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15 Awesome Dog-Friendly Midwest Road Trip Destinations

Best buds make the best travel companions—especially when they let you call all the shots and pick the snacks. We sniffed out our top 15 Midwest Fido-friendly road trip destinations for when your doggo’s wanderlust just can’t be held at bay any longer. Read on to find out about these dog-friendly road trips including what to bring, where to stay, and more!

Before You Hit the Road…

Make sure you are PAW-pared! Here are just a few tips to make sure your road trip is a success.

Think about a trip to the vet

First, make sure  sure pup is up to date on her vaccinations and physically able to take a road trip. Also, ensure fren’s flea and tick treatments are up to snuff! If your pup is an anxious shot-gun rider, ask your vet about meds or other solutions to make him more comfortable.

Always come prepared 

Not sure what to pack for the pup? Here is a list of essentials to consider adding to the luggage.

• Identification papers and vaccination records
• Collapsible dog bowls 
• Plenty of food and treats
• Leash with collar or harness 
• So many poop bags
• A towel or two (for muddy paws) 
• A first aid kit 
• Any medications that Fido might be taking 

For more information about how to prepare your pup for an amazing road trip, check out Dog Road Trip Essentials: 5 Tips for Your Drive before you hit the road! 

Buckle Up, Pups! It’s Road Trip Time

From Minnesota to Ohio, and back around the Dakotas, the Midwest is a region like no other! If you’re ready to see what you’ve been missing, or revisit some amazing sites, then check out these dog-friendly vacation destinations.

More than simply fun to say, Bemidji has a lot to offer to road-tripping pups and humans. We recommend checking out Lake Bemidji State Park for its over-water sunsets and pup-friendly hiking trails.

After that, head over to the patio of Bemidji Brewing for some delicious beer and food, plus complimentary treats and water for your pup.

Our dog-friendly lodging pick: Candlewood Suites Bemidji . This spot allows two pups up to 80lbs for $25 the first night, followed by $15 for each subsequent night.

Duluth is your quintessential MN vacation spot, and it’s one of the dog-friendliest as well. Duluth is home to a number of fantastic dog-friendly restaurants and breweries: We love the patios of At Sara’s Table Chester Creek Café or Ursa Minor Brewery in paw-ticular.

As for outdoor activities, check out Ely’s Peak for a leisure hike with some amazing views. If you are feeling adventurous, Duluth offers a unique experience for you and your pooch; Lake Country Air & Beaver Air Tours is an air tour company that showcases water plane rides up the North Shore! Adults can fly for just $119 per person, and doggos fly free!

Our dog-friendly lodging pick: Sheraton Duluth Hotel . Allows dogs up to 80 lbs, and a guest waiver must be signed at check-in.

4. Wisconsin Dells

The Dells is a Midwest must-see for both you and you pup. Start off your vacation with a river ride from Dells Boat Tours , and if you and Fido are still on the prowl, head out to Devil’s Lake State Park for some terrier-iffic views.

Hungry after all of that fresh air? The Keg & the Patio and the Brat House Grill both have dog-friendly patios, and the latter has a special menu just for pups. If you’re in the mood for a brew, hit up the dog-friendly beer garden at Port Huron Brewing Company . 

Our dog-friendly lodging pick: While there is no shortage of pet-friendly lodging options in the Dells, our recommendation is Baker’s Sunset Bay Resort , where you can bring up to two pets for $15 a day per floof. 

5. Door County

A famous, stunning slice of land surrounded by Lake Michigan, Door County is home to a fabulous hiking opportunity in Whitefish Dunes State Park , which even has access to a dog-friendly beach area on Lake Michigan.

After you get in some walking, swimming, and socializing, consider a stop by the Gibraltar Grill for delicious food and fantastic music. Maybe pup’ll even get a feature on the Dog Pals page of their website!

Our dog-friendly lodging pick: Hillside Inn of Ephraim . Allows pups with approval, so be sure to call ahead. Other great lodging options can be found here .

6. Mackinac Island 

Hit the water with a trip to Mackinac Island in the UP of Michigan. Soak up the sun with a ferry ride from Shepler’s Mackinac Island Ferry (Fido rides for free). We know your history hound has been beggin’ to see a recreation of an 18th-century fort and fur trading village, and he’ll get his fill at Colonial Michilimackinac . 

Looking for something to cure your sweet tooth on this vacation? Head to the famous Ryba’s Fudge Shop and experience some delicious T-R-E-A-Ts for pups and humans. It’s the best of both worlds. 

Our dog-friendly lodging pick: Stay right on the island at the Mission Point Resort , or the Holiday Inn Express Mackinaw City is just a short ride to the mainland of Michigan (one-time $30 pet fee). 

7. Cleveland 

Ready to have a ball? Cleveland is home to tons of dog-friendly excitement including the Ohio & Erie Canal Towpath which has access to some of the most beautiful views of the canals and wildlife. If pup is more of a city slicker, get tickets to Cleveland Scavenger Hunt: A Ball Round The Mall where you and Fido can search the city for landmarks, artwork, and more!

Bring your woofer to the dog-friendly patios at Nano Brew Cleveland and Luxe Kitchen , which are both top rated in the city for both food and dog-friendliness

Our dog-friendly lodging pick: Hotel Indigo Cleveland Downtown is a great place to unwind, and they’re dog-friendly! Their pet-policy allows for 2 dogs up to 50lbs for a $35 deposit and $35 nightly fee per dog. 

8. Indianapolis

Let’s set our road trip GPS to Indy! First stop is Broad Ripple Park which is home to a beautiful view of the White River and lots of doggos. From there, check out the Cultural Trail , which connects Indy’s six Cultural Districts. You’ll find pup tons of dog-friendly breweries, coffee shops, and stores along the way (Mass. Ave is a mutts visit!).

You’re sure to be hongryafter your day of play, so zoomie over to Cafe Patachou for some top-rated breakfast and lunch! After your meal, hit up Hotel Tango Distillery for a few cocktails with your pal.

Our dog friendly lodging pick: Ironworks Hotel Indy LOVES dogs, and if you call them in advance, they’ll even prep your room with dog bowls, a custom Ironworks mat, and a treat!

There’s no dog-friendly vacation station like the Windy City for your road trip! If your pup has been cooped up on your long ride, head over to Puptown Dog Park in Margate Park! Chicago has some of the best gardens and outdoor shopping in the Midwest; take Fido to Farmers Market Garden Center for some retail therapy. 

Pizza is a Chicago staple, and 6 Mutts Chicago food truck is slingin’ pizza options for you AND your pup. What goes great with pizza? Beer. Lake Bluff Brewing welcomes both you and your pooch on the patio for views and brews!

Our dog-friendly lodging pick: the Staypineapple Hotel is an iconic spot in The Loop of Chicago! Not only are they pet-friendly, but according to their website they are, “Pet Obsessed!” 

10. Des Moines

Treat your pup to a road trip to Des Moines. We recommend checking out the dog-friendly and scenic Kruidenier Trail , a relatively short hike which passes beautiful Grey’s Lake and connects to other local trails.

After that, consider a stop at the dog-friendly patio of Gazali’s , a Mediterranean spot which churns out gyros, wraps, salads, and sandwiches.

Our dog-friendly lodging pick: La Quinta Inn & Suites Des Moines West Clive . Like almost all La Quinta locations, this spot allows pups—with some restrictions. Find deets here .

11. St. Louis 

Another great pet-friendly road trip destination is St. Louis! Get outdoors and go to the Ellen Clark Sculpture Park & Dog Park for a peek at the St. Louis University campus.You should also add the iconic Gateway Arch National Park for some fun and very cute photo-ops! 

Head to Boathouse at Forest Park to enjoy an American style dinner on their pooch-loving patio. If you’re looking for more variation in your menu, try Tamm Avenue Grill for the largest dog-friendly patio around.

Our dog-friendly lodging pick: Magnolia Hotel St. Louis offers a unique lodging experience, and is also proudly pet-friendly.

12. Kansas City 

Put Kansas City on your Midwest road trip vacation checklist. You and your pooch can catch a flick at the Boulevard Drive-In Theater or take a stroll at the Shawnee Mission Off-Leash Dog Park .

You can’t leave Kansas without tasting some KC BBQ. Woodyard Bar-B-Que has tons of amazing KC-style options, and the dog-friendly patio is perfect for you and pup to enjoy a meal together. 

Our dog-friendly lodging pick: The Residence Inn Kansas City at the Legends is a comfortable stay that allows 2 pets (50 lb max) per room for a $150 fee. 

If you’re looking for some history on your dog-friendly road trip, Omaha is a great place to stop. Memorial Park showcases trails and monuments that honor the fallen soldiers from WWII, Korea, and Vietnam. Then head to Omaha Dog Bar where your dog will get a chance to socialize with tons of other pooches while enjoying the “bar” of dog treats. 

J. Coco is a great place to settle down from your busy day to a nice lunch or dinner on their patio with your bud. They serve up great organic fare and will tell your pup how pretty she is (even tho she already knows).

Our dog-friendly lodging pick: The Element Omaha Midtown Crossing is an affordable hotel with great amenities, including being very pet-friendly. 

South Dakota

14. Rapid City

Rapid City is one of the Midwest’s great, often-overlooked gems. While you’re in town, make a stop at the in-progress, ten-times-larger-than-Mount Rushmore Crazy Horse Memorial , which will be among the world’s tallest monuments once completed. You’ll enjoy the short walk, the breathtaking view, and the look at the Midwest’s Native American heritage. 

Consider a stop at the sprawling, gorgeous patio of Murphy’s Pub and Grill for some drool-inducing eats like street-style tacos, unique sliders, chicken wings with wacky flavors like strawberry-habanero, and much more.

Our dog-friendly lodging pick: Grand Gateway Hotel . Up to two dogs allowed per room for a nightly fee of $10 per dog.

North Dakota

When traveling to North Dakota, Fargo is a must-see destination. Your pup will love joining you at the Fargo Air Museum where you can both see some airplanes and fascinating memorabilia. When your hound is ready to roll, get some fresh air at the Village West Dog Park . 

Fargo has many dog-friendly breweries and restaurants, and one that should be on your radar is Wild Terra Cider . From sweet spiked ciders to street tacos and nachos, this bar is one that you and your furry friend will definitely enjoy. 

Our dog-friendly lodging pick: Red Roof Inn offers a homey atmosphere while also being super welcoming to four-legged frens.

Woof to the Wise

Not every road trip is going to be ideal for your furry friend—nor your furry friend for every road trip. Remember to consider your dog’s individual personality and needs when deciding whether or not they should tag along. And, as always, never ever leave your dog unattended in a vehicle—especially during the scorching summer months.

There you have it, friends. You now have a summer’s worth of pup-lovin’ road trip inspiration to keep you and your best bad busy.

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HOME / BLOG / Travel Destinations 49 Places To See On A Pet Friendly American Road Trip

49 Places To See On A Pet Friendly American Road Trip

• By Amy at GoPetFriendly.com
• May 8, 2023

The American road trip … it’s iconic! And there’s no better way to see some of the most special places across the country. But what if you want to include your pet in the fun? Here are 49 breathtaking sights you’ll love exploring together on a pet friendly American road trip!

Road trip vacations are as American as apple pie. And yet, planning to see the “best” the United States has to offer can be overwhelming. Your trip could focus on cultural sites, national parks, state capitols, scenic landmarks, or sports venues.

But if you’re looking for a truly special experience, why not plan the best pet friendly American road trip? Visit the top pet friendly attraction in each state, and collect precious memories with your best friend along the way!

A Pet Friendly American Road Trip

The most difficult part of planning an epic road trip is choosing the stops. From beaches to mountain tops, bustling cities to secluded retreats, you want to see the very best places across the country.

We traveled full-time with our dogs for twelve years, spending time in all of the lower 48 states. And we’re happy to share what we’ve learned!

Whether you’re planning to see the whole country in one trip, or checking out one region at a time, the itinerary we’ve laid out for your pet friendly American road trip will give you a good feel for what each state is about. And very stop is guaranteed to be fun for you and your pet! Click on the name of each location for more details and photos.

READ MORE ⇒ How To Plan A Pet Friendly Road Trip

The Ultimate Pet Friendly American Road Trip

This itinerary covers nearly 15,000 miles and would take at least a couple of months to complete. If you can do it all at once, it’s absolutely the trip of a lifetime!

If you’re looking for shorter trips, choose one or two regions and do a deeper dive in each area. Any combination will make a fantastic pet friendly vacation.

The Northwest

We start this pet friendly American road trip in the northwestern United States. From Washington’s green isles to the heights of Beartooth Highway, this region has something for everyone!

READ MORE ⇒ Tips for Traveling Alone with a Pet

Washington – The San Juan Islands

In the far northwest corner of the contiguous United States, off the coast of Washington, lies a confetti of emerald jewels in the Salish Sea. Known as the San Juan Islands, the landscape is a patchwork of pine forests, stoney beaches, verdant pastures and fields, and sparkling lakes.

Each of the islands has its own charm, and no matter which you visit, you won’t be disappointed.

Oregon –  Portland’s Parks and Gardens

With eclectic neighborhoods, great eateries, and one of the most extensive urban park systems in the country, Portland, Oregon is a pet friendly playground!

Boasting 10,000 acres of natural areas and parks scattered around the city, there’s a treasure around every corner. And if your pup enjoys being social, don’t miss some of the 20+ off-leash areas!

Idaho –  Lake Coeur d’Alene

Among the rugged peaks of northern Idaho, where pine trees far outnumber people, lies one of the most beautiful lakes in the world. Unfolding over 26 miles with more than 135 miles of shoreline, Lake Coeur d’Alene is a sparkling blue jewel.

From scenic boat tours to miles of pet friendly trails, there are as many ways to enjoy Lake Coeur d’Alene as your imagination allows.

Wyoming –  Bighorn National Forest – Medicine Wheel

You’ll find some of Wyoming’s most diverse terrain in the Bighorn Mountains. It would be easy to spend weeks hiking the 1,500 miles of pet friendly trails and enjoying the three scenic drives. But for us, nothing speaks to the timelessness and beauty of the Bighorns like a visit to Medicine Wheel.

Montana –  Beartooth Highway

For 68 miles, between Cooke City and Red Lodge, Montana, the Beartooth Highway winds through some of the most awe inspiring terrain in the United States. This road, one of the highest in the lower 48 states, passes 20 peaks that rise over 12,000 feet.

You’ll experience pristine mountain landscapes, lush forests, and alpine tundra – all within a few miles. And there are numerous places to park the car and hit a pet friendly trail with your furry travel buddy!

The Southwest

The southwest section of this pet friendly American road trip starts with a romp on Carmel’s spectacular dog beach. The next two stops at Red Rock Canyon and the Grand Canyon offer fantastic pet friendly hiking. And we top it off with a trip up Telluride’s gondola. You and your active pets are going to love this adventure!

California –  Carmel’s Dog Beach

Carmel’s crowning glory is its magnificent beach. This mile-long stretch of sand begins just steps from downtown and runs to just below the 9th hole at Pebble Beach Golf Course. And it’s all pet friendly!

Dogs are welcome to romp off-leash on the beach. Or visit Carmel River State Beach, just down the road, where leashed pets will find plenty to explore.

Nevada –  Red Rock Canyon National Conservation Area

It’s only 17 miles from the Las Vegas Strip, but Red Rock Canyon feels like a completely different world! From the 13-mile scenic loop road to the 30+ miles of pet friendly trails and picnic areas with great views, you’ll have a fantastic day here with your pet!

Arizona –  Grand Canyon National Park

Traveling to any national park is a wonderful experience, but seeing the Grand Canyon with your pet will make your vacation unforgettable!

The pet friendly South Rim Trail runs for 14 miles and is paved for easy walking. Make sure to allow plenty of time to take in the panoramic views!

Colorado –  Telluride Gondola to Mountain Village

Tucked high in Colorado’s San Juan Mountains, the village of Telluride is ideal for a Rocky Mountain adventure with your pet. Offering spectacular scenery, miles of hiking trails, a pet friendly gondola, and a nice selection of eateries and lodging that welcome pets, it might be the highlight of your pet friendly American road trip!

Utah –  Dixie National Forest’s Red Canyon

Covering almost 2 million acres, every inch of Dixie National Forest is pet friendly! And with 1,600 miles of hiking, horseback riding, and bike trails, and hundreds of miles of scenic byways, backways, and drives, you and your pet could spend a lifetime exploring here.

While you’re in the area, be sure to check out Bryce Canyon and Zion National parks. And don’t miss the chance to visit Best Friends Animal Sanctuary in Kanab, Utah !

READ MORE ⇒ Tips For RVing With Pets

The South Central

Bustling San Antonio is balanced by serene natural wonders on the South Central section of our pet friendly American road trip.

If you’re considering skipping the pet friendly paddle on the Buffalo National River … DON’T! We did it with Ty and Buster, and loved every minute. Though it was our dogs’ first time in a canoe, they did great. And now it’s one of our favorite memories with them.

New Mexico –  White Sands National Park

The name “White Sands” might be a little misleading, but that doesn’t make this pet friendly national park any less impressive! The shimmering dunes here are actually made of gypsum – not sand. And thanks to an ancient sea and some very fortunate geography,  it’s now the world’s largest dunefield!

You’ll find pet friendly trails and plenty to keep you busy at White Sands. And be sure to stay for sunset. It’s unlike any other you’ll see!

Texas –  San Antonio River Walk

Providing access to some of the city’s most precious historical and cultural sites, the 13-mile, pet friendly San Antonio River Walk is one of the most unique parks in the country!

It would be easy to spend several days exploring different sections of the River Walk, hopping on and off to visit all the connected neighborhoods.

Oklahoma –  Wichita Mountains Wildlife Refuge

As if watching the grazing bison, elk, and white-tailed deer weren’t enough reason to visit Wichita Mountains Wildlife Refuge, you and your pet will also find 18 pet friendly hiking trails and lakes for boating and paddling!

Arkansas –  Canoe the Buffalo National River

Canoeing the Buffalo National River with your pets is easier than you might think! Pet friendly canoe rentals are a cinch to find, and the calm water will put every paddler at ease.

When you’re back on solid ground, there are also miles of pet friendly trails to hike along the river’s course and in the nearby Ozark National Forest.

READ MORE ⇒ Tips for Canoeing or Kayaking with Dogs

Kansas –  Monument Rocks

Monument Rocks is what’s left of a sea floor that formed millions of years ago when water covered the continent from Montana and the Dakotas to Texas and Louisiana. The chalk spires, buttes, and arches that remain now stand 70 feet tall on the Kansas plains. And your pets are more than welcome to explore them with you!

The Plains – North

The Northern Plains section of this trip takes you through the heartland and reveals what America was like before Europeans arrived.

You’ll spend time appreciating the vastness of Lake Superior and the powerful Mississippi River. Then walk in the footsteps of the Native Americans who lived in Iowa and North Dakota.

Minnesota –  Split Rock Lighthouse State Park

Split Rock Lighthouse State Park sits on Lake Superior’s northern shore. Providing breathtaking views of one of the most photographed lighthouses in the country and 14.5 miles of pet friendly trails, it’s a great place to stretch your legs or camp on the beach.

READ MORE ⇒ Camping With Dogs – A Beginner’s Guide

Wisconsin –  Trempealeau National Wildlife Refuge

Trempealeau National Wildlife Refuge is located in the Mississippi River flyway, the migration route of about 40% of all waterfowl and shorebirds. The refuge serves as a “bed and breakfast” for the birds as they travel through and is home to the magnificent bald eagle.

In addition to some spectacular bird spotting, there are miles of pet friendly trails to explore.

Iowa –  Effigy Mounds National Monument

Standing atop the bluffs overlooking the Mississippi River, it’s easy to see why American Indians chose to make this breathtaking place their home. Covering 2,500 acres along the western bank of the Mississippi River, Effigy Mounds National Monument now protects 206 prehistoric earthen mounds built by Indigenous People, 31 of which are in the shape of animals.

You and your dogs are welcome to explore all the trails. But remember to be respectful and never walk on (or allow your pet on) the mounds.

North Dakota –  Knife River Indian Villages National Historic Site

Interpretive plaques help you imagine what life was like at the Knife River Indian Villages. This is where Captains Lewis and Clark first met Sacagewea and her husband, Toussaint Charbonneau. Once a bustling community of nearly 400 people, this is now a quiet place to reflect and enjoy the scenery.

South Dakota –  Custer State Park

Custer State Park protects 71,000 acres of South Dakota’s most magnificent landscapes. It also provides habitats for a dazzling array of wildlife. Whether you prefer picturesque drives or multi-day hikes, wildlife viewing or kayaking, elegant dining or campfires under the stars, Custer has something to please traveler.

Nebraska –  Fort Robinson State Park

Fort Robinson State Park is a rare combination of stunning landscapes, fascinating history, a variety of recreational opportunities, and pet friendly accommodations. 

Spread over 22,000 acres, with rugged buttes as the backdrop, it’s a wonderful place to unwind and enjoy the expansive wild prairies during the day and the star-filled skies at night.

The Great Lakes

Three of the five stops on this section of our pet friendly American road trip are on the Great Lakes! Absorb the energy of downtown Chicago at Navy Pier. Then contrast it with the leisurely atmosphere of Mackinac Island. You’ll enjoy both ends of the spectrum!

West Virginia –  Monongahela National Forest

The Monongahela National Forest covers more than 900,000 acres, preserving a rugged and wild paradise unlike any other. With an extensive backwoods road system, oodles of campgrounds, and 825 miles of pet friendly trails, you and your pet will find plenty to explore!

Ohio – Holden Arboretum

Holden Arboretum is evidence of the beauty that results when humans and Mother Nature work together. Encompassing 3,600 acres, it’s one of the largest arboreta and botanical gardens in the country and a fabulous place to explore with your pet.

Wander the garden paths or hit the miles of trails through native forests with your furry travel buddy!

Illinois –  Chicago Lakefront Trail & Navy Pier

Chicago’s pet friendly Lakefront Trail runs for 18 miles along the spectacular shore of Lake Michigan. Connecting vibrant neighborhoods, expansive parks, popular beaches, and famous attractions like Navy Pier, Buckingham Fountain, and Soldier Field, it’s fun to choose a section and spend a day exploring it with your pet!

READ MORE ⇒ Tips for a Cross-Country Road Trip with Pets

Indiana –  Indiana Dunes National Park

Caribbean blue waters and miles of pet friendly beaches await you at Indiana Dunes National Park. But the beaches are just the beginning!

This dynamic landscape also features dunes, ponds, marshes, creeks, prairie, and forests for your exploration. Whether you decided to hang out on the shore or hike the trails, you’re sure to have a great time.

Michigan –  Mackinac Island

Hop aboard the pet friendly ferry for a trip to Mackinac Island. Automobiles aren’t allowed, but you and your pet won’t have any trouble getting around!

Main Street is just steps from the ferry docks, pets are welcome on the horse-drawn carriages rides, and bikes with pet trailers are available for rent. So all of Mackinac’s most popular attractions are within easy reach!

The Plains – South

Road tripping pets are going to adore this route through the southern plains. Romp at the incredible off-leash dog park at Shelby Farms, then stiff along the 444-mile Natchez Trace! Finally, spend an afternoon relaxing in the shadow of the Gateway Arch in St. Louis.

Louisiana –  State Capitol Gardens in Baton Rouge

Standing 34 stories tall, Louisiana’s capitol in Baton Rouge is the tallest state capitol building in the United States. It’s surrounded by 27 acres of pet friendly grounds and gardens that offer picturesque views from every angle.

Stroll the paved paths under massive live oaks and palm trees or plan a picnic with your pet!

Mississippi –  The Natchez Trace Parkway

The Natchez Trace Parkway stretches 444 miles, from Natchez, Mississippi to Nashville, Tennessee. It’s a blissfully quiet, billboard-free retreat from our fast-paced highways.

But a slower pace doesn’t mean you’ll be bored! There’s something to sniff around every bend with countless exhibits and 28 pet friendly trailheads along the route.

Tennessee –  Shelby Farms Park Off-Leash Area

Shelby Farms Park in Memphis is one of the country’s largest urban parks. With a massive off-leash dog area, 40 miles of pet friendly trails winding through 4,500 acres, a disc golf course, canoe, kayak, and paddle board rentals, and a lovely visitor center, you could easily spend an entire day here!

Kentucky –  Abraham Lincoln Birthplace National Historic Park

President Abraham Lincoln’s life is an inspiration, and visiting his simple birthplace fosters an even deeper appreciation of his accomplishments.

Pets are welcome to join you on the grounds of the historic park. And together you can explore the trails there and at the Lincoln Boyhood Home at Knob Creek, just ten miles away.

Missouri –  Gateway Arch National Park

Leashed pets are welcome to explore the extensive grounds at St. Louis’ Gateway Arch National Park. Enjoy the Riverfront Trail, embark on a one-hour scenic riverboat cruise, and be sure to ask now your pet can become a BARK Ranger during your visit.

