Best Happy Hour in Chicago: Cheap Drinks and Great Deals

You asked. The Haute Seeker delivered! We are (re)introducing an ongoing list of Haute Happy Hours in Chicago.

This list of local happy hour spots seeks to highlight new and diverse restaurants while spotlighting popular Chicago neighborhoods. Whether you’re WFH(working from home) or working on the roam, save yourself a few dollars and enjoy these Chicago happy hours.

Note: Changing menus, changing COVID-19 regulations in the city of Chicago. As you visit these happy hour spots keep in mind that both are well, subject to changes. Be sure to contact the restaurant or visit their website for additional details before heading out to the happy hour of your choosing.


WICKER PARK – Estelle’s, 2013 W North Ave. 

Enjoy happy hour every day at Estelle’s. All drinks are half-price. Estelle’s also offering other weekly specials like 1/2 burgers on Mondays and $10 Patty Melt with Fries and $7 High Life + Four Roses shot combo on Sundays.

Happy Hour specials are available Monday – Friday from 4:00 PM – 6:00 PM.

RIVER NORTH – STK CHICAGO, 9 W KINZIE ST. 

Ditch work early, head to STK, and take the edge off with Half Off Drinks and $2-$8 Bite and ½ Off Specialty Cocktails and $10 Justin Cabernet and Whispering Angel Rosé.

Happy Hour specials are available Monday – Friday 3:00 PM – 5:00 PM.

RIVER NORTH – BRANDO’S SPEAKEASY, 343 S. DEARBORN AVE.

Enjoy a happy hour for only $5 at Brando’s Speakeasy. The South Loop karaoke lounge and cocktail bar offers daily drink specials. Choose from a selective list of cocktails including a 1792 Old Fashion, Paloma, or your choice of White Claw Flavors or Revolution Beers.

Happy Hour specials are available daily from 5:00 PM – 7:00 PM.

RIVER NORTH – BERNIE’S CHICAGO, 660 N ORLEANS ST.

Bernie’s is a chef-driven restaurant in River North that offers a selection of a seasonal and progressive array of food and drink items. Stop by for a happy hour and sample this menu at a discounted price. Sample small bites from the menu like Tenderloin Sliders for $14 and Handcut Fries with sea salt, rosemary, and garlic for $7. Drink specials include $8 wine and bubbles, $6 drafts, and house cocktails for $10.

Happy Hour specials are available weekdays from 4:30 PM – 6:30 PM.

WEST LOOP – CABRA CHICAGO,  200 N GREEN ST.

Happy Hour takes on a new meaning at Cabra Cevicheria at the Hoxton Hotel. ‘Golden Hour’ at the Peruvian-inspired restaurant by Chef Stephanie Izard, welcomes all patrons to watch the sunset and sip on specialty cocktails weekly at the hotel’s rooftop bar.

Happy Hour specials are available Tuesday – Friday from 4:00 PM – 6:00 PM


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