underground bar tour chicago

Explore Chicago’s hidden underground

Last updated on October 30, 2018 by Choose Chicago

There’s so much to see on the streets of Chicago. But most people never see what’s lurking just below the surface.

The city hides layers of tunnels, passages, businesses and more, all beneath our feet. Explore the hidden layers of our city with this deep-dive into Chicago’s underground world.

The Pedway System

Savvy Chicagoans and visitors can make their way around the Loop without ever emerging above ground. That’s thanks to the Pedway, one of the most-visited parts of subterranean Chicago. It’s a series of passageways that connects 50 office buildings, shopping centers, train stations, and parking structures — a particularly handy route during Chicago’s winters.

The Pedway, open from 7 a.m. to 5 p.m. on weekdays, links over 40 blocks and 5 miles beneath the heart of the city. It’s also home to variety of vendors, from coffee shops to food stalls, so you can grab a bite as you explore beneath the city streets.

Subterranean streets

One of the most famous aspects of Chicago’s underground: the subterranean streets. While names like Lower Wacker may ring a bell, their real claim to fame is their supporting role in The Dark Knight . The Batman film was shot in Chicago, using the lower levels of streets throughout downtown for dramatic car chase scenes.

However, the street’s most common use is a little less glamorous. They allow freight transport and trash disposal vehicles easy access to the Loop’s many large buildings, making the street level less congested and more pleasant for drivers and pedestrians alike.

Abandoned freight tunnels

Chicago is known for its elevated train lines, but lesser known is the network of century-old freight tunnels that criss-cross beneath the city.

Built by the Chicago Tunnel Company, the vast system was inhabited by little electric trains that could be used for an array of services, such as carting away ashes, delivering mail, and connecting phone lines. They even offered “tunnel air” as a form of natural air conditioning for theaters and hotels.

The Tunnel Company’s clients included dozens of iconic buildings, including the Board of Trade, City Hall, Merchandise Mart, Chicago Tribune, Civic Opera House, Field Museum, and more.

The freight lines stopped operating around 1959 and were largely forgotten — until catastrophe struck.

On April 13, 1992, construction workers driving wood pilings into the Chicago River accidentally punctured a tunnel roof, causing thousands of gallons of water to gush into the system. Massive flooding ensued in buildings across the city, eventually causing more than $2 billion in damage. Today, the tunnels are sealed off and all-but impossible to enter.

Water Tower and Pumping Station

In the mid-1800’s, Chicago officials were seeking a better way to provide clean water for a booming population. The solution: a two-mile tunnel beneath Lake Michigan that could transport fresh water into the city, an innovative feat of engineering for the time.

The tunnel was completed in 1866, along with the ornate Water Tower and Pumping Station. Both structures managed to survive the Great Fire of 1871 and became icons of the city’s resilience. The structures are now home to an art gallery and Tony-award winning theatre company, standing tall atop the now-defunct tunnel that still lies deep beneath the city.

The Deep Tunnel project

What’s the lowest you can go within Chicago’s city limits? That distinction lies with the Calumet TARP Pumping Station deep beneath the Riverdale neighborhood. The subterranean room lies 365 feet below the surface, making it the lowest inhabitable point in the city.

This pumping station is part of a massive underground system known as the Tunnel And Reservoir Plan (TARP). More commonly known as the Deep Tunnel project, it was built to minimize flood risk and improve water quality in the area’s lakes and rivers.

Today, the series of tunnels spans more than 110 miles and has become one of the largest and longest civil engineering projects in American history. If you’re interested in seeing it for yourself, the Calumet station and several other points of the system are open to the public for tours .

Underground bars

While some aspects of Chicago’s underground are difficult to access, anyone can stop for a drink in one of these below-ground bars.

The Underground This sultry nightclub and bar is tucked away beneath the bustling streets of the River North Neighborhood. With an ever-changing line-up of DJs and themed events, The Underground is best known for its late-night dance floor.

Three Dots and a Dash If you spot tiki torches in the alleyway, you’re in the right place. And if you come on a weekend, the line is probably a dead giveaway, too. The downstairs tiki bar has an award-winning cocktail menu, featuring fresh fruits and flavors that will transport you straight to the islands.