READ MORE ⇒ 60 National Parks Where Your Dog Can Be A BARK Ranger

New England

You can see a lot without traveling far in New England! Enjoy Central Park in the heart of Manhattan, then explore the trails in Acadia National Park. Finally, take a splash in the pond at Dog Mountain. From beginning to end, this section of our pet friendly American road trip is a pet’s dream come true.

New York –  Central Park

There’s no place like New York! Central Park is the third most visited attraction IN THE WORLD – and it’s even better with your pet. Whether you choose to lounge on a bench, enjoy the conservatory gardens, or explore the wooded trails in the Ramble, it will be a day to remember.

Connecticut –  Mystic Seaport

Spread over 19 spectacular acres on the banks of the Mystic River, Mystic Seaport is the largest maritime museum in the United States. You and your pet can view magnificent old boats and learn what life was like for seaport dwellers in this part of New England in the 1800s.

Rhode Island –  Newport Cliff Walk

Newport is known as the City by the Sea. And a stroll along the pet friendly Cliff Walk proves that she more than lives up to her nickname!

Winding for 3.5 miles with the rocky shoreline on one side and the lush gardens of historic mansions on the other, the Cliff Walk Trail provides you and your pet with unforgettable views.

Massachusetts –  The Freedom Trail

Boston’s Freedom Trail connects 16 of our country’s most significant historic landmarks – locations that played a pivotal role in America’s rebellious beginning.

The pet friendly 2.5-mile path starts in Boston Common where you can pick up a map. Here pups will also find two off-leash areas for sniffing and socializing in America’s oldest public park. Then follow the red brick path through the city at your own pace, taking in each site as you go.

Maine –  Acadia National Park

As one of the countries most pet friendly national parks, you and your pet will find plenty to love in Acadia. There are more than 100 miles of trails to sniff, carriage roads to explore, and pets are even welcome on the free shuttles that run throughout the park and around the island!

READ MORE ⇒ America’s Best Dog Friendly National Parks

New Hampshire –  Mount Washington

Visiting Mount Washington can be tricky. More than 100 days a year the wind at the summit exceeds hurricane force, the peak is enveloped in clouds 60% of the time, and snow can fall year round. But if you’re lucky enough to be there on a pleasant day, you and your pet will never forget the pet friendly trails and stunning views.

Vermont –  Dog Mountain

At Dog Mountain, pets aren’t just welcome – they’re cherished! This 150-acre former dairy farm is always open to the public and dogs are welcome to shed their leashes while they run, play, and swim in the pond.

There are also hiking trails, peaceful retreats, and a pet friendly chapel and art gallery.

The Mid-Atlantic

The theme of this section of the trip is early American history with a lot fun thrown in! Learn about the first Europeans to arrive in the New World in Colonial Williamsburg. Then stroll through Washington, DC, where history is made every day. Next enjoy a day on the Jersey shore before heading to the Pocono Mountains for a scenic train ride!

Virginia –  Colonial Williamsburg

Colonial Williamsburg welcomes you and your pets to step back in time. View historic homes, watch demonstrations at the trades shops, enjoy the fife and drum corps, and get a bite to eat at one of the taverns or restaurants.

Washington, DC –  The National Mall

There are few places in the America more inspiring than our National Mall & Memorial Gardens. And because this national park sits in the middle of a living city, it’s more pet friendly than you might expect!

From the U.S. Capitol to the Lincoln Memorial, you and your pet can view dozens of iconic sights all within walking distance.

Maryland –  Cruise on Chesapeake Bay

Explore the Chesapeake Bay with your travel buddy aboard a pet friendly cruise! Arrange a tour from Annapolis, Baltimore, or St. Michaels. Or contact one of the countless privately-operated charter boats available in harbors up and down the bay, most of whom are happy to welcome your pets.

READ MORE ⇒ 5 Questions To Ask BEFORE Taking A Dog On A Boat

Delaware –  Walking Tour of Historic New Castle

Do you love strolling with your pet along tree-lined streets? Would you like to admire beautiful examples of colonial Dutch and Federal architecture? And what if you could learning a bit about the early history of our country at the same time?

It sounds like a walking tour of New Castle will be right up your alley! Be sure to check the local calendar for pet friendly events when planning your trip.

New Jersey –  The Jersey Shore at Wildwood Dog Beach

New Jersey has many popular beaches, but Wildwood’s beach stands out. It’s lovely, spacious, family-friendly, and free to use. And the best part is that your pets can come along!

Dogs on leashes are welcome from dawn to dusk, every day on the Wildwood dog beach between Glenwood and Maple Avenues. Just look for the gigantic fire hydrant and enjoy a day of sand and surf together.

Pennsylvania –  Lehigh Gorge Scenic Railway

All aboard! The Lehigh Gorge Scenic Railway welcomes pets on their vintage coaches. Powered by diesel engines and departing from the old railroad station in historic downtown Jim Thorpe, the narrated trips lasts about 70 minutes and follow 16-mile route along the Lehigh River as it winds through the gorge.

The Southeast

Beautiful gardens await your arrival on this pet friendly road trip through the Southeast. Wander the paths through Rock City, where on a clear day you can view seven states! Then admire the last large-scale romantic-style garden at Magnolia Plantation. Finally, spend a day exploring the formal gardens and wooded trails of the 8,000-acre Biltmore Estate.

Alabama –  Little River Canyon National Preserve

On a flat-top mountain in northeastern Alabama, Little River Canyon National Preserve protects 15,000+ rugged acres along the Little River.

Be prepared for stunning scenery and a taste of southern hospitality, because the preserve is incredibly pet friendly. Not only can your furry travel buddy join you on all the trails — he’s also welcome inside the visitor center, and the staff has dog treats!

Georgia –  Rock City Gardens

Visitors from around the world come to admire Rock City’s botanical and geological features. And your pet is welcome to join you on the trails. You can even have lunch together on the patio at Café 7, a seasonal restaurant with amazing views!

Florida –  Fort De Soto Dog Beach

Fort De Soto’s beaches are acclaimed for their white sand and clear blue waters. But the best part of this quarter-mile stretch of beach is that it’s dedicated to the dogs!

Pups can romp leash-free here and in the adjacent enclosed dog park. Then rent a kayak and paddle the 2.25-mile water trail, peddle the 7-mile bike trail, or hit the hiking trails to see more of the island.

South Carolina –  Magnolia Plantation & Gardens

Founded in 1676 by the Drayton family, Magnolia Plantation and Gardens is America’s last large-scale Romantic-style garden. You and your pup are welcome to enjoy the trails, grounds, gardens. Plan accordingly to see your favorite flowers in bloom!

North Carolina –  Biltmore Estate Gardens and Grounds

At the Biltmore Estate, pets cannot tour the historic home. However, you and your pet can stroll the lush garden paths, or hit the 23 miles of hiking trails that criss-cross the 8,000-acre estate.

When you’ve worked up an appetite, head over to Antler Hill Village and choose a table on the patio at one of the pet friendly restaurants!

READ MORE ⇒ Training Your Dog To Be A Great Traveler

How long will it take and what will it cost?

In total, our entire pet friendly American road trip is 15,000 miles and will take at least two months. That’s assuming you have great luck with the weather and don’t mind driving about 8 hours a day.

The cost of the trip depends on how you travel. And where you are comfortable staying is a factor that has a big impact. Car camping or tenting will be least expensive. And staying at pet friendly hotels will cost more. Luckily, pets aren’t picky about where you sleep – as long as you’re together.

READ MORE ⇒ Car Camping With Pets: Prep The Car, What to Pack, and More

Most of the attractions we’ve recommended are fairly inexpensive (free – $20), with a few exceptions. So figure around $500 per person for all the admission fees.

Gas will cost another $1,500 to $2,000.

Then there’s food, which can also vary a lot. To save money, plan to spend time shopping and preparing your own meals rather than eating out. If you can eat for $15 per day, that adds about $900 per person for a two-month trip.

In total, this trip could be done by one person for around $4,500. Bring a buddy to split the lodging and gas costs and the cost is even less for you both.

So, there you have it – our Ultimate Pet Friendly American Road trip! Now all that’s left to do is pack the car, crank up the tunes, and hit the road. Waggin’ trails to you!

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The ultimate dog-friendly summer road trip guide

Not every dog mom or dad has an easy time leaving their pup behind (hi!). When it comes to summer road trips , why not bring Buddy along for the ride?

For pups that do well in the car (my Frenchie Jaxson loves soothing jams and good vibrations), road trips are a great way to include your canine companion in your adventures.

Unlike air travel, most vehicles provide plenty of room for your pooch. It also provides freedom and flexibility to plan and pivot as you see fit, along with increasingly appealing options when it comes to dog-friendly accommodations .

Still on the fence? We've broken down everything you need to know, prepare and pack so you can bring your favorite tail-wagger along on your next exciting road trip.

Buckle up Fido

The term "precious cargo" applies to more than just the little ones. Ensure your four-legged friend is safe and secure before you leave your driveway. Lucky for you, there's a plethora of options that cater to your dog's security while on the road.

Secure a seat belt

My personal preference is a dog-friendly seat belt, including an actual harness seat belt or seat belt restraints like the EZYDOG. If your dog does well cozied up on the actual seat of your car, this is a great choice. Make sure the seat belt is tightly fastened to the dog and that it properly clicks into the seat belt jack before you get moving.

Use a car seat or booster

Yes, doggy car seats are a thing. These typically also buckle into the seat belt and can be tethered to the dog's harness or collar for a second level of security. Or you can opt for a booster seat like the Kurgo , which also buckles in and offers a bit more space while keeping your doggo in place.

Fasten a hammock

Looking for a cool lounge vibe for your pup by creating a padded cradle to keep your dog contained? Strap up a hammock — also great for keeping dog hair and treat crumbs contained. However, this option is best paired with a dog seat belt because the hammock alone won't secure your pup.

Set up a crate

If you have a larger vehicle with plenty of breathing room and your dog does well crated, this may work for you. Keep in mind you will need to find a way to secure the soft crate so it stays in place. Consider a travel crate that is impact-safe. Note that crating may not be the best option for anxious pups.

Build a barrier

If you have a large dog and an even larger cargo area, you can secure a barrier made of netting or metal bars. This also works if you have more than one dog and a designated section of the vehicle reserved just for them. The cargo bars may keep the dogs from traveling within the vehicle, but they won't secure your dog, so use a seat belt.

Create a comfort zone

Dogs sleep an average of 14 hours per day, which means once safely fastened, your pooch needs a comfortable place to rest and relax while you're taking in the scenery. Make sure your dog has enough space to stand up, turn around and adjust as needed.

A good rule of thumb is to provide a space as large as their standard dog bed. In fact, taking your dog's actual bed is one easy solution. Don't want to take the regular dog bed on the road? Buy one for the trip and let your pup cuddle up in prep so they know exactly what to expect on departure day. Bonus: they'll have infused the bed with not only their scent but familiar ones from inside your home.

Help your dog feel cozy by adding a blanket or a few soft toys.

Breaking down the basics

With so much packing and planning, don't forget the bare necessities, as well as toys and chews that will keep your dog happy throughout your journey.

Necessary accessories

Typically, these include a collar/harness (with current ID tag) and leash, pet waste bags and food and water bowls. Collapsible silicone bowls are also handy and great for excursions.

Soft, plush toys are the safest for road travel. Consider soft toys your dog cannot tear into easily. Perhaps leave the squeaker toys at home, as well as rope toys – both are choking hazards, and no incessant squeaking may preserve your zen mode.

Bones and chews

Stock up on bones, chews, bully sticks and rawhides. However, make sure you stow them for long stops or once you are at your lodging accommodations – these are choking hazards, too. Fillable cones like rubber Kong toys also fall into this category.

Outdoor toys

If your pup loves playing fetch, make sure to pack tennis balls, frisbees and ball launchers for fenced stops and dog parks.

Related: A comprehensive guide to traveling with pets

Food, glorious dog food

Everybody's got to eat, including Bowser. Dogs consume two kinds of foods: dry and wet. The most convenient food is dry kibble. Many brands sell 5-pound bags, which makes it easy to grab one (don't forget the measuring cup) and keep it with you for a long haul. If you're taking a shorter trip, you can portion the food ahead of time into meals in reusable silicone bags.

In terms of wet food, it should be as easy to purchase the cans or packets you need. However, be cautious of temperature advisories. For example, if your pup takes wet food (or freeze-dried food) that should be stored at or below a certain temperature, you will need to make this accommodation. Pack a small cooler dedicated solely to your dog's food.

If you forget your dog's food, run out or thought you'd be able to purchase it when you arrived at your destination but can't find it, buy a food with a similar ingredient list and arm yourself with one secret ingredient: organic, canned pumpkin.

"The fiber in the pumpkin may help avoid any digestive disturbances the new food may cause," offers Johnna Devereaux, clinical pet nutritionist and director of nutrition and wellness for Bow Wow Labs.

Don't forget about dog treats. You should include these in your food inventory. Also, consider packing some extra to reward your pup for being a good boy or girl throughout the journey.

Additionally, make sure to pack your pup's vitamins and supplements. It's important to keep up with your dog's regular nutritional routine – the road is no exception. If your dog tends to have a nervous belly when traveling, consider ginger root as a solution. "Ginger root may help calm and unsettle stomach and is best given just before departure," Devereaux suggests.

TPG tip : Store the dog food and treats out of range from where your pup will be seated in your vehicle so they aren't tempted by the familiar scent.

Pack an emergency stash

Just like you packed yourself an emergency sustenance stash of protein bars and trail mix, you should the same for your loyal companion. There are a lot of unknowns associated with the open road. You could be delayed by weather or a car issue, and you will need to prepare extra dog food just in case. (I like to pack two additional days of food, at minimum.)

Splurge a little

Obviously, stopping for special treats and indulgent meals is one of the best parts of a road trip. When your pup accompanies you, they should be no exception to the rule. Once you've carved out your route and itinerary, do your due diligence to find some pitstops for Spot. (While the occasional Starbucks puppuccino can be fun, it's best not to make that a daily treat.)

Pet bakeries

For fresh gourmet treats, bookmark these bark-worthy bakeries with outlets nationwide:

Woof Gang Bakery & Grooming: Not only will you find gourmet mix-and-match treats, but if your companion could use a refresh, jump into the grooming schedule. Founded in Florida, this barkery now has 200 locations in 18 states, from North Carolina to New Jersey and Colorado to Las Vegas.

Three Dog Bakery : Find fresh-baked treats from "collieflower pupcakes" to eggs-and-bacon-shaped cookies in Indiana, Tennessee, Kentucky, Missouri, Texas, Minnesota and other states.

The Dog Bakery : Want to celebrate your pup's birthday on the road? Order a celebration cake. Or, settle for delicious biscuits, jerky and assortment treat packs with locations across California.

Hotel pampering and doggy socials

Want to spoil your pup? Plan a hotel stay where you can treat your pup to a gourmet meal or just stop for a relaxing dinner at a doggy social club.

Loews Hotels : In addition to a check-in care package featuring treats, bowls, placemats and waste bags, there's a full gourmet room service menu for dogs developed by the hotels' executive chefs. Serve up bow wow tenderloin of beef, a mix of filet, eggs and rice, or chicken puppy bites, tender shredded chicken with carrots.

Four Seasons Resort Orlando at Walt Disney World : Once you're done devouring Mickey Mouse pops and jumbo turkey legs, order K-9 crudite, the hot diggity dog (scrambled eggs, rice and veal stock), and frozen peanut butter and banana bites for the doggy.

Lazy Dog Restaurants : In Florida, Virginia, Texas and Colorado, this casual dining chain services pup-friendly brown rice bowls with grilled hamburger or grilled chicken.

Boozehounds in Palm Springs , California : This restaurant features dog-friendly outdoor spaces, as well as a dedicated dog menu that includes teriyaki salmon bowls, gazpacho, loaded sweet potatoes and doggie TV dinners.

Pacific Hideaway in Huntington Beach, California : Inside the Kimpton Shorebreak Resort, Pacific Hideaway welcomes dogs on the outdoor patio where they can enjoy three savory menu items: chicken and white rice, fish and sweet potato, and beef and vegetable.

Bark Social in Bethesda and Baltimore, Maryland : This social club for dogs serves craft brews, nachos and pizza for you, and pupcakes, pupsicles and chicken strips for your doggo.

Don't forget the H2O

It goes without saying that water is a necessity for summer road-tripping dogs and humans alike. Even though you may have done your research about your trip ahead, it's likely you won't know much about the water quality at each stop.

According to Illinois-based veterinarian Dr. Allison Pepich, your dog needs a rough estimate of at least 1 ounce of water per 0.5-1 pound of body weight. For example, a 30-pound dog would need between 15-30 ounces of water per day at a minimum, but it could be more depending on their fluid losses throughout the day.

"If they will not drink water while in the car, giving them water at rest stops throughout the journey is recommended," Dr. Pepich said. "The more panting, activity, or just general fluid loss that your pet has, the more water they will need."

Always store a few extra gallons of water in your car — in a cooler is even better.

Avoiding the dehydration danger zone

As the weather warms up through the summer months, Dr. Pepich says dehydration and overheating could be a concern during extended car travel.

"If you feel that your pet is experiencing either, the safest option is to get them to the nearest veterinary clinic for evaluation," she said. "Pets can often mask signs that they are not feeling well, especially if they are already anxious from travel. Watch for signs of reduced energy, poor appetite, not drinking well, tacky mucus membranes (gums), or heavy panting."

A normal temperature for a dog is between 100-102 degrees Fahrenheit, and the most accurate way to check this is with a rectal thermometer – add this to your first-aid kit (more on that below), according to Dr. Pepich.

In order to avoid dehydration and overheating, Dr. Pepich says never to leave your pet alone in the car during travel. Also, keep the car at a comfortable temperature while traveling. If you spend time outdoors, make sure your pet has a cool, shady area to go to for rest. Dr. Pepich also recommends paying extra attention to breeds that may be at significant risk for heat stress. These are typically brachycephalic dogs like French bulldogs, pugs, shih tzus, boxers, Boston terriers and others.

Meds and first aid

Before you head out, make sure you have medication and first-aid options for your pup, too. The Red Cross offers a comprehensive list of what to pack , which includes many household items that will come in handy. Some include latex gloves, gauze, tweezers, a muzzle, rubbing alcohol, antibiotic ointment, a baby-dose syringe, 3% hydrogen peroxide, an emergency blanket, sterile saline wash, petroleum jelly, cotton swabs and needle-nose pliers. As mentioned above, make sure to pack a rectal thermometer for temperature checks.

De-stressing your doggo

Additionally, take extra precautions if your dog tends to get easily stressed.

"There are a few over-the-counter products that can be used for stress reduction during car trips," Dr. Pepich said. "My favorite products are Rescue Remedy and Adaptil pheromone products. You can also use CBD products, but I've found success varies considerably across different products."

If your dog gets carsick, Dr. Pepich recommends using an anti-nausea medication or one aimed at treating motion sickness may help calm their car-related anxiety. Before your trip, discuss prescription anxiety medications for car travel with your vet, "though the specific product prescribed may vary greatly depending on your dog's needs," according to Dr. Pepich.

For the record

Whether digitized or hard copies, keep your dog's latest vaccination records on hand. If your dog is microchipped, make sure you have the ID number and registration information before you leave. Confirm you also have a collar with an ID tag that displays your most up-to-date contact information for peace of mind.

TPG tip : Work in advance to help your dog get comfortable in the car. If there are signs of car-related anxiety, employ a trainer to help desensitize your pup to car trips.

Keep 'em clean

Grooming on the go can be a pain, so make sure your car is stocked with the essentials. You can very easily craft a handy DIY travel grooming kit with these necessities:

Shampoo : Whether your furry friend enjoys regular puppy spa appointments or bath time at home, it's important to pack a bottle of your pup's shampoo – just in case. If your hotel or lodging doesn't happen to have a bathtub or sink to refresh Sparky, opt for a dry shampoo. Test out any new products in advance so you aren't dealing with any unpleasant surprises like allergies or skin reactions.

Wipes : Pet wipes can be a lifesaver when traveling. They're great for muddy paws at a rest stop to avoid caking dirt onto your leather seats and a full wipe-down from outdoor dander, pollen and the elements. Try these out at home before the road trip and opt for scented or unscented based on what works best for the doggy.

Nail clippers : Either a manual tool or an electronic device, a set of dog-friendly nail clippers are handy. Just like human nails, dog nails and dewclaws (essentially the thumbs and big toes) can split while adventuring and be painful for your pup.

Toothbrush : It's important to stay up on your doggy's dental hygiene. Grab a small travel-size toothbrush for longer trips.

Scissors : While you may pack these for your own emergency kit, you can also use them to remove fur tangles on long-haired dogs.

Dog waste bags : Do the math on the length of your trip and how many times your dog does his or her business per day to determine how many poop bag rolls you need. Pack a couple of extra rolls for any surprise messes along the way.

Related: The 15 best dog-friendly hotels in the US you need to know about

Bottom line

Don't let hitting the road with your favorite furry friend intimidate you. There may be plenty of prep work, but once you're en route, it will be worth it.

Dogs make amazing summer road-trip companions, whether heading out solo, as a couple or even with the kids. With so many dog-friendly lodging, activity and dining accommodations, there's no reason to board your bestie or spend hundreds on a dog sitter this summer.

The best part about dog-friendly road trip travel is that you never need to "ruff" it because everything is accessible along the way. So, what are you waiting for? Rev up, hit the cruise and lift that sun "woof."

Related reading:

Top pet-friendly Marriott hotels for animal lovers World's top pet-friendly Hilton hotels for animal lovers 8 things to consider before flying with your pet Your pet travel primer: Answering questions about vaccination records, EU pet passports and how to find dog-friendly restaurants

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The 17 best road trips from Chicago

Need a change of scenery? Load up the car and embark on one of the best road trips from Chicago.

No coast? No problem. Chicago can sometimes feel like a Midwest oasis, but there's plenty to see just a scenic road trip away. With summer quickly approaching, you can spend a few weekends sipping bourbon in Louisville, hiking  in Eau Claire or sunbathing in Door County. So if you're not sure where to start, check out our list of unique nearby destinations , load up the car, turn up "Life is a Highway" and hit the road—one of these routes from Chicago could quickly become your preferred weekend getaway . 

RECOMMENDED: The best day trips from Chicago

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Best road trips from Chicago

1.  St Louis, MO

Driving time from Chicago:  Four and a half hours

While beer, blues and BBQ are likely on the top of your St Louis bucket list (and rightfuly so), there's a lot more to discover in the Gateway to the West—like custard from Ted Drewes and a walk around Forest Park. There's also a ton to see on the five-hour drive from Chicago: Stop off in Springfield to see attractions like the Illinois State Capitol, or in Atlanta, IL to take a photo with Paul Bunyon holding a massive hotdog. 

2.  Eau Claire, WI

Driving time from Chicago:  Five hours

Folks head to the Chippewa Valley in northern Wisconsin for its rolling hills and colorful foliage (plus plenty of beer and cheese to smuggle back to Chicago), but there are some worthy sights along the road as well. Snap a selfie with Pinkie the Elephant in DeForest, WI and sample cranberry-flavored everything at the Wisconsin Cranberry Discovery Center   in Warrens, WI. Once you're in Eau Claire, trade in the car for a kayak:  Riverside Bike & Skate   in downtown Eau Claire rents canoes and kayaks and has shuttles that will drive you upstream so you can hit the Chippewa River. 

3.  Traverse City, MI

The charming resort town of Traverse City, located at Michigan’s northern tip, offers plenty to do for nature enthusiasts. Clinch Park and Bryant Park have gorgeous, popular beaches while the more remote Haserot and North Bar Lake beaches offer the chance for a secluded getaway. You’re also within a stones throw of the coastal M-22, one of the most scenic drives in America, as well photo-ops at the Grand Traverse and Little Sable lighthouses. 

4.  Detroit, MI

Driving time from Chicago:  Four and a half hours

Despite what Blackhawks fans may chant, there is plenty about Detroit that doesn’t suck. You could easily spend a day or two on art alone, thanks to world-class museums like the Detroit Institute of Arts and the Museum of Contemporary Art Detroit ; powerful, immersive public art like the Heidelberg Project and colorful, whimsical folk art like Hamtramck Disneyland . Enjoy a leisurely morning browsing at Eastern Market showcasing dozens of artisan food producers, makers and crafters, and then check out the tempting restaurant and bar options nearby. On the way home, stop in neighboring Dearborn, home to the largest and most diverse Arab community in the U.S., for delicious food at spots like Al-Ameer , Sheeba and Shatila Bakery . 

5.  Galena, IL

Driving time from Chicago : Three hours

At the top of many Chicagoans city escape must-visit list is Galena, Illinois. This charming town just under three hours from the city is known for its history, 19th-century architecture and resorts. There are hundreds of unique and antique shops in the city center to add some vintage pizzazz to your living room. History buffs can head over to the  Ulysses S. Grant Home  to tour the city’s proudest attraction. Once you’ve worked up an appetite, stop into  Log Cabin Steakhouse , which has been in operation since 1937. During the third weekend of June, tourists and locals alike gather for the annual  Great Galena Balloon Race .

