The Ultimate Guide to Chicago Happy Hour

I live for happy hour in Chicago. It’s that special time of day when appetizers and fancy craft cocktails are cheap across the Windy City.

happy hour in chicago with friends toasting drinks

It is the best way to transition from my work day self into the fun version of me who likes spending time with friends and colleagues.

Chicago is a cultural hub, with high-quality eats and unique bars on every corner.

No matter what part of the city you’re in, I guarantee there is a spot nearby that offers a fantastic happy hour you and your loved ones will enjoy.

Check out my best happy hour spots in Chicago below!

Brando’s Speakeasy

343 S Dearborn St, Chicago, IL 60604
Visit Website

Happy hour is a festive occasion that pairs well with karaoke. Brando’s Speakeasy, located between Willis Tower and the Art Insitute of Chicago, offers one of the best happy hour experiences.

Brando’s is a vintage tavern with a dimly lit cocktail lounge and separate karaoke room.

The space has a romantic feel to it, from the dazzling crystal chandeliers over the bar to the intimate lounge seating.

Drinks are the main focus at Brando’s, however, they offer customizable small and large pizzas. They also have a daily happy hour from 5-7 pm.

Select canned seltzers and classic cocktails are on sale for $5 each. I recommend the Paloma or the Moscow Mule.

Cafe Ba-Ba-Reeba!

2024 N Halsted St, Chicago, IL 60614
Phone: 773-935-5000
Visit Website

Nothing says happy hour quite like authentic Spanish tapas. At Cafe Ba-Ba-Reeba guests can enjoy a wide range of tapas, pintxos, and paella.

They also have an extensive sangria, beer, and cocktails menu in addition to a selection of authentic Spanish wine.

This beloved Chicago restaurant has indoor and outdoor seating. Both spaces are thoughtfully designed and atmospheric.

Happy hour at Cafe Ba-Ba-Reeba lasts from 4-6 pm in the bar area. They serve bite-size tapas popular in Northern Spain, such as deviled eggs with crispy Jamon serrano.

Other tapas dishes include chilled gazpacho soup, garlic potato salad, or spicy potatoes with tomato aioli.

The featured drinks at Cafe Ba-Ba-Reeba’s happy hour include a selection of beer for less than $5 and pitchers of classic red sangria.

Gilt Bar

230 W Kinzie St, Chicago, IL 60654
Phone: 312-464-9544
Visit Website

If you’re in the mood for a romantic, dimly lit bar with happy hour specials, you will love Gilt Bar. The atmosphere here alone makes it one of the best happy hours in Chicago.

Crystal lamps, dark floral wallpaper, and private leather booths fill the space. It feels intimate no matter where you sit or how busy the bar is.

The bar is on the south end of the River North neighborhood, only a couple of blocks away from the river.

Gilt Bar’s happy hour takes place every day from the time the bar opens until 5:30 pm. Guests who order online take 20% off their bill.

Gilt Bar also offers Wine Wednesday specials, with 50% off all bottles throughout the day.


12 W Elm St, Chicago, IL 60610
Phone: 312-725-0732
Visit Website

Sparrow is a recently renovated lobby bar in the historic Gold Coast neighborhood.

The building has been around since 1927 and is currently home to several apartments.

The art deco bar is frequented by the building’s residents but is open and welcoming to all. Sparrow offers an extensive list of spirits, liqueurs, beer, and wine.

They also have a list of incredible craft cocktails. My favorites are the La Floridita, a rum-based drink, and the Mandarin Punch made with citrus, mint, clove, and soda water.

They offer guests happy hour specials Wednesday through Friday from 4-7 pm. Wines by the glass are $10 during happy hour, and draft beers are $5.


112 W Grand Ave, Chicago, IL 60654
Phone: 312-846-6654
Visit Website

Arbella hosts happy hour from 5-7 pm Monday through Saturday. They have one of the best happy hour menus in Chicago, with several cocktails, wine, beer, and small plates to choose from.

Arbella is a fun and youthful establishment that serves several casual American-style foods and unique craft cocktails.

During my visit to Arbella, I tried the potato tacos and the Chicago Fire Extinguisher, a cocktail with scotch and smoked bitters.

The Walk-In

2727 N Milwaukee Ave, Chicago, IL 60647
Phone: 773-697-8726
Visit Website

The Walk-In is the best happy hour in Chicago if you like fun, good service, and great drinks.

The restaurant sits in the northern part of Logan Square near The Logan Theatre. They are a cocktail bar and liquor store.

At The Walk-In, guests can expect to enjoy the best cocktails in the city.

Daily happy hour specials include discounted cocktail creations such as the Go-Go Gimlet, Lucky’s Explanation, or the Rosey Cheeks.