Booze Box It’s easy to miss Booze Box — but it’s worth the effort to find. Nestled below the popular Sushi Dokku in the West Loop neighborhood, Booze Box is hidden behind an unmarked door in an alleyway behind the restaurant. Just keep an eye out for a neon red arrow, and you’ll be rewarded with creative Japanese cocktails and bar snacks.

Subterranean This bi-level music venue hosts a variety of live musical acts, from reggae nights to burlesque shows to DJ acts. Head downstairs to get up close and personal with the performers, or hang back and watch from the surrounding balcony.

The Drifter One of the oldest bars in the city is hiding an authentic 1920’s-era speakeasy just beneath their floorboards. Head inside The Green Door Tavern, find the secret door, then go down. That’s where you’ll find The Drifter , a cozy cocktail haven where the nightly menu is written out on tarot cards.

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The best Chicago speakeasy bars to discover

Sneak into these covert speakeasy bars for classic cocktails and old-school entertainment.

Photograph: Courtesy of Adalina

The secret drinking days of the Prohibition era are long behind us, but Chicago is still home to a thriving network of underground bars perfect for grabbing a drink away from the crowds—and best of all, you (probably) don’t have to worry about the feds raiding these contemporary speakeasies. Venture beneath Chicago's most romantic restaurants , behind closed doors and through alleyways to find clandestine bars offering intimate, dimly-lit settings and cocktail menus dreamed up by some of the city’s best mixologists, plus live music and other tempting attractions. Ready to drink on the down low? Here are some of the best speakeasies in Chicago, no secret password required.

RECOMMENDED: Uncover more of the best bars in Chicago

Been there, done that? Think again, my friend.

Chicago's top speakeasies

1.  the drifter.

• River North
• price 2 of 4

The Green Door Tavern used to be patronized by Chicago gangsters, taking its name from the discreet entrance on the side of the building. If you walk down the metal staircase leading to the bathroom, you’ll notice a knickknack-covered door to a room that housed a speakeasy in the ’20s. Today it's the entrance to the Drifter, a craft cocktail bar with live entertainment and funky decor. Guests are invited to order from a stack of custom-made tarot cards that act as a constantly rotating menu. Sit back, sip your drink and take in old-school entertainers like contortionists and belly dancers.

2.  Milk Room

Many of the watering holes on this list are intimate, but the Chicago Athletic Association's Milk Room is a true micro-bar, with just eight seats available to guests. Though the cocktails here cost a pretty penny (upwards of $40–$50 a pop), they're crafted with rare vintage spirits like 1970s Cointreau, 1960s rum and 1950s Fernet Branca. After you're done with the boozy history lesson, get some fresh air and take in the views upstairs at rooftop lounge Cindy's.

3.  The Violet Hour

• Cocktail bars
• Wicker Park
• price 3 of 4

You won't see any signs for Violet Hour, only a long line of people waiting outside of an ever-changing, abstractly painted building. Once inside, the first thing you'll spot is a list of "house rules," which limits cell phone use (take your calls outside the bar) and outline contraband (domestic beer, White Claw, top shelf vodka and late ‘90s club cocktails). Seating areas are designed to be cozy and private so that guests don't have to shout over ambient noise. Plus, the crew behind the bar comprises some of the city’s most talented bartenders, who mix classics and seasonal concoctions.

4.  Osito’s Tap

• South Lawndale

Moreno's Liquors has stocked Little Village with shelves upon shelves of tough-to-find tequila and mezcal for more than 40 years. Head to the back of the store, though, and you'll find a neon Chihuahua sign guiding you to Osito's Tap, a tucked-away space that once housed a Bohemian bar (true to the neighborhood's old Czech heritage) and an underground bookie joint. Nowadays, the bar serves a drink and food menu inspired by Little Village's Latinx community, with an especially strong showing of agave cocktails and michelada options, plus a hefty selection of draft beer. Cozy up in high-backed leather booths indoors or venture outside to the not-so-secret patio for a drink in the sunshine.

5.  The Office

You won't soon forget an evening at the Office, a tiny speakeasy hidden below lauded cocktail bar the Aviary in the West Loop. Your best bet is to reserve one of four bar stools for the Office Hour, a 60-minute guided experience that includes two bespoke cocktails and snack pairings (ideal for pre- or post-dinner tipples). Can’t decide on a drink? Opt for the Dealer’s Choice and let the expert bartenders craft a concoction tailored to your preferences.

