Near North Side

Unwind from a long work day at this sultry library themed spot. Their $5 happy hour specials include everything from tasty high-end bites to delicious drinks. Wanna lean into the vintage vibe? Order the old-fashioned.  

Location: 230 W Kinzie St

Happy Hour: Everyday from 4pm-5pm

Hours: Sunday - Thursday 4pm-10:30pm, Friday-Saturday 4pm-11pm

For more information on Gilt Bar.

River North

Wait, is this Chicago or Tulum? This trendy Mexican restaurant is like a tropical hideaway in the middle of the city, and it’s the perfect spot to forget your worries while soaking in the good vibes. From 4 to 6 pm on Tuesday through Friday there are plenty of great deals, but the best of the best is their margarita and taco bundle — a marg and a taco of your choosing for just $10. 

Location: 601 N Wells St

Happy Hour: Tuesday-Friday from 4pm-6pm

Hours: Tuesday-Thursday 4pm-12am, Friday 4pm-1am, Saturday 12pm-1am, Sunday 12pm-5pm

For more information on Diver.

Andersonville

Uvae’s upscale American fare is delicious at any price, but their $2 oysters and shrimp is also one of the best happy hour deals in the city. Pair those with their $5 draft prosecco and stylish bar and you’ve got the makings of a truly fantastic post-work nosh that will make you feel more than a little bougie.

Location: 5553 N Clark St

Happy Hour: Wednesday-Saturday from 5pm-6:30pm, Sunday from 3pm-6:30pm.

Hours: Wednesday-Saturday 5pm-10pm, Sunday 10:30am-9pm

For more information on Uvae Kitchen & Wine Bar.

Fulton Market District

Considering this massive former meatpacking factory offers everything from shuffleboard to ping pong to bocce to bowling and even virtual reality games, it’s easy to forget that it also has one of the best happy hours in the city! From 4 to 6 pm every Monday through Thursday, Punch Bowl Social offers a wide selection of snacks ranging from just $6 to $11, and a slew of beers, wines, and mixed drinks like — naturally — punch, for just five bucks! 

Location: 310 N Green St

Happy Hour: Monday-Thursday from 4pm-6pm

Hours: Monday-Thursday 11am-12am, Friday 11am-2am, Saturday 10am-2am, Sunday 10am-12am

For more information on Punch Bowl Social.

Old Town

There is no better spot for a casual (yet extremely fun) happy hour than Happy Camper. This funky industrial pizza shop knows how to start the party with half-off glasses of wine, espresso martinis, and salads from 3 to 6 pm Monday-Friday, plus a killer charcuterie board for a mere $10 and a few other tasty $5 sides. 

Location: 1209 N Wells St

Happy Hour: Monday-Friday from 3pm-6pm 

Hours: Monday-Wednesday 10:30am-12am, Thursday 10:30am-1am, Friday 10:30am-2am, Saturday 10am-3am, Sunday 10am-11pm

For more information on Happy Camper.

Motor Row District

This whimsical yet modern rooftop lounge comes with incredible views of the lake and all of downtown, but if the ambiance isn’t enough for you, the happy hour sure will be. Some of their lighter bar fare is just $5 a plate, and they all pair perfectly with their drink deals, like $8 sangrias and $5 Miller High Lifes.

Location: 133 E Cermak Rd

Happy Hour: Mondays-Thursdays from 4-6pm

Hours: Wednesday-Thursday 4pm-11pm, Friday 4pm-1am, Saturday 11am–1am, Sunday 11am-11pm.

For more information on VU Rooftop.

Gold Coast

This sophisticated art-deco Cuban restaurant will have you feeling fancy while sipping their rum cocktails and craft beers. From Wednesday through Friday from 4 to 7pm, grab $5 drafts and $10 wines by the glass! 

Location: 12 W Elm St

Happy Hour: Wednesday-Friday from 4pm-7pm

Hours: Sunday-Friday 4pm-2am, Saturday 4pm-3am

For more information on Sparrow.

