The Best Happy Hours in The Loop - Explore Downtown Chicago

May 20, 2025

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.



Woman drinking wine


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.



Cauliflower wings on tortillas


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.



Oysters on ice


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.


Martini


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.



Ping pong table


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.



Man playing darts


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.


Pizza


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.

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