6.  Dorothy Downstairs

• Ukrainian Village

Tucked away beneath the former space of Split-Rail sits this LGBTQ+ cocktail den that’s decked out in vintage furniture and ‘70s-style decor. You’ll find good vibes all around and a rotating selection of intriguing libations, such as the Cup of Cheer made with baking spice bitters, persimmon and bubbles. There are also regular events and programming like Fruit Salad, Dorothy’s monthly queer open mic night.

7.  Golden Teardrops

• Logan Square

Located in the basement of Tex-Mex restaurant Lonesome Rose, this dark and intimate establishment welcomes guests in for a cozy nightcap after a round of tacos and truck stop nachos. Belly up to the mahogany bar, which is illuminated by a neon sign that reads “Weddings & Funerals,” order a drink—mostly spirit-forward riffs on classic cocktails—and then try to grab one of the few available seats. It’s an inviting hideout that beckons you to stay a while.

8.  Dorian’s

Venture through a petite record shop storefront in Wicker Park to discover Dorian’s, a cocktail bar built around music (or behind music, if you want to get literal). The elegant space boasts an Italian-made hi-fi sound system for vinyl DJ nights and a stage for live music—where the bar has hosted performances from luminaries like Jeff Parker and Makaya McCraven—plus a narrow menu of house cocktails perfect for sipping while you listen. 

9.  Room 13

Perhaps one of Chicago's most exclusive speakeasies, Room 13 is accessible to members and guests of the Old Chicago Inn, where the bar is housed. Make friends with someone who's in the know and obey the strict dress code (cocktail or business casual) before sidling up to the bar for classic cocktails that are crafted from recipes that date back to the Jazz Age. Hotel guests can opt to experience Room 13's cocktail flight, a tasting of four tipples along with historical commentary from your bartender.

10.  The Library at Gilt Bar

Ever feel like going somewhere where no one knows your name? That's the vibe at the Library, which is located below Gilt Bar in River North. The dark, library-themed bar slings classic cocktails and hearty bites from upstairs. Reservations for each weekend are released on Wednesdays, though you can also try your hand a snagging one of the bar’s limited walk-in slots. 

11.  The Gatsby

• Lincoln Park
• price 1 of 4

Hidden away on the second floor of Lincoln Park’s Bourgeois Pig, this intimate cocktail den is filled with bookshelves, 19th and 20th century oil paintings, chandeliers and a fireplace. To gain access, you’ll first have to solve a riddle to find the secret entrance and then recite a password. Once inside, indulge in bespoke concoctions and light bites while being serenaded by jazz, electro swing and crooner tunes. If you’re looking for a romantic date night destination, this is it.

12.  Nightshade

• Portage Park

On Friday and Saturday nights, visitors to Moonflower in Portage Park can saunter down to the bar’s subterranean space to discover Nightshade, a speakeasy-style grotto serving a sophisticated selection of cocktails. Choose from creative sippers like the Late Bloomer (purple rice-washed Ford’s Gin, coconut, cinnamon, lime) and Sneaking Suspicion (chamomile, cinnamon, lemon, clarified yogurt, rum, vodka and “fancy ice”) or go all-out and order from a menu of fanciful cocktails made with fluffy mounds of shaved ice.

13.  The Alderman

• Lower West Side

Try googling “The Alderman Chicago” and you’ll be lost in a sea of city websites—and maybe that’s intentional. The 16-seat speakeasy-style bar, tucked away in an tiny, candlelit side room of Pilsen Yards, offers an intimate hideaway for sipping through beverage director Lance Bowman’s sophisticated cocktail menu, plus a long list of spirit pours. Overwhemed by the thick menu and dim lighting? Staff are eager to help indecisive visitors sort through the not-insignificant cocktail list. A word to the wise: Don’t show up without a reservation, especially on the weekends.

14.  Rose Lounge

• Rush & Division

Take the golden elevator at Adalina down to Rose Lounge, where you can grab a seat at the horseshoe-shaped central bar or the plush velvet couches around the perimeter. Lit by candles and chandeliers and decorated by floral art to go with the name, the bar offers an extensive selection of Champagne and spirits plus complex cocktails. You’ll also find premium spins on classics like the Walnut Old Fashioned made with walnut liqueur, hazelnut and chocolate-walnut bitters. Reservations are required for most of the night to ensure it doesn’t get too crowded for intimate conversations.