My favorite cocktail at The Walk-In was the Green Light, a refreshing mixture of rum, lime, and mint.

The Walk-In also does shot specials, including bourbon, tequila, and a house shot for only $3.

The Press Room

1134 W Washington Blvd, Chicago, IL 60607
Phone: 331-240-1914
Visit Website

In the heart of Chicago’s West Loop sits The Press Room. The Press Room is a stunning, sophisticated restaurant known for good vibes, great service, and the best wine in town.

The menu consists of fresh seafood, pasta, grilled veggies, and customizable charcuterie boards.

Everything pairs well with The Press Room’s exceptional wine bar.

Happy hour takes place on Tuesday and Wednesdays from 4-6 pm. Guests enjoy a dozen freshly shucked oysters for $1 and several traditional cocktails.

I recommend the gin martini or the Old Fashioned.

Logan 11 Bar & Kitchen

2230 N California Ave, Chicago, IL 60647
Phone: 773-252-1110
Visit Website

Logan Square’s Logan 11 Bar & Kitchen is a cool and funky place to hang out.

They believe in cultivating a hospitable culture where everyone can experience acceptance and belonging.

They also support the local community.The restaurant is a large, open space with a glass roof, exposed beams, and decorative Edison bulbs.

The atmosphere is warm and welcoming, no matter when you stop by. They serve an eclectic mix of comfort and American-style food.

From nachos and southwest chicken salad to chicken wings and burgers. Logan 11 also serves plenty of vegan and vegetarian options alongside craft cocktails, wine, and beer.

Happy hour at Logan 11 is Monday through Friday from 4-7 pm. Appetizers are ½ off and there are many drink specials.

2Twenty2 Tavern

222 S Wabash Ave, Chicago, IL 60604
Phone: 312-878-9994
Visit Website

2Twenty2 is a happening spot in Chicago’s downtown loop. The restaurant and bar are an awesome place to let off some steam after work.

There are numerous video games, TVs broadcasting sports, and shuffleboard. In addition to a delightful daily happy hour, 2Twenty2 serves signature, hand-crafted cocktails with top-quality tequila and aged whiskey.

There are over 30 beers on tap which can be enjoyed alongside burgers and fries, wood-fired pizzas, and signature bar food.

Happy hour specials run daily, and each day is something different. $6 liquor drinks rotate, but all house lagers are $2.22 Monday through Sunday.

Broken Shaker at Freehand Chicago

19 E Ohio St, Chicago, IL 60611
Phone: 312-940-3699
Visit Website

Broken Shaker is a hotel bar inside Freehand Chicago in the River North neighborhood.

The bar serves award-winning cocktails made with garden infusions, housemade syrups, and unique elixirs.

The food menu is reminiscent of street food from around the world. There are so many cocktails to choose from.

I recommend the Flores Guava Old Fashioned, Eye of the Storm, and the Velvet Revolver. They also have an extensive wine and beer list.

I sampled a glass of superb Spanish wine called Orelgi De Luberri that any wine lover will appreciate.

Happy hour at Broken Shaker runs Monday through Saturday from 4-6 pm and Sunday from 6-8 pm. The Happy Hipster is the happy hour signature drink, and the chef’s burger is cheap.

Cindy’s Rooftop

12 S Michigan Ave, Chicago, IL 60603
Phone: 312-792-3502
Visit Website

The best happy hour bar in Chicago’s rooftop bar scene is Cindy’s Rooftop. The bar is on top of the Chicago Athletic Association Hotel.

Every seat in the bar offers gorgeous panoramic views of the city, including Millenium Park and Lake Michigan.

The bar serves seasonal, family-style comfort food and fresh seafood. It is open year-round and has a comfortable ambiance enjoyable for all.

The plates are bright and colorful, which compliment the glass walls and ceilings, exposed brick walls, and outdoor fire pits.

Whether you enjoy your cocktails inside or out on the balcony, you can enjoy one of the best happy hours in Chicago. Happy hour specials are seasonal and run daily.

There are many places to enjoy the best happy hour in Chicago. From fancy rooftop bars to moody craft cocktail establishments, there is something to suit every happy hour craving.

In the mood for ramen? Check out these Chicago ramen spots for a delicious bowl of noodle soup!

Did we leave a restaurant off of the list? Make sure you leave us a comment and we’ll check it out!

Leave a Reply

Your email address will not be published. Required fields are marked *

Written by Brian Nagele

Brian has over 20 years experience in the restaurant and hospitality industry. As a former restaurant owner, he knows about running a food business and loves to eat and enjoy cocktails on a regular basis. He constantly travels to new cities tasting and reviewing the most popular spots.