6.  Door County, WI

The road trip doesn't end when you reach Door County; There's plenty to navigate by car as you wander the series of small towns located on a beautiful 75-mile peninsula surrounded by Lake Michigan and Green Bay. There are also 53 public beaches, five state parks, and 300 miles of shoreline so get ready to put some miles on your car. Need a pit stop? Milwaukee is a little less than half way. 

7.  Louisville, KY

Kentucky’s largest city, located just across the Ohio River from southern Indiana, is steeped in bourbon and long on charm. The home of the old fashioned and mint julep embraces its role as the gateway to Bourbon Country. The city now has over 10 tourable distilleries, including   Evan Williams,   Angel’s Envy   and  Old Forester . If bourbon and honkytonk aren't for you, downtown Louisville has an incredible art scene and is booming with independent businesses and charming shops. 

Discover the best things to do in Louisville

8.  Madison, WI

Driving time from Chicago: Three hours

Sure the Midwest loves its college towns, but Madison's proximity to five surrounding lakes make it one of the more of the scenic ones. The abundance of waterways make kayaking, rafting and canoeing especially popular—you can book them directly through Madison Boats . For those averse to using their sea legs, there's the 16-acre Olbrich Botanical Gardens for all ages or the National Mustard Museum (yes, you read that correctly). It wouldn't be a trip to Wisconsin without trying blocks and blocks of cheese, so make sure to stop by the "Capital of Cheese" known as Fromagination in downtown Madison. 

9.  Cincinnati, OH

If Skyline Chili is not your bag, don’t worry—there’s a whole lot more to the Queen City than its most famous tourist foodstuff. Cincy has been undergoing a major glow-up over the past decade or so, from the ever-evolving Smale Riverfront Park, which offers lots to do and gorgeous views of the skyline and the Ohio River to the revitalization of the historic Over-the-Rhine neighborhood. There, you'll find a number of must-visit spots, including the popular Rhinegeist Brewery, the vibrant Findlay Market , the stunning Music Hall and Washington Park , which sports a sweet playground and community events throughout the year. Plus, the Cincinnati Zoo is one of the best in the country, and the only place you can see Internet icon Fiona the Hippo in person. That in itself is worth the trip.

10.  Shawnee Hills Wine Trail, IL

Driving time from Chicago:  Six hours

Not going to make it to Napa this year? Opt for the just-as-beautiful Shawnee Hills Wine Trail instead. The 3 5-mile scenic drive meanders through Shawnee National Forest in southern Illinois and features over 10  award-winning wineries in cute towns like Cobden, Alto Pass, and Pomona. If you need more than wine to prompt a trip, there's plenty of nature in the vicinity and the nearby town of Murphysboro is home to some of the finest BBQ in the Midwest at 17th Street Barbecue . 

11.  Bloomington, IN

Driving time from Chicago:  Four hours

This cozy college town offers some big-city amenities, but it's the surrounding hills, forests and lakes that make it special. A short itinerary could look like: Hike the Deam Wilderness trails ; s ee the Morgan-Monroe State Forest wildflowers; admire the Cedar Bluffs Nature Preserve limestone bluffs; g o fishing at the reservoir lakes. Just don't forget to leave room for a meal at  Feast Market & Cellar , a family-owned kitchen with a lovely corner porch where everything is made from scratch daily. 

12.  Saugatuck, MI

Driving time from Chicago:  Two and a half hours

This dreamy lakeside town (and next-door neighbor Douglas) has long been a favorite of Chicagoans looking to spend time on the water, whether it’s a boat on the Kalamazoo River or a relaxing day on one of the area’s six clean, inviting beaches. From hiking the Saugatuck Dunes to window shopping on Butler Street to enjoying dinner and drinks alfresco, there are many ways to get some much-needed fresh air here. It’s also one of the Midwest’s best queer-friendly vacation destinations, home to more than 100 LGBTQ-owned and friendly businesses. 

13.  Ann Arbor, MI

Driving time from Chicago:  Four hours

If you'd rather stick to less-crowded cities, skip Detroit and opt for Ann Arbor instead. Foodies and beer nerds will love this low-key vacation spot for its plethora of good restaurants and breweries. Home to the renowned University of Michigan, this city’s quaint downtown is full of unique shops, spots to eat and so much more (make sure Blank Slate Creamery is on your list). 

14.  Toledo, OH

The road from Chicago to Ohio is filled with worthwhile attractions, including Indiana Dunes State Park and the Hall of Heroes Super Hero Museum in Elkhart, Indiana. Once you arrive in Toledo, you'll be greeted with picturesque churches, wild urban parks, a trendy jazz culture and plenty of microbreweries to keep you busy. Just outside the city you'll also find fall-harvest overload in the way of apple and pumpkin farms where you can pick your own fruits and veggies and gorge on baked treats.

15.  Shipshewana, IN

Driving time from Chicago:  Two hours

OK, just hear us out. The heart of Indiana Amish country is a great option for a convenient road trip perfect for families, history buffs and, most of all, antiquers. The Shipshewana Trading Place Flea Market is a bargain-hunter’s dream—the largest flea market in the Midwest, with lively auctions Wednesday mornings. After a morning of browsing and bargaining, you’ll work up an appetite for some Amish home cooking, which you can even sample in a  literal Amish home . For outdoorsy types, nearby Mongo offers canoe and kayak rentals for a relaxing day on the water. 

16.  Des Moines, IA

Driving time from Chicago: Five hours

There's a surprising amount to explore over a weekend in Des Moines, from more than 20 breweries in the metro area to the six-mile Art Route , which showcases 87 public art pieces from sculptures to murals. But what really makes Des Moines worth visiting are its summer events, like the eclectic 80/35 music festival, and, of course, the festive juggernaut that is the Iowa State Fair , where you can get 69 different food-on-a-stick creations (nice). When you're heading back on I-80, don't miss the World's Largest Truck Stop in Walcott, truly a site to behold.

17.  Columbus, IN

Driving time from Chicago : Three and a half hours

In the heart of Southern Indiana, Columbus is an unexpected center for boundary-pushing architecture—in fact, the American Institute of Architects ranked the city sixth in the nation for architectural innovation. Roughly 70 different constructions sprinkled around the city and county make this city an architectural wonder. Take an  Architectural Highlights Tour  of more than 30 of Columbus' structures and learn how this city became the state's award-winning arts and design destination. Make another pit stop of striking constructions with a stroll through Mill Race Park , an 85-acre riverfront park near the city's center. Once you’ve worked up an appetite, stop by  Columbus Bar , the oldest bar and restaurant in town.

Need more travel inspiration?

The best weekend getaways from Chicago for families

Take a break from the city and find family-friendly activities throughout the Midwest on these weekend getaways.

The best places to go camping near Chicago

• Things to do

Make a quick escape and spend a few nights amidst nature. 

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Dog-Friendly Chicago Roadtrips for Peak Fall Foliage

Doggo’s been itchin’ to get out of the city. Time for a road trip! Unfortunately, pup failed her driver’s test (holding the wheel is hard without thumbs!), so you’ll have to be DD for this one. We promise these destinations are worth it. Curious about where to see fall foliage near Chicago? Check out these dog-friendly autumn road trips.

Chicago Day Trips

Ottawa, illinois.

View this post on Instagram A post shared by ᴍᴀᴄ (@___intothewoods) on Aug 8, 2019 at 11:19am PDT

Ottawa is an easy 90-minute drive from Chicago and a must-stop for every true Chicago dog. With three state parks in the vicinity, you won’t get more fall foliage opportunities than this. Buffalo Rock State Park features nearly 300 acres of trails and riverside views, and a short 20 minutes away are lush, wooded Matthiessen and Starved Rock State Parks. Fill your days with hikes and adventures and take a snoozle at the dog-friendly Starved Rock Lodge .

Naperville, Illinois

Pup’ll ruv going to Naperville for a day trip! Make your way to the Springbrook Prairie Forest Preserve to experience fall in native prairieland with your buddy. Then, let him explore it off leash in the enclosed dog park. It can get muddy, so don’t forget to bring a towel for later. Another perk of Naperville is its proximity to the granddaddy of fall foliage: the Morton Arboretum. Dogs are welcome on their special Dog Admission Days !

Afterward, take a trip to downtown Naperville for a snack break and some shopping at any of the dog-friendly stores .

Chicago Weekend Trips

Door county, wisconsin.

View this post on Instagram A post shared by Rüfüs | RuRu (@rufus_theminiweenie) on Sep 4, 2020 at 12:35pm PDT

You know what they say, Explore the Door! Your pup will be giving you a million kisses as thanks for this fun trip up the Lake Michigan coast. The five-hour trip up north is made easier with a scenic drive of forestry and Wisconsin beaches. Once you get to Door County, we recommend the Ellison Bluff State Natural Area to get into the autumnal mood with their forested trails, rock terrace, and gorgeous views of the lake. Experts recommend visiting the third week in October for peak foliage.

Three Oaks, Michigan

View this post on Instagram A post shared by Ollivander🐾✨ (@accio_ollivander) on Sep 20, 2019 at 5:08am PDT

Over here at Sidewalk Dog Chicago, we love talking about Lake Michigan, so take a weekend trip to explore the other side of it. Less than two hours away, take your pup to Warren Woods State Park in Three Oaks to see autumn underneath towering tulip and beech trees. When you’re done marveling at Mother Nature, swing by Journeyman Distillery to marvel at the nature of their handcrafted spirits.

On the way back, of course you need to visit the Indiana Dunes National Park! There are plenty of trails, lake shore, and of course dunes to explore, but if you’re on the hunt for fall foliage, be sure to stop by the Taltree Arboretum and Gardens.

Chicago Spots for Indoor Dog Walks

Cleveland, ohio.

We’re not gonna say that Lake Michigan is overhyped, but let’s not forget that there are other lakes. This city is right on Lake Erie and is the home of several dog-friendly breweries such as Great Lakes Brewing and Terrestrial Brewing Company. You’ll find all the foliage you can ask for at Cuyahoga Valley National Park, a short 20-minute drive away with 33,000 acres of forest to explore.

What are your favorite places to for autumnal vibes? Woof at us in the comments and be sure to tag @SidewalkDog in all your adventures! Oh, and pass this on to anypuppy wonderin’ where to see fall foliage near Chicago.

Featured photo: Claudio Schwarz

Sidewalk Dog’s mission is to help dog parents spend more time with their puppers by discovering and sharing activities they can do and places they can go—together! Sniff out our award-winning  newsletter  and  Instagram , and join our  dog-obsessed Facebook group .

More reads you’ll ruv:

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Looking to have your last summer adventures before fall begins? Amy Burkert, author of “ The Ultimate Pet Friendly Road Trip ” and creator of pet travel site, gopetfriendly.com has a list of jaunts where pet owners and their four-legged friends can enjoy the outdoors on road trips from Chicago.

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Your Family Will Love These 30 Road Trips Near Chicago

• Updated: 04/03/2024

Chicago and US Midwest families, we feel you. Airplane tickets are pricier than ever. Though, your need for a getaway has never been greater. 

You want to get out of town with minimal effort and do not want to spend a small fortune to do it. 

To help, I share my favorite short to medium-distance driving destinations and those recommended by regional experts—other travel bloggers and planners passionate about places in the Midwest. 

Together, we came up with this list of the 30 best road trip destinations for the summer and the fall, from big cities to small charming towns to blow-you-away natural wonders, all within a five-hour drive of Chicago.

Table Of Contents

Check out our destination recommendations by state below. 

• Michigan & Ontario

Or view all 30+ places we recommend going in the map below.

How to use this map:  In the map header, click the square tab to the left of my logo or click the enlarge frame to the right to view detail. You can save the map to “Your Places” on Google Maps by clicking the star next to the map name. Or you can share it by clicking the share icon.

Wisconsin: Top Road Trips Within 5 Hours of Chicago

Welcome to Wisconsin, or the “Dairyland State,” loved by visitors for its rich dairy heritage, delicious cheeses, and beautiful landscapes, including miles upon miles of lakeshore coastline.

Check out these six Wisconsin destinations shared in more detail below.

• Madison, WI
• Milwaukee, WI
• Sheboygan, WI
• Door County, WI
• Wisconsin Dells, WI
• Lake Geneva, WI

Also, consider adding Green Bay (a 4-hour drive) and the lake-perfect Northwoods towns of Manitowish Waters and Boulder Junction (a 5.5-hour drive) to your driving trip wishlists.

Madison, Wisconsin

Approximate drive time from Chicago: 2.5 to 3 hours

Recommended by: Rebecca Gade Sawicki of VeggiesAbroad.com

At just two and a half hours from Chicago, Madison is the perfect destination for a quick day trip or a weekend away . This sustainability-focused college town offers families tons of outdoor activities, diverse dining, and art and culture.

If you’re a family that loves the outdoors, visiting Madison during the summer is best. This is the prime time to enjoy the city’s prized lake life (five lakes surround it) and over 200 miles of paved bike trails. Madisonians love to bike (even in the winter), which is one of the best ways to see the city.

Another great activity to see Madison’s unique and eco-friendly side is to explore the independent boutiques that line Willy Street. You’ll find plenty of vintage shops, locally created art, zero-waste products, and clothing that’s been ethically produced and sourced.

While you’re in the area, don’t miss an iconic Madison treat, Nutkrack — this sweet and salty snack was actually created by accident! And, around the corner from Nutkrack is Madison’s oldest vegetarian restaurant , Green Owl Café — don’t miss their loaded vegan cheese fries.

When deciding where to stay in the city, the best place is downtown. This will put you within easy walking distance of many shops, restaurants, and events.

The Hyatt Madison/Downtown offers spacious rooms and suites, perfect for families, along with continental breakfast, and has multiple sustainability initiatives to reduce its and its guest’s carbon footprint. Or search for more Madison lodging options here .

Sign up for my monthly Discovery Newsletter & get a free Trip Budget Calculator !

Milwaukee, Wisconsin

Approximate drive time from Chicago: 1.5 hours

Recommended by: Lisa of WavesandCobblestones.com

Milwaukee, Wisconsin , is the perfect city to visit on a family road trip from Chicago. Milwaukee is an easy 1.5-hour drive from Chicago, located to the north along the banks of Lake Michigan.

There are plenty of great things to do in Milwaukee to keep your family entertained! Rent kayaks and paddle along the Milwaukee Riverfront for some fresh air and exercise. Or show some team spirit and take the family to a ball game and watch the Brewers play baseball at the American Family Field or the Bucks on the basketball court at the Fiserv Forum.

There are many fun museums to visit in Milwaukee with your family, such as the Milwaukee Art Museum , a top-notch fine arts museum, where admission is free for children 12 years and younger. Or Discovery World , Milwaukee’s science museum, and Reiman Aquarium. Or the National Bobblehead Hall of Fame and Museum—a one-of-a-kind museum with over 10,000 bobbleheads from across the globe!

Stay at the Plaza Hotel , centrally located in Milwaukee’s historic Lower East Side, with suites that include a pull-out sofa and accommodate up to four people. The Plaza rooms have full kitchens, and with a large grocery store just a block away, you can save money on meals and snacks during your stay.

Or search for more Milwaukee lodging options here .

Sheboygan, Wisconsin

Approximate drive time from Chicago: 2.5 hours

Recommended by: Theresa Goodrich of TheLocalTourist.com

Sheboygan, Wisconsin, is a surprising destination only two and a half hours away from Chicago and a great road trip for families because of the variety of things to do. Begin your visit at the Visit Sheboygan Visitors Center and see Science on a Sphere , a suspended globe that acts as a projector screen displaying programs provided by the National Oceanic and Atmospheric Administration. You can also get tips for places to visit and pick up brochures and souvenirs.

One of the best things to do in Sheboygan for families is Bookworm Gardens. This whimsical garden is a haven for book lovers and children alike, where literature comes to life through vibrant displays and interactive exhibits. Another must-stop for families is the Above and Beyond Children’s Museum . You can’t miss it—there is a ship’s hull sticking out of the building! While downtown, stroll 8th Street for delicious pizza at Il Ritrovo , and don’t miss the Victorian Chocolate Shoppe . Since Sheboygan is on the shores of Lake Michigan, it is also a great summer vacation spot, with sandy beaches and lakefront parks .

Make Blue Harbor Resort your base camp. With its own waterpark, an arcade, mini-golf, a beach, and outdoor games—the kids will love staying at this resort. Or search for more Sheboygan lodging options here . 

Door County, Wisconsin

Approximate drive time from Chicago: 4 to 5 hours

Recommended by: Janice Moskoff of GatherandGoTravel.com

This Wisconsin peninsula just north of Green Bay, surrounded by Lake Michigan, boasts beautiful beaches, scenic hiking trails, and family-friendly activities that will keep everyone pleased for days. 

We visited Door County in the fall , and it was gorgeous. The leaves had not quite fully changed, though we took full advantage of the pretty outdoors to bike and hike at several of the peninsula’s five state parks . 

We even visited Cave Point County Park , one of the Door’s nearly 20 county parks, and were treated to an easy-to-access spectacular scene of Lake Michigan waves crashing against a stunning rocky coastline on a windy day. The beauty of this experience blew us away. Expect the Door to do the same to you.

In the summer, the Door truly shines. Families flock here for the beaches, events, and the abundance of outdoor activities. 

With over 300 miles of shoreline , you can swim, kayak, and fish in the crystal-clear waters of Lake Michigan, especially gorgeous on a sunny day.  Plus, the towns dotting the peninsula are charming, full of shops, galleries, and many restaurants.

Visit or stay on the west or bayside of the peninsula, where you can catch sunsets in towns like Fish Creek or Sister Bay . Or opt for the eastside—where we stayed—and catch the sunrises in or around Bailey’s Harbor . Top family-friendly resorts include Newport Resort , Ephraim Shores Resort , and Scandinavian Lodge . Though, know that the Door books early. So, if you plan your trip last minute, grab the best lodging you can get from Sturgeon Bay or further north and use it as a base to drive around and explore the Door. 

Search all family-friendly Door County lodging options on VRBO or Booking.com .

Wisconsin Dells, Wisconsin

Approx drive time from Chicago: 3 hours

Recommended by: Hannah & Adam Lukaszewicz of GettingStamped.com

The Wisconsin Dells is the ideal road trip destination from Chicago as it is known as the Waterpark Capital of the World . The driving distance from Chicago to Wisconsin Dells is just under three hours, making it the perfect length for a weekend getaway . Kids love to splash and play in the water, so why not visit multiple waterparks in one road trip?

The Wisconsin Dells is home to the first-ever indoor waterpark and currently has the largest concentration of waterparks in the world. No matter if you are visiting in the summer or the winter, you will find an amazing waterpark for your family to visit and enjoy, as the area is home to 12 different indoor water parks and over 20 water parks in total.

The best place to stay in Wisconsin Dells is one of the Waterpark Hotels . Our favorite waterpark hotel is Great Wolf Lodge as not only does it have a fantastic waterpark with a 6000 ft outdoor pool, 1000 gallon tipping bucket, a wave pool with three-foot-tall waves, a toddler pool, and a variety of slides for kids of all ages.

The Great Wolf Lodge has unique themed rooms and fun activities, including magi-quest, live shows, and an arcade, making it a kid paradise!

Lake Geneva, Wisconsin

Approximate drive time from Chicago: 2 hours

Recommended by: Diana of TravelsinPoland.com

With an approximate driving time of 2 hours, Lake Geneva is a short drive from Chicago and one of the best cities to visit in Wisconsin. The small-town atmosphere combined with a variety of activities make it a perfect choice for families with children of all ages.

Families can enjoy a day on the water, renting boats, kayaks, or paddle boards, or opt for a scenic boat tour around the lake. Or walk along a portion of the Lake Geneva Shore Path , a 21-mile trail that offers stunning views of grand estates and natural beauty. Spending time on the lake is the best way to experience the area, particularly during warmer months. Shopping in downtown Lake Geneva can keep families occupied for hours. The shops along the main roads have unique items such as art and handcrafted goods. There are also mom-and-pop cafes, ice cream, and candy shops in town.

For accommodation, The Abbey Resort , located in the heart of town, offers a great choice. It is a full-service family-friendly resort offering spacious rooms, indoor and outdoor pools, a game room for the kids, and a full-service spa for the adults. Or search for more Lake Geneva lodging options here .

Michigan & Ontario: Top Road Trips Within 5 Hours of Chicago

Experience the best of the Mitten State , a northern gem and a truly ideal destination for vacationing families. The Michigan coastlines—particularly to the west, with sandy beaches, spectacular sunsets, and towering dunes —will wow you with their beauty. Plus, the vibrant cities and small towns in Michigan will offer enough activities and culinary delights to keep you busy and satisfied for days.

Check out these four Michigan & Ontario destinations shared in more detail below.

• Saugatuck, MI
• Ann Arbor, MI
• Detroit, MI, into Ontario, Canada (a loop driving trip)
• Traverse City, MI (with a day trip to Sleeping Bear Dunes National Lakeshore)

To expand your options—consider adding these Michigan Southwest coastal towns to your road-trip-and-relax lists, like New Buffalo, St. Joseph/Benton Harbor, South Haven, Holland, and Grand Haven. Or spend time exploring more urban centers like Detroit or Grand Rapids .

Saugatuck, Michigan

Approximate drive time from Chicago: 3 hours

We love Saugatuck. We have visited for weekend trips several times in the fall and keep returning for more.  What draws us? The unbelievably beautiful beaches and dunes, the quaint downtown area filled with art galleries and boutiques, and the concentration of seriously elevated cuisine.

Our favorite beaches are Oval Beach , which consistently ranks as one of the top beaches in the country, and offers soft sand, clear water, and stunning views of Lake Michigan.  Additionally, we love the nearby and dog-friendly Saugatuck Dunes State Park , which is perfect for hiking and exploring, with over 1,000 acres of dunes, forests, and beaches.

When not visiting the beaches or getting ice cream, or shopping the galleries on Butler Street, Saugatuck’s main thoroughfare, we spend our time apple picking (in the fall), boating on the Kalamazoo River, or dining at one of the truly fantastic eateries in and around town. I share more things we love to do in Fall Trip: 10 Wonderful Family Things to Do in Saugatuck, MI “

Visiting families also love going on Saugatuck Dune Rides . This thrilling ride takes you on a tour of the dunes, with steep climbs and drops, which the kids will love. And bonus! The knowledgeable guides will share the history and ecology of the area, making it both fun and educational. 

For meals, you cannot go wrong nearly anywhere you choose to eat, but our favorites include The Southerner , where the biscuits alone are worth repeat visits, Pennyroyal Cafe & Provisions , and a short 15-minute drive to enjoy drinks and snacks at Virtue Cider .

Booking a stay in Saugatuck can be surprisingly pricey, so I share helpful information on where you can stay in the surrounding areas for less in “ Saugatuck, MI: 8 Amazing Areas to Search for Lodging .” Then, and especially because many local inns do not allow children as guests, I detail my top choices for family lodging in “ Roundup of the Best Family-Friendly Places to Stay in Saugatuck .”

Ann Arbor, Michigan

Approximate drive time from Chicago: 4 hours

Whether you’re a University of Michigan sports enthusiast or just looking for a hip town surrounded by gorgeous natural beauty, Ann Arbor is the ideal Michigan town to visit!  From Chicago, the trip via car or train (Amtrak offers service from Chicago’s Union Station to Ann Arbor) is just under four hours , making it a perfect road trip for a few days away!

Ann Arbor is well known for its thriving arts and culture scene . Year-round, it hosts a variety of art, music, and film festivals, including one of the largest outdoor art fairs in the nation, The Ann Arbor Art Fair . The Art Fair takes over Ann Arbor every July and spans 30 city blocks with over 1,000 artists! You’ll also find food and music throughout the fair.

For families who enjoy outdoor activities, you’re in luck! Ann Arbor is surrounded by natural beauty, with parks, nature reserves, and the Huron River flowing through it. Head to the Argo Livery during the summer and rent a canoe, kayak, or stand-up paddle board. You can go out on your own, or Argo offers multiple group river trips that range in time and distance from just under 4 miles and 1.5 hours to almost 6 miles and 2.5 hours.

When it comes to dining, you’re in for a treat — the city is well-known for its eclectic mix of cafes and restaurants. From the famous and funky sandwiches at Zingerman’s Delicatessen to the veggie eats at Ann Arbor’s best vegan restaurant, Detroit Street Filling Station.

When choosing a place to stay, it’s best to stay right in the heart of the city (especially if it’s your first visit). Two terrific family options include the Residence Inn by Marriott Ann Arbor Downtown and The Graduate Ann Arbor . Or search for more Ann Arbor lodging options here .

Detroit to Southwestern Ontario Loop Trip (a 5 Day, 4 Night Itinerary)

Approximate drive time from Chicago to Detroit: 4.5 hours

Recommended by: Erie Conners of EverywhereOntario.com

For a unique road trip that takes you into another country, consider making the trip from Chicago to Southwestern Ontario , Canada.  This southernmost region of Canada is filled with quaint small towns, sandy beaches , an abundance of fruit farms and wineries , and incredible historic sites that tell important stories from the Underground Railroad that delivered many slaves to freedom in the 1800s. 