15.  Nine Bar

• Armour Square

Chinatown’s first cocktail bar doubles as one of the city’s coolest speakeasies. Located in the former dining room of longtime neighborhood restaurant Moon Palace (now offering takeout as Moon Palace Express), Nine Bar is a moody, Blade Runner -esque space—think neon lighting, sleek furniture and touches of industrial decor—with a killer menu of cocktails and bar bites that owners Lily Wang and Joe Briglio have dubbed “Asian-ish.” We’re especially fond of Paradise Lost, a buttery-smooth concoction made with cachaçha (a fermented sugarcane spirit from Brazil), Rhine Hall mango brandy, ube, pineapple and Thai coconut milk, then clarified to crystal-clear perfection.

16.  The Bamboo Room

The folks behind Three Dots and a Dash surprised us with a bar-within-a-bar concept called the Bamboo Room, where guests can sip cocktails mixed with rare and high-end rums. The 22-seat area offers a menu curated by beverage director Kevin Beary; expect simple, well-balanced beverages that are more refined than their Three Dots counterparts. In the mood for something bespoke? Order a Dealer's Choice and your bartender will create a custom, off-menu rum cocktail based on your imbibing preferences. 

17.  Lulu’s Chambre Privée

Named for Lulu White, one the most successful French Quarter madams, the basement space below New Orleans-inspired restaurant Storyville creates a boudoir vibe with couches, gilded mirrors and tasseled lamps. Settle in and order a classic cocktail like a negroni or sidecar or a signature sipper such as Be My Druidess, mezcal blended with papaya, lime and activated charcoal. Burlesque dancers, magic shows and live music add to the sexy fun.

18.  BORDEL

• East Village

Up leopard-print stairs and behind a hidden door, Wicker Park’s Bordel is a speakeasy that seeks to revive the intrigue of Paris’s belle époque. Order one of the classics, like the Spanish coffee, and settle into the plush red seats as you take in the bar’s nightly entertainment. The large format porróns are the perfect accompaniment to watching the scantily-clad fire dancers and burlesque performers that frequent the stage at this lively bar late into the evening.

19.  Brando's Speakeasy

True to form, Brando’s Speakeasy is not what it seems. It’s a lounge, yet conversation flows more like a neighborhood haunt. The cocktail menu features interesting drinks, like the root beer old fashioned. The decor and vintage posters throw it back to yesteryear, but the karaoke and late-night dance music add modern flair.

20.  Blind Barber

• Things to do

Hidden behind a fully functioning barber shop, this raucous late-night spot is dark and outfitted with wood paneling, a checkered floor and divey lounge furniture. It's where the beard trims end and the imbibing begins. Grab a seat at the bar and order a cocktail and a grilled cheese. A rotating cast of DJs keeps the dance floor packed into the wee hours of the morning.

21.  Punch House

Concealed in the depths of Thalia Hall, this dark, ’70s-themed bar is decorated with a fish tank, wood paneling and a huge fish on the wall. Think of it as an upgraded, boozy version of your grandparents' basement. Like its name suggests, punch is the main draw here—and you can order most cocktails by the glass, carafe or bowl. Whether you go big or small, you'll experience the genius and precision happening behind the bar at Punch House. If you're looking for a good place to start, order Space Juice for Jered, a blend of tequila, grapefruit, lime, black pepper, sparkling wine and sage.

22.  Pigtail

The menu at this underground speakeasy—located beneath celebrity chef  José Andrés' flagship restaurant, Jaleo— centers around one ingredient: Jamón ibérico, the dry-cured Spanish ham that's prized for its smooth, nutty taste. You'll find the jamón nestled into dishes like a "taco" with caviar, quail egg and ibérico de bellota as well as on the drink menu, which includes savory beverages like the Consomé Cocktail, a combination of a house-made pork consomé with palo cortado and amontillado sherries topped with egg foam. 

23.  Soif

Styled after the intimate bars of Paris, Soif—pronounced "swaf," like the French word for thirsty—is a romantic hideaway for wine lovers, with a rotating wine list of around 50 to 60 bottles served in a subterranean space below Testaccio in Logan Square. Sidle up to one of the bar's plush velvet banquettes to peruse a menu that highlights  small batch and limited production wines (like grower Champagne, which is produced in small volumes by the same person who grew the grapes) as well as natural and orange wines.

