Where to Drink

Where to find the best happy hours in Chicago

Looking for pocket friendly places to have drinks and food in Chicago? Don't look away, we have just the bars to refuel the fun.

When it comes to saving the bucks for value deals, Chicago has plenty of options to turn to for happy hours. From bars in Wicker Park to game lounges in River North, certain windows pop open every now and then for you to capitalize on mouth watering deals.

Here are a few imbibing spots in Chicago where you will be treated with combo deals, cheap drinks, and discounted dishes. 

Brando’s Speakeasy

Attending all your needs, from on demand karaoke sessions to having conversations in a subtle cocktail room, Brando’s Speakeasy is a vintage tavern serving house crafted cocktails and small bites.

Some delightful concoctions you will find for $5 each in the happy hour special menu include the Paloma, Moscow Mule, and Old Fashioned along with hard seltzers from White Claw and beers from Revolution Brewing. 

Happy hours - 5 pm to 7 pm

Location - 343 S Dearborn St, Chicago, IL 60604.

Timings - 5 pm to 2 am (Monday to Sunday)

View on maps. 

The Walk In

chicagobarswithhappyhours The Walk In

All smiles at The Walk In, Source: Facebook

Relish a happy hour cocktail such as the Lucy’s Explanation made with Lucy Pistolas Mezcal, grapefruit, orange, lime, and cinnamon, while nodding to Rock n Roll music at this watering hole. The Walk In is settled in a century old vintage building, welcoming guests to its modern industrial setting that would make most diners look outdated.

Other cocktails that can be found on the happy hour menu are Green Light, Rosy Cheeks, Go-Go Gimlet, and Old Fashioned ($6 each).

Happy hours - 5 pm to 8 pm

Location - 2727 N Milwaukee Ave, Chicago, IL 60647.

Timings - 5 pm to 2 am (Sunday to Friday)
12 pm to 3 am (Saturday)
12 pm to 2 am (Sunday)

View on maps. 

Old Town Pour House

chicagobarshappyhours Old Town Pour House

Cheers to the happy hours at Old Town Pour House, Source: Instagram

Whether it's lunch, dinner, or a private party, Old Town Pour House will keep you company with over 90 craft beer options and modern American food. 

To make the most of their wide selection, visit during the happy hours to get $2 off all local drafts, the backyard flight, selected hard seltzers, well drinks, and wine glasses. 

Additionally, enjoy tasty small bites like the kung pao cauliflower, chicken popcorn, pretzel bites, and more for half the price.

Happy hours - 4 pm to 6 pm (Monday to Friday)

Location - 1419 N Wells St, Chicago, IL 60610.

Timings - 4 pm to 11 pm (Monday to Wednesday)
4 pm to 12 am (Thursday)
11 am to 2 am (Friday)
10 am to 3 am (Saturday)
10 am to 11 pm (Sunday)

View on maps.

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chicagobarshappyhours Highline

Drinks and games at Highline, Source: Website

Famous for an upscale bar fare and a dynamic gaming lounge, Highline attracts patrons of all kinds in the River North. Choose to play standout arcade games like the NBA Jam, WWF Wrestlemania, pac man, and more as you reach a high point with their signature dishes like the smash burger, fish tacos, and skillet cookie.

For drinks, draft beer, shareable cocktails, wine, and hard seltzers are there to entertain, especially when the happy hour special event kicks in. (Valid till 31st January, 2022)

Tuesday: $4 domestic drafts, $5 craft drafts, $40 shareable cocktails
Wednesday: $8 Moscow mule bar
Thursday: $8 classic margaritas
Friday: $15 burger, draft beer & whiskey shot

Location - 169 W Kinzie St, Chicago, IL 60654.

Timings - Closed (Monday)
11 am to 2 am (Sunday, Tuesday, Wednesday, Thursday, and Friday)
11 am to 3 am (Saturday)

View on maps.


chicagobarshappyhours Arbella

Drinking at Arbella, Source: Facebook

Apart from the elusive $16 cocktails on the list, Arbella has a separate menu for happy hours that turns to different wine varietals, beers, and spirits with each passing day. From a glass of vino to the Kentucky Old Fashioned cocktail made with bourbon, house bitters, and simple syrup, there are a variety of drinking options you can go for.

Although, chicken tenders with a dip of your choice is the only snacking option on the happy hour menu.

Happy hours - 5 pm to 7 pm (Monday to Saturday)

Location - 112 W Grand Ave, Chicago, IL 60654.

Timings - 5 pm to 12 am (Monday)
5pm to 2 am (Tuesday to Friday)
5 pm to 3 am (Saturday)
Closed (Sunday)

View on maps. 

Easy Cocktail Bar

chicagobarshappyhours Easy Cocktail Bar

Easy Cocktail Bar, Source: Facebook

Submerged in the electric and entertaining atmosphere of Wicker Park, Easy Cocktail Bar passes a warm and unpretentious vibe. You will find a fully stocked bar in the backroom area and old school music waves dispersing from a jukebox.The half price happy hour runs daily along with $8 beer and shot combos. 

Happy hours - 5 pm to 7 pm (Monday to Friday)

Location - 1944 W Division St, Chicago, IL 60622.

Timings - 5 pm to 2 am (Monday to Thursday)
4 pm to 2 am (Friday and Sunday)
4 pm to 3 am (Saturday)

View on maps. 


chicagobarshappyhours Bernie's

Outdoor patio at Bernie’s, Source: Facebook

Cornered by the streets of Erie and Orleans, Bernie’s is a roomy space with a right balance of traditional and modern styling. Offering the thoughtful presentations of owner and chef, Zack Sklar, you will be set in the motion with a procured wine list, micro brewed beers, and craft cocktails. 

Dive straight into the happy hour special menu catering cocktails like the classic G&T and Moscow Mule or go for a featured wine if that is your go to drink. The chicken wings, tenderloin sliders, and hand cut fries make awesome companions with the drinks. 

Happy hours - 4.30 pm to 6.30 pm (Monday to Friday)

Location - 660 N Orleans St, Chicago, IL 60654.

Timings - 11 am to 9 pm (Monday to Thursday)
11 am to 11 pm (Friday to Saturday)
10 am to 4 pm (Sunday)

View on maps.

Header image - Bernie’s Chicago, Source: Facebook

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