From Chicago, you’ll drive 4 hours to the Detroit-Windsor border. In Detroit, you’ll cross the Ambassador Bridge or take the Detroit-Windsor Tunnel to get into Canada. 

Depending on how long you’ll be staying in Canada, here are the sites I recommend according to a path that takes you from the Detroit-Windsor border to the Sarnia-Port Huron border , where you’ll loop back to Chicago:

• Optional overnight at Caesar’s Windsor Hotel , or search for other Windsor lodging .
• Or, Pelee Island : Take the ferry to Canada’s southernmost landmass, Pelee Island. Visit Pelee Island Winery and bike around the island before taking the ferry home. Overnight in Leamington at a beautiful B&B , or other lodging . 
• Grand Bend Beach : Visit one of Ontario’s top beaches in the summer months. Lounge on the beach, participate in water sports, or walk along the Grand Bend Strip for boutique shopping.
• Sarnia: Walk along the waterfront to see Port Huron from the Canadian side. Overnight at The Insignia Hotel , in Sarnia . Or stay search for other nearby lodging .
• Cross the Bluewater Bridge back to Port Huron and drive 5 hours back to Chicago.

Traverse City, Michigan

Approximate drive time from Chicago: 5 to 5.5 hours

We visited vibrant Traverse City, MI , picturesquely nestled at the southern u-shaped end of Grand Traverse Bay , for five days in the heart of summer with our family dog and loved every minute of our trip. 

In addition to enjoying the lakeshore views that front the length of the town and strolling the shops and restaurants of bustling Front Street, our favorite activities were biking along the wooded TART trails—especially the Leelanau Trail, and hiking. 

We walked the paths in Grand Traverse Commons Natural Area , located behind the outdoor shopping plaza, making our way to the Hippie Tree, a massive old willow tree at the center of the trail network. Painted in bright colors by locals representing living artwork, the tree is rumored to have a haunted history that we only learned about after our visit. 

On another day, we drove out to the Old Mission Point Peninsula to spend the day enjoying the sweeping lake views from the lighthouse, hiking the trails in the adjacent Old Mision Point Park , stopping to buy fresh farmstand cherries, picking blueberries with the kids, and to enjoy a late al fresco lakeside lunch at the Jolly Pumpkin Restaurant & Brewery .

Another highlight was taking a day to visit the Sleeping Dunes National Lakeshore (a 40-minute drive), where we climbed dunes, hiked the Empire Bluff Trail , one of many in the area , and relaxed and picnicked on dog-friendly Esch beach. 

In addition to the outdoor activities, which could also include boat trips on Lake Michigan or kayaking on local lakes or rivers, your family will love the varied collection of breweries and wineries with outdoor dining areas ideal for families. When visiting, you can stay at a centrally located and family-friendly hotel, like the Bayshore Resort . Or search for a rental in the area. Find more available Traverse City hotels and lodging here . 

Indiana: Top Road Trips Within 5-Hours of Chicago

Hang out in the Hoosier State in one of these two top destinations:

• Indiana Dunes National Park, IN
• Indianapolis, IN

Additionally, consider staying in French Lick, IN, at the French Lick Resort  (a 5-hour drive), located in the hills of Indiana’s Hoosier National Forest. It is a classic family-friendly Americana resort offering loads of activities including, golf, biking, hiking, spa treatments, and supervised drop-off kid activities.

Indiana Dunes National Park, Indiana

Approximate drive time from Chicago: 45 minutes

Recommended by: Caitlin Dismore of TwinFamilyTravels.com

If you are in the Chicago area and looking for a family-friendly trip nearby, definitely consider visiting Indiana Dunes National Park and the surrounding area. Just 45 minutes outside of the city, the park offers a beautiful setting with plenty of beach access points and hiking trails.

In addition to the fabulous activities within the park, the surrounding towns offer a variety of attractions, shopping, and dining to keep the whole family entertained. West Beach is the perfect place for a family outing. It’s the largest beach in Indiana Dunes National Park and is great for swimming, sunbathing, or just relaxing. The Lake Michigan water is clean and clear, and there’s plenty of sand for kids to play with.

Hiking is another popular activity while in the park. Explore Indiana Dune’s biodiversity by hiking along the boardwalks, past historic homes, and even through marsh areas. If you are up for it, complete the 3 Dune Challenge at the nearby Indiana Dunes State Park .

If you are traveling with young children, consider staying at the Country Inn & Suites By Carlson Portage . The hotel has both a standard indoor pool and a shallow pool specifically designed for children, complete with a frog slide. Or search for other lodging options in the nearby Portage, Indiana area.

Indianapolis, Indiana

Approximate drive time from Chicago: 3 to 3.5 hours

This lively Midwestern city offers a wide range of activities and attractions ideal for families. From world-class museums to racetracks , expect a visit to Indy will be a memory-making trip your kids will love.

Top spots include the Indianapolis Children’s Museum , which has 472,900 square feet and five halls of exhibit space, making it the largest children’s museum in the world!  While there, kids can explore science, history, and art exhibits. Or they can ride a carousel, board a train, or climb a giant treehouse.

Prefer outdoor activities?  Be sure to visit the Indianapolis Zoo and White River Gardens , where the kids can roam, see amazing things, and do fun activities. In addition to seeing tigers, dolphins, and orangutans, the kids can visit the petting zoo, ride trains, join for animal feedings, or watch cheetah racing. 

For families who love cars and racing, include a visit to the Indianapolis Motor Speedway . Known as the “Racing Capital of the World,” the speedway is home to the famous Indianapolis 500 race and offers tours of the track and museum. When in the area, stop for burgers and root beers at the Mug ‘n Bun, a nearby vintage drive-in.

On where to stay, consider booking a room at the five-star Conrad Indianapolis tops the list with its spacious rooms and prime downtown location. Prefer something less splurgy? The more budget-friendly Homewood Suites by Hilton Downtown Indianapolis , with a complimentary breakfast, makes for an excellent alternative. Or search for other lodging options in the Indy area here .

Illinois: Top Road Trips Within 5-Hours of Chicago

Check out these top locations in the Land of Lincoln: 

• Starved Rock State Park, IL
• Shawnee National Forest, IL

Also, consider a visit to Galena (a 2.5 to 3-hour drive) with a historic downtown full of shops and restaurants, nearby outdoor activities like walking and biking along the Galena River, and lots of family-friendly lodging , some with pools.

Starved Rock State Park, Illinois

Recommended by: Alyssa of AnAppleaPlane.com

Only 1.5 hours by car outside the bustling city of Chicago, Starved Rock State Park transports visitors into another world. Dramatic canyons and cascading waterfalls are not the first things you picture when you think of the Midwest!  

If you do not plan to drive your own car, renting one will be most effective for your time and budget. Or, you can get to the area by taking a train from Chicago’s Union Station to Mendota Amtrak Station and hailing a 30-minute cab to the park. A huge draw to Starved Rock is its easy-to-access features . Many of Starved Rock’s most famous waterfalls provide drive-up parking lots, so the walk to the waterfall is only a couple of minutes.

Alternatively, consider parking at the main visitor center lot and hiking to your waterfalls of choice. Waterfalls at Starved Rock flow after rainfall or snow melt, so be mindful that these will not be here year-round. The longest-lasting waterfalls are at St. Louis Canyon and La Salle Canyon.

Other top features of the park include hiking, boat tours, and camping . And perhaps the park’s biggest draw—the entrance is free !

Consider staying in the highly-rated Starved Rock Lodge for either cabin or hotel room options. Or search for other nearby family-friendly lodging options here .

Shawnee National Forest, Illinois

Approximate drive time from Chicago: 5 hours

Recommended by: Melissa of HelloWanderlustFamily.com

Located in southern Illinois, Shawnee National Forest is about a 5-hour drive from Chicago, making it an easy and accessible destination for families. 

One of the best things about Shawnee National Forest is its variety of activities , such as hiking, fishing, ziplining, or just relaxing in nature—it offers something for everyone.  Two must-see attractions are Cave in Rock and Little Grand Canyon Trail. Cave in Rock is a 55-foot-wide cave formed over thousands of years by the forces of the Ohio River and the wind, and a highlight of Little Grand Canyon Trail is you get to hike in and around a series of waterfalls that cascade down the rocky cliffs. 

When looking for a place to stay, consider the location of your planned activities . Shawnee National Forest is huge, with some attractions only 15 minutes away, while others may take an hour to reach. Because of this, choose accommodation closer to the area where most of your activities will be. One excellent lodging option for families is Home2 Suites in Carbondale , which not only provides larger room sizes and access to a pool but is in a city that offers plenty of amenities. Or search for more Carbondale lodging options here . Alternatively, for a more unique and memorable experience, consider staying at the Timber Ridge Outpost & Cabins , which offers cozy treehouses perfect for families seeking a one-of-a-kind stay.

Gurnee, Illinois

Approximate drive time from Chicago: 45 minutes to 1 hour

Recommended by: Lisa of PlanningAway.com

If you are looking for a fun short road trip from Chicago, Gurnee Illinois is just the place! There are lots of fun things to do in Gurnee, Illinois !  Gurnee is about 45 minutes north of the city. Home to Six Flags Great America and Great Wolf Lodge , it is the perfect place to spend a fun weekend.   

Six Flags Great America is the highlight of a trip to Gurnee. There are over 30 roller coasters and rides to explore. There is also a water park inside Six Flags called Hurricane Harbor. Six Flags has great shows and entertainment options for all ages.  

To relax after a fun day at Six Flags, stay nearby at Great Wolf Lodge , where you can enjoy many activities, including an indoor water park, Magiquest game, rock climbing, ropes course, arcade, bowling, and mini golf.  Kids will also love character meet and greets, dance parties, and many other fun activities by Great Wolf Lodge, and included in your stay. The lodge is perfect for kids under the age of 12 . 

There are some places to eat inside Great Wolf Lodge, but if you want to really experience Gurnee, you will want to venture out and try some local favorites. Kaiser Pizza is delicious, and Oberweis Ice Cream is a must. Gurnee Mills shopping and outlet mall is a good stop for families too. Shop at the Bass Pro, eat at the Rainforest Cafe, and enjoy many more fun shopping options. If you do not want to stay overnight—Gurnee also makes for a great day trip from Chicago.

Missouri: Top Road Trips Within 5-Hours of Chicago

Saint louis, missouri.

Approximate drive time from Chicago: 4 hours 30 minutes

Recommended by: Lynli Roman of Wanderbig.com

With less than five hours between cities, Saint Louis is a family getaway that feels far away but is easy to drive from Chicago in a half-day! Book a room at the railroad depot turned hotel , Union Station , and spend your time exploring the many family-focused activities that Saint Louis offers.  First, take your family to explore the City Museum . Described as “weirdly wonderful,” the City Museum is the crown jewel of family-friendly fun in St Louis. Housed in an old shoe factory, the City Museum boasts a huge network of slides, tunnels, and caves for all ages. All ages love the rooftop, where you can ride the Ferris wheel or climb a giant praying mantis for perfect views of the St Louis skyline. 

Next, wander through Soulard Farmers Market and taste your way through the city. The Soulard Farmers Market is one of the oldest markets in the United States, with roots dating back to 1779! Most alive during the weekends, you’ll find 147 stalls filled with unique vendors selling everything from local Missouri produce to handmade gifts. Nearby grounds include a playground and plenty of space for an impromptu picnic with your market spoils. 

No family road trip to St Louis is complete without a trip to Forest Park— one of the nation’s largest and most-visited urban parks. The park is home to the Saint Louis Art Museum , the Saint Louis Science Center , the Missouri History Museum , an outdoor theater, and the Saint Louis Zoo . Entrance fees vary, but many amenities, including general admission to the zoo, are free!

Want to see more St. Louis lodging options ? Search for other family-friendly accommodation options here .

Ohio: Top Road Trips Within 5-Hours of Chicago

From city trips to world-class amusement parks to under-the-radar natural gems, Ohio regularly delights visitors , and especially families, with all it offers as a vacation destination.

Four Buckeye State destinations to consider for your next road trip include:

• Cincinnati, OH
• Cleveland, OH
• Cuyahoga Valley National Park, OH
• Cedar Point Amusement Park, OH

Cincinnati, Ohio

Approximate drive time from Chicago: 4.5 to 4.75 hours

Recommended by: Linda of MidwestExplored.com

If you’re looking for one of the best family road trips near Chicago—you can’t beat Cincinnati, Ohio.  After all, this underrated city is located just four and a half hours, or 297 miles, away from Chicago and is a well-priced, family-friendly destination brimming over with fun Cincinnati things to do that everyone will love.

So, start your visit with a trip to The Cincinnati Art Museum , founded in 1881, and in the Eden Park area.  Not only is the museum free to visit, but there are over 67,000 works that cover 6,000 years, ensuring there is something for everyone at this incredible institution. 

Next, grab a picnic lunch and explore Ault Park , which spans an impressive 220 acres of land and is the city’s fourth-largest park, and features a wealth of picnic areas, playgrounds, and walking trails that will help keep energetic kids busy. Finally, learn more about the Underground Railroad at the National Underground Railroad Freedom Center before taking in the electric hue of the cool signs on display at the American Sign Museum.

Then, when you’re ready to call it a day, return to your room at the Hyatt Regency Cincinnati , where you can take advantage of their family-friendly suites, indoor pool and catch up on laundry at their on-site facility. Or search for more Cincinnati lodging options here .

Cleveland, Ohio

A visit to Cleveland truly offers the best of all worlds—thrills at nearby Cedar Point Amusement Park (1-hour drive), cultural chills, and hills made for hiking at Cuyahoga Valley National Park (30-minute drive).  Stay in town at a place like centrally located and highly-rated Roost Cleveland , which offers fully furnished apartments with hotel-like perks,  and use it as a base to explore the area. 

The city, on the shores of Lake Erie, is home to the Rock and Roll Hall of Fame, the Cleveland Museum of Art, and the Cleveland Orchestra—great destinations and cultural institutions for families to experience and explore.  And when your crew gets hungry, head to the historic West Side Market to grab a bite from local food vendors and souvenir shop for artisanal products.

For families with outdoor enthusiasts, pair a visit to Cleveland with a day trip to Cuyahoga Valley National Park , a 30-minute drive away, where you can hike one of many highly rated wooded or waterfall trails.

Want to see more Cleveland lodging options ? Search for other family-friendly accommodation options here .

Cuyahoga Valley National Park, Ohio

Another must-see destination for families visiting Ohio is Cuyahoga Valley National Park .  Located just outside Cleveland (a 30-minute drive), this park offers over 33,000 acres of natural beauty and outdoor activities. 

Families can explore the park’s hiking trails , go fishing or kayaking on the Cuyahoga River, or even take a scenic train ride.  With its pretty waterfalls, wooded paths, and diverse wildlife, Cuyahoga Valley National Park is a perfect destination for families looking to get outside, get moving, and enjoy the best of what nature and national parks offer.  

If you do not plan on staying in Cleveland, consider booking rental lodging in tiny and historic Peninsula Village , a private island of town surrounded by Cuyahoga Valley National Park.  Top rental picks in Peninsula, OH, for families include a few three and four-bedroom homes that can sleep up to ten. Search “Peninsula, OH” on VRBO  to find them.

Cedar Point Amusement Park, Ohio

Approximate drive time from Chicago: 4.5 hours

Cedar Point Amusement Park , located on a peninsula extending into Lake Erie near Sandusky, Ohio, is surrounded by water and overflowing with family-style fun. 

Known as the “ Roller Coaster Capital of the World ” with over 70 rides, including 18 roller coasters—thrill-seeking families will love it. The park also features a water park, live entertainment, and plenty of family-friendly dining.  Take at least two days to enjoy all it has to offer.

Stay on-site at one of the Cedar Point resorts like the beachfront Hotel Breakers , Lighthouse Point offering cottages and campgrounds, Castaway Bay with an indoor water park, or the budget-friendly Cedar Points Express Hotel .

Kentucky: Top Road Trips Within 5-Hours of Chicago

Louisville, ky.

Need a reason to visit Louisville, KY? How about six? Your family will love visiting the Louisville Zoo or strolling along Waterfront Park facing the Ohio River and adjacent to downtown Louisville, stopping to play in playgrounds or cool down in hot summers at the splash park. 

While in the area, catch a ride on a riverboat like the Belle of Louisville , which offers several different types of cruises, including historic narrated ones to picnic lunch cruises . Or your whole crew might love the Hometown Music Kids Cruise , designed especially for families.

Kids and parents who love baseball—or love to see how things how are made—will enjoy a visit to the Louisville Slugger Museum & Factory , conveniently located downtown. Your tickets give you access to the museum and a tour of the factory—kids even get a free mini-bat at the end of the tour.

Need an indoor day activity? Explore the Mega Cavern , a former limestone quarry, now an underground adventure park offering ziplining, ropes courses, and a bike park, just a 15-minute drive from downtown and near the Zoo.  Or visit the downtown Kentucky Science Center , where your kids can engage with exhibits about the human body and outer space.

For places to stay, The Grady Hotel and Homewood Suites by Hilton Louisville Downtown are great choices. Both hotels are centrally located downtown and highly rated. Or search for more Louisville lodging options here . 

Related Reading

For traveling families, check out my related articles below for more trip ideas and tips that will help smooth your travels and get out the door with less hassle.

• Need An Itinerary For A Spring Trip To Europe? Here Are 25 Amazing Ideas
• 31 Warm Winter Break Vacation Ideas Your Family Will Love
• Enjoy the Ride: 12 Tips for Better Family Road Trips
• 15 Tips on How to Raise the Bar on Rental Cars
• Pack Faster & Better With This Universal Printable Packing List
• 25 Expert Packing Tips to Help You Travel Better
• Pre-Trip: A Practical Checklist to Close the House & Pack

Additional Trip Planning Resources

To further help you with travel planning, I share my go-to resources for every trip below. 

Google Flights. My first research stop for affordable flights for every trip. Learn why here . 

Google Hotels . Use its “ Where to stay ” button to discover the best neighborhoods to base your visit.

Booking.com. For hotel and rental bookings, I appreciate its flexible cancellation, candid user reviews, discounts, loyalty program, and easy-to-use interface.

Viator , Get Your Guide , & Airbnb Experiences . Quickly find and book highly-rated tours and activities on these sites.

Google Travel Things to Do & Google Maps . Find more things to do in your destination on Google Travel, then record where you want to visit on a custom Google Maps list. 

AllTrails . Love to hike? Me too. I religiously use AllTrails to discover hiking and biking trails and download its offline maps to manage my hikes.

Guide Along . 5-star self-guided audio tours that are GPS-compatible for US road trips and national parks. We loved the Glacier National Park tour .

Insure My Trip. I never travel internationally without trip insurance. Learn why here . My preferred place to shop and compare policies is InsureMyTrip.com . 

Plus, check out the 15 travel apps I use on trips, my preferred guidebooks , and my free customizable travel itinerary template , downloadable in four file formats.

About the author:  Janice Moskoff is a travel writer and blogger who loves hiking, exploring the world, and reading. She writes to inspire travel-loving families, adult friends, and couples on her blog,  Gather and Go Travel . Check out  her bio , learn how she became  a blogger , and discover how to  work with her . Sign up for her monthly  Discovery Newsletter  to get her latest travel recommendations and  how-to’s .

Love to travel? Sign up for m y monthly Gather & Go Travel Discovery Newsletter and get a free trip budget calculator .

Affiliate Disclosure: Some of the links on this page may be affiliate links, and at no additional cost to you, I earn a commission if you make a purchase. I only recommend products and companies I use. And the income goes to keeping the site community-supported and ads minimal.

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Welcome to Gather and Go Travel , a blog inspiring families, adult friends, and couples to explore US and international destinations and to get outdoors. I am Janice, an experienced traveler to over 50 countries and a travel writer, book lover, and blogger. Learn more about me , read our story , and how to work with me .

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9 Dog Friendly U.S Road trips

Explore the top 9 dog-friendly U.S road trips with your furry friend! Tips on accommodation, parks, and keeping your pup happy on the go. Perfect for pet-loving travelers.

Your dog is your companion, your friend and boy do they love a good road trip! There head out the window with the wind in their hair, most dogs love a great road trip across the U.S.A.

However, it can be difficult finding the most "Dog friendly hotels" & dog friendly parks in the U.S.A, many simply will say no to your pooch. Also, it's good to know some tips to stop you from going barking mad along the way!

Can you take a dog on a road trip?

Lots of dogs suffer from car sickness, so a top tip is to  feed your dog  a few hours before you set of on your road trip! Then take your dog your a nice, long walk so he/she is tired & relaxed ready to hit the road.

Dog friendly Road Trip USA

On the road trip try and remain as consistent as you would at home with walk/mealtimes, it will keep your dog in a better pattern, ready to travel.

What can I give my dog on a road trip?

Before setting off, put your dog in the back seat or cargo area. Pet them, praise them and  give them treats  if they look nervous. Make it fun & not forced.

Should I sedate/Drug my dog before setting off?

Sedating/drugging your dog/pet is not necessary, some choose to do this if they are flying with there dog...but precautions should be taken either way. According to the  American Veterinary Medical Association (AVMA ) , "sedating dogs or cat during air travel may increase the risk of heart and respiratory problems.

Except in unusual circumstances, veterinarians should not dispense sedatives for animals that are to be transported. Speak to your veterinarian before hand.

Dog Friendly Road Trip USA

Which type of Road Trip should I take my dog on?

Shorter road trips, with lots of scenic nature around are the ideal road trips to take your dog on.

These are great as you can pull up anytime and take a wonderful walk through a national or state park! I would prefer to stay away from big cities to be honest, but it can be done!

Top 9 Road Trips with your dog:

9. montana road trip:.

Montana is heaven for Dogs! With plenty of nature & breath taking scenery its the ideal place to hop out of the car for some hiking with your dog!

A. Missoula

Begin your road trip in  Missoula,  a college town with a heap of dog friendly accommodation & restaurant patios.

Afterwards take the drive 50 miles north to the  National Bison Range  in  Dixon,  MT. Here your and your doggie friend can take the 2 hour loop through scenic meadows & hills.

Jack Dykinga | Wiki

This is the ideal place to do some wildlife watching. You & your pooch can spot birds, bison and even the odd bear!

Dog Road Trip Tip:

While driving through the National Bison range there are plenty of place to park up and enjoy a walking trail where your dog can go to the toilet. (Dog must stay on its leash)

C. Big Fork,Montana

Nearby to Dixon is the town of Big Fork MT, located on the northeastern edge of Flathead lake. Here you can enjoy some fine dining (dog patios), camping & canoeing around the lake. There is also some great hikes through  Flathead National Forest.

D. Glacier National Park

Finish of your road trip with a drive north to Glacier national Park and take the epic  Going to the Sun Road  which runs for 50 miles.

pray-lake-Glacier National Park

Insider Tip:

Going to the Sun Road  opens when the snow has melted, which sometimes doesn't happen till late july so aim for road trip later in the summer.

Dog Road Trip:

Dogs aren’t allowed off-leash at Glacier National Park, but you’ll see the best scenery in the park from the comfort of your car.

8. Great Lakes Road Trip: Chicago, Michigan

There are some epic great lakes loop tours, but I would recommended starting in dog friendly Chicago before driving up the eastern shore in Lake Michigan and then looping through Indiana before reaching the  dog hiking trails  of Michigan. This is a great midwest road trip where you will get to see most of the great lakes!

There is also plenty of  State Parks within 1 hour of Detroit.

The Haunted Tunnel of trees Michigan, is a ghostly drive.

Round Barn Winery, Distiller & Brewery

As you drive over the state border between Indiana and Michigan, be sure to stop by   Round Barn Winery, Distiller, and Brewery  for some drink tasting.

Dogs are allowed to explore the area on a leash.

As you drive father north, check out   Sleeping Bear Dunes  close to the town of Glen Arbor. At this state park, you & your dog can enjoy some nature walks, with view of lake Michigan.

7.  Chicago to Iowa Road Trip : Wicked Mid West!

Another great Midwest road trip you can combine with the above is from Chicago to Iowa. This will take you to the following stops along the way.

• Iowa City, Iowa
• Bonus: Amana Colonies

Dog Friendly highlights:

For Hiking on a series of historic & scenic trails at the  Mines of Spain state Recreation area.

dog road trip usa

Davenport (Dog Road Trip Heaven!)

Drive South on a scenic drive along the Mississippi River to reach Davenport City. Davenport was founded in 1836 and is known as a very green city with  pleathora of 50 local parks! These are great for walking your Dog!

Credit Island:

Credit Island is a island on the Mississippi to the south west of Davenport. This was an historic native american trading area and spans 420 acres!

These days it’s a vibrant community park which offers its own golf course including rugby, soccer and softball areas.

Credit Island-Davenport Iowa

Vander Veer Botanical Park

Vander Veer Botanical Park is a lush 33-acre botanical garden. It was established in 1885 and features a range of displays.

Location:  215 W Central Park Ave, Davenport.

Terry Trueblood Recreation Area (Iowa City)

A 5,870 square foot  recreation area   great for dog walking and it even has a large lake great for Kayaking & paddle boarding.

