11 Spots for best happy hours in Chicago in 2023

The Best Happy Hours in Chicago: We present to you the Ultimate Guide to Chicago Happy Hour in this post. The absolute greatest drink deals and food specials anyone could ask for.

In Chicago, happy hour is a way of life. Throughout the city, snacks and upscale artisan beverages are on offer at happy hours.

It’s the greatest method for me to transform from the serious person I am throughout the workday into the sociable one I am when I’m among my friends and coworkers.

You can find excellent restaurants and interesting pubs on every street corner in this cultural hub.

There is always a great happy hour somewhere in the city, and it doesn’t matter what area of town you happen to be in.

If you’re in Chicago, you should check out the places I recommend for happy hour.

Spots for best happy hours in Chicago

The Ultimate Guide to the best happy hours in Chicago

So, here’s a guide to the best Happy Hours in the city with all the details you’ll need on days, times, and drink and food deals.

Spots for best happy hours in Chicago

1. Cindy’s Rooftop

Cindy’s Rooftop is the greatest rooftop bar in Chicago for happy hour. The rooftop bar of the Chicago Athletic Association Hotel offers great city views.

All of the bar’s patrons can take in breathtaking views of the city, including Millenium Park and Lake Michigan, from every seat in the establishment.

Comfort cuisine for the whole family that changes with the seasons and delicious fish are what you can expect to find at this pub. It’s welcoming and pleasant environment makes it a popular destination at any time of year.

The colorful plates are a nice touch to go with the clear ceilings and walls, brick accents, and fire pits outside.

One of the best happy hours in Chicago can be had here, whether you choose to drink inside or on the balcony. Seasonal and ongoing daily happy hour discounts.

2. 2Twenty2 Tavern

In the heart of Chicago’s downtown, you’ll find 2Twenty2. Both the bar and the restaurant are great places to unwind after a long day.

There are many other options for entertainment, including video games, televisions showing sporting events, and shuffleboard. Signature cocktails made with premium tequila and aged whiskey are available at 2Twenty2 every day, along with a lovely happy hour.

Burgers, fries, wood-fired pizzas, and other classic bar foods complement the more than 30 beers on tap.

Every day at happy hour, there will be a varied selection of discounts. Monday through Sunday, all house lagers are $2.22 while specialty cocktails with liquor are $6.

Spots for best happy hours in Chicago

3. 1308 Chicago

After a stressful day at work, like when you accidentally left your microphone on during a company-wide Zoom, this is the type of relaxing spot you want to unwind in.

There are just around 30 seats at this little bar and restaurant, which is located in the courtyard of a tiny office building and serves excellent drinks and delicious Southern-inspired cuisine.

Dishes like corn ribs and grits with sweet roasted carrots and crispy dukkah are just a few examples. We apologize in advance if listening to some great neo-soul and sipping an Old Fashioned doesn’t let you forget about the meeting your boss requested for this Friday at 4 o’clock.

Spots for best happy hours in Chicago.

4. Amaru

It doesn’t matter if you had to get up at 6 in the morning; Amaru, a casual Latin American restaurant in Wicker Park, will keep you awake with its lively atmosphere. 

They provide the best Happy Hours in Chicago that will make you want to go out instead of spending the rest of the day lounging at home.

Ceviche, piononos with sweet plantains, and chorizo wrapped in bacon are among of the meals on the $10-or-less menu, and there are also drinks and wines available for under $6.50. 

There’s no shame in making a complete dinner out of Happy Hour snacks, as our former roommate who was always late with the rent used to remark.

Spots for best happy hours in Chicago.

5. The Press Room

The Press Room is located in the middle of the action in Chicago’s West Loop. It’s common knowledge that the atmosphere, service, and wine list at The Press Room are unmatched in town.

Fresh seafood, spaghetti, grilled vegetables, and charcuterie boards with your choice of toppings are on the menu.

The Press Room’s superb wine bar complements any meal.

On Tuesdays and Wednesdays from 4 and 6 o’clock, we have the best happy hours in Chicago here at the press room. 

There are a variety of classic drinks and a dozen freshly shucked oysters for only $1.

6. Brando’s Speakeasy

Karaoke is a fun and social activity that goes well with a happy hour atmosphere. Between Willis Tower and the Art Institute of Chicago is where you’ll find Brando’s Speakeasy, a top-notch happy hour hotspot.

Brando’s is a dive bar featuring a karaoke area and a separate cocktail lounge.

Every detail, from the glittering crystal chandeliers hanging over the bar to the plush lounge seating, contributes to the room’s sultry atmosphere.

Brando’s specializes on alcoholic beverages, but they also provide small and big pizzas that may be made to order. As an added bonus, they have a daily happy hour every day between the hours of 5-7 pm.

There is a $5 can deal on select canned seltzers and vintage drinks. The Paloma or the Moscow Mule are two excellent choices.

 7. Gilt Bar

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.

8. The Walk-In

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.

Spots for best happy hours in Chicago.

9. Ema’s

When we’re having a bad day, we prefer to chill at Ema’s bar. It is well-lit, filled with greenery, and laid-back (by River North standards) without having an eerie, desolate vibe. 

All of the mezze platters (especially the hummus and labneh) and the Happy Hour wines at this Mediterranean restaurant are top-notch. 

After doing one of those things, you won’t even remember the email your boss sent you as you were leaving the office.

10. Logan 11 Bar & Kitchen

The Logan 11 Bar & Kitchen in Logan Square is a trendy and happening spot. To them, it’s important to foster an environment where everyone feels welcome.

They’re also big on giving back to the neighborhood.

This restaurant features a glass ceiling, wooden beams, and Edison light fixtures for ambiance.

At whatever time of day or night, you’ll find the ambiance to be friendly and comforting. The menu is a mishmash of homey fare and classic American dishes.

Everything from burgers and wings to nachos and southwest chicken salad. Vegan and vegetarian alternatives are abundant at Logan 11, alongside creative cocktails, wine, and beer.

Monday through Friday, from 4 to 7 p.m., Logan 11 hosts the best happy hours in Chicago. There are various beer promotions and appetizers are half price.

Spots for best happy hours in Chicago

11. Uvae Kitchen And Wine Bar

Uvae Kitchen and Wine bar is a great place for a relaxed supper, especially if you arrive for Happy Hour and enjoy the restaurant’s extensive wine selection and tasty fare. 

This Andersonville restaurant has the feel of a pleasant neighborhood dinner party, with intimate, comfortable seating and helpful servers. 

They have $5 glasses of prosecco to help you relax between seafood courses.

Best happy hours in Chicago

Final Thoughts:  Best happy hour in Chicago

Chicago is home to some of the world’s top happy hours, and you can find them all around the city. There is a wide variety of bars to satisfy your happy hour needs, from upscale rooftop lounges to sultry artisan cocktail dens.

Hopefully, you have enjoyed our Ultimate Guide to Chicago Happy Hour.