10 Best Happy Hour Hot Spots in Chicago
Happy hours can be the perfect way to end your work week.
And, in Chicago, there’s no shortage of excellent options for happy hours when you’re ready to unwind, enjoy some drinks, and have fun with friends and coworkers.
In fact, no matter what you drink or who you happy hour with, you can get some killer deals in some of the hottest spots in town.
Here are our 10 favorite spots to happy hour in Chicago.
1. The Franklin Room
Nestled in River North, The Franklin Room is a charming tavern with a swanky speakeasy vibe.
Offering classic cocktails, beer, and an array of whiskey, The Franklin Room also features independent distillers and limited-edition rare releases to create “a uniquely Chicagoan experience.”
Beyond being a dream come true for any whiskey lover, The Franklin Room is the place to be if you’re looking for happy hour deals that offer fresh oysters on the cheap.
Happy Hours: Daily 4:30 p.m. to 6:30 p.m.
Deals: $1 whiskey drinks, $1 oysters, $15 Wine Carafes
2. The Walk In
Looking for a cozy, funky watering hole where the staff is “friendly as f*ck”? Head over to Logan Square for a retro Rock N’ Roll happy hour at The Walk In.
Sitting in a century-old building, The Walk In blends a 1960’s vintage-style bar with a contemporary-industrial lounge, creating a fun vibe that’s all its own.
With inspired cocktails and full beer and wine menus, The Walk In can serve up pretty much anything you’re in the mood for while giving you a rad, funky place to happy hour.
It’s also worth noting that The Walk In has rolling garage doors that open up to a patio — and it has a walk-in cooler door that opens up directly into Red Star Liquor next door (hence, the bar’s name).
Happy Hours: Monday to Friday, 5 p.m. to 8 p.m.
Deals: $6 specialty cocktails (Green Light, Go-Go Gimlet, Old Fashioned, Rose Cheeks & Lucky’s Explanation)
3. Brando’s Speakeasy
Another cool happy hour spot where you can kick back, drink up, and get down is Brando’s Speakeasy. When you walk into this vintage tavern and lounge, you’ll feel like you’ve stepped back into the 1920s.
You’ll also be able to enjoy exquisitely crafted cocktails, tasty small bites, and on-demand karaoke —meaning you and your buddies can belt out your favorite tunes at happy hour or well after.
Whenever you want to take a break from karaoke, move into The East Room. With the motto “Cocktails & Conversation,” The East Room is a stunningly elegant lounge that can be the perfect place to relax, chat, and unwind after a long day at work.
Happy Hours: Monday to Sunday, 5:00 p.m. to 7:00 p.m.
Deals: $5 Absolut Moscow Mule, 1792 Old Fashioned, Paloma, Revolution Beer, White Claw Seltzer
4. The Violet Hour
Calling all cocktail enthusiasts! If you love a great artisanal cocktail, make plans to happy hour at The Violet Hour.
Located in Wicker Park, The Violet Hour has won a James Beard Award for its bar program, which features “a seasonally rotating cocktail list” and “an extensive selection of approachable and sought-after spirits.”
From its exclusive, thoughtfully crafted cocktails to its chic décor and single exterior entryway, The Violet Hour oozes of everything cool in the prohibition era while putting a fresh, creative, ritzy spin on it.
Happy (“Golden”) Hours: Wednesday to Sunday, 5:00 p.m. to 7:00 p.m.
Deals: $13 Daiquiri, Gin Gimlet, Tom Collins, Margarita, Sidecar, Manhattan, Negroni, Vieux Carre
5. Broken Shaker
For one of the hippest happy hour scenes in town, you’ve got to check out River North’s Broken Shaker.
With fancy cocktails, infusions, elixirs, and syrups, the Broken Shaker serves impeccable drinks that can electrify any happy hour.
It also has a diverse, street-food-inspired menu that’s full of international flavors, exquisite ingredients, and tasty treats.