Map of Chicago to Iowa Road Trip (Dog Friendly)

6. dog friendly new england road trip.

New England is perfect road trip area for your dog! Here you will find plenty of states with short driving distances in between and plenty of dog friendly attractions along the way!

• Portland, Maine
• Dog Mountain, Vermont.
• Newport, RI
• Martha Vineyard, MA
• New Haven, CT

A. Portland, Maine:

Begin your road trip in Portland Maine, where you and your dog and hop on a  ferry  to explore all the nearby islands.

Afterwards head northwest to New Hampshire before stopping at the  White Mountain National Forest  for some dog-friendly  hiking  (on leash) and camping.

B. Dog Mountain, Vermont

Afterwards continue driving towards Vermont before stopping at the world renowned  Dog Mountain   this is a farm and art galley in St Johnsbury with plenty of scenic trials, ponds, sculptures and even a Dog Chapel!

Alan Sandercock | Wiki Commons

Many choose to leave a note for a previous dog which has passed away & is in doggie heaven.  The entire area is DOG FRIENDLY all year round!

Dog Friendly Lodging?

For one of the most Dog friendly lodges you will ever see head to the  Paw House Inn , a farm country inn which catering to dogs and their owners

Fun Fact:  Paw House actually charges a $10 fee to anyone staying  without  a dog!

Afterwards, take the drive to Boston and head to its most famous food halls,  Quincy Market,.  Here you will find which houses nearly 40 gourmet food vendors. Just 10 mins walk from there is Faneuil Hall, in Bostons little Italy district.

Dog Friendly Road trip usa

D. Newport, Rhode Island

Take the drive down to Newport road island to the Dog friendly Brenton Point State Park. Here you and your pooch can sit back and watch the  kite flyers.

E. Marthas Vineyard

Take the drive to beautiful Marthas Vineyard here you can check out dog friendly activities in Edgartown:

• Edgartown  Lighthouse.
• Norton Point Beach.
• Manuel F. Correllus State Forest.
• South Beach State Park.
• Kalmus Beach. Barnstable, MA.
• Craigville Beach. Centerville, MA.
• Island Queen Ferry. Falmouth, MA.
• Black  Dog  Tavern.  Vineyard  Haven, MA.

Brando | Wiki Commons

F. New Haven

East rock park.

You & your pooch can check out the epic views of New Haven from East Rock Park. You can drive right up to the summit and take in the breath taking scenery. This is especially beautiful during the fall.

Map of Dog Friendly New England Road Trip:

5. route 66: with your dog.

We can't have any road trip post without including Route 66!  There is a section of the route which still exists this will take you from Chicago southwest to Los Angeles. The southwest is the most memorable part!

It can really hot in the South so DON'T leave your Dog unattended in the Car and its even recommended you take your road trip during the cooler month.

Enroute be sure to check out the dog friendly  Big Texan  in Amarillo, Texas. A retro restaurant (great steaks!) with an adjacent motel. they welcome well behaved pets.

Route 66 is the number one most Iconic American road and Historic Legend.[/caption]

Also enroute be sure to check out  Petrified Forest State Park , where leashed dogs are welcome to explore the trails and backcountry with their owners. Remember to bring lots of water!

For more on Route 66, check out:  25 Most Epic Driving Roads in the U.S.A: Road Trip Ideas!

4.  New York to Niagara falls Road trip

If you fancy exploring New York State with your Dog I would recommended a road trip to Niagara Falls.

I would avoid New York city though! They recently introduced a law where if you wish to take your dog on the subway it must fit inside a bag! Classic New Yorkers saw this as a challenge so started to cut holes in giant bags for very big dogs!

A. Gilbertsville (Otsego County)

Enroute to Niagara be sure to drive through Gilbertsville (Otsego County) and head down to  Wagner Farm State Forest  offers with over 450 acres to stroll through.

However, be aware that  hunting & trapping allowed during appropriate seasons in designated areas, so keep your dog on a lease if your unsure or ask the visitors centre/warden.

B. Milford ( Otsego County )

Just nine miles south of Cooperstown and just a 20 minute drive from Oneonta, NY, you will find Milford. You and your pooch should head down to  Middlefield Orchard , for some Raspberry, strawberry and apple picking!

C. Coopers town  ( Otsego County )

Cooperstown  in Ostego County is a quaint village area which packs a big punch in New York state. Baseball fans will know the town as home of  National Baseball Hall of Fame  which celebrates the legendary players & managers from yesteryear.

The best place for dogs is  Glimmerglass State Park ,  a 593 acre park which offers year round activities including swimming and camping on the wood lined shores.

D. Fly Creek:

Fly Creeks lies just 4 miles (6 min) drive north west of Coopers town. The town was founded by Dutch traders who harnessed the power of the fast moving creeks by building 8 mills in the 19th century.

Be sure to check out  Fly Creek Cider Mill,   which is 163 years old and still open to visitors today. There is also the Cooperstown Beverage Trail and variety of tasty restaurants.

E. Richfield Springs ( Otsego County )

As you drive out of Coopers town or cherry valley be sure to take the drive to  Canadarago Lake  which is just one mile south of the village,  this is known as the second cleanest lake in NYS, and is 7 miles long/2 miles wide.

Unknown | Wiki

Insider Tip:   Head to  Deowongo Island  in the center of the lake for a picnic & some exploring.

F. Worcester, NY

Small town Worcester offers a indoor flea market, quilt zoo and quaint 1 screen theatre (Wieting Theater).  Decatur State Forest  spanning 582 acres and is the perfect place for hunting, bike rides and picnics.

G. Go wild at Seneca County

Drive west into New York’s Seneca County, and be sure to check out  Montezuma National Wildlife Refuge  an area which offers of 10,000 acres of swampland and has been a national landmark since 1973.

H. Finger Lakes

Take the short drive to the Finger Lakes Regions where I suggest you spend a few days.

Fun Fact:  The name “ Finger Lakes ” comes from the finger shape of two lakes Seneca and Cayuga, which are some of the deepest in the US.

I. Niagara Falls

You & your dog have now made it to the wonderful Niagara Falls!

• Niagara Falls is over  15,000 years old,  formed just the last  Ice age
• The  Largest Fall (Horse shoe falls)  is on the Canadian side 176 feet / 53.6 meters high.
• 600,000 U.S. gallons / 2,271,247 litres per second  flow over Horse shoe falls.

Are Dogs allowed at Niagara Falls?

Yes, Dogs are allowed at Niagara Falls, however there are a couple of conditions. Dogs need to be leashed and rabies vaccinated. You can walk your dog along the footpaths & green spaces.

3. Western National Parks Road Trip

On the West Coast of the U.S.A, are some of the most epic National Parks which stretch from Sequoia National Park and Yosemite National Park in the south west, to Olympic National Park & Mt Rainer National Park in the north west.

Cost Saving  Tip:

If you plan on traveling to alot of National Parks then I suggest purchasing a “America the Beautiful Pass” which renews annual for $80. This pass will get you into every national parks and also into any federal lands which charge fees.

You could explore any of americas western National park for an eternity with your dog! Here are some ideas below!

A. Grand Canyon National Park – Arizona

With over 6.38 million visitors in 2018, Grand Canyon National Park is the MOST popular National Park in the U.S.A.

Aerial Photo over horseshoe river at the Grand Canyon. Awe-inspiring!

Are dogs allowed at the Grand canyon National Park?

According to the  NPS :  Pets  must be leashed (up to 6 feet) at all times. On the South Rim, leashed  pets  are allowed on trails above the rim, Mather Campground, Desert View Campground, Trailer Village, and throughout developed areas.  Yavapai Lodge  is the only in-park lodge that has pet friendly rooms.

B. Yosemite National Park – California

Yosemite National Park is a real west coast highlight, located in the Sierra Nevada Mountains, it is best known for it’s massive sequoia trees and the granite cliffs of El Captain & half dome! Head up to the famed cliffs and you will find an incredible glacier valley with majestic waterfalls.

Yosemite-National-Park-[/caption]

Are dogs allowed in Yosemite National Park?

Dogs are allowed in Yosemite National Park. However, there are some restrictions & regulations, dogs are allowed on fully paved trails and roads, on a leash 6 feet or shorter, and cannot be left unattended.

C. Crater Lake National Park – Oregon

Crater Lake National Park, is Oregons only National Park and they are so proud of it! Highlights include the deepest lake in the United States (Crater Lake) (1,949 feet) which is also the ninth deepest lake in the world!

"Phantom Ship" rises above the surface of Crater Lake. | By Glenn Scofield Williams, via Wikimedia Commons.

Are dogs allowed at Crater lake National Park?

According to the  NPS  dogs are welcome at Crater Lake National Park, but only in certain areas. Pets are not allowed on other park trails or off-trail. They are also not allowed inside park buildings, including Crater Lake Lodge and The Cabins at Mazama Village.

D. Olympic National Park/National Forest – Washington

As we drive further up the north west we enter the Olympic National Park. One of the most diverse in the United States. Here you can find everything from glacier clad mountains such as Mt Olympus to vast expanses of wilderness, rainforests and even secluded beaches!

Are Dogs Allowed at Olympic National Park?

Though much of the peninsula is pet friendly, the trails in the Hoh Rain Forest  do  not allow  dogs!  However, you should head to the  Dog Friendly Olympic National Forest , where dogs on a leash are welcome!

E. Mt Rainier National Park – Washington

We’ve left the biggest till last at 14,410 feet above Sea level Mount Rainier is one the  tallest peaks in the United States. ..it is also an ACTIVE volcano.  Mount Rainier National Park offers the most glaciated peak in Contiguous U.S.A. In addition to wildflower meadows, five meandering rivers, ancient forests and an abundance of wildlife.

Mount-Rainier-National-Park. Source: the great ww.beyondthetent.com[/caption]

Are dogs allowed at Mount rainier National Park?

Dogs are not allowed on trails, or in any buildings. However dogs on a leash are allowed on the Pacific Crest Trail near the park's eastern boundary.

2. California State Park Road Trips

State Parks are generally more relaxed when it comes to dogs compared with National parks. However, alot of them tend to state "Dogs on leash" and "Paved Road Only" just so your aware. However, often there is dog friendly areas very close by to these great parks. Here are some of the most Dog Friendly state parks.

Julia Pfeiffer Burns State Park

Julian Pfeiffer Burns is probably the biggest bang for buck State park in California. After just a short 1/2 mile round trip along  Waterfall Overlook trai l, you will find a fantastic oceanfront views and jaw dropping views of the cascading McWay Falls. The water falls over 80 feet from the granite peak to the bottom.

julia-pfeiffer-burns-state-park-California

Are Dogs allowed at Julian Pfeiffer Burns state park?

At Pfeiffer Big Sur SP (four miles south on Highway 1),  dogs are allowed on leash  in the developed  campground  and  day use areas . Dogs are also allowed on United States Forest Service (USFS) property, including Pfeiffer Beach.  Source

Salt Point State Park

A great fusion between the land and sea, Salt Point State Park offers 6000 acres of wave carved cliffs & headlands stretching along the Sonoma Coast, 95 miles north of San Francisco.

Are dogs allowed at Salt Point state park?

Dogs of all sizes are allowed at the campgrounds  and in any of the developed areas. Dogs are not allowed on the trails or on the beaches, and they must be inside at night. There is no additional pet fee.

1. Road trip to  Woofstock!

This has to be the most Dog Friendly Festival in North America! Its designed to celebrate all things great about your pooch, so a road trip here, is the ideal place to go.

Dubbed as one of the best festivals in Canada and winner of numerous awards, Woofstock is a barking mad, fun packed event which draws thousands from all over North America.

Over 200,000 people from all over the U.S and Canada ascend upon Woodbine Park in Toronto for this annual two day event with their furry friends!

Peace and Love at Woof stock Dog Festival!

According to Melissa Granite, from Woofstock:

“Woof stock is to celebrate dogs as companions in our lives and, as well, bring together a community of people who are passionate about dog ownership and looking for the best dog products”

Activities/Events at Woofstock:

There are so many crazy events at Woofstock, from dog fashion shows to dog concert and even a Mr. and Mrs. Canine Canada Pageant!! Other events include:

• Running of the Pugs!
• Best Costume Contest
• Dog Racing Arena
• On-Stage Competitions
• Celebrity Dog Show
• and many more!

For more info check out our ultimate guide to  Woofstock: Largest Dog Festival in North America!

Want a great Car rental deal?

For the best rental car deal for your road trip be sure to check out:

Ultimate Car Rental Travel Hacks!

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Have you got everything you need??

Check out our   Travel Essentials .   (Things You can’t travel without!)

• Recommended  Backpacks
• Recommended  Camping Gear
• Recommended  Hiking Boots.
• Recommended  Photography Gear  (Capture Instagrammable photos!)

A high quality Backpack is essential to any traveling trip![/caption]

Wish to Book a trip?

To get the best hotel prices check out:   Hotel Deal Secrets!

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19 Awesome Road Trips from Chicago (with Timings)

Keeping your introduction to road trips from Chicago short and simple, let’s take a look at the summer, winter and weekend favourites!

The city of Chicago is awesome and all, but it’s also a great starting point for some great Chicago road trips. The city’s prime location acts as a portal to the Midwest – from historical cities to sprawling state parks and urban-stress-relieving beer. 

Best Chicago Road Trips in Summer

If you’re looking for one of the longest Chicago road trips, how about driving from Chicago to New Orleans ? If you’re thinking a little shorter, then read on…

Distance: as far as you can go

No American road trip is complete without covering some part of classic Road 66 – of which, lucky for us, kicks off in Chicago!

Snap a selfie at the official sign between East Adams and South Michigan Avenue then check-off stops such as the Gemini Giant, the Pontiac murals, Lincoln Presidential Library and more. If you can spare a month, make it all the way down to the Pacific Ocean.

2. Illinois’ Great River Road

Distance: 3.5-hour drive

In a seemingly never-ending chain of historical sites and activities, the drive along Mississippi River to East Dubuque is one of the best road trips from Chicago.

Moline and Rock Island are two cool detours but you can head straight for East Dubuque for its Chicago Great Western Railway Depot Museum. John Deere Pavilion lets you hop from car to farm machines, while the city Nauvoo shows off many historic homes. 

3. Lake Michigan to South Haven

Distance: 2.5-hour drive

Escape the heat by packing your car with beach gear and setting off for a nice drive around Lake Michigan and towards South Haven.

There are plenty of berry farms along the way so you can stain your hands with blueberries; or maybe you prefer to climb up a lighthouse?

To take your road trip even further, bring a bike! Cruise along the water front; take a dip or two. 

Do you have a favourite road trip quote? Click for the best long drive quotes to inspir e your next adventure!

4. Shawnee National Forest

Distance: 6-hour drive

One of the longest Chicago road trips on the list, it’s more than worth it to visit Shawnee National Forest. In fact, plan to camp amidst the spectacular range of landscapes for one of the best driving trips from Chicago!

Local favourites include the Garden of the Gods – you’ll find super special rock formations like Anvil Rock. Little Grand Canyon and Bell Smith Springs feature moderate hikes; Inspiration Point offers panoramic views over the prairie, Mississippi River and the forest.

Not convinced? Shawnee Hills Wine Trail is a brilliant drive that links up vineyards and wineries in the area – a great stop on a road trip from Chicago.

How about driving from Chicago to Atlanta? Here’s my guide to the best stops on a Chicago to Atlanta road trip , just for you.

Best Chicago road trips in Winter

If you want the best road trips from Chicago when it’s colder and darker, then these are the best ones for you.

5. Grand Rapids

Distance: 3-hour drive

After just long enough of a drive, pull into Grand Rapids for a nice sweep of activities. The Beer City Ale Trail will keep you road-tripping on foot (or car, if you have a Designated Driver); or wander through Downtown Market for food adventures instead.

Warmed by booze, drop by the 158-acre Frederik Meijer Gardens & Sculpture Park where their installations are bright pops of colour against an all-white backdrop. 

6. Muskegon

Speaking of unusual winter activities, I’ve heard so much about Muskegon Winter Sports Complex. Just an hour from Grand Rapids, it’s a great next stop on your Chicago road trip.

Their Olympian-designed ice-luge course is perfect for beginners, spanning 850 feet of forested speed racing. Muskegon is also home to USS Silversides Submarine Museum if you’re into marine vehicles, and there’s a great pier and lighthouse too.

7. Indianapolis

When temperatures are cold, cold, cold – you might opt for staying indoors. The city of Indianapolis is one of the best road trips from Chicago during winter because of its incredible indoor entertainment: museums.

From the Indianapolis Museum of Art to the Indianapolis Children’s Museum to quirky Indiana Medical History Museum, you can escape the cold all day!

Of course, drop by famous City Market for great eats and then maybe go on a catacombs tour underground too. This makes for one of the best road trips from Chicago.

8. Boyne Mountain Resort

Distance: 5-hour drive

Michigan winters are best captured with the ski resort of Boyne. Drive past snowy landscapes to reach 850 acres of skiing, snowmobiling, dogsledding and photography escapades.

While the forested grounds offer romantic snow-covered views, don’t miss out on the epic zip lines that take you through the trees and slopes. 

If you like your road trips from Chicago with a bit of snow and ski thrown in, then this is a great option for you.

Your ESTA for the USA

Before you go to the USA make sure you have your ESTA organised. You can find help with this on this link: https://www.application-esta.co.uk/ESTA-guide . It doesn’t take long and organising it beforehand will make things go that bit smoother at the airport.

9. Apostle Islands

Distance: 7-hour drive

Does driving over ice count as going off-road?

It’s an unforgettable journey to Apostle Islands National Lakeshore as winter ice freezes thickly to transform water into road, ending with stunning ice caves!

Make sure to visit the only inhabited Madeline Island as well for a cool wind sled experience and hot tub stay. 

Day Road Trips from Chicago

10. lake geneva.

Distance: 1.5-hour drive

Chicago’s number one when it comes to day trips, Lake Geneva is one of the best lake town’s in the US.

Downtown boasts all the food and drinks you need for the inevitable food baby; you might even land a booze cruise.

Hot air balloon rides, Lake Shore Path, ziplines and even ski slopes make it a year-round place to visit. It’s a multi-visit destination for sure!

11. Harbor Country

Distance: 1-hour drive

Wind between the towns of Michiana, Grand Beach, Three Oaks, New Buffalo, Lakeside, Union Pier, Harbert and Sawyer. This Chicago road trip will have you hopping between wineries and breweries, not to mention the beach.

It’s so close to the city, but the sand dunes and soft grasses make it a wholly different world. 

12. Starved Rock State Park

Distance: 2-hour drive

Families and romantics will love Starved Rock State Park for reasons that include: 13 miles of hiking, 18 canyons, free entry and nature-surround lodge.

It’s a great location to unplug for a day as you hunt down natural rock pools, waterfalls and incredible moss-strewn glades. You can even visit in the winter for cross-country skiing and cuddles in front of expansive mountain views. 

13. Saugatuck 

Making up Lake Michigan’s “art coast of Michigan”, Saugatuck and its neighbours (Fennville and Douglas) are house dozens of art galleries!

Unique and LGBTQ+-friendly shops feature alongside artsy hubs to make it a super welcoming town. Of course, famous Oval Beach appeals with soft dunes and paddleboat rides too. From craft booze tours to fruit picking and corn mazes, it’s one of Chicago’s best road trips.

14. Elkhart Lake

I won’t spoil it for you but this 292-acre lake and nearby Kettle Moraine State Forest is truly a place to unwind from the crowds.

You can hike the epic Ice Age National Scenic Trail or bike down Old Plank Road Trail. Pumpkin patches, race-tracking and fishing are all inclusive!

Want a charming hideaway? This is it.

Road Trips 4 hours from Chicago

Want your road trips from Chicago for a special weekend? Then these Chicago road trips are only 4 hours away.

15. Ann Arbor

If you’re looking for an all-season destination, Ann Arbor is the perfect road trip from Chicago.

Huron River entertains with kayaking, paddle-boarding, tubing and swimming; Matthaei Botanical Gardens and Nichols Arboretum displaying beautiful foliage. Definitely spare some time for Kerrytown Market and Shops for all their indie offerings! 

16. Door Country

Also called ‘Cape Cod of the Midwest’, Door Country is a 70-miles-long basket of fun!

You’ll never get tired of exploring its orchards, coves, lighthouses and wineries. Away from the light pollution, Newport State Park offers stunning starlit skies while Ephraim is all the small-town charm you need. Just imagine – 300 miles of coastline.

You can reach Galena under 4 hours but I recommend taking your time. Pull up through scenic rolling hills to go back in time because the Galena Historic District is made up of cobblestone streets and over 1,000 buildings from the 19 th century.

For those non-history buffs, Chestnut Mountain opens as a ski resort in the winter; Stagecoach Trail and Apple River Canyon State Park are open year-round. 

18. Richland County

To really escape from people, Richland County is a rural road trip destination where you can bunk for the night. But away from the isolated and lush property of Candlewood Cabins are fields and hills that keep you outdoors all day.

The Ridge Road and Pine River Recreation Trail fulfils all your adventurous needs – where else would you find wildlife while biking over abandoned railroads?

You also have three rivers and five state parks within an hour’s distance, and the lovely 100-mile Lower Wisconsin River Scenic Byway for more driving way. 

19. Huron-Manistee National Forest

Michigan really surprises us again and again!

Along the peninsula is the expansive Huron-Manistee National Forest, one of the best road trips from Chicago if you are a nature enthusiast. A single paved road takes you through dense forest (beautiful in the fall) to parking areas so you can hike your way through the serene space or canoe on the rivers. 

Road trips from Chicago

Of course there are loads of great things to do in Chicago but visiting Chicago really opens up a world of opportunities when it comes to road trips.

Whether you’re taking the car out for an hour-long spin or you’re willing to buckle down for a few hours, you won’t be disappointed by the scenery along your journey or the fantastic destinations ahead. 

Related Posts:

• 7 Ways to Make the Most of Your Road Trip Budget
• Planning a Road Trip in the USA: 13 Best Routes!
• 57 Coolest Things to Do in Chicago for 2023
• Christmas Things to Do in Chicago in Winter: 21+…
• 14 Awesome Stops on a Chicago to New Orleans Road Trip
• 11 Unique Stops on the Drive from Chicago to Atlanta

Hi, I'm Vicky! I wrote this. You can find me on all the social media @VickyFlipFlop. I love a bit of adventure, will try anything once, and have a strong passion for the local food and drink, whatever it may be. I'm here to help inspire you to travel to places a little out of your comfort zone, or at least to explore the usual destinations in a different way. Stay, have a look around, and if you have any questions – let me know below.

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The Best Road Trips from Chicago with Itineraries

Looking to get out and explore? There are so many unique places to visit that are just a car ride away! From quaint small towns to interesting cities to exciting outdoor adventure and everything in between, here are the best road trips from Chicago.

Afterward, you may also be interested in reading suggestions for

Fun Spring Break Trips from Chicago .

The Best Road Trips from Chicago

Starting with quick weekend getaways, this list is ordered by distance and ends with long road trips from Chicago.

HERITAGE TRAIL, INDIANA

This 90-mile scenic route will take you through northern Indiana's off-the-beaten-path towns where time slows down. The loop rambles through the communities of Goshen, Elkhart, Middlebury, Nappanee, Bristol, Wakarusa, and Shipshewana.

You'll discover winding country roads, talented artists, old-fashioned entertainment, recreational areas, blossoming gardens, and delicious treats.

From mid-May to mid-September, the trail coincides with the colorful Quilt Gardens project. 16 gigantic gardens and 23 painted murals embellish the trail with dazzling flowers in unique designs.

Drive Time: 2 hours to Elkhart Visitor Center

On the Way: University of Notre Dame, The Oliver Mansion, and Bonnie Doon Drive-In.

What to Do: Quilt Gardens, Wellfield Botanical Gardens, RV/MH Hall of Fame & Museum, Pumpkinvine Bike Trail, Ruthmere Mansion, Old Bag Factory, Linton's Enchanted Gardens, Bonneyville Mill County Park, and Menno-Hof.

Where to Eat & Drink: Rise N' Roll, Blue Gate Restaurant & Bakery, Iechyd Da Brewing, Das Dutchman Essenhaus, and Dutch Country Market.

Where to Stay: Excellent Hotel with a Great Location and Free Buffet Breakfast

SOUTH HAVEN, MICHIGAN

If you're looking for a relaxing destination with beach access, good restaurants, and a bike trail, South Haven is it. With its close proximity, southwest Michigan is amongst the top one day road trips from Chicago.

The walkable idyllic small town is right down the street from the Lake Michigan waterfront where you can see some of the best sunsets in the Midwest. There's plenty of opportunities to get out on the water: charter a fishing boat, take a sailing excursion or rent a jet ski.

If you'd like to do more than hit the beach then check out the Kal-Haven Trail, a former railroad route, that runs 33.5 miles from South Haven to Kalamazoo. It's a quiet and easy ride through blueberry fields, tree tunnels, and across a few bridges.

Drive Time: 2 hours, 15 minutes

On the Way: Four Winds Casino

What to Do: Kal-Haven Trail, DeGrandchamp Farms, Michigan Maritime Museum, Friends Good Will Tall Ship, and the Farmers Market.

