When: Weekdays, 4-6pm
If your happy hour excursion calls for sports on flatscreens and 90+ beers on draft, point your GPS towards this sprawling emporium of booze for $5 select beers and well drinks, $6 wine glasses, and half-off appetizers including cheese curds and pretzel bites.
When: Weekdays, 4-7pm
Stop by one of Chicago’s premier soccer bars to discover a lost art of the happy hour special: the $1 Jello shot. Pair that gloriously ridiculous item with half-price appetizers, half-price wines by the bottle or glass, and $2 off all drafts, and suddenly soccer is looking a lot more interesting.
When: Daily, 5-7pm
This dimly lit karaoke lounge provides the perfect escape from another interchangeable work week with $3 small pizzas and $4 flatbreads, $4 Three Floyds bottles and Absolut Moscow mules, and $5 Bulleit Rye Old Fashioneds and Carlsberg/Jameson boilermakers.
When: Mon-Sat, 3-5:30pm
Kickstart your after-work routine at this affable neighborhood hang with $3 champagne followed by $5 well drinks, drafts, and wine, plus $5 off pizzas and starters and $5 off select wine bottles.
When: Monday-Friday, 3-6 pm
One of the few actually not-terrible bars in Wrigleyville offers this not-terrible happy hour special: $3 shots of Malort (along with $1 off draft beer, well drinks, and freezer shots.) Because nothing goes down better at 3 pm on a Monday than a shot of pure gasoline that causes you to make this face.
When: Fri-Sat, 8-10pm
Ready to get the night rolling, but need to get off the couch before The Shawshank Redemption pops on? Head to Late Bar and throw back $1 PBRs at this anything-goes dance spot.
When: Tues-Fri, 5-6pm
Stop in at this stylish neighborhood haunt’s self-proclaimed “infamous” happy hour for half-price beer, wine, cocktails, and bar snacks in the bar and lounge during the week (except Monday, when the place is closed).
When: Daily, 5:30-6:30pm
This industry favorite offers its happy hour all week. Stop in for $5 local craft drafts from Off Color, Dovetail, Spiteful, and more, plus $5 wines, $6 select snacks including duck fat fries, and $6 select cocktails including Moscow mules.
When: Weekdays, 3-6pm
Oysters and beer on the cheap? No, you haven't died and gone to Belgium. Cold Storage offers $1 oysters and daily drink specials on weekdays.
When: Mon-Fri, 4-7pm
The Gold Coast location of this small tri-state chain (with locations in Florida and Texas) is serious about happy hour with a menu that includes $4 fries, $7 mini margherita pizzas, $4 Amstel Lights, Miller Lites, and Pacificos, and $6 rotating drafts, wines, and well drinks.
When: Mon-Fri, 4-7pm
This cool little spot from the crew behind Bangers & Lace and Spilt Milk offers what might be the best Monday night tradition in Chicago: the $5 daiquiri. Stop by the rest of the week for half-price wines and drafts.
When: Mon-Wed 4:30-6 pm; Thurs-Fri 2-6 pm
This delicious happy hour special offers everything you need after a long day in the salt mines. Their “$10 Pre-Six” happy hour special includes a burger, fries, and craft beer (normally priced $5 or under) for one solitary Alexander Hamilton, with well cocktail and non-alcoholic options also available if you’re not into beer.
When: Weekdays 5-8 pm
If you’re looking to end your work day with a fancy craft cocktail that won’t break the bank, hit up this loungey spot connected to Red Star Liquor store via a walk-in cooler door for expertly crafted $6 cocktails including Old Fashioneds, gimlets, and more, plus $4 select drafts.
When: Daily, 4-6:30pm
This popular downtown happy hour go-to offers a large menu of selections in its bar and patio areas (we highly recommend the patio area) including $3.50 truffle fries and $5.50 burgers daily in addition to $7 select cocktails and wines, plus $1 oysters and shrimp on Wednesdays and $2 fish tacos on Tuesdays. Happy hour specials are available with a minimum beverage purchase of a very random $3.40.
When: Mon, Wed & Fri 5-6pm; Sat-Sun 3-5pm
Who doesn't like $1 oysters? No one, and Frontier has them, along with $3 High Life drafts, $3 dealer’s choice whiskey shots, $5 house wine pours, and $6 draft cocktails.
When: Daily, 5-6:30pm
River North is actually packed with great happy hours, but this little under-the-radar spot snags top honors thanks to its affordability, as many River North happy hour “specials” hover around the $7-$10 range for drinks. Union Sushi + BBQ solves that problem with $1.50 oysters, $3 beef filet skewers, $5 Moscow mules and glasses of rose, plus $6 spicy shrimp sushi rolls.
When: Weekdays 3-6 pm
This no-frills spot offers a no-frills happy hour that gets right to the point when it comes to helping you forget the work day: $3 domestic bottles and $4 Jagermeister and Fireball shots. Yep, Fireball before 6pm. It’s a thing.
When: Weekdays, 4-7pm
Rogers Park Social is as good a spot as any to bring your Tinder Tuesday date, and as a bonus, you can order pick-your-own mules for $6 (vodka, gin, rum, bourbon, or tequila). Also: $6 wines and $1 off Illinois draft brews.
When: Weekdays 5-7 pm
When you want to hit a cool downtown rooftop bar but don’t want to deal with the seemingly mandatory $13 cocktails that come with the honor of boozing from on high, hit up one of Chicago’s finest cocktail bars for $5 select beers, $8 select wines, and their $10 signature cocktail of the day.
When: Thurs-Fri, 7-9pm
This unique German/Southern-styled food joint wins the award for the most fun happy hour special in Chicago: a boot of beer. As in, a $9 16-ounce boot of 18th Street Brewery’s Partyboi Oktoberfest, which you can also upgrade to house in 34-ounce footwear for $18. Additional specials include $3 spicy smoked chicken legs and $5 16-ounce Krombacher Pils.
When: Mon-Thurs, 4-6 pm
Instead of spending your post-work hours in some interchangeable Lakeview sports bar, spice up your weekday routine at this neighborhood Mexican joint with $3 imports, $5 house margaritas and sangrias, and a range of food options including $5 empanadas and tamales.
When: Mon-Thur, 4-6pm
Four days a week, this happy hour has your basics covered with $5 select drafts paired with buy one, get one half-off appetizers. Gluttony encouraged.
When: Mon-Thurs 5-6pm, Fri-Sun 4-5 pm
This cool neighborhood music venue/restaurant (operated by the folks behind Empty Bottle and Thalia Hall) keeps it classy with a happy hour menu that includes $5 Goose Island 312 and IPA ales, $7 cocktail and wine specials, and select bites including $5 chickpea fries with curry ketchup.
When: Mon-Fri, 4-7pm
Sepia is one of the finest restaurants in Chicago, and that sometimes overshadows the fact that its bar staff is also exemplary. Offering a “Greatest Hits” menu that showcases items from the past 12 years, Sepia's happy hour invites patrons to enjoy $7 cocktails, wines, and beer. Bites such as crispy chicken panisse and shishito peppers are also available for $7.
When: Mon-Fri 5-7pm, Sat-Sun 3-5:30pm
Pound for pound, Easy Bar has one of the best drinking happy hours in Chicago. From Monday-Friday, enjoy half of EVERYTHING from 5-7pm, with additional daily specials including $2 High Life bottles on Sundays, $2 PBRs on Mondays, and $4 select craft cans on Wednesdays.