Happy Hours: Monday to Saturday, 4 p.m. to 6 p.m. Sundays, 6 p.m. to 8 p.m.
Deals: Daily drink specials vary, $14 “The Happy Hipster” (a beer, a burger, and house fries)
6. Highline Bar + Lounge
Are you game for a happy hour that will keep you on your toes? If so, your next stop should be the Highline Bar + Lounge in River North.
Featuring several classic arcade games that you can play for FREE — including Skee-ball, Pac Man, pinball, Donkey Kong, and so much more — Highline is a fun, upscale bar with an excellent menu.
Whether you’re stopping in for a cocktail or you stay for dinner, you’re going to be entertained and enjoy yourself at Highline.
Happy Hours: Tuesday to Friday, 3 p.m. to 5 p.m.
Deals: Daily food and drink specials vary
7. Celeste
For a posh scene with a ritzy, unpretentious vibe, stop in for happy hour at Celeste.
Marked by a timeless, modern décor, Celeste has “three uniquely appointed floors” — The Pub, The Deco Room, and The Roof Garden.
In any of these vibrant, elegant spaces, you can enjoy Celeste’s turn-of-the-century drink menu that features craft cocktails, rare vintages, and hand-selected barrels.
Happy Hours: Tuesday to Friday, 5:00 p.m. to 7:00 p.m.
Deals: $8 select signature cocktails, $5 select beer, $8 select wines (by the glass), 50% off select dishes (chef's choice)
8. Earl’s Kitchen + Bar
Promising “irresistible food and drink and an engaging experience,” Earl’s Kitchen + Bar is a contemporary, sophisticated scene where you can savor innovative creations cooked up by world-class bartenders and chefs.
When it’s nice out, you and you friends can sit by the firepit while sipping on mojitos or your favorite wine. Or take the party inside Earl’s stylish lounge where you can kick things up with a spicy watermelon margarita or a signature Marilyn Monroe cocktail.
Want something to munch on? The Chipotle calamari and buffalo cauliflower are perfect for sharing!
Happy Hours: Monday to Friday, 2 p.m. to 5 p.m. & 9 p.m. to close
Deals: $5 well drinks, select craft pints & select wines, along with several other drink and food specials
9. AceBounce
If you love games and you’re looking for entertainment during your happy hour, you have to make a trip to AceBounce.
With shuffleboard, wonderball, ping pong, and beer pong, your whole group can get in on the fun while taking advantage of some great drink deals.
Plus, AceBounce has a thoughtful menu that can please almost any palette — beyond beer, wine, cocktails, and mocktails, AceBounce has a full menu, complete with vegetarian and gluten-free dishes.
That’s why it’s a nice go-to place for bigger groups, private events, and even corporate events.
Happy Hours: Monday to Friday, 4 p.m. to 7 p.m.
Deals: $5 Ketel One cocktails, $5 Lagunitas
10. Gideon Welles Craft Beer, Bar + Kitchen
Whether you’re a foodie or a beer lover looking for a chill happy hour spot, you’ll dig happy hours at Gideon Welles Craft Beer, Bar + Kitchen.
Inviting and relaxing, Gideon Welles is a modern gastropub that offers special and seasonal beers, as well as meads, ciders, cocktails, and mocktails.
Whether you’re loyal to ordering your favorite drink or you’re looking to try something you, Gideon Welles can serve up mouth-watering delights and highly enjoyable happy hours.
Happy Hours: Monday to Friday, 4 p.m. to 6 p.m.
Deals: $5 cocktails & tap beer, $7 select appetizers
Beyond Happy Hour
Happy hours could be just one event you’re planning for your colleagues.
If you’re putting together a corporate event — anything from a staff appreciation party to a live music event, a speaking engagement, a product launch, and beyond — we’ve got you covered.
Our expert corporate event team can help you with everything from venues and booking a corporate DJ to commercial AV equipment, sonic branding, music licensing, playlists, social media marketing services for venues and events, and more.
Just contact The Music Trust today to get more information and/or a free quote from our trusted pros.
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