When the workday winds down in Downtown Chicago, the hunt for the perfect happy hour spot begins. Whether you’re commuting from the office or just looking to enjoy a drink in the city, The Loop offers plenty of options. Chicago’s central business district is famous for its iconic architecture, world-class theaters, public art installations, and bustling energy. To help you navigate your next happy hour outing, we’ve rounded up some of the best spots in Downtown Chicago - each with its own charm and reason to visit.

The Gage

24 S Michigan Ave, Chicago, IL 60603

WHEN: Monday through Thursday: 2pm-5pm

Situated across from Millennium Park, The Gage combines a gastropub atmosphere with a sophisticated twist. During happy hour, indulge in $10 cocktails, discounted wines and beer, and inventive $10 bites crafted with locally sourced ingredients.



Roanoke Restaurant

135 W Madison St, Chicago, IL 60602

WHEN: Monday through Friday: 4pm-6pm

Located in The Loop's historic Monadnock Building, Roanoke Restaurant exudes old-world charm. Their happy hour features $10 artisanal cocktails and $8-$10 small plates crafted with a contemporary twist, like flatbread and buffalo cauliflower.



Mercat a la Planxa

Located in The Blackstone Hotel, 638 S Michigan Ave, Chicago, IL 60605

WHEN: Every night: 4pm-5:30pm

Bringing a taste of Catalonia to Chicago, Mercat a la Planxa offers a vibrant setting with Spanish-inspired tapas and cocktails. Their happy hour menu includes discounted drinks and $8 bites, including spanish tortillas, pintxo solomillo, and oysters.



Untitled Supper Club

111 W Kinzie St, Chicago, IL 60654

WHEN: Tuesday through Friday: 5pm-6pm



Discover a speakeasy-inspired ambiance at Untitled Supper Club , where happy hour transports you to the Prohibition era with discounted martinis, $1.50 oysters, and live jazz performances. Located on Kinzie Street, it's a hidden gem in Downtown Chicago.

AceBounce

230 N Clark St, Chicago, IL 60601

WHEN: Weekdays: Open-7pm

A lively spot for post-work fun, AceBounce is a ping-pong bar with a high-energy vibe and a full menu of drinks and bites. During happy hour, enjoy $5 beers and mixed drinks, along with shareable plates starting at just $8. It’s perfect for team outings or letting off steam after a long day.



Flight Club

111 W Wacker Dr, Chicago, IL 60601

WHEN: Monday through Friday: 3pm-6pm

This social darts bar combines games, chic décor, and strong happy hour offerings. At Flight Club , enjoy $8 liquor and discounted bites while you challenge your friends to a few rounds of darts. It’s got a stylish, energetic feel that’s great for groups.



ROOF on theWit

201 N State St 27th Floor, Chicago, IL 60601

WHEN: Monday through Friday: 4pm-6pm



Enjoy a rooftop lounge that brings panoramic views and stylish ambiance to your after-hours plans. ROOF’s happy hour features $12 wine and mixed drinks and gourmet pizza priced at $10, all set to a backdrop of skyline views and curated music.

Whether you're craving competitive games, international flavors, or a rooftop atmosphere, The Loop and Downtown Chicago offer a diverse array of venues for happy hour enthusiasts. Check out a full list of our communities to find out how far they are from these local gems. 



Note: Happy hour offerings are subject to change. It's recommended to check with each venue for the most current information.