7 Best Cocktail Bars in Chicago – Hotspot Guide

Our search for the best cocktail bars in Chicago began one cool evening, with the city’s famous skyline serving as our backdrop. Known for its rich history and active nightlife, Chicago seemed the perfect place to explore the world of cocktails. We were on a mission, filled with excitement and curiosity, to discover what makes each bar in this city stand out.

Navigating through Chicago’s streets, we encountered a mix of old and new. From the quiet, historical neighborhoods to the more active downtown areas, every corner of the city had its own version of a cocktail story to tell. Our goal was simple: to visit and experience the seven best cocktail bars in Chicago, renowned for their creativity and exceptional drinks.

As we moved from one bar to the next, we realized that these places were more than just spots to grab a drink. Each bar had its own character, reflecting a piece of Chicago’s diverse culture and history. This journey wasn’t just about tasting great cocktails; it was about understanding the heart of the city, one drink at a time.

The Aviary

Location: 955 W Fulton Market, Chicago, IL 60607
Link: theaviary.com

The Aviary is more than just one of the best cocktail bars in Chicago; it’s a haven for mixology innovation. Located in the trendy West Loop neighborhood, it features a sleek, modern interior with an open kitchen allowing guests to observe the art of cocktail making.

The Aviary is celebrated for its inventive cocktails, notably “In the Rocks,” a bourbon drink encased in an ice sphere. This spot is a testament to Chicago’s avant-garde cocktail culture.

The Berkshire Room

Location: 15 E Ohio St, Chicago, IL 60611
Link: theberkshireroom.com

In the heart of Chicago’s River North neighborhood, lies a hidden gem known as “The Berkshire Room.” This cocktail bar, nestled inside the Acme Hotel, is a fusion of old-world charm and contemporary elegance.

The interior of The Berkshire Room exudes a classic, sophisticated feel with its dark wood paneling, plush leather seating, and vintage accents. It’s a place where the past and present meet, creating an ambiance that’s both inviting and stylish.

The Berkshire Room is renowned for its innovative approach to cocktails. It specializes in barrel-aged creations, offering a unique twist on classic drinks. Their signature cocktail, the “Dealer’s Choice,” is a testament to their creativity. Patrons simply choose a spirit, a flavor profile, and a glass type, and the skilled bartenders craft a personalized drink on the spot.

It’s this combination of a prime location, a refined interior, and a focus on bespoke cocktails that sets The Berkshire Room apart as one of the best cocktail bars in Chicago.

The Violet Hour

Location: 1520 N Damen Ave, Chicago, IL 60622
Link: theviolethour.com

Hidden behind an unmarked, mural-covered facade in Wicker Park, The Violet Hour stands out among the best cocktail bars in Chicago.

Its high-backed chairs, velvet curtains, and soft lighting create an intimate ambiance. Renowned for its meticulously crafted cocktails and seasonal menu, The Violet Hour offers a modern twist on classic drinks.

Three Dots and a Dash

Location: 435 N Clark St, Chicago, IL 60654
Link: instagram.com/threedotsandadash

Three Dots and a Dash in River North is a unique addition to the best cocktail bars in Chicago.

Its lively, island-themed setting, complete with Polynesian decor, makes it a fun escape. Known for its creative tiki drinks, it’s a vibrant spot for those looking for a lively cocktail experience.

Cindy’s Rooftop

Location: 12 S Michigan Ave, Chicago, IL 60603
Link: cindysrooftop.com

Cindy’s Rooftop, located atop the Chicago Athletic Association, combines stunning views with exquisite cocktails, making it one of the best cocktail bars in Chicago. Overlooking Millennium Park, its airy, open space and communal tables are perfect for enjoying a sunset drink in the Loop.

Billy Sunday

Location: 3143 W Logan Blvd, Chicago, IL 60647
Link: billy-sunday.com

In the heart of Logan Square, Billy Sunday is a standout among the best cocktail bars in Chicago for its vintage charm. The cozy, dark-wood interior provides a warm, inviting atmosphere. Known for its extensive collection of rare spirits and classic cocktails, it’s ideal for a more laid-back evening.

Punch House

Location: 1227 W 18th St, Chicago, IL 60608
Link: punchhousechicago.com

Punch House in Pilsen offers a unique approach to the best cocktail bars in Chicago, specializing in craft punch bowls perfect for groups. Its quirky, retro space with an underwater theme adds to the charm, making it a great spot for a fun night out.