24.  Booze Box

From the outside, you wouldn’t guess that Sushi Dokku in West Loop has something to hide, but insiders know about the subterranean bar with izakaya-style small plates that waits below. Once you know what you’re looking for, you’ll feel like a covert spy on a mission for boozy cocktails and quality hip-hop music. Head to the alley just behind Sushi Dokku (not sketchy at all) and look for the red light above a door—you've successfully found Booze Box. Psst! If you can’t find it, the staff will be happy to escort you downstairs.

25.  The Cauldron

Have you ever wanted to be a witch or wizard? Well, make your dreams come true at this magic-themed concept in Wicker Park. Housed inside an old bank, The Cauldron is a full-service restaurant and bar offering immersive potion-making experiences—cocktail classes–plus British comfort fare and a creative selection of concoctions. The highlight of the space, though, is the Vault: a speakeasy located inside the bank’s safety deposit vault. There, you can exchange wizard currency for a wand-poured drink from the bank teller.

26.  The Bassment

Head below The Hampton Social in River North for this speakeasy and music lounge with a swankier vibe than most typical nightclubs. Expect to hear everything from live jazz and acoustic sessions to DJ sets, plus there are comfy leather couches and chairs for when you want to take a break. If you need a refreshment, try The Bathtub—a cutesy vodka-based cocktail served in a tiny bathtub.

27.  Fifth Province Pub

• Irving Park

In addition to its library and museum, both packed with historical acquisitions, the Irish American Heritage Center boasts a cozy limited-hours pub with free live music (Irish, of course) and Guinness-absorbing classics like fish and chips. If everyone were as beer-minded as the Irish, cultural institutions would be flooded with the thirsty and eager to learn.

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The 5 can’t miss hidden Chicago Speakeasies

Step into the captivating world of Chicago speakeasies, where the city’s rich history intersects with its vibrant nightlife scene. In the heart of Chicago, speakeasies thrived during the Prohibition era, offering an escape from the restrictions of the time. 

Concealed behind discreet entrances and hidden within the city’s unassuming buildings, speakeasies in Chicago became havens of secret revelry. While we didn’t get a chance to visit them all (damn livers!), we were able to indulge in some amazing craft cocktails at the ones we did visit. 

Short on Time? Here are the key takeaways: 

• Most Chicago Speakeasies don’t open until 5 PM (even on the weekends)
• Almost all of the speakeasies on this list have food
• In our opinion, don’t miss The Booze Box or The Drifter

Boozing Abroad contains affiliate links throughout the site. If you choose to purchase items through these links, we will earn a small commission at NO extra cost to you. Read the full disclosure policy here **

Map of the 5 Speakeasies in Chicago

HOW TO USE THIS MAP: To view the layers and see the names of the places on this map, click the tab in the top left corner. You can select the check marks to show or hide certain layers. If you select the icons on the map, you will get more information about the point of interest.

HOW TO SAVE THIS MAP: If you select the star icon next to the map name, you can save this map to your Google Maps account. To view it, open Google Maps in desktop or on your phone, select the menu button, go to “Your Places,” scroll to the right to Maps, and you will see this map.

The 5 Can’t Miss Chicago Speakeasies

1. the drifter.

• Wednesday – Friday: 5PM – 2AM
• Saturday: 5PM – 3AM
• Sunday – Tuesday: Closed
• Food Available: Snacks only
• Reservations Available: No, first-come, first-serve

Nestled beneath the unassuming exterior of The Green Door Tavern, The Drifter offers a speakeasy experience like no other. This hidden bar invites patrons on a nostalgic journey back to the Prohibition era.

The Green Door Tavern was built in the late 1800s but has been open and operating since 1921 making it one of the oldest bars in Chicago. Many of the tavern’s original fixtures are still in place to this day and it offers decorative memorabilia from the past century throughout the bar. 

Descend the stairs as if you’re heading to the restroom, and find yourself transported back to the bygone era behind a hidden door that resembles a bookshelf. Inside, the 45-seat bar oozes with 1920s charm, complete with live entertainment and more vintage decor. 

