The 6 Best Spots to Enjoy a Cocktail in Chicago

Chicago may be referred to as the Second City but when it comes to cocktails, it’s second to none. Sip to your heart’s content at these top Chicago bars.


1. Howells and Hood

Michigan Avenue
Tucked into the famed Neo-Gothic Tribune Tower, Howells and Hood pays homage to the architects, John Howells and Raymond Hood, and features an extensive craft beer and cocktail selection. This is a top spot for locals looking to enjoy after work drinks or a boozy weekend brunch.
Order: Heliostat Zwickel Lager from Chicago’s own Metropolitan Brewing

luxde-189794-Wine Cocktail Collection Textures

2. Lost Lake

Avondale/Logan Square
This 1930s throwback has everything a vintage tiki bar deserves: bamboo décor, handsome bartenders in aloha shirts, banana leaf-print wallpaper and, of course, tropical drinks. It’s the brainchild of Paul McGee — voted the city’s best bartender year after year — so no wonder. Enjoy the good island vibes and the even better cocktails.
Order: The Beachcomber’s Rule No. 2, a shareable $50 rum masterpiece

mer1866rf-191902-SPG Cravings - Summer Cocktail

3. Estereo

Logan Square
Pick your Latin poison at this new, bright bar; you’ve got pisco, tequila, mezcal, rum and cachaça to choose from. With strong pours, a Caribbean soundtrack and top-notch bartenders (what more can you ask for?), you’re sure to spend more time than anticipated at Estereo.
Order: The smoky mezcal cocktail, with agua de jamaica and pina bitters

mer1866ls-191900-SPG Cravings - Cocktail preparation

4. Galway Bay

East Lakeview
Chicago has neighborhood bars for days, and Galway Bay is sure to please any dive bar enthusiast. The basement pub feel is enhanced by free popcorn, old school Nintendo video games, darts, pool and vintage Blockbuster favorites on repeat. You’ll find a good mix of professionals, locals, neighbors and college students.
Order: A $2 PBR, because really you’re here for Duck Hunt

shels-174405-Friends toasting with beer

5. The Violet Hour

Wicker Park
The Violet Hour is one of Chicago’s best-kept secrets and reminiscent of its speakeasy days with an inconspicuous entrance marked only by an ever-changing large mural and lamp. In a time where technology reigns, high-backed chairs, velvet curtains and dim lighting enhance the intimate feel.
Order: Rangoon Fizz, a crisp Violet Hour classic with gin, ginger and mint

mer1919rf-167258-Sparkling Cocktail Mint Lemon

6. Moneygun

West Loop
While we normally wouldn’t recommend waiting in line to drink, sometimes it’s worth it. Moneygun’s certainly inconspicuous from the outside, but the inside is just right. You’ll likely find old school hip hop, an understated atmosphere and food just as good as the drinks.
Order: Anything on a Monday, when drink specials are aplenty

wes1064de-83131-Cocktails at Compass Rose Lobby Lounge

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