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Best Cocktail Bars in Old Town

Discover the best restaurants in Old Town

Explore must-try spots, new openings, and hidden gems.

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54 restaurants available nearby

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A photo of Three Dots and a Dash restaurant
1. Three Dots and a Dash
4.8
Exceptional(1923)
Price: Expensive
• Cocktail Bar • River North (Chicago)
Booked 58 times today
With a secret alleyway entrance, Three Dots and a Dash is a speakeasy-style take on the traditional island bar—ready to transport you to the glamorous bygone eras of Trader Vic, Stephen Crane and Don the Beachcomber. Descend underground to discover a subterranean hideaway featuring a rum-soaked menu of more than two dozen classic, modern and original tropical cocktails and a selection of island fare. We are a 21+ venue.
A photo of The Violet Hour restaurant
2. The Violet Hour
4.7
Exceptional(199)
Price: Expensive
• Cocktail Bar • Bucktown / Wicker Park
Booked 27 times today
The Violet Hour, nestled in the heart of Wicker Park, Chicago, is a paragon of Dining Bar excellence, known for its "inventive and perfectly balanced" cocktails and impeccable service. The James Beard award-winning bar program dazzles with seasonally-driven libations, crafted under the expert guidance of trailblazing head mixologist Toby Maloney. Guests rave about the "amazing ambience" and "intimate experience" that make it a perfect spot for date nights or special occasions. With bartenders who are "true cocktail enthusiasts," The Violet Hour elevates the cocktail culture, earning it a reputation as one of the best craft cocktail bars in the city.
A photo of Fioretta restaurant
3. Fioretta
4.7
Exceptional(1023)
Price: Very Expensive
• Cocktail Bar • West Loop
Booked 72 times today
Fioretta in Chicago's vibrant West Loop district is a cocktail bar that truly stands out with its "incredible drinks crafted to perfection." The bar experience is enhanced by the lively atmosphere, often featuring live music that adds to the allure of an unforgettable night out. Patrons rave about the attentive and friendly bartenders who ensure each cocktail is a masterpiece, making you feel like a "VIP in an establishment like this." Fioretta's cocktails are seamlessly integrated into the overall dining experience, providing an exquisite balance of flavors that mirror the restaurant's opulent and nostalgic ambiance. Perfect for those seeking a sophisticated yet inviting setting, Fioretta is a must-visit destination for cocktail enthusiasts.
A photo of Pandan restaurant
4. Pandan
4.8
Exceptional(50)
Price: Moderate
• Cocktail Bar • Gold Coast / Streeterville
Booked 8 times today
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.
A photo of Lazy Bird restaurant
5. Lazy Bird
4.8
Exceptional(19)
Price: Expensive
• Cocktail Bar • West Loop
Booked 21 times today
Located in the cellar level of The Hoxton, Chicago hotel, Lazy Bird is a cocktail and music lounge in Chicago’s Fulton Market District. Known for its extensive signature cocktail program, luminary bartenders, live music, and low lighting, Lazy Bird hums with energy every evening, making it the perfect start, middle, or end to a night on the town.
A photo of Chateau Carbide restaurant
6. Chateau Carbide
4.2
Awesome(223)
Price: Expensive
• Cocktail Bar • River North (Chicago)
Booked 6 times today
At Château Carbide, the Tapas / Small Plates cuisine shines with an authentic, botanical twist that elevates the dining experience to new heights. Nestled on the rooftop of Pendry Chicago, diners can savor light bites crafted by expert Pendry Chefs, all while enjoying breathtaking city views. Guests rave about the "outstanding presentation" and "so many flavors" present in dishes like the cheese and meat hors d’oeuvre and uniquely seasoned fries. This al fresco destination captures the quintessential charm of the French countryside. With a vibrant ambiance and staff known for their "amazing service," Château Carbide is a must-visit for tapas enthusiasts.
A photo of The Berkshire Room restaurant
7. The Berkshire Room
4.4
Awesome(63)
Price: Moderate
• Cocktail Bar • River North (Chicago)
Booked 6 times today
The Berkshire Room, nestled within River North's chic ACME Hotel, offers an unparalleled Bar and Lounge experience with its exceptional craft cocktails. Guests are consistently dazzled by the "Dealers' Choice," where skilled bartenders create personalized concoctions tailored to each patron’s preferences. The retro classy atmosphere provides the perfect backdrop for a memorable night out, whether you're on a date or enjoying a nightcap with friends after a show. Visitors rave about the "best drinks in town" and the engaging mixologists who bring a touch of magic to every glass. For those seeking an authentic and innovative cocktail experience, The Berkshire Room is a must-visit gem.
A photo of Bordel restaurant
8. Bordel
4.3
Awesome(58)
Price: Moderate
• Cocktail Bar • Bucktown / Wicker Park
Booked 13 times today
Bordel, nestled in the vibrant Bucktown/Wicker Park area of Chicago, is an exceptional cocktail bar that has redefined nightlife with its impeccable blend of creative cocktails and captivating cabaret. Celebrating its 10th anniversary, Bordel has earned a reputation for crafting some of the most unique and delicious drinks in the city. With glowing reviews highlighting the cocktail experience as “phenomenal” and “fantastic,” diners are in for an unforgettable evening. Bordel's cocktails are not just drinks; they are an art form, complementing the seductive atmosphere and live performances that have made it a beloved cultural landmark. "Highly recommend" for an unmatched night out!
A photo of Ghost Donkey - River North restaurant
9. Ghost Donkey - River North
4.6
Exceptional(47)
Price: Moderate
• Cocktail Bar • River North (Chicago)
Booked 17 times today
A warm and inviting space with a healthy dose of city grit, Ghost Donkey is rich with vibrant colors and a carefree, fun-loving attitude that evokes notions of Mexican celebration. A true high-low nightlife destination with elevated mezcal and tequila-focused cocktails, classic bites with just enough twist to keep your palette guessing, and an extensive mezcal and tequila list. Ghost Donkey creates an experience-driven, unforgettable moment for every guest that joins the fiesta. Immerse yourself in the heart and soul of Mexican Hospitality while savoring sips of agave-based spirits. Kick back, relax, and enjoy the show, or break out a dance move underneath the sway of the swinging lights.
A photo of Celeste restaurant
10. Celeste
4.6
Exceptional(193)
Price: Moderate
• Cocktail Bar • River North (Chicago)
Booked 4 times today
Celeste, nestled in the vibrant River North neighborhood of Chicago, offers an exquisite take on modern American cuisine. This refined establishment blends upscale dining with a contemporary twist on classic American bars. Guests rave about the "fantastic cocktails" and commend the "wonderful food" that perfectly complements the lively atmosphere. Diners are particularly impressed by the steak tacos, which are touted as "the best" by many. Celeste's unique four-level design, inspired by architectural and artistic nuances, creates an immersive experience that elevates the dining scene. With its exceptional service and stylish ambiance, Celeste stands out as a must-visit for American cuisine enthusiasts.
‘About the restaurant’ descriptions have been generated using an artificial intelligence model comprised of OpenTable proprietary data that has not been independently verified by OpenTable. The content is presented as-is, for informational purposes only.

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