Their extensive cocktails list of over 100 options changes daily with each night’s offerings depending on which tarot cards are selected for that day. We hesitate to name the cocktails we had because they very well may not be available when you visit, but regardless, they are going to be expertly crafted cocktails that are delicious – all while relishing in the intimate setting and vibrant energy of the crowd.

The Drifter promises a unique experience and live entertainment every night. As mentioned above, the rotating selection of tarot cards dictates the evening’s libations which ensures an element of surprise and excitement for visitors. And as for that live entertainment, when we visited, we were delightfully surprised with a more-risque-than-expected burlesque “show” (it was only a couple of minutes long).

With its commitment to preserving history and providing patrons with an unforgettable evening of revelry, The Drifter captures the essence of Chicago’s rich and storied past and is a must-visit speakeasy in Chicago (in our humble opinion). 

Note : since there are live performances every hour, there is a $7 charge per person added to your bill. However, we thought it was worth it for the performance we saw. 

2. The Booze Box

• Tuesday & Wednesday: 5PM – 10PM
• Thursday: 5PM – 11PM
• Friday & Saturday: 5PM – 12AM
• Sunday & Monday: Closed
• Food Available: Full menu, Japanese food
• Reservations Available: Yes, for parties of 2-8

We found the Booze Box by accident on our first trip to Chicago back in 2019. We were next door for a drink and saw this neon sign in the alley. After 5 years, the memory of this Chicago speakeasy stayed with us and we were anxious to try to it again. 

In the back alley of the sushiDokku restaurant, look for a bright red neon sign. Enter through the door (don’t be alarmed that the door is between a bunch of dumpsters), down the staircase and you’ll find yourself in a secret Japanese oasis offering an incredible selection of Sake and Japanese Whiskey.

The Booze Box doesn’t have a website. If you try to google the location, the restaurant will pop up. You just gotta trust us, this place is worth the visit. 

While the upstairs sushiDOKKU offers a fine-dining experience, venturing downstairs to Booze Box sets the stage for an unforgettable evening. Dim, warm lighting and low ceilings create an intimate atmosphere and while we didn’t eat here, the food looked scrumptious and we found ourselves growing hungrier with every passing dish. We arrived around 7 on a Friday and it was packed. There are limited seating options so we highly recommend making a reservation if you want to eat here as well. 

In our opinion, the cocktails we ordered here blew away every other cocktail that we tried on this list. Sam got the Muraski crafted with Dry White Rum, Ube Syrup, Egg White and Lime, while Chris opted for the Eastern Medicine made with Glenfiddich 12 year scotch, Islay Scotch, Ginger Wasabi and Lemon. 

Between the drinks, the back alley entrance and the incredible selection of Japanese libations, we think Booze Box might be one of the most underrated speakeasies in Chicago. 

3. Blind Barber

• Tuesday – Saturday: 5PM – Close
• Food Available: Yes, small bar bites
• Reservations Available: Yes, through their website

Step into the whimsical world of Blind Barber , a hidden bar in Chicago’s bustling West Loop neighborhood. The Blind Barber is a novel fusion of barbershop and speakeasy. 

By day, it operates as a traditional barbershop, but by night, it transforms into a vibrant speakeasy with a cozy, dark ambiance and plush leather seating. 

At first glance, Blind Barber appears to be just another barber shop, complete with the iconic spinning multi-color spiral tube outside. We’ll admit, we were completely fooled when we walked by it as people were legit getting their hair cut when we peered through the window! 

Once inside the barber shop, ask for the speakeasy. You’ll be escorted through an unmarked door inside the barber shop which opens to this sophisticated bar. 

We visited during happy hour and enjoyed two of their HH cocktails: Southside Richie and Paradise Ginza. Both were simple, yet delicious and hit the spot for both of us. 

Despite its unassuming facade, Blind Barber harbors a not-so-secret speakeasy that’s become a hotspot for party-goers in the city. Whether you’re popping in for a haircut during the day or craving some late-night snacks and cocktails, this Chicago speakeasy has you covered.

4. Three Dots and a Dash

• Sunday – Wednesday: 4PM – 12AM
• Thursday & Friday: 4PM – 1AM
• Saturday: 2 PM – 1 AM
• Food Available: Yes, mostly shareables
• Reservations Available: Yes, via OpenTable

Tucked away in Chicago’s River North neighborhood, Three Dots and a Dash is a speakeasy-style paradise, offering a unique blend of island charm and tiki cocktails. 

