Chicago is a city with a long-history and spirited spirits. Whether it was gangsters smuggling rum across Lake Michigan during Prohibition, cool cats enjoying some cocktails during the birth of jazz, or a modern craft brewery, this city has always loved a good sip.
See also: Where To Get The Best Martinis In Chicago
Toast to the good life and have the best of any era at one of these top-notch bars, cocktail lounges, pubs and brewhouses. No matter what style or flavor you prefer, there’s a good night to be had on the town—or a daytime drink to be had.
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1664 N Ada Street / Website
Atmosphere: Warm and intimate with small tables and a long bar, and a full menu of New American and Mediterranean plates.
Best For: Dinner and drinks.
The Drink To Order: The cocktail menu is always changing and updating, but we like the El Diablo with blanco tequila, fresh pressed ginger, blackberry and lime.
Pro Tip: Do not miss out on the whipped burrata.
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112 W Grand Ave. / Website
Atmosphere: Hip and stylish, with leather-seat booths and small tables, seving international-inspired craft cocktails and light bites. Definitely a place for the in-crowd.
Best For: After-dinner drinks with a cool date.
The Drink To Order: The Globe Trotting is the hallmark signature, with Voyage 24 Jefferson's Ocean aged bourbon, jerez Spanish sherry, madagascar bourbon vanilla, brazilian banana, and Trinidad and Tobago bitters
Pro Tip: Come Tuesday through Saturday to enjoy music by a live DJ.
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1670 W Division Street / Website
Atmosphere: Chic, vintage vibes with indoor and outdoor seating, a pool table, snacks and more.
Best For: Meeting up with friends.
The Drink To Order: Something off the extensive craft beer menu.
416 N Des Plaines Street
Atmosphere: A cozy, intimate hidden speakeasy that’s worth the search.
Best For: Dancing and drinks, thanks to the live DJ.
The Drink To Order: The Punch Bowl, if you’re ready to get serious.
Pro Tip: This place is only open Thursday, Friday and Saturday. Follow the red lights.
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Chicago Athletic Association Hotel, 12 S Michigan Ave. / Website
Atmosphere: Light, bright and airy, with a full menu of seasonal favorites.
Best For: Day drinks with friends, or a romantic evening.
The Drink To Order: The Peach Perfect, with pau maui vodka, aperitivo, amaro nonino, peach cordial, lemon and trinity bitters.
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The Drake Hotel, 140 E Walton Place / Website
Atmosphere: All the glamor of the 1930s with historic architecture and cutting-edge taste.
Best For: Dinner and drinks with friends, or a classy date.
The Drink To Order: The Drake namesake cocktail with Drage Few rye whiskey, sweet vermouth, bitters and simple syrup.
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1944 W Division Street / Website
Atmosphere: Casual neighborhood bar with an extensive beer list and a jukebox.
Best For: Catching up with old pals for some good, old fun.
The Drink To Order: Something seasonal served ice cold from the draft counter.
4802 N Broadway / Website
Atmosphere: A cool yet unpretentious spot to catch live jazz and nightly jam sessions.
Best For: Sipping, grooving and enjoying the show.
The Drink To Order: The sidecar is a real classic.
Pro Tip: The bar is cash only, so come prepared. The nights to dance are Tuesday and Thursday.
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1354 W Wabansia Ave. / Website
Atmosphere: A casual hangout with regular events from live music to bingo, vintage markets and more.
Best For: Getting together with friends after work.
The Drink To Order: Like the sign says, a cold beer.
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5148 N Clark Street / Website
Atmosphere: An adults-only Belgian brewhouse with a host of craft beers from around the world.
Best For: Drinking with friends and watching the game.
The Drink To Order: With more than 400 bottles of brew to choose from, you’re best off picking something you can’t get anywhere else.
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630 W Lake Street / Website
Atmosphere: Japanese luxury in a stylish setting, where the omakase is as good as the sips.
Best For: Dinner and drinks with a cultured date.
The Drink To Order: One of Kumiko's curated cocktail flights.
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The Chicago Athletic Association, 12 S Michigan Ave. / Website
Atmosphere: Medieval chandeliers and modern cocktails for the discerning palate.
Best For: Cozying up to a date or spending time with your hippest pals.
