Diners' Choice: Cocktail Bar restaurants in Chicago

OpenTable

Updated May 05, 2026

Looking for restaurants with the best overall Cocktail Bar cuisine in Chicago? You’re in the right place. Each month OpenTable analyzes more than 400,000 new diner reviews. We sort the results by category to help you discover new favorites. It's a great partnership: you reserve, eat, and review. We listen...and deliver the results for all to benefit. Enjoy!

Kitty’s Cosmopolitan Club

4.8

4.8 (50)

$50 and over

Cocktail Bar

River North (Chicago)

About the restaurant

Tucked into the lower level of Crying Tiger in River North, Kitty's Cosmopolitan Club is a cocktail lounge from Beverage Director Kevin Beary and the award-winning team behind Gus' Sip & Dip. The opulent interior, designed in collaboration with David Collins Studio, sets the stage for an elevated experience where all cocktails are ordered, crafted, and served by expert bartenders.

The bar program is organized around three experiences: From the Cold Room, cocktails held in Chicago's first -16°F walk-in freezer for concentrated flavor and luscious texture; From the Bar, made-to-order classics elevated through modern technique and spirit selection; and From the Trolley, cocktails prepared tableside and served in fine crystal. Low- and no-alcohol options are also available, alongside coffee and tea.

The food menu is a collaboration between James Beard-nominated Chef Thai Dang and Chef Bob Broskey, featuring a raw bar and curated dim sum designed to complement the cocktail program.

Top review

TaylorGold

Dined 2 days ago

Amazing cocktails the 20th Century martini is INSANE! Eli is also the absolute best!

Three Dots and a Dash

4.8

4.8 (2195)

$31 to $50

Cocktail Bar

River North (Chicago)

About the restaurant

Three Dots and a Dash is an award-winning tiki bar and speakeasy in Chicago’s River North neighborhood, hidden behind a secret alley entrance. Inspired by the legendary tropical bars of Trader Vic and Don the Beachcomber, this underground cocktail destination transports guests to a vintage island escape with immersive décor, vibrant energy, and one of the best rum programs in Chicago. Guests can enjoy more than two dozen classic tiki cocktails, modern tropical drinks, rare rums, and shareable punches crafted by expert bartenders. Popular menu items include the signature Three Dots and a Dash cocktail, Jet Pilot, Painkiller, coconut shrimp, poke, bao buns, and island-inspired small plates perfect for sharing. Known as one of the best cocktail bars and nightlife destinations in Chicago, Three Dots and a Dash is ideal for date nights, birthdays, celebrations, happy hour, and late-night dining in River North. Reservations are highly recommended. 21+ only.

Top review

David

Dined 3 days ago

What an amazing experience. Drinks and food and are on point. Service was great.

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Thai Curry Crab Rangoon Dip

The Gatsby Speakeasy - Chicago

4.8

4.8 (22)

$31 to $50

Cocktail Bar

Lincoln Park

About the restaurant

The Gatsby is a prohibition era inspired speakeasy hidden directly above The Bourgeois Pig Cafe, in the center of the historic Lincoln Park neighborhood of Chicago. As fortune would have it, The Gatsby just so happens to be a block away from where the infamous bank robber and gangster John Dillinger was shot and killed by federal agents nearly 100 years ago.

You are invited to Gatsby’s party!
As you pass through the hidden entrance and authentic, period steel door, sounds of classic jazz, crooners and big band fill the velvety rooms, and antique portraits in the library study are illuminated by the gentle glow of flickering candles. In some far away room a grandfather clock chimes on the hour. As you ponder the century, our expert bartenders create bespoke prohibition-era cocktails crafted to match the literary vibe of this Great Gatsby inspired speakeasy.

Top review

MattGold

Dined 2 days ago

I love the full experience of hidden entrance, cozy atmosphere, great drinks and amazing staff.

Parachute HiFi

4.6

4.6 (93)

$30 and under

Cocktail Bar

Avondale

About the restaurant

Parachute HiFi is a Korean-American listening bar in Avondale from James Beard Award-winning chefs Beverly Kim and Johnny Clark. Come for bold bar food, creative drinks, and analog vibes powered by vintage speakers and curated vinyl.

We set aside some seats on a nightly basis for walk-ins on a first come first serve basis. If you’re planning to walk in on the weekend, we recommend arriving as close to opening as possible for the best chance at seating.

Top review

Kelcey

Dined 6 days ago

Delicious cocktails and amazing food! The hand roll by far was the best item on the menu!

The Alderman

4.9

4.9 (292)

$30 and under

Cocktail Bar

Pilsen

About the restaurant

Winner of the 2022 Jean Banchet Award for Best Bar, THE ALDERMAN is an intimate, 16-seat cocktail bar tucked away, behind closed doors, within Pilsen Yards. The cocktail list rotates some of its original cocktail features, while the twists on American classics are staples of the cocktail list.

With a plush velvet banquette and a 4-seat counter, it’s the perfect room for a night cap, a date, or a casual evening of one to several astonishingly good cocktails.

Top review

JorgeGold

Dined on Apr 29, 2026

Visit here frequently. Amazing ambiance to sit for cocktails and the actual cocktails are always on point.