Where to Eat & Drink: Golden Brown Bakery, Harbor Light Brewery, Chomp Gourmet Hot Dogs, Captain Nemo's, Phoenix Street Cafe, Idler Riverboat, Clementine's, and 12 Corners Vineyards.

Where to Stay: Historic Hotel in the Heart of Town walking distance to the Beach

GALENA, ILLINOIS

Galena is a must-experience destination in the Midwest especially if you live in Illinois. It is one of the unforgettable places to visit near Chicago with rolling hills, historic landmarks, and a super charming Main Street that will make you feel like you stepped into a Hallmark movie.

Start your visit at the historic Old Market House built in 1845 and now serves as Galena's Welcome Center. You'll learn about the fascinating history of the area and find information for your visit.

From springtime through fall, bike the River Trail, hike at Casper Bluff Preserve, or paddle the Galena River. The Alpine Slide, a 2,050-foot outdoor track, is a unique 2-minute adventure on the banks of the Mississippi River.

When the snow starts to fall, hit the slopes at Chestnut Mountain, one of the most popular ski destinations in the Midwest, or ice skate, sled or snowshoe at The Nordic Center at Eagle Ridge Resort.

While in town, hop on a trolley for a tour, visit wineries, and browse all the specialty and boutique shops.

Galena is on the Great River Road in Illinois along with some other special stops that make the scenic byway a unique Midwest road trip. Click on the link to read all about it!

Drive Time: 2 hours, 45 minutes

On the Way: Rafters Restaurant, Apple River Fort State Historic Site, Highway 20 Brewing Company, Horseshoe Mound Preserve, and Long Hollow Scenic Overlook.

What to Do: Galena Cellars Vineyard, Ulysses S. Grant Home, Galena Trolley Tour, and Grant Park

Where to Eat & Drink: Frank O'Dowd's Irish Pub & Grill, Durty Gurt's, The Log Cabin Steakhouse, Fried Green Tomatoes, Otto's Place, and Gobby's Sports Pub & Eatery.

Where to Stay: Cozy Hotel with an Indoor Pool & Spa and Cool Bar

PARKE COUNTY, INDIANA

Indiana has 98 historic covered bridges and Parke County is home to 31 of them. The central west area is also home to Indiana's largest festival, The Parke County Covered Bridge Festival, held every October in honor of the famous crossings.

Here, you'll also find quaint towns among rolling hills and two state parks to hike with deep gorges, wooden ladders, rocky hollows, and natural arches making the area one of the best fall road trips from Chicago.

Drive Time: 3 hours

On the Way: Kankakee Sands Bison Viewing

What to Do: Bridgeton Mill, Turkey Run State Park, Mansfield Roller Mill and Covered Bridge, Narrows Covered Bridge, Rockville Lake Park, Roseville Covered Bridge and downtown Rockville.

Where to Eat & Drink: Wheel House Donuts, Cross at Walk Winery, Thirty-Six Saloon, Big Berry, and Drunk Tank Winery.

Where to Stay: Cabin or Hotel Stay with an Indoor Pool

HAMILTON COUNTY, INDIANA

Under 200 miles away from Chicago and just 23 miles north of Indianapolis, Hamilton County is a fantastic option for a weekend getaway.

With lively communities bursting with arts and entertainment districts, outdoor activities, historic squares, boutique shopping, and diverse restaurants, Hamilton County deserves its own place on the list.

If you like to eat and drink, you can dedicate an entire weekend chasing giant pork tenderloins, local donut shops, and/or craft breweries. Make sure to spread your time evenly within the cities of Westfield, Carmel, Noblesville, and Fishers.

On the Way: Fair Oaks Farm, Cairo Skywatch Tower, Wildcreek Winery, and Jerry E. Botanic Gardens.

What to Do: Monon Bike Trail, Carmel Arts and Design District, Strawtown Koteewi Park, Hamilton County Courthouse & Old Sheriff's Residence and County Jail, Center of the Performing Arts,

Where to Eat & Drink: Urban Vines Winery and Brewery, Wolfies Grill, Rosie's Place, Cafe Patachou, Books & Brews, and Divvy Restaurant.

Where to Stay: Upscale Boutique Hotel in a Great Location

INDIANAPOLIS, INDIANA

Home to the state capitol, the world's oldest continuously operated racecourse, and the world's largest children's museum, Indianapolis has endless vacation potential.

Kick off your visit at Monument Circle, an impressive centerpiece circling the 284- foot tall Soldiers' and Sailors' Monument. The spectacular views from the observation deck will get you pumped to explore the city.

Once back on the ground, don't miss The Indianapolis Motor Speedway Museum, home of the Indy 500, for a chance to learn all about the history of racing, fast cars, and to see the track up close and personal.

For those looking for outdoor adventure, the Central Canal and White River State Park offer quiet respites from the bustling urban atmosphere with biking, pedal boat rentals, kayaking and segway tours.

If traveling with kids, spend an entire day at the gigantic Children's Museum of Indianapolis. Each exhibit will entertain the whole family.

What to Do: Indianapolis Motor Speedway, The Children's Museum, Monument Circle, Connor Prairie Interactive History Park, Canal Walk, Indiana State House, White River State Park, and Indianapolis Zoo.

Where to Eat & Drink: St. Joseph Brewery, Cafe Patachou, BRU Burger Bar, The Rathskeller, St. Elmo Steak House, and Slippery Noodle Inn.

Where to Stay: Hotel with Ideal Downtown Location & Indoor Swimming Pool

LAKE ERIE OHIO COASTAL TRAIL & CEDAR POINT

It's time to ditch Lake Michigan and discover another one of the Great Lakes. You can pick up the Lake Erie Ohio Coastal Trail in Toledo and follow the shoreline to Conneaut.

Along the 293-mile route, you'll discover the second-oldest operating amusement park in the United States (which happens to also be the best in the Midwest), old-time lighthouses, water parks an underrated cool city, swimming beaches, coastal towns, and beautiful state parks.

Being along the lake, there are numerous outdoor activities to choose from, plus historical and entertaining options on the drive. You'll have a newfound love and appreciation for Lake Erie after this sensational road trip.

Drive Time: 4 Hours to Toledo

On the Way: University of Notre Dame, Shipshewana, RV/MH Hall of Fame & Museum

What to Do: Marblehead Lighthouse State Park, Cedar Point Amusement Park, Rock n' Roll Hall of Fame, and Fairport Harbor Marine Museum and Lighthouse.

Where to Eat & Drink: Dock's Beach House Restaurant in Port Clinton, New Sandusky Fish Company, Mary's Kitchen in Geneva-on-the-Lake, Old Prague in Vermilion, Madsen Donuts in Geneva, and White Turkey Drive-in.

Where to Stay: Waterfront Property near Cedar Point

BLOOMINGTON, INDIANA

Bloomington tops the list of coolest college towns in the Midwest. There's always something going on between outdoor festivals, sports games, and music events.

Take a tour of one of the most beautiful campuses in the nation, go brewery hopping, or explore the area's natural beauty.

There's a reason Bloomington is referred to as the "Gateway to Scenic Southern Indiana," just twenty minutes away is the beautiful Lake Monroe and the Hoosier National Forest.

Drive Time: 4 hours

What to Do: Hickory Ridge Fire Tower, B-Line Trail, Indiana University Tour, and Tibetan Mongolian Buddhist Cultural Center.

Where to Eat & Drink: Nick's English Hut on Kirkwood, Laughing Planet Cafe, Oliver Winery, Crazy Horse, Cardinal Spirits, Upland Brewing Company, and Switchyard Brewing.

Where to Stay: Nice Hotel Walking Distance to University with Free Breakfast

HANNIBAL, MISSOURI

The river town of Hannibal is all about Mr. Samuel Clemens, aka Mark Twain. The prolific American writer grew up in this charming small town and many of his tales were inspired here.

Take a ride on the Mississippi, tour Twain's boyhood home and climb in the caves he played in and helped shape his imagination.

If you want to make your trip extra memorable, visit Memorial Day Weekend when the family-friendly Twain on Main Festival takes place featuring an arts and craft event, live music, Mark Twain performers, and a wine & beer garden with local favorites.

Drive Time: 4 1/2 hours

On the Way: Route 66 (see below for stops) to Springfield (Lincoln attractions)

What to Do: Mark Twain Boyhood Home & Museum, Mark Twain Cave, Lovers Leap, Mississippi Riverboat, Memorial Lighthouse, and Cave Hollow West Winery.

Where to Eat & Drink: Fiddlesticks Food & Spirits Company, Mark Twain Brewery, Becky's Old Fashioned Ice Cream Parlor and Emporium, Becky Thatcher's Diner.

Where to Stay: No-frills Chain with Indoor Pool and Free Breakfast

Unique and Romantic B&B with Breakfast and Full Bar

ROUTE 66: CHICAGO TO SPRINGFIELD, ILLINOIS

Route 66 is the most popular road in the United States and it begins in Chicago! For a fun weekend getaway, take a ride to the state capital of Illinois.

On the way, you'll find quirky roadside attractions along with interesting small towns. There are a ton of fun photo opportunities, colorful murals, and historical places along the route.

Once you arrive in Springfield, learn about one of America's most beloved presidents, Abe Lincoln, and see where he lived and worked.

Read here for a complete Springfield Itinerary to make the most of your time in the city.

Drive Time: 5 hours

On the Way: Old Joliet Prison, Gemini Giant, Launching Pad, Funks Grove Pure Maple Sirup, Route 66 Hall of Fame, World's Largest Covered Wagon, and Paul Bunyan Statue.

What to Do: Lincoln Home, Abraham Lincoln Presidential Museum, Lincoln Tomb, Ergadoozy Creative Play Center (kids under 12), Henson Robinson Zoo, Illinois State Capitol, and Knight’s Action Park.

Where to Eat & Drink: Cozy Dog Drive-In, Obed and Isaac's Brewery, Incredibly Delicious, Engrained Brewery & Restaurant, Mel-O-Cream Donuts, and Route 66 Motorheads.

Where to Stay: Downtown Hotel with Indoor Pool

ST. LOUIS, MISSOURI

Saint Louis has it all - good food, unique museums, craft breweries, and outdoor activities.

This Midwest destination is easy on the pocketbook too with most of the attractions and museums being free.

Don't miss the Gateway Arch; one of our newest national parks with a new state-of-the-art visitor center, the City Museum; the wackiest "museum" I've ever been to, and Anheuser Busch Brewery; a tour where you can also see the famous Clydesdales.

St. Louis is a great destination for couples, families, and solo travelers with an array of vacation activities to choose from.

On the Way: For a delightful lunch on the way down, stop halfway in Bloomington at Rosie's Pub. It's a popular restaurant serving up delicious sandwiches and burgers in one of the oldest buildings in town.

What to Do: St. Louis Zoo, The Arch, City Museum, Anheuser-Busch Brewery, Forest Park, Cathedral Basilica of St. Louis, Ballpark Village, and the Missouri Botanical Garden.

Where to Eat & Drink: Bogart's Barbecue, The Fountain on Locust, Crown Candy Kitchen, Hodak's Restaurant and Bar, Civil Life Brewery, and 360 rooftop bar.

Where to Stay: Well Reviewed Hotel near the Arch with a Free Hot Breakfast & Swimming Pool

CLEVELAND, OHIO

Cleveland provides an array of attractions from action-packed sporting events to interesting museums and even a few quirky stops like Ralphie's house in A Christmas Story.

Progressive Field, the Cleveland Indians' turf, is right near the pedestrian-friendly East 4th street which is the entertainment district downtown lined with restaurants and pubs. Down the street, take your chances with Lady Luck at a casino which also happens to be in the department store where the infamous 1983 Christmas movie was filmed.

And no visit to Cleveland would be complete without the Rock and Roll Hall of Fame experience . The museum launches visitors through the evolution of the shake-rattle-and-roll era that exploded in America.

And lastly, only 20 miles south is a national park to check off your list, Cuyahoga Valley. You can explore the park on a side trip from Cleveland or Akron.

Drive Time: 5 hours 20 minutes

On the Way: Cedar Point Amusement Park

What to Do: James A Garfield Memorial, Cleveland Botanical Garden, Cultural Gardens, Rock & Roll Hall of Fame, and A Christmas Story House.

Where to Eat & Drink: Collision Bend Brewery, West Side Market, Mabel's BBQ, Great Lakes Brewery, Lindey's Lake House, Alley Cat Oyster Bar, and Fat Cats.

Where to Stay: Reasonably priced 4-star hotel with indoor pool and lake views

SHAWNEE NATIONAL FOREST, ILLINOIS

You won't believe you're still in the Prairie State once you arrive in Shawnee National Forest. It is one of the best-kept secrets in Illinois.

It's a great destination to unplug and get back to nature. Start with the 1.7 mile Rim Rock Trail which will guide you through 300-year-old oak trees and narrow crevices to a beautiful canyon.

Explore the Cave-in-Rock overlooking the Ohio River, the historic cavern provided a safe haven for frontier outlaws back in the day. Take the Cave in Rock Ferry across the river to the small Amish village in Marion.

Don't miss a sunset at Garden of the Gods and a hike up Triggs Tower for more beautiful views.

What to Do: Rim Rock Recreation Trail, Burden Falls, Triggs Tower, Bell Smith Springs Recreation Area, Cave-in-Rock, Inspiration Point, and Garden of the Gods.

Where to Eat & Drink: The Diver Down, Garden of the Gods Outpost, E'Town River Restaurant, and Hogg Hollow Winery.

Where to Stay: A Beautiful Cabin with Private Bathroom and Deck

PATOKA LAKE, INDIANA

One of the best road trips from Chicago during Covid we took was to Patoka Lake. It is a destination that offers outdoor activities, that isn't very busy especially midweek, and where you can get out on a lovely lake.

Combine the trip with visiting the small towns of French Lick, known for its historic mineral springs, and Jasper, home to the Indiana Hall of Fame.

Make sure to rent a pontoon for a day on the lake and to take a walk through the stunning French Lick Resort and West Baden Springs Hotel for a glimpse into the past.

Drive Time: 5 1/2 hours

On the Way: Stop for lunch in a booming college town - either Lafayette or Bloomington.

What to Do: French Lick Casino, French Lick Scenic Railway, and Patoka Lake State Park.

Where to Eat & Drink: Patoka Lake Winery, 33 Brick Street, German Cafe, and French Licks Ice Cream.

Where to Stay: A 3-bedroom Country Cabin on the Lake

SANTA CLAUS, INDIANA

If you are looking for a fun wholesome summer trip for the family, head over to Santa Claus, Indiana.

With free soft drinks, free parking, free sunscreen, and free Wi-Fi, you can't go wrong with a visit to Holiday World and Splashin' Safari.

Home to the world's longest water coaster and America's only launched wing coaster, both amusement parks will keep the whole family entertained.

In between, make sure to track down all the festive spots that'll have you celebrating Christmas in July.

On the Way: Lincoln Boyhood National Memorial

What to Do: Holiday World Amusement Park, Splashin’ Safari Water Park, Lincoln State Park, Santa Claus Christmas Store, Santa’s Candy Castle, Santa’s Stables, Santa Claus Museum, and Holiday Drive-In.

Where to Eat & Drink: Frosty's Fun Center

Where to Stay: Santa's Lodge just not far from the Amusement Park

Rental RVs and Holiday Cabins

PUT-IN-BAY, OHIO

Where should I go for a weekend getaway from Chicago? Let me introduce you to South Bass Island in Ohio that is home to the small charming village of Put-in-Bay.

Even though there's plenty to do for families, this Midwest must-experience destination is best for couples or friend getaways. It's where golf carts roam and drinks flow with over 25 bars, breweries, and wineries.

From boating to paddle boarding, water activities are one of the best things to do when visiting. Along with catching a sunset at South Bass Island State Park, touring the wineries, and eating and drinking your way through town.

Drive Time: 5 1/2 Hours

On the Way: Shipshewana, Indiana's cutest Amish town.

What to Do: Observation Deck at Perry’s Victory and International Peace Memorial, island tour by tram, bike, or golf cart, Heineman’s Winery and Cave Tour, the monument view from Oak Point State Park, swimming at The Sand Bar, and the Massie Cliffside Preserve.

Where to Eat & Drink: Put-in-Bay Brewery, Chocolate Cafe & Museum, The Forge, Put-in-Bay Winery, Biergarten at the Boathouse, The Boardwalk, and Topsy Turvey's Bar & Grill.

Where to Stay: A Private Guesthouse with Free Bikes and a Fabulous Breakfast

AKRON, OHIO

Where can I go 6 hours from Chicago? Akron, Ohio that's where!

This is a city that surprised us in so many ways, not to mention, it's right next door to one of the few national parks in the Midwest.

Catch a minor league baseball game, tour an incredible historic mansion, chase waterfalls in Cuyahoga National Park, and visit an impressive art museum.

Drive Time: 6 hours

What to Do: Akron Art Museum, Cuyahoga Valley National Park, Akron Rubber Ducks, Stan Hywet Hall, and Akron Civic Theatre.

Where to Eat & Drink: The Peanut Shoppe, Mr. Zub's Deli & Bar, Lock 15 Brewing Company, and El Patron Tequileria & Cuisine.

Where to Stay: Modern Hotel with Lounge and Indoor Pool

TWIN CITIES, MINNESOTA

Saint Paul and Minneapolis, commonly called the Twin Cities, have a lot to offer for a vacation.

St. Paul is a little quieter with the state capitol and more daylife. While Minneapolis is where you go for art, theater, and nightlife. Both have a ton of breweries and great food options.

Discover the area through fun attractions like the Mall of America, the Science Museum of Minnesota, Como Zoo, Can Can Wonderland, and the Walker Art Sculpture Garden.

And do not miss the most beautiful places like the Cathedral of Saint Paul, the Minnesota State Capital, Como Conservatory, the historic homes of Summit Avenue, Lake Phalen, and Minnehaha Falls.

On the Way: Eau Claire, an Underrated Wisconsin Destination.

Where to Eat & Drink: Band Box, Summit Brewing Company, Keg and Case Market, Bad Weather Brewing, The Anchor Fish & Chips, and The Nook.

Where to Stay: Hotel with a Free Shuttle and Modern Rooms

CLEAR LAKE, IOWA

Clear Lake is a little hidden gem in the state of Iowa and it's another destination only 6 hours away from Chicago.

Cruise the Lady of the Lake, an authentic paddlewheel boat, while taking in the sights and learning some fun facts about the area.

Take in a show and tour The Surf Ballroom, where Buddy Holly, Ritchie Valens, and JP “The Big Bopper” Richardson played their last concert. Frozen in time, it'll transport you right back to 1959.

Eat, drink, and shop along Main Avenue, the hub of this friendly lakefront community.

And before you leave, drive north to Buddy Holly's Crash Site, you can't miss the giant Holly's iconic black eyeglasses.

On the Way: Galena's Helluva Half Mile Main Street

What to Do: Lady of the Lake Cruise, The Surf Ballroom & Museum, Clear Lake State Park, and Central Gardens of North Iowa.

Where to Eat & Drink: Cabin Coffee, Starboard Market, PM Park, South Shore Donuts, Lake Time Brewery, and Sevens Steak House.

Where to Stay: Adorable Rental with Free Bicycles walking distance to the Surf & Downtown

PORCUPINE MOUNTAIN STATE PARK, MICHIGAN

Michigan's Upper Peninsula is pleasant in the spring and summer, but it is also one of the best fall road trips from Chicago. And no trip there is complete without a visit to the Porcupine Mountains Wilderness State Park.

With 60,000 acres of old-growth forest, meandering rivers, jaw-dropping vistas, and flowing waterfalls, the “Porkies” will impress any traveler. It's kind of hard to believe you can find these views in the Midwest!

Drive Time: 6 hours 40 minutes

On the Way: Oshkosh, Wisconsin.

What to Do: Bond Falls, Lake of the Clouds, Escarpment Trail, Presque Isle Falls, Summit Peak Observation Tower, Big Carp River Trail, Union Spring Trail, and Porcupine Mountains Chairlift.

Where to Eat & Drink: White Pine's Yooper Diner, Antonio's Restaurant, and Hoop'n Holler Tavern.

Where to Stay: Chain Hotel only 15 minutes from the Park

RED RIVER GORGE, KENTUCKY

Listed on the National Register of Historic Places and a National Natural Landmark and National Archaeological District, Red River Gorge is a place that should not be overlooked as a road trip from Chicago.

Located in the Daniel Boone National Forest, there are over 100 natural sandstone archways, waterfalls, dense woodlands, exposed limestone ledges, tunnels, and bridges. 

Red River Gorge is an outdoor enthusiast's dream destination.

Drive Time: 7 hours

On the Way: Kentucky Horse Park in Lexington

What to Do: Nada Tunnel, Sheltowee Trace National Recreation Trail, Gladie Historic Site and Visitor Center, Sky Bridge Trail, Angel Windows Trail, Chimney Top Rock Trail, Cliff Trail, and Hidden Arch.

Where to Eat & Drink: Sky Bridge Station, Red River Rockhouse, Thatcher Barbecue Company, and Miguels Pizza.

Where to Stay: Great Resort surrounded by Natural Beauty

KANSAS CITY, MISSOURI

We are moving onto longer drive times so anything below here are my recommended best road trips from Chicago for a week or more.

Kansas City has culturally rich areas, bold and modern architecture mixed with distinguished historic buildings, a flourishing arts scene, and finger-licking-good barbecue.

If that doesn't convince you, it is also home to the best World War I Museum in the country and a highly rated art museum admired by all that visit.

Drive Time: 7 hours 45 min

On the Way: Springfield, Illinois.

What to Do: Crossroads Art District, National World War I Museum, Nelson-Atkins Museum of Art, City Market, Rose Garden at Loose Park, and Country Club Plaza.

Where to Eat & Drink: Arthur Bryant's, Cinder Block Brewing Company, Gillis Cafe and Hangout, Pigwich, Joe's Kansas City Bar-B-Que, and Boulevard Brewing Company.

Where to Stay: Hotel with Ideal Location and Free Breakfast

BRANSON, MISSOURI

Branson is probably one of the most underrated road trips from Chicago for families.

It's not just cheesy musicals and religious shows, there's a lot of natural beauty, fun attractions, and cool things to do for kids and adults alike. 

Drive Time: 8 hours

On the Way: St Louis and the quirky stop of Uranus.

What to Do: Titanic Museum, Silver Dollar City Amusement Park, Table Rock Lake Trail, Dick’s 5 & 10 Store, Top of the Rock, Shepherd of the Hills Fish Hatchery, and Branson Landing.

Where to Eat & Drink: Danna’s BBQ & Burger Shop, White River Fish House, Andy’s Frozen Custard, The Paddlewheel, Clockers Cafe, and Mel's Hard Luck Diner.

Where to Stay: Modern Hotel on the Branson Landing

FINGER LAKES, NEW YORK

If you are interested in 10 hour road trips from Chicago, Finger Lakes is the place to go especially if you enjoy hiking, lakes, and drinking.

The region is renowned for its wine trail but it also has more than 75 craft breweries! Don't miss the wonderful state parks and the interesting towns of Hammondsport and Corning.

Drive Time: 10 1/2 hours

On the Way: Rock n Roll Hall of Fame in Cleveland.

What to Do: Watkins Glen State Park, Corning Glass Museum, Hammondsport, Robert H. Treman State Park, and Mark Twain's Study and Burial Site.

Where to Eat & Drink: Market Street Brewing Company and Restaurant, Glenora Wine Cellars, Rooster Fish Brewing Tasting Room, Nickel's Pit BBQ, and Wagner Vineyards Estate Winery.

Where to Stay: Inn with a Beautiful Grounds & a Free Breakfast

BLACK HILLS, SOUTH DAKOTA

If you're planning a 2 week road trip from Chicago, head to the beautiful Black Hills of South Dakota.

You'll find scenic drives, history, wildlife, and natural beauty throughout the entire region. And, some goofy roadside attractions on the way!

Drive Time: 14 hours

On the Way: Austin, Minnesota

What to Do: Wildlife Loop in Custer State Park, Mount Rushmore, Wind Cave National Park, Evans Plunge Hot Springs, Crazy Horse Memorial, and Badlands National Park.

Where to Eat & Drink: Chuck Wagon Dinner Show, Baker’s Bakery & Cafe, Black Hills Burger & Bun Co, Wall Drug, and Legion Lake Lodge. 

Where to Stay: Bavarian Inn with an Outdoor Pool

THEODORE ROOSEVELT NATIONAL PARK, NORTH DAKOTA

If you like cool roadside attractions, quirky vibes, outdoor adventure, and getting off the beaten path then this is one of the best long road trips from Chicago.

Don't put off North Dakota as your last state because it has a lot going for it. The Theodore Roosevelt National Park has sprawling natural beauty with winding waterways and painted canyons along with free-roaming bison and wild horses.

The neighboring town of Medora is one of my favorite small towns in the U.S. with an authentic Western energy. Visit the Cowboy Hall of Fame to learn about cowboy culture, catch a show at the famous Medora Musical, an outdoor extravaganza with the real badlands as its backdrop, and stroll the streets of this tiny charming town.