River North

This colorful Roman pizza bar is a can’t-miss. Try their next-level Italian fare, and wash down your pie with $5 drinks Wednesday through Friday from 4pm to 6pm. 

Location: 605 N Wells St

Happy Hour: Wednesday-Friday from 4-6pm

Hours: Wednesday-Thursday 4pm-10pm, Friday 4pm-12pm, Saturday 11am-12am, Sunday 11am-9pm

For more information on Bar Cargo.

West Loop

Authentic Japanese grub with a killer drink deal on the side? What more could you want! Kinton Ramen offers Sapporos for $2, sake for $3, glasses of wine for $4, and cocktails for $5 every weekday from 4 pm to 7 pm. 

Location: 163 N Sangamon St,

Happy Hour: Monday-Friday from 4pm-7pm

Hours: Monday-Thursday 5pm-9pm, Friday-Sunday 12pm-9pm

For more information on Kinton Ramen.

Fulton Market District

Stepping into Trivoli Tavern feels like stepping into a different world with its dim lighting, lush palms, and unique antler chandeliers. The ambiance screams “Old World,” and their happy hour prices feel like a throwback, too! Every day from 4:30 to 5:30 pm, tavern dwellers will find $5 deals for everything from mussels to sliders to mixed drinks and brews.

Location: 114 N Green St

Happy Hour: Everyday from 4:30pm-5:30pm

Hours: Sunday-Thursday 4:30pm-10:30pm, Friday-Saturday 4:30pm-11pm

For more information on Trivoli Tavern.

River North

This bright American brasserie offers some truly unique beverages as part of their happy hour special. Weekdays from 3 to 6 pm, patrons can try their tasty French 75 slushie, make their own mule, or taste their cucumber loco or Gatsby concoctions. One thing to note: the happy hour deals are only at the bar, so skip the table and keep it casual! 

Location: 400 N Clark St

Happy Hour: Monday-Friday from 3pm-6pm

Hours: Monday-Wednesday 8:30am-9pm, Thursday-Friday 8:30am-10pm, Saturday 9:30am-10pm, Sunday 9:30am-9pm

For more information on The Smith.

River North

Cafe Ba-Ba-Reeba! bills itself as Chicago’s original tapas bar, and their Spanish food still remains some of the best in the city. You’re going to want to try one of everything at this legendary spot, and their awesome happy hour allows you to do just that — on a budget! Taste their pintxos for $1.50, tapas from $2.50-$3.50, and red sangria pitchers for $20. 

Location: 2024 N Halsted St

Happy Hour: Everyday from 4-6pm in the bar and lounge area only

Hours: Monday-Thursday 4pm-9pm, Friday 11:30am-11pm, Saturday 10am-11pm, Sunday 10am-9pm

For more information on Cafe Ba-Ba-Reeba!.

Wicker Park

This industrial-yet-airy grill has an onsite brewery, so, naturally, their happy hour is the perfect time to taste test some of their incredible house brews. On Monday through Thursday from 2 pm to 5 pm, pints are $5 and flights are just $8. Oh yeah, and you can also pay just $10 for a snack plus a beer and a shot. 

Location:1932 W Division St

Happy Hour: Monday-Thursday from 2pm-5pm

Hours: Monday-Thursday 11:30am-9pm, Friday 11:30am-10pm, Saturday 9am-10am, Sunday 9am-9pm

For more information on The Perch.

Theater District

City Social prides itself on having “something for everyone,” from modern bar food to classic drinks with a twist. If you stop by this upscale-but-casual theater district hang on Monday through Wednesday between 4 and 6 pm, you can snag $4 Draft Krombachers, $6 glasses of bubbly, $4 City Pale Ales, and $5 mini black & tans.

Location:120 N LaSalle St

Happy Hour: Monday-Wednesday from 4pm-6pm

Hours: Monday-Friday 11am-8pm

For more information on City Social.