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Experience

Industry Night - 35% Off Sundays

The Berkshire Room

4.8

4.8 (87)

$30 and under

Cocktail Bar

River North (Chicago)

About the restaurant

The Berkshire Room is an upscale lounge specializing in craft cocktails all created by a talented team. The atmosphere is retro classy and definitely worth a visit before or after dinner for cocktails with friends. There is ample seating either in the private side rooms, the booths in the lounge area or at the bar. The clientele that frequent the Berkshire Room rave about the dealers' choice, which allows guests to choose the spirit, flavor profile and glassware. The bartender then customizes a unique and customized cocktail.

Besides the tasty cocktails and the relaxing ambiance, the Berkshire also offers bar snacks and small dishes. The Berkshire room is located within River North's swanky ACME hotel.

Top review

Jason

Dined 7 days ago

My wife and I celebrated our 29th anniversary at The Berkshire Room, and it was an outstanding experience from start to finish. The ambiance was exceptional—great music, a wonderful vibe, and the perfect atmosphere for enjoying cocktails and conversation. It felt special without being pretentious, making it an ideal setting for a memorable evening. The mixologist was fantastic, creating custom cocktails tailored to our preferences. Each drink was expertly crafted and showcased both creativity and skill. Our server, Brandon, was attentive, personable, and added to the overall experience with excellent service. The manager was also warm and welcoming, helping make our anniversary celebration even more memorable. As for the food, the kettle chips were very good, but the real standout was the house-made onion dip. It was absolutely delicious and is something I would highly recommend ordering. Overall, this was a 10 out of 10 experience. Between the atmosphere, exceptional cocktails, outstanding service, and thoughtful hospitality, The Berkshire Room exceeded our expectations. My wife and I both agreed that we will definitely be back, and we would highly recommend it to anyone looking for one of the best cocktail experiences in Chicago.

After

4.7

4.7 (107)

$31 to $50

Cocktail Bar

West Loop

About the restaurant

High Craft, Low Key

After isn’t about white tablecloths or hushed voices. It’s about unmatched cocktails, loud laughter, good music, and an authentically laid-back spirit. It’s a come-as-you-are bar—because a great drink should make you feel something, not just impress you.

Opened by Michelin-starred Chef Curtis Duffy reinventing what a cocktail bar can be—seasonal, boundary-pushing drinks, grounded in technique, built for fun. After is where culinary precision meets barroom revelry.

After was named one of the United States' Top 15 bars by Food & Wine in Spring 2024. In 2023, Esquire put After on their Best Bars in America list. The New York Times featured After in their 2023 "36 Hours in Chicago."

Top review

baltimorestudent

Dined 7 days ago

Awesome, unique cocktails. Great ambiance. Would need to come back 3 more times to try everything we wanted to try!

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4.6

4.6 (137)

$31 to $50

Cocktail Bar

Hyde Park

About the restaurant

Cantina Rosa is a tropical Cocktail Bar focused on agave spirits from Virtue Hospitality. Stationed in the historic Hyde Park neighborhood of Chicago, Cantina Rosa offers craft cocktails and botanas (snacks) that appeal to sophisticated palates and newcomers alike. Its humble yet creative atmosphere seamlessly blends modern sensibilities with traditional influences.

Cantina Rosa draws inspiration from diverse regions across Mexico, enriched by the expertise of Virtue’s most experienced Mexican team members. The name "Rosa" holds deep personal significance, paying tribute to Rosetta, the grandmother of Erick Williams—who profoundly shaped his life.

Top review

KantehGold

Dined on May 15, 2026

Food was amazing and drinks were great! A bit expensive but I’d definitely come back!

Pandan

4.7

4.7 (76)

$30 and under

Cocktail Bar

Gold Coast / Streeterville

About the restaurant

Venture to the 18th floor of Viceroy Chicago to discover a seductive world where the sky is your ceiling and gorgeous city views unfold from every angle. Welcome to Pandan, a lush cocktail experience in the heart of the Gold Coast. Bask in what seems like infinite sunshine and starlight as you share baos and buns from the menu of Southeast Asian cuisine. The cocktail menu is as vast as the skyline itself and full of alluring flavors you haven't yet imagined. Sink into a lounge chair surrounded by botanicals and greenery. You'll quickly see: Pandan is a world unto itself -a haven for secluded celebrations, important connections, and whispered secrets. And the undercurrent of exclusivity is undeniable. Pandan is not just a scene. It's a satisfying new perspective. Come up. Elevate.

Top review

BecaGold

Dined on May 21, 2026

A beautiful interior with delicious cocktails, friendly servers, and tasty finger foods. I loved this place so much. The corn fritter, pork bbq, and fried chicken were all delicious. Love the plating and theme of this place. Especially love the small details.

Vol. 39

4.5

4.5 (111)

$31 to $50

Cocktail Bar

Downtown / Loop

About the restaurant

Tucked away in the The Kimpton Gray Hotel is our library of spirits. Vol. 39 is an upscale bar and cocktail lounge in Chicago’s Loop where friendly faces serve classic drinks like Old Fashioneds and Expresso Martinis. For a speakeasy feel with the comfort of your neighborhood bar, Vol. 39’s collection of wine, whiskey and other craft spirits is the ideal spot for an intimate date night, networking with colleagues, pub crawl or your first drink of the night.

Top review

LindsayGold

Dined on Apr 28, 2026

Great place to meet after work for a quick cocktail.

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