To enter this oasis, walk down the alley directly next to Firecakes on West Hubbard. You’ll see the tiki art painted on the building; then look for a door among the artwork.  As you descend into the tropical hideaway, you’ll find yourself surrounded by unique Polynesian artifacts, a bamboo and straw roofed bar and colorful Caribbean decor. 

Their menu boasts an impressive selection of over two dozen classic and original tropical drinks, meticulously crafted using the freshest ingredients served in statuesque ceramic mugs. 

Sam ordered the Royal Hawaiian which was served in a massive bowl complete with a smoking tiki statue, flower, umbrella and a large chunk of pineapple. This delicious concoction was made of Gin, Almond Orgeat, Lemon and Pineapple. Chris ordered their signature drink, Three Dots and a Dash, made of Aged Martinique Rhum Agricole, Aged Guyana Rum, Lime, Orange, Falernum, Allspice. 

While we didn’t eat on this visit, the table next to us ordered the Pu Pu Platter that is served with a tiny grill so you can skewer your food over an open small flame right at your table. 

If you are looking to escape the bustling streets into an immerse tropical atmosphere, Three Dots and a Dash should be on the top of your Chicago speakeasies list! 

• Wednesday: 6PM – 1AM
• Thursday – Saturday: 6PM – 2AM
• Food Available: No

Curl up into Fox Bar , an intimate, cozy hideaway concealed within the mezzanine level of Soho House Chicago. 

Once inside the Soho House, look for a large fox painting hanging along the staircase on your right. Walk up the stairs and look for the saloon doors with the words “Bar Service Only”. Swing through the doors to enter. 

Despite its smaller size, Fox Bar offers a seasonal craft cocktail menu that perfectly compliments each season. We happened to be visiting in the winter and their menu offered a variety of drinks to warm you back up (think Hot Toddy). 

Chris ordered the La Estrella Del Norte, a Mezcal-based drink with lemon cacao, mole bitters and orange oil while Sam was feeling something a bit more classic and went with a vodka gimlet. 

The bar has very limited seating so get there early or be prepared to wait. We were very lucky to snag 2 seats at their bar, but this place was packed when we left. 

Boozy Tours in Chicago

If the idea of trying to find these speakeasies in Chicago is intimating OR you are looking for more boozy fun, check out these tours on Viator:

• Private Speakeasy Pub Crawl in Chicago with Local Historian : If history and speakeasies are your passion, this tour was made for you. Complete with a driver, this is a solid option for a large group looking to bar hop. Note: It’s a bit pricey.
• Haunted Chicago Booze and Boos Ghost Walking Tour : If you want to put the boo in boozy, this much more affordable option combines history, haunts and libations. While the speakeasies aren’t on this guide, you’ll get to learn the secrets of Chicago’s past.

Watch the Adventure on Youtube

Tired of reading? We don’t blame you. Watch the whole thing here:

In wrapping up our exploration of Chicago speakeasies, it’s evident that these stealthy establishments offer more than just cocktails—they provide a captivating journey into the city’s storied past. From hidden alleyway entrances to glamorous underground lounges, each speakeasy reveals a unique facet of Chicago’s Prohibition-era heritage. 

Whether you’re a local seeking a new haunt or a traveler craving an authentic nightlife experience, delving into the world of speakeasies in Chicago promises an unforgettable adventure through the city’s hidden gems. 

Ready to visit to Chicago? Read hotel reviews, check current prices and then  book your room here !

But where do we personally recommend?  Kinzie Hotel  is super walkable to the speakeasies, restaurants and other bars  PLUS  it won’t break your bank.

Don’t forget to pick up a  Chicago guidebook  for your other boozy adventures.

Love this guide? Have questions? Get in touch with us on  Facebook  |  Twitter  |  Instagram  |  Pinterest

Samantha and Chris fell in love with traveling together back in 2015. They met, married, and lived together in Richmond, VA for 7 years before becoming full-time travelers in 2020.

Along the way, they've traveled to over 40 U.S. states and 20 countries while drinking local beers, wines, and spirits during their journeys.

Join them as they share travel resources, stories, and guides based on their personal experiences drinking locally when traveling globally.

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