Where to Quench Your Thirst in the Windy City

Where to Quench Your Thirst in the Windy City

By Lola Mendez

After exploring all that Chicago has to offer on a Fat Tire Tour and checking out the city’s unique cultural activities, and the newest restaurants, it’s time to check out the Windy City’s best drinking holes. It’s bottoms up in Chicago. Beer lovers, wine snobs, caffeine addicts, and tiki tipplers will all find a place to unwind with their beverage of choice at these Chicago bars. From neighborhood taverns to high-end cocktail lounges, you can quench your thirst at these cocktail lounges, dive bars, speakeasies, and beer halls.


Location: 630 W Lake St

Drink your way around the globe in Chicago by hitting up locales inspired by foreign destinations. For a beverage or two with a Japanese twist head to Kumiko. This formal cocktail bar in the West Loop is the mastermind of the team behind the two Michelin-starred Oriole. Since opening last December, patrons have enjoyed mixologist Julia Momose’s curated selection of upscale spirits and expertly crafted beverages with Japanese ingredients.

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Location: 2450 N Milwaukee Ave

Looking for a mid-day drink? Head to the all-day Estereo bar, the laid-back spot in Logan Square known for its selection of unaged Latin spirits, including mezcal, sotol, pisco, rum, and tequila. Order a flight to try a few spirits or a farm-to-glass drink off the innovative cocktail menu featuring spirits blended with farm-fresh seasonal fruits. As the drinks rely on the local produce offerings, the menu tends to rotate weekly. Even better, this bar is dog-friendly!

Queen Mary Tavern

Location: 2125 W Division St #4150

Queen Mary Tavern first started serving beverages in Wicker Park back in the ’70s when Division Street was lined with seven taverns. A forty-year hiatus following a family tragedy shuttered the local institution, but it was revitalized back to its original glory in 2015. The tavern is a bit of a time capsule and honors the age-old tradition of British maritime pubs and offers many vintage bottles.

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Pink Squirrel

Location: 2414 N Milwaukee Ave

If you like your booze in the form of a milkshake then head to the Pink Squirrel in Logan Square. The eclectic drink menu features alcoholic milkshakes served in vintage glasses at the two-lane bowling alley for serious throwback vibes. Try the Grasshopper (it’s bug-free, we promise).

Three Dots and a Dash

Location: 435 N Clark St

One of the most beloved spots in town is Three Dots and a Dash in River North. Folks love the speakeasy-style tiki bar named after a popular tiki drink from the ’40s. Once you’ve thrown back a few rum drinks, you’ll know exactly why the bar has been named one of The World’s 50 Best Bars by Drinks International. Try Camp Anawanna made with Overproof Jamaican Ru, lime, pineapple, maple, and cinnamon served in a Fijian Mermaid tiki mug with a toasted marshmallow on top.

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Utopian Tailgate

Location: 1608 N Wells St

If you’re traveling in Chicago with a group of friends and want to go somewhere spacious, make your way to the 10,000 square foot year-round rooftop bar Utopian Tailgate. The venue located on top of The Second City building opened this summer and is a fun place to party and an ideal spot to watch sporting events. Order a tableside keg and grab your buds for a round of giant board games like Connect Four and Jenga, or get in touch with your inner child in bouncy houses or on mechanical bull rides. The winner of the game has to buy a round of paletas La Michoacana out of Blue Island serving boozy Mexican fruit ice pops!


Location: 1059 W Wrightwood Ave

If you’ve never poured your own beer at a bar, don’t miss the chance to have this experience at Tapster. The self-serve bar in Lincoln Park allows guests to pour their own craft beers, wine, cider or kombucha. Many of the offerings come from local breweries.

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Bad Hunter

Location: 802 W Randolph St

Vegans will love Bad Hunter in the West Loop on Chicago’s trendy Restaurant Row. Bad Hunter’s bar program has low or no-ABV cocktails and an extensive wine list of natural, organic, and biodynamic wines. Bad Hunter’s cocktails are sustainable with a focus on local seasonal produce and kitchen scraps to enhance alcoholic beverages.

Pipeworks Brewing

Location: 3912 W McLean Ave

Pipeworks Brewing near Logan Square was a community-funded Kickstarter project. The brewery operation has a heavy-metal flair with its artistic labels and obscure beer names. Pipeworks was the dream of two friends who started by borrowing equipment to try their hand at making beer—which was a major success. They’ve released one beer a week since 2012 on an exclusive limited-edition basis. The Emerald Grouper IPA with honey is a fan fave.

The Violet Hour

Location: 1520 N Damen Ave

The Violet Hour is a Wicker Park institution that sparked the craft cocktail renaissance in Chicago over a decade ago. With a speakeasy vibe and pre-prohibition concoctions to match,

this den is a great spot for a date night. In the fall try the By The Sea cocktail, which is the autumn sister to a margarita but made with mezcal and curation of spices such as clove and cinnamon.

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Location: 60 E Ontario St

If you like your drinks with a side of adrenaline, make your way to the Safehouse in River North. The spy-themed bar features scenes from Get Smart, James Bond, Austin Powers and Mission Impossible movies—and you get to be one of the undercover spies in an interactive espionage task. Libations are also themed such as the Vesper Lynd Martini and Agent Chi whiskey cocktail.

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