The Drink To Order: One of the rare whiskeys served straight up, or a vintage spirit mixed to your taste.
Pro Tip: Reservations are required, so plan ahead.
219 W North Ave.
Atmosphere: A no-fuss, old-school pub that Roger Ebert once called “the best bar in the world, that I know about.”
Best For: Gathering with friends and family.
The Drink To Order: The craft beer selection is extensive and impressive.
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2125 W Division Street / Website
Atmosphere: Rich and warm, with wooden interior and sea-fairing charm.
Best For: Drinking with your best mates.
The Drink To Order: The menu is seasonal, but we recommend the Bay Watch house cocktail with lunazul blanco tequila, lime, soursop, bay leaf, vanilla and Thai chili
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2323 N Milwaukee Ave. / Website
Atmosphere: A hip yet casual brew-pub with fresh sips and tasty bites.
Best For: Hanging out with friends and enjoying a summer day.
The Drink To Order: A tasting flight of the latest brews.
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3201 W Armitage Ave. / Website
Atmosphere: A gin-focused cocktail bar with cozy vibes and welcoming smiles.
Best For: Intimate conversation and friendly evenings.
The Drink To Order: The Hot Polloi with Scofflar old tom gin, Jamaican rum, lucky falernum, campari and pineapple.
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12 W Elm Street / Website
Atmosphere: Tropical and cozy, with vintage, Cuban-inspired decor and a unique menu.
Best For: Sophisticated sips with friends, colleagues and dates.
The Drink To Order: La Floridita signature cocktail with white rum, maraschino, lime and grapefruit.
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435 N Clark Street / Website
Atmosphere: Hip speakeasy vibes with tropical tiki drinks that may or may not be served on fire.
Best For: A fun Friday night with the crew.
The Drink To Order: The signature namesake Three Dots and a Dash with aged martinique rhum agricole, aged guyana rum, lime, orange, falernum and allspice.
955 W Fulton Market / Website
Atmosphere: High-end and modern with complex cocktail creations and show-stopping presentation.
Best For: Making a big impression, whether that’s with a date or friends from out of town.
The Drink To Order: The Rocks cocktail served inside a ball of ice, with absinthe, tart cherry, vermouth and rye.
Pro Tip: Try the Aviary three-course cocktail menu and let the chef take over.
955 W Fulton Market / Website
Atmosphere: Tucked just beneath The Aviary, this dim-lit hideaway serves sophisticated drinks to discerning drinkers.
Best For: After-dinner drinks and cozy conversation.
The Drink To Order: The Office serves classic cocktails, or you can tell the bartender your tastes and let them create something to your liking.
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2202 W Lawrence Ave. / Website
Atmosphere: Hip, vintage decor alongside seriously-fun cocktails, served with specialty ice and lots of flair.
Best For: A fun time with friends.
The Drink To Order: Try the Sherry Baby with sherry, spiced pears, blueberry, lemon juice and mole bitters.
Pro Tip: Get adventurous and order the Dealer’s Choice, which allows you to pick the spirit, flavor profile and glassware, then the bartender does the rest.
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2018 W North Ave. / Website
Atmosphere: A sky-high sanctuary with floor-to-ceiling windows in a sophisticated setting.
Best For: Impressing out of towners, dates and colleagues.
The Drink To Order: Toast to sunset with the Golden Hour, featuring rum, bourbon, citrus, honey, angostura and salt.
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1520 N Damen Ave. / Website
Atmosphere: Classic glamor, velvet curtains and delightful cocktails served with a hint of modern edge.
Best For: The cool playlist creates fun for friends and dates, but isn’t too loud for intimate conversation.
The Drink To Order: It's called Easy To Love for a reason, with corazon reposado, ruby port, lemon, house pomegranate and hibiscus, lemon and cherry.
Pro Tip: The entrance is hidden in the large mural facade.
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The Kimpton Gray Hotel, 39 S La Salle St #200 / Website
Atmosphere: Swanky sips served in a luxurious atmosphere. Silver-cart champagne and caviar service is available.
Best For: Special occasions and important dates.
The Drink To Order: The Vol. 39 Vintage Old Fashioned offers a rare sip indeed, with a blend of aged French brandies, banana-nut demerara, chocolate bitters and legal precedent.
Photography by: Louis Hansel / Unsplash