On the Way: Fargo-Moorhead Visitors Center, Fargo Air Museum, Frontier Village, World's Largest Buffalo, Lewis and Clark Riverboat, Fort Abraham Lincoln State Park, North Dakota Heritage Center and State Museum, North Dakota State Capitol, and the Enchanted Highway.

What to Do: The Medora Musical, Chateau de Mores State Historic Site, Pitchfork Steak Fondue, ND Cowboy Hall of Fame, South Unit 36-mile Loop Drive, Sunset at Wind Canyon, Painted Canyon Visitor Center Overlook, Ridgeline Nature Trail, Roosevelt’s Maltese Cross Ranch Cabin, Boicourt Trail, Buck Hill Trail, Oxbow Overlook, River Bend Overlook, Cannonball Concretions Pullout, and 14-mile North Unit Scenic Byway at the Theodore Roosevelt National Park.

Where to Eat & Drink: Sandy's Donuts, Drekker Brewery, Tower Travel Center, Little Missouri Saloon & Dining Room, Medora Uncork'd, and Hidden Springs Java.

Where to Stay: Ranch Cabin in the Heart of Medora

Hotel with Free Breakfast and Indoor Pool

One of the most beautiful Midwest states is just a short drive from Chicago, here are fun day trips in Michigan to help you plan. 

I hope you enjoyed my favorite road trips from Chicago 2021 edition! If you have any other recommendations, please let us know in the comments below!

• About Author
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Angela E. is a travel writer from the Chicagoland area who has visited all 50 states in the US and has traveled extensively around the world. She is passionate about exploring the great outdoors and hiking in particular. Her love for nature has taken her to some of the most beautiful locations on the planet. She has written extensively about her travels on her own website, Dang Travelers, and has been published in collaboration with other travel websites and multiple visitor bureaus around the country.

Latest posts from Angela

• The Best Road Trips from Chicago with Itineraries - April 15, 2024
• The Best Restaurants in Celebration, Florida - January 15, 2024
• Restaurants Open for Christmas Dinner in Orlando - November 4, 2023

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6 Best Road Trips From Chicago

Waterfalls, storybook towns, incredible food, and more await just a short drive from Chicago.

Cities can sometimes feel like endless stretches of concrete — especially in the hot summer months — and Chicago is no exception.

Fortunately, there's a whole world out there beyond the city limits. While it doesn't always feel like it, there are so, so, so many worthy escapes within a few hours' drive of Chi-town: storybook towns studded with ice cream parlors, lakeside cities with entirely different cultures, and even places where you can connect with nature among waterfalls and lush trees. Waterfalls! Outside Chicago!

The Windy City's location, in this case, is your ally. Pack your car with some picnic accoutrements, and maybe some hiking gear just in case, and head off. You're within driving distance of some truly great, out-of-the-ordinary places that make for wonderful road trips. Here are six of them.

Madison, Wisconsin

Imagine a state already known for its beer and cheese having to cater to over 30,000 college students, and you've got some idea of the earthly delights that await in Madison, Wisconsin. This state capital could have been a destination in its own right for its unique geography — located on a narrow isthmus surrounded by two large lakes, it's beautiful even during cold Wisconsin winters — or its remarkable breadth of shopping, cultural events, and festivals, and architecture, but its food scene is virtually unrivaled for a city of its size.

The streets are filled with an eclectic mix of professors, politicians, businesspeople, street performers, and health nuts, and if you ask any of them for their favorite spot, you'll likely get a range of answers as large as the city's 250,000-plus population: American small bites at the new and renowned Mint Mark, tacos and margaritas at Canteen, Lao-Thai noodles from Vientiane Palace, and the list goes on and on.

Most students, however, will drive you toward craft-beer watering holes like The Malt House or Dotty Dumpling's Dowry, which purportedly serves one of the best burgers anywhere. Wash it down with some Wisconsin beer from New Glarus as well as some fried cheese curds, and you'll have yourself a real Madison, Wisconsin, night.

Madison is about two and a half hours from Chicago.

Starved Rock State Park, Illinois

Yes, Illinois isn't known for its natural beauty like some other states. Yes, its highest natural point is Charles Mound, a diminutive 1,235-foot hill. But that doesn't mean that hidden gems don't exist here. For a true escape from Chicago's steel-and-stone skyscrapers that is still within the state limits, drive to the area around Starved Rock State Park.

Visitors expecting more flat Illinois farmland will be surprised to find an incredible valley around the Illinois River, with lush trees, striking bluffs, and 14 gorgeous waterfalls feeding into the roaring waters. Starved Rock is a choice destination for camping, hiking, kayaking, and white-water rafting, and after you're exhausted from a day of physical exertion, it's also got a place to hang your hat: the Starved Rock Lodge .

However, if you feel like experiencing a bit more of the local flavor, the towns around the river valley provide it in buckets. Tiny, charming Utica is home to the August Hill Winery and some wonderful antique stores, while the historic towns of Oglesby and Ottawa are chock-full of Americana: small museums, galleries, and great food, particularly at the Red Dog Grill in Ottawa and The Rootbeer Stand in Oglesby.

Starved Rock State Park is about an hour and a half from Chicago.

Allegan County, Michigan

Lake Michigan is huge. And in the summertime, when the heat gets a little unbearable, you could easily just jump into the lake in Chicago. But there's something to be said for taking a jaunt out to Michigan to visit a string of lakeside towns that bring some truly unique qualities to the mix.

Douglas, Saugatuck, and Holland — and Fennville, though it's not right on the water — epitomize small-town charm, while still offering some truly city-sized amenities for city-sized appetites. Fennville is known as the fruit basket of Michigan, with apple orchards, vineyards, and berry farms alongside delightful creameries and even corn mazes, while Saugatuck and Douglas consistently take the cake as two of the best lakeside towns in the Midwest, with incredibly charming downtown areas, gorgeous undulating sand dunes, pristine blue water, and more art galleries than you can shake a stick at. In fact, it's here that two School of the Art Institute of Chicago instructors founded their own art school and residence, Ox-Bow, establishing an artists' colony right on the shores of Lake Michigan. Their legacy endures to this day.

Further up the road, you'll find a truly unique destination in Holland, where Dutch colonists established a foothold in the 1800s, bringing with them their culture, architecture, pastries (check out DeBoer Bakkerij), and even fields' worth of tulips, which you can find at Veldheer Tulip Gardens.

Fennville is about two hours from Chicago.

Indianapolis, Indiana

Among the many types of travelers out there — people who crave solitude, people who don't want to leave the 100-foot radius of their resort's pool — there are those who are fascinated by city life, jumping from one urban area to another. If you count yourself among them, a road trip from Chicago to Indianapolis is certainly warranted.

First off, it's the 15th-largest city in America, with a vast population and penchant for festivals, parties, and overall pageantry (it is the Racing Capital of the World, after all, and its famous month of May includes tons of smaller celebrations leading up to the Indy 500). No matter the time of year, though, you'll find Indianapolis in full swing, whether you're in the midst of its rollicking IndyFringe Festival in August and September or its Wine & Food Festival in June. It's also a museum hub, with the world's largest children's museum, several art museums with broad and granular focuses, and small museums focusing on its favorite children, from Vonnegut to President Benjamin Harrison.

But one of the main reasons visitors flock to Indianapolis is its incredible food scene, which has, in recent years, exploded into national prominence. Hot new restaurants like Bluebeard, Milktooth, Crispy Bird, Oca, and more have all contributed to its reputation as a gastronomical powerhouse, while iconic institutions like Workingman's Friend have been, well, working behind the scenes to keep Hoosiers well-fed for decades. It's about time their city gets noticed.

Indianapolis is about three hours from Chicago.

Traverse City, Michigan

If you're craving a real getaway, you can't do much better than northern Michigan — it's still within driving distance of Chicago and not as remote as the state's Upper Peninsula, while still providing a wilderness-tinged escape for city dwellers. The de-facto capital of the region, Traverse City, is a city in name, but its population of around 15,000 means it's got small-town charm and accessibility, making it a perfect gateway to the region's breathtaking sights. Stop in for a glass of beer or wine at one of the many famous wineries and brewpubs, like Mari Vineyards or Mackinaw Brewing Company, before heading into the wilderness.

From Traverse City's quaint streets, you can head north and explore the Leelanau Peninsula, or veer west to Sleeping Bear Dunes National Lakeshore. Better yet, take scenic M-22 to tick off both boxes. Sleeping Bear Dunes is one of the country's best stretches of shoreline, with incredible dunes and westerly views that mean it's got some of the best sunsets east of the Mississippi.

From there, mosey up M-22 to continue exploring the Leelanau Peninsula, where wilderness encroaches a bit further and small towns, each with a population under 1,000, dot the roads. Hike through the dense forests, pick apples and berries at the region's many farms, and be sure to grab a heaping sandwich from the Village Cheese Shanty in the county seat of Leland (population 377).

Traverse City is about five hours from Chicago.

Galena, Illinois

In rare cases, a road trip doesn't just mean traveling great distances — it can also mean traveling back in time. That's what's figuratively the case when you drive west from Chicago to Galena, consistently rated as one of the best small towns in America. For decades, Galena has been on a mission to preserve its rich history, meaning it has one of the most unspoiled historic town centers in the country.

The town's good fortune started back in the mid-1800s, when it was the beneficiary of government grants to begin mining precious minerals located under the town. Since then, the town has focused on maintaining the buildings from that boom time, and there are architectural landmarks around every corner. The Galena Historic District is a particular delight, comprising more than 1,000 buildings, including the home of Ulysses S. Grant, a prime example of the Italianate style and now a dedicated memorial to his legacy. The town even has trolley tours that take you to its major historical and architectural benchmarks, contributing to its overall throwback feel.

Galena's best eating institutions don't necessarily date all the way back to 1850, but that doesn't mean they aren't also great — Durty Gurt's Burger Joynt was founded in 2007 and serves gigantic, almost architecturally impressive stacks of meat and cheese. Looks like everyone's concerned with building a legacy here.

Galena is about three hours from Chicago.

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Best Dog Route Planner (Planning A Road Trip With Your Dog)

Last Updated on January 30, 2023 by Rose Morah

To plan a successful cross-country road trip with your dog, you will need a good dog route planner. 

This article discusses one of the best dog route planner websites that helps you plan a trip in just under 5 minutes.

But first, the following are the advantages of using a dog road trip planner:

• It helps you to save time and is less stressful. 
• It helps you choose the best route for your road trip.
• You get a clear picture of what your trip will look like.
• It helps you enjoy a smooth and seamless dog road trip.
• It is flexible. You can plan an emergency route that includes dog clinics.

Petswelcome is one of the best dog trip planner websites that helps you plan your route. It allows you to add stopovers and dog-friendly hotels within your route.

The following are steps for planning a road trip with your dog on Petswelcome.

1. Add your starting point and destination

• How to select the hotel's pet fee on Petswelcome dog route planner.

How to check the dog weight limit on these hotels

How to check the maximum number of pets allowed per room, how to add stopovers on your route, how to get hard copy directions for your trip, how to plan an emergency route on a road trip with a dog.

(Check out the screenshot below)

What I love about this dog route planner is the fact that it allows me to select hotels near my main route. I just need to adjust the miles, as seen in the screenshot below.

See also: 8 Best Pet Transportation Services – Best Pet Shipping Companies .

2. Select your preferred hotel along your route

So, once you’ve entered your starting location and your destination, go ahead and click on ‘Go.’ 

Your route will be automatically mapped- as seen below.

See also: 10 Best Road Trip Planner Apps/Websites (As Recommended by Travelers) .

How to select the hotel’s pet fee on Petswelcome dog route planner.

Select “Add to your trip,” as seen in the screenshot below

You may also like 15 Tips for Taking Your Dog Camping For The First Time .

See also 13 Must-Have Dog Camping Accessories .

If you are traveling with a big dog, then this will be important.

The screenshot below is about how to check the weight limits.

Once you have identified the ideal hotels for you and your dog, you will need to find out the maximum number of dogs allowed and the fee you will pay per night. This is important, especially if you are traveling with more than one dog.  

Refer to the screenshot below.

So, to check, click on “more info” just below the hotel. 

See also: 28 Best and Must-have Road Trip Car Accessories .

Remember, frequent stopovers are a must when you’re planning a long road trip with your dog!

This dog route planner website comes in handy when planning your stopovers.

What I love most about this dog route planner is the fact that it gives you a detailed guide to the location of dog-friendly hotels. Therefore, I don’t get lost along the way. 

Additionally, it allows you to save , share and print a copy of it. The screenshot below will show you exactly what I am talking about. To get this feature, you just need to click on “Get directions with Selected Hotels.”

Anything can happen while on your road trip. For example, your dog might get sick. This is common for some dogs, especially those that have not been on long drives. 

The Petswelcome app will help you plan an emergency route with facilities/services you may need during your road trip.

You just click on ‘plan an emergency route,’ as seen below.

This will enable you to plan your route, as seen below.

You can also get the dog/pet clinic contacts by clicking on “more info,” just below the Pet clinic.

That’s it. I hope this guide will help you plan your next road with your dog. In less than 5 minutes, you are done.

Hello there! My name is Rose. I’m passionate about electric cars and clean energy. My adventurous spirit and journalistic pursuits make each day fascinating and far greater. I consider traveling not just about the grandeur moments, but the little elements that transform the whole experience.

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12 Best Spring Break Road Trips from Chicago

Chicago is known for its world-class museums, including the Field Museum and the Museum of Science and Industry, but after the cold Chicago winter, most people will have exhausted the city's many indoor attractions. That makes spring break the perfect time to take a trip.

Whether you have a day, a weekend, or longer, there's a fabulous choice of spring break trips from Chicago. Drive to Cincinnati, Traverse City, Cleveland or Columbus, follow Scenic Route 61, or chase the sun south the Nashville, Hot Springs or Atlanta.

There's something for everyone in reach of Chicago, with great spring break road trips to suit if you're traveling with children, teens, or childfree. Keep reading to find out some of the best places you can get to from the Windy City this spring break.

Best spring break road trips from Chicago

Chicago makes a great place for a spring break staycation, and with its museums, parks and the attractions around Navy Pier to enjoy you might even be heading there as your main spring break destination. But if you're ready to explore a little further afield after the St Patrick's Day party, or looking for a day trip or two while you spend spring break in Chicago itself, you have some amazing destinations to choose from.

After the long winter, why not head out for an adventure when spring break rolls around again? We've listed some of our favorite spring break destinations, so keep on reading to decide what kind of trip awaits you this spring break.

If you're thinking of taking a road trip from Chicago in another season, check out our Best Road Trips from Chicago article for ideas and inspiration! We also have a detailed guide for traveling from Chicago in winter, if you want to plan ahead.

Day trips (about 3 hours each way)

1. Indianapolis, Indiana

3 hours 10 minutes from Chicago (180 miles)

Why you should visit: This is the shortest trip on the list, but there's plenty to see in the city whether you're traveling as a family with young kids or taking a break from college.

The Children's Museum is sure to be a hit for younger travelers – it's the world's largest children's museum. With a visit here your spring break can take you to modern Europe, ancient Egypt, or even into space.

Baseball fans might like to time the trip to catch the home opener of the Indianapolis Indians, which usually takes place in early April.

How to get there: Head out of Chicago on I-90 E then pick up I-65 which you'll follow south past Remington and Lafayette. After around 130 miles on the interstate you'll cross the White River to arrive in downtown Indianapolis.

Our highlights: The Indianapolis Children's Museum will definitely appeal to families on spring break. This huge space has engaging interactive exhibitions covering space travel, history, pop culture, science and technology, and dinosaurs.

Families and college athletes alike will also appreciate the NCAA Hall of Champions, which even has sports simulators where you can try your hand at new activities.

Elsewhere, Indianapolis Museum of Art blossoms in springtime when the thousands of bulbs planted at Newfields' gardens burst into life.

Indianapolis also has breweries, wineries and distilleries which you can visit with the Indy Craft Pass – something that might appeal if you want to party during spring break.

Bonus: You won't be able to see the famous Indy 500 automobile race during your spring break visit, as this usually takes place in May. If you decide to make a return trip to see the race, you'll be in good company – more than half a million people watch from around the Speedway.

Our travel tips: Weather can be variable during spring break, from 32 degrees F right up to 65 degrees. April is one of the wettest months of the year too, so pack accordingly.

2. Springfield, Illinois

3 hours 30 mins from Chicago (200 miles)

Why you should visit: This is a really easy drive out from Chicago, and with its presidential history it's a fascinating contrast to the Windy City. It's also a great place to spend a weekend, especially if you fancy following the Capital City Bourbon Journey.

Springfield is a great family getaway, especially if your kids have started to learn about the country's history.

You can immerse yourself in stories of the country's 16th President, Abraham Lincoln, who lived in the city for many years – his legacy as the country's Civil War-era president is sure to inspire grade schoolers and older teenagers alike, especially when you can visit the places where he lived and worked for real.

How to get there: This is a really simple trip to navigate – just pick up I-55 S from your departure point in Chicago, and follow it all the way to Springfield, Illinois.

Our highlights: You could easily spend the whole trip exploring Lincoln-related sites. There's the Lincoln Home National Historic Site, where he lived until becoming President in 1861, and the unique, interactive Abraham Lincoln Presidential Library and Museum. You can also tour both the old and new state capitol buildings.

Younger kids will enjoy Kidzeum, a colorful museum where they can learn about keeping themselves and the planet healthy. Many of the exhibits are play-based – a perfect pick-me-up if they're getting fidgety after all that history.

With its vintage fighter planes, the Air Combat Museum might also appeal. Check ahead for opening times.

Alternatively, if you need to run off some energy, head to Knights Action Park, where you'll find arcade games, rides and mini-golf.

Springfield isn't just for families though – older visitors might like to follow the Capital City Bourbon Journey, which takes you on a tour of some fabulous bars and restaurants to try locally-produced makes.

Bonus: Springfield didn't invent the corn dog, but it does claim to be the birthplace of the iconic cozy dog – that's a hotdog on a stick covered in tasty batter for out-of-towners. For one of the best in town, head to the Cozy Dog Drive-In.

Our travel tips: Springfield will feel chilly if your spring break falls earlier in the season, with March temperatures rarely topping 50 degrees Fahrenheit. You might even see a little snow.

Click here to skip back to the top.

Weekend trips (about 5 hours each way)

3. Cincinnati, Ohio

5 hours from Chicago (290 miles)

Why you should visit: Cincinnati is a beautiful riverside city which is at the longer end of the one-day range – it's also a great place for an overnight trip. There's plenty going on so it will appeal to visitors of all ages.

If your spring break coincides with Opening Day, come and join the party in Cincinnati. With unbeatable baseball heritage, the first pitch of the season sees the Findlay Market Parade and other events to celebrate the Reds (who always play their opening game at home).

How to get there: Follow the interstate as far as Indianapolis. You can stop for a break here but if you'd rather head straight to then bypass the city on I-465 which takes you onto I-74. Follow this road all the way to Cincinnati.

Our highlights: Baseball fans should head straight to the Cincinnati Reds Hall of Fame & Museum, where you can also take a tour of the Great American Ballpark.

If you're not in town for Opening Day, there's still plenty to see and do. Cincinnati Zoo holds its popular free Tunes & Blooms sessions on Thursday evenings through April. Enjoy live music among the colorful spring blooms in a family-friendly atmosphere. You can also enjoy the blooms in the daytime if you need to hit the road back to Chicago by the evening.

At Krohn Conservatory, the spring sees the arrival of thousands of butterflies which are fascinating to watch when you visit the tropical glasshouse.

With its Dinosaur Hall and interactive science exhibits, Cincinnati Museum Center is also a great family day out. Head to the Children's Museum for some play-based fun.

Bonus: For many years, the baseball season was officially opened with a first pitch in Cincinnati, whose team, the Reds, was the first in the country to go fully professional.

Our travel tips: The city will be really busy if you do visit for Opening Day, so expect some queues and leave extra time to park (we'd suggest arriving early). Book early if you want to try to get tickets for the game.

4. Traverse City, Michigan

5 hours from Chicago (320 miles)

Why you should visit: This is the only destination on our list that lets you carry on exploring the shores of Lake Michigan.

After the long winter, the wildflowers start to blossom around Sleeping Bear Dunes National Lakeshore, making this a fabulous weekend destination for fans of the great outdoors.

How to get there: The interstate runs parallel to the shore of Lake Michigan most of the way to Traverse City. You'll start out on I-90 E before switching on to I-94. Follow this past Benton Harbor then change onto I-196 where the interstate divides. When you reach Grand Rapids join US-131 and continue north until you reach your destination.

Our highlights: You could spend days exploring the fabulous lakeshore, but seeing as you're only here for the weekend we'd suggest starting at Sleeping Bear Dunes with a hike along the Old Indian Trail or spending some time exploring Old Mission State Park. You can also visit the historic lighthouses – six in all – to enjoy more atmospheric views out across the lake.

It's too early in the year to swim in the lake but kids of all ages will love the huge indoor water park at Great Wolf Lodge.

If you're here without the family, visit a winery or two or taste some of the wine produced along the Traverse Wine Coast at one of the city's tasting rooms or bars.

Bonus: Traverse City is known as the Cherry Capital of the World. Spring break is out of both the cherry blossom and picking seasons, but don't miss the chance to try a slice of cherry pie while you're in town.

Our travel tips: Temperatures often dip below freezing even in April, and this can be a wet time of year, so plan for some indoor activities if you're making a spring trip here.

5. Columbus, Ohio

5 hours 30 mins from Chicago (350 miles)

Why you should visit: Ohio's state capital and largest city is packed full of things to do during spring break. The length of the drive means you'll probably want to stay at least a night (or maybe longer) but there's so much to do when you arrive that you definitely won't be bored.

You'll find a whole host of family-friendly attractions in Columbus, including one of the best science museums in the country at the Centre of Science and Industry.

How to get there: Follow I-65 away from Chicago then at Indianapolis change onto I-70 to head east into Ohio. As you approach Columbus, merge onto I-670 to make your way to the downtown area.

Our highlights: The Center of Science and Industry (COSI) – named "America's number one science museum" – is packed full of interactive and informative exhibits which are guaranteed to keep children entertained for hours.

Another surefire hit with children is the LEGOLAND Discovery Center. It doesn't just appeal to kids, though. There's a 3D cinema featuring Lego characters, as well as the chance to build and explore interactive displays.

Just outside town, Columbus Zoo & Aquarium is another entertaining attraction, and if your spring break coincides with Easter there are extra egg-themed activities and attractions

If you're feeling active, head to Hocking Hill State Park, where you can escape the busyness of the city and hike through a fascinating sandstone landscape.

Staying outside, you can also visit Franklin Park Conservatory & Botanical Gardens, where the spring flowers will be starting to burst into life. It's a relaxing place to escape the hustle and bustle, and if you're traveling as a family children love exploring the tropical conservatory too.

Finally, to celebrate the spring sunshine, round off the afternoon or evening on one of the city's rooftop patios.

6. Cleveland, Ohio

Why you should visit: As well as spending time by another of the Great Lakes, this trip from Chicago to Cleveland also lets you follow one of “America's most scenic drives” with a detour along Indiana's Heritage Trail that starts at Elkhart.

If your spring break falls over the Easter period, come and join in the Dyngus Day celebrations! Held on Easter Monday, this Polish festival includes polka dancing, accordion music and beer tents – a really unique way to spend the spring break whatever your age!

Another interesting event that coincides with spring break is the Cleveland Thyagaraja Festival, a celebration of Indian classical music that brings international stars to the city.

How to get there: From the center of Chicago, join I-90 and keep going. You'll drive all the way across Indiana and then into Ohio, passing to the south of Toledo and Lake Erie before arriving in Cleveland.

If you're following the marked Heritage Trail, leave the interstate at Elkhart then head east on IN-120 to Bristol. Carry on to Middlebury and Shipshewana before looping back around to visit Goshen and Nappanee. Wakarusa is the final stop on the trail, which then passes through Elkhart again before you rejoin I-90 to continue east towards Cleveland.

Taking this detour along the Heritage Trail will add around 2 hours and 30 minutes to your driving time, plus any time for stops in the towns you'll pass along the way.

Our highlights: On your way to Cleveland, take a break from the interstate to travel along Elkhart County's Heritage Trail. Taking you through small towns and beautiful landscapes, you can download a free audio guide which gives you some of the background to this peaceful part of Indiana.

Once you've arrived in the city, you should definitely try out Maple Sugaring if you're visiting in March. This takes place at a number of locations in and around Cleveland.

If you're traveling with children, check out the themed trips on the Cuyahoga Valley Scenic Railroad, which run through April.

If the weather's good enough to spend more time outdoors, go for a longer hike through Cuyahoga Valley National Park where Brandywine Waterfall should be in full flow. You could also spend a peaceful half hour walking through the daffodils that carpet Lake View Cemetery.

Bonus: Cleveland Thyagaraja Indian classical music festival is the biggest festival of its kind that you'll find without visiting India.

Our travel tips: As with some of the other destinations listed so far, spring weather in Cleveland can be unpredictable, ranging from late snow to bright sunshine.

READ MORE - Road Trip from Chicago to Cleveland

Long weekend trips (6-8 hours each way)

7. Nashville, Tennessee

7 hours 15 mins from Chicago (480 miles)

Why you should visit: Nashville is the first of our road trip destinations where you're likely to be able to enjoy some warmer spring weather, and the first one outside the Midwest.

Nashville is a great place to party , and with live music and warm weather likely to feature, it's perfect for a short spring break road trip from Chicago. It's a straightforward interstate drive south for the weekend, and once you arrive, you can immerse yourself in the party atmosphere until it's time to leave.

It's also a fun place to take children, especially if they're happy to soak in the atmosphere. Many of the live venues on Lower Broadway welcome families during the daytime.

How to get there: Although it's a pretty long drive, this 475-mile route is really easy to navigate. Just hop onto I-65 as you exit Chicago to the south, and follow it all the way through Indiana and Kentucky. Just after you cross the Cumberland River, turn onto I-40 to make your way into Nashville's downtown where you'll complete your drive.

Our highlights: You can't visit Nashville without seeing a live show or two, so head to Music Row and take your pick before partying late into the night on Broadway. Some venues host special spring break parties, but if these don't match the kind of vibe you're after there are plenty of other venues to choose from.

A great all-year-round attraction that's a must-see in Nashville is the Country Music Hall of Fame. If really you want to immerse yourself in the heritage of Music City, you can carry on to the Johnny Cash Museum, RCA Studios or the Grand Ole Opry House.

When you're ready to take a break from wall-to-wall music, head to the Cheekwood Estate where the springtime Cheekwood in Bloom event sees over 100,000 tulip bulbs filling the peaceful gardens with bursts of color.

Just outside the city, Treetop Adventure Park is great for couples, groups and families alike – test your nerves as you travel across bridges, ropes and ziplines high up in the canopy (children must be over 7 to take part, and an adult has to climb with them).

Bonus: Book a stay at the Gaylord Grand Ole Opry Resort to enjoy a host of springtime activities for families.

Elvis recorded dozens of songs in Nashville, and with so many live acts performing in the city, you might one day be able to say you saw the next big music star before they were famous.

Our travel tips: This part of Tennessee is known for its spring tornadoes. It's unlikely that you'll see one but watch out for local advisories while you're in town.

Even this far south you'll need to pack warm clothes as the evenings will be cool and the weather can still sometimes be unsettled, especially in early spring.

READ MORE - Road Trip from Chicago to Nashville

8. Knoxville, Pigeon Forge and Gatlinburg

8 hours from Chicago (550 miles)

Why you should visit: With the mild Tennessee spring weather in your favor, you can leave your winter gear behind and enjoy time in the great outdoors on this trip.

The Great Smoky Mountains will be bursting with color in the spring, from the lush new leaves on the trees to the carpet of wildflowers.

In between the winter snow and sometimes humid summer heat, spring break is the perfect time to lace up your hiking boots and explore. If you need to keep teens or older kids entertained too, the fun attractions at Gatlinburg and Dollywood will be just the ticket.

How to get there: Follow the route toward Cincinnati along I-65 and I-74, then take I-275 to bypass the city itself. You'll cross the Ohio River to enter Kentucky, then follow the interstate south towards Lexington. Continue along I-75 and you'll reach Knoxville around an hour after crossing the state border into Tennessee.

To reach Pigeon Forge and Gatlinburg, take I-40 out of Knoxville then turn south on TN-66. From Sevierville, turn onto Parkway which takes you to both towns. This part of the trip will add just over an hour to your drive time.

Our highlights: While you're in Knoxville, enjoy the city's nightlife under the beautiful dogwood blossoms, and check out April's Chalk Walk which sees colorful art on sidewalks across downtown.

When you're ready to head out of town, make for Great Smoky Mountains National Park where trails and lookouts are abundant, or follow the Newfound Gap Road for a spectacularly scenic drive through the mountains.

Just outside nearby Pigeon Forge, Dolly Parton's Dollywood amusement park is a firm favorite with visitors of all ages.

Thrill seekers should definitely head to Gatlinburg's Mountain Coaster, which races rollercoaster-style down the side of the mountain, or Smoky Mountain Ziplines, where you can get a whole new view of this beautiful part of the world.

Bonus: Great Smoky Mountains National Park receives more visitors than any other national park in the United States – more than 11 million a year.

Our travel tips: Because of its popularity the roads into the national park can feel a little crowded at busy times, especially during spring break. Parking lots fill up and you might hit traffic delays. Visit early in the day or in the evening if you want to avoid the crowds – you're also more likely to see wildlife at these times.

READ MORE - Road Trip from Chicago to the Great Smoky Mountains National Park

Longer trips (Over 8 hours each way)

9. Chattanooga, Tennessee

9 hours 20 mins from Chicago (610 miles)

Why you should visit: Built around the Tennessee River and overlooked by Lookout Mountain, Chattanooga is a city where you can easily combine active adventures with big-city entertainment.

For a longer spring break trip, stop in Nashville as well to enjoy even more of Tennessee's southern charm and hospitality.

Attractions in Chattanooga put on special events as part of the Spring Break Safari, making the city the perfect family spring break destination. There are child-focused art, science and nature activities on the itinerary, as well as the chance to explore caves, ride the Tennessee Valley Railroad or visit the Tennessee Aquarium.

How to get there: Follow I-65 all the way to Nashville, where you'll merge onto I-24 after a brief stretch on I-40 as you cross the city. I-24 then takes you all the way to Chattanooga, crossing the Tennessee River Bridge then dipping into Alabama for about a mile before you complete your journey in the far south of Tennessee.

Our highlights: Tennessee Aquarium is one of the stops on the Spring Break Safari and the world's biggest freshwater aquarium. Check out the penguins, otters, and alligators, as well as plenty of underwater favorites.

The Creative Discovery Museum is a firm favorite with younger children. It features fun, interactive science-based exhibitions that will keep them entertained for hours.

Another must-see in Chattanooga is Ruby Falls, a waterfall and cave system which sits under Lookout Mountain. The mountain itself towers above the city and if you're feeling energetic you can hike right up to the top for amazing views across Chattanooga and into Georgia.

A great activity for families or groups of friends, you can take a small pedal-powered boat out to enjoy food and drinks on the Tennessee River.

Bonus: Miniature golf was invented in Chattanooga nearly a century ago, so why not play a round during your stay in the city?

Our travel tips: Chattanooga is notorious for its traffic so avoid traveling in the morning or evening rush hours if possible

10. Hot Springs, Arkansas

10 hours 40 mins from Chicago (700 miles)

Why you should visit: As well as being a great spring break destination, you can turn the drive to Hot Springs, AR, into a fabulous longer road trip with stops in Springfield and St Louis along the way.

People have been coming to Hot Springs in search of the healing powers of its naturally heated spring water for nearly 200 years, so if you're in need of some relaxation and downtime during spring break, this is the place to come.

How to get there: Follow I-55 southeast through Illinois, passing Springfield before you cross the Mississippi River at St Louis, Missouri. After following the interstate south out of the city, turn onto US-67 which winds its way through the gently rolling hills of Missouri and into Arkansas.

At the town of Corning, turn right to continue along US-67/US-62, sticking with US-67 when the highways divide at Pocahontas. At Bald Knob the road merges with US-167 which takes you to the state capital Little Rock. Follow I-30 W out of the city, then turn onto US-70 for the final stretch of your drive to Hot Springs.

Our highlights: Top on most people's list in Hot Springs is a visit to a spa or geothermal spring. There are plenty to choose from, depending on whether your want a traditional bathing experience or a full day of pampering and relaxation.

Bathhouse Row is a National Historic Landmark District where 8 historic bathhouses still stand. Most no longer operate as bathhouses, but at Buckstaff Bathhouse you can still experience the same hot spring bathing experience that the first visitors here in 1912 would have enjoyed.

If some of your group are less interested in spa time than others, Adventureworks Hot Springs is a more active alternative. Ride zip lines and tackle a treetop rope course.

Crystal Ridge Distillery offers informative tastings and free tours where you can find out about the history of the moonshine that's traditionally been produced in this part of the country.

Bonus: The mineral-rich water from the hot springs is said to have healing qualities, and there are fountains across the city where you can take a drink or fill a bottle.

If you happen to be in Hot Springs over St Patrick's Day you can watch “the world's shortest St Patrick's Day Parade”. The event travels less than 100 feet but features several lively Irish-themed entertainment acts.

Our travel tips: Although there are a few natural open-air pools where the hot spring water travels down the mountain, bathing in them is not permitted. You can only soak in the geothermal water at Hot Springs at indoor bathhouses and spas.

11. Highway 61 Scenic Drive

11 hours from Chicago (710 miles)

Why you should visit: This trip takes you right up to Grand Portage on the Canadian border, which is the northernmost point on our list.

Spring is one of the best times of year to see the Northern Lights, which are visible along this route. It's an unforgettable spectacle which is definitely worth the long drive out from Chicago. With the weather still feeling wintery, book into a cozy cabin and enjoy quality time together over spring break.

How to get there: Follow I-90 W out of Chicago for around 100 miles until you reach Wisconsin, then continue for another 100 miles to merge with I-94. From here the road takes you through Eau Claire before arriving in the twin cities of St Paul and Minneapolis.

Exit the city via I-35 W for a couple of miles, before continuing on I-35 N in the direction of Duluth. The interstate ends here and you'll complete your road trip by following Highway 61 Scenic Drive, which follows the shore of Lake Superior all the way to Grand Portage at the Canadian border.

Our highlights: If there is still snow on the ground, that means you can take a scenic dog sledding trip to explore the wild landscapes of the scenic north shore.

The scenic drive along the North Shore is one of the main attractions of this road trip, so make sure you leave plenty of time to stop and enjoy the views along the way.

If the snow has melted, pack your hiking boots and set out to explore Tettegouche, Temperance River or Cascade River State Parks, which are all easily accessed from Scenic Route 61 along the lakeshore.

At Lutsen you can ski in colder months or, if spring has come early when you visit, head up to the peak via gondola to enjoy stunning views.

Bonus: You can't drive this route without stopping off in Grand Marais to visit World's Best Donuts, a local legend.

Our travel tips: As you might expect this far north, temperatures can be cold especially if your spring break falls early in March. Heavy snow is possible but not guaranteed during March and April, so stay flexible in your choice of activities if you take this trip.

This trip is probably best suited for travelers who can visit a little later in the season if they want to comfortably spend more time outdoors.

12. Atlanta, Georgia

11 hours from Chicago (730 miles)

Why you should visit: Atlanta is the southernmost destination on our list and is an amazing place to visit from Chicago during spring break .

You're almost certain to enjoy some much-needed spring sunshine here, without the large crowds that you'll find further south in Florida or on the coast.

How to get there: Head south through Nashville to Chattanooga on I-65 and I-24. As you enter Georgia just south of Chattanooga, I-24 merges with I-75 which takes you as far as the suburbs of Atlanta.

Depending on your final destination in Atlanta, you'll probably join up with I-85 to complete your journey in the city's downtown.

Our highlights: Families should head straight to Centennial Park, a huge outdoor space which covers the site of the 1996 Olympic Park. The Children's Museum of Atlanta is on the edge of the park too.

Zoo Atlanta is a must-see for visitors of all ages. It's one of the only places in the United States where you can see Giant Pandas, alongside many other endangered species.

There's also a wealth of sites dedicated to modern US history and the Civil Rights movement in Atlanta, including the National Center for Civil and Human Rights and Martin Luther King Junior National Historical Park.

If you're traveling with older spring breakers, Six Flags Over Georgia theme park is a great stop, and sports fans should definitely check out the College Football Hall of Fame.

Bonus: Coca-Cola originated in Atlanta in the 1880s, which is why you'll find the World of Coca-Cola in the city today.

Our travel tips: “Rush hour” in Atlanta lasts all day. Allow plenty of time for your journey if you're using your car to get around the city.

READ MORE - Road Trip from Chicago to Atlanta

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Stopping On The Way To AC from Chicago- Is Rivers a Good Opt - Pittsburgh Forum

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Stopping On The Way To AC from Chicago- Is Rivers a Good Opt

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I spent like 5 hours researching and using the Road trips Forum and it seems Pittsburg is my best stop. I don't want to just spend the night in a motel, I want some liveliness and entertainment, How is Rivers? Also, the hotel there is $200 for a Wednesday in July and there is a Residence Inn 6 blocks away for $130. Is it safe to walk? Do they charge to park in Pittsburg?

5 replies to this topic

Do you mean The Landing? If the only entertainment you want is casino based then I'm sure it's fine. I would check the Rivers Casino website to see what they offer. You might be disappointed on a July weekday night.

If your itinerary isn't casino based, I would pick the Residence Inn. There are plenty of restaurants and bars around there and it's poised close to the end of the Roberto Clemente bridge that will take you right over into downtown in a short walk.

I assume the Pirates aren't in town because I would expect the prices to be higher if they were. If they are in town, a Pirates game is great (fantastic ballpark and great food).

I highly expect a parking charge because land is at a premium but I am sure their websites say.

Safe to walk. I would personally walk along the river as it is more scenic.

Pittsburgh comes with an "h" at the end. :)

I hope the H is for HAPPY! : ) THANK YOU for the info. So we can walk from Residence Inn then? It seems like there are a ton of other hotels but Google Maps makes them seem on the other side of the expressway and I don't wanna drive after driving 7 hrs to get there. :)

Pull it up on google streetview- the highway is elevated there. :) There's a whole network of other roads below it as well as the riverfront walking trail. :)

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9 of the best road trips in the USA

US road trips remain ever-present on travel bucket lists the world over.

A true pillar of American folklore, their routes are steeped in history and paint a picture of the USA through the ages, from the Gold Rush to the Cold War.

In the modern day, these routes remain on the travel lists of Americans and tourists alike, all longing to head out on the open road to discover vibrant cities, desert plains, attractive coastlines and enormous mountain ranges.

In a nation that stretches over 3,000 miles from east to west, there are hundreds of routes to take you across the country, whether you want to follow the coast north from California or take a more remote route in Alaska.

Lesser known odysseys such as Route 101 or the Lincoln Highway quickly capture the imagination, while famed highways such as Route 66 dominate the dreams of would-be road trippers. To help you decide which route suits you, we’ve rounded up a list of the best trips across the country.

Chicago to Santa Monica

The USA’s most famous route has been immortalised via a combination of pop culture and nostalgia, despite no longer officially being classified as highway. Today, it remains the holy grail of US road trips.

Stretching for around 2,500 miles from Chicago to the beachfront of Santa Monica (just next to Los Angeles), it provides a taste of times gone by in the US, from kitsch gas stations to the Wild West-like emptiness of the Arizona and New Mexico desert.

This retro feeling is lost at either end of the ‘Mother Road’, especially when arriving into LA, but the marked contrast means that those travelling the route get to experience a quintessential slice of the States, including beautiful desert landscapes, the vintage Americana of Texas and two of the country’s foremost modern cities.

Read more on North America travel :

• The best time to visit Hawaii for a holiday – and how to avoid the rain
• Affordable New York: How to do the notoriously expensive city on a budget
• Canada travel guide: Everything you need to know before you go

The Great River Road

Minnesota to louisiana.

This winding route follows the equally serpentine Mississippi River for a total of over 2,300 miles through 10 states. It starts (or ends) in Louisiana, near the Gulf of Mexico, before coursing through Mississippi, Tennessee and ending up in Minnesota, near the Canadian border.

At its start, the route takes travellers across two of of the US’s most famous cities. It begins in New Orleans , the centre of Cajun and Creole culture, and shortly after passes through the capital of blues, soul and rock’n’roll: Memphis , Tennessee.

The rest of the route is renowned for showcasing an abundance of different natural landscapes that only a country as geographically diverse as the US could provide. The wetlands and bayous of Mississipi and Louisiana, including the Atchafalaya Basin, will be the most alien environment to many visitors, with a distinctly eerie, almost rainforest-like feel.

Following along the Mississippi, drivers will see flat plains, mountains and extensive woodland as the route crosses Arkansas, Kentucky, Iowa and Wisconsin, before finishing in Minnesota, “the Land of 10,000 Lakes”.

Lincoln Highway

New york to san francisco.

Though no longer in existence as a single route, a little research will help you take on a section – or all – of the 3,389-mile long transcontinental route that was originally conceived in the 1910s. The route started in New York City and extended all the way to Lincoln Park in San Francisco , taking in 14 states including Ohio, Illinois, Nebraska, Utah and Nevada. Today, much of the road is now Route 30, from Pennsylvania to Wyoming – avoid the freeways of the I-80 for a trip with less motorway and more character.

Today, driving the route is easier in some states than others due to different standards in maintaining the route’s heritage, but this highway will take you across roughly 700 cities and towns, from small-time American settlements to big-hitters like Chicago and Pittsburgh. Along the way, you can learn about the history of both the highway and early America, visit 19th-century mining towns and see some delightful nature, including parts of Lake Tahoe and the Utah desert.

Los Angeles to Olympia, Washington

Route 101 traces the US’s Pacific Coast from California up into Washington, offering some of the best coastal views in the country. Though it technically starts in Los Angeles , you can begin the route from near the Mexican border, close to San Diego, all the way up to the border with Canada.

The route is split into different sections of road in each state. The first section is California State Route 1, also known as the Pacific Coast Highway, which offers the first uninterrupted sightings of the turquoise waters of the Pacific. It carries on through San Francisco and across the Golden Gate Bridge, passing through the famous wine regions of the Napa Valley and Sonoma County, before picking up the Oregon 101.

Oregon’s coast is home to raw natural beauty, captured in the rugged, unspoilt coastline of areas like Cannon Beach and the valleys of the Columbia River. You continue along the river as you enter Washington, eventually circling the Olympic Peninsula and its mountains before finishing near Olympia’s State Capitol Building.

Richardson Highway

Valdez to fairbanks.

Shorter than many US trips, but certainly no less scenic, the Richardson Highway extends for “just” 364 miles between the cities of Valdez and Fairbank. Alaska offers some of the wildest natural landscapes in America, perhaps best compared to parts of Iceland when viewing its large glaciers, towering peaks, dramatic gorges, steep waterfalls and the Valdez glacier lake.

Various locations offer a host of activities such as white water rafting, hiking, fishing and even ice climbing (as well as views of the Trans-Alaskan Pipeline). Both Valdez and Fairbanks have a range of things to keep you busy too, from lake cruises and whale watching to skiing and Northern Lights spotting.

The Atlantic Coast

New york to florida keys.

Another road trip that gets to roughly 2,000 miles but can easily be split up into manageable sections, a trip down the Atlantic Coast is a worthy alternative to its Pacific counterpart. There is no defined route, with some beginning as far north as Bar Harbor in Maine, and others starting in NYC . If you do start in Maine, you’ll have the option to explore Boston, Rhode Island and the Hamptons, as well as the Big Apple.

Continuing south towards Miami , you can travel through Philadelphia, Washington D.C. and Atlantic City, the East’s answer to Las Vegas. If you stick to the coast rather than heading to the capital, you’ll go through Delaware before crossing a tiny section of the Atlantic over into Virginia Beach.

Carrying on through North and South Carolina, you’ll eventually reach Florida , first via Jacksonville and then Orlando if you fancy a small detour. From Miami you’re on the home stretch, but not before you cross arguably the highlight of the entire trip – the 113-mile Overseas Highway, which extends over the Atlantic between Miami and Key West, the final stop.

Road to Hana

Hana to kahului.

Hawaii may not be the first destination that comes to mind when thinking of road trips, with the Polynesian-influenced State home to a fascinating local culture, laid-back towns and coastline so picturesque it’s scarcely believable. But one small route stands out on Maui that’s as beautiful as those famed beaches – the Hana Highway, which links the towns of Hana and Kahului.

Running for just 64 miles, this coastal route usually takes around three hours to drive due to speed limitations and around 600 bends, winding through dense jungle and passing over imposing cliffs while tantalisingly close to the emerald waters of the Pacific.

Western Highlights

San francisco to las vegas.

This trip takes in some of the US’s most famous landmarks and cities, passing through California , Nevada and Arizona.

Begin in charming San Francisco, where innovation, forward-thinking and counterculture have combined to form a bohemian city backed by national landmarks like the Golden Gate Bridge. The first stop on your route will be Yosemite National Park, a land of surreal landscapes including giant sequoias, the 914-metre vertical rock face of El Capitan and North America’s tallest waterfall, Yosemite Falls.

Continue on a slightly longer drive southeast towards Los Angeles, where you’ll need a few days to take in the sights of Hollywood, Santa Monica, Malibu and the rest, before continuing on to the Grand Canyon via the I-10 or I-40 freeways.

Red rock hills and desert plains will quickly come into sight before you reach what is undeniably one of America’s most famous, and impressive, natural sites. Explore, hike and marvel at the vast sandstone cliffs and winding waterways, before spending the night in a rustic mountain cabin. This grandiose trip finishes in equally extravagant Las Vegas , the US’s undisputed home of hedonism.

Read our reviews of the best USA hotels

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Some of Chicago's Best Hot Dogs Are Hiding in Home Depot

Taste legit Chicago hot dogs, from a jumbo frank to a Maxwell Street Polish, at these four destination stands.

Redhot Ranch

At the little hot dog stand around the corner from my house, my order always starts with the same song and dance:

“One hot dog with everything on it, no fries.”

“One ‘dragged through the garden.’ Fries come with it. Free.”

“Don’t bother, I don’t want them.”

“Same price.”

“Charge me, that’s fine.”

“Okay, one dollar off.”

If, like me, you reside in Chicago, chances are you also have the good fortune to live around the corner from a little hot dog stand. You’ve learned to count on it for a quick lunch, a big snack, a late-night liquor sop and — during warm weather when picnic benches seem to sprout from the earth — a kind of perfect al fresco dinner. In this situation, you do want the fries and perhaps a “double dog” with two side-by-side links sharing a bun under all those garden draggings. 

In Chicago that means diced onions, pickle relish dyed a shade of science-fiction green, mustard, tomato slices, snappy little sport peppers, a pickle spear, and a sprinkling of celery salt. Ketchup is famously left off, but if you think about it, all these flavors kind of add up to ketchup. 

Vienna Beef — the city’s most ubiquitous brand — made its debut during the Columbian Exposition at the World’s Fair in 1893, but the iconic composition of the Chicago dog didn’t really start to coalesce until the Great Depression, when the Jewish, Italian, Greek, and Eastern European vendors around the once-bustling Maxwell Street fruit and vegetable market all contributed their preferences. The “Depression Dog,” a hearty belly filler sold from push carts for a nickel, sported mustard, onions, relish, and peppers, and it’s still a style favored by some today. The celery salt, pickle spear, and tomatoes joined the party later, after World War II when push carts gave way to the stands and small corner joints that still dot the city today. 

Since moving to Chicago I’ve learned that hot dog menus, simple though they may be, are calibrated for perfect satiety. Depending on your hunger level, you may want a frank, a jumbo frank, a double dog, or a pair of dogs, often listed on the menu as such, with a side of fries and a drink. You may want a more seasoned, juicier, snappier Polish but you might not care for all the toppings, so you order a Maxwell Street Polish that arrives simply with griddled onions and mustard. Sublime. 

A hot dog from any stand in Chicago will scratch the itch, but these are some to look out for:

Fatso's Last Stand

This is the best choice for char dogs — hot dogs cooked until they start to sweat and shrivel over a charcoal-fueled grill. Before going on the grill, the cooks notch the ends of the dogs with a crisscross, so the ends turn into crispy-crunchy nubbins. The first bite and the last bite are the best.  fatsoslaststand.com

Red Hot Ranch

The freshly cut fries and the burgers have their own fan clubs, but it’s the Depression Dogs here that afford the best taste of Chicago. These natural-skin sausages are extra snappy and juicy — so good that you need the sharper pitch of the toppings. Make sure to go for the sport peppers, even if you’re not a major spice fan. Their vinegary snap is the crowning touch.  redhotranchchicago.com

Fixin' Franks at Home Depot

Fixin' Franks

Yes, yes, yes: One of Chicago’s best hot dog chains can be found in 17 branches of Home Depot. If you’ve got 10 bucks, then let these weenie wizards prepare you a gourmet Wagyu beef “steak dog” to order. I’m perfectly happy with the regular version, which I find to be the most carefully constructed in town. There is a way to fit all the garnishes into the bun and not just pile them atop. It’s like solving a tangram, and these folks are experts. These dogs are best eaten in your car in the parking lot, where you can relish the perfect chunk of pickle in every bite and not worry about an errant tomato popping out.  instagram.com/fixinfranks

The Weiner's Circle

At Chicago’s most famous hot dog stand, foul-mouthed attendants have been known to spew invective at patrons waiting in line, and folks come here for the experience as much as for the hot dogs. I’ve been once and found they serve the standard Vienna Beef you get at countless hot dog stands throughout the city — never an unwelcome sight. Sadly, the woman who waited on me was perfectly nice. They may need to fire her. wienerscirclechicago.com

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