Cheers to These 12 Chicago Bars With The Best Happy Hour Deals

The Happy Hour spread at Cold Storage
The Happy Hour spread at Cold Storage. Photo courtesy of

In 1989, a string of traffic fatalities involving drunk drivers created a moral panic in Illinois, leading legislators in Springfield to formally ban all happy hours in the state.

For the next 26 years, budget-minded drinkers languished under their own form of prohibition, legally barred from unwinding after work with a specially discounted cold one.

But in 2015, Gov. Bruce Rauner signed a bill that liberated Chicagoans from the tyranny of paying full price for a can of Old Style at 5 p.m. on a Tuesday. And since then, the city’s bars have provided its residents with a multitude of reasons not to go straight home from the office.

Here are a few of the best.

Downtown Drink Deals

All of those big buildings downtown are filled with thirsty workers, and there are lots of bars and restaurants in the area that are more than happy to cater to them.

The suit-and-tie set might enjoy the classy Rosebud Prime, which from 4 p.m. to 6 p.m. on weekdays offers $5 wine glasses, $3 domestic beers and half-off every food item on its “Prime Time Menu.”

You can loosen your tie (and your vocal chords) a bit more at Brando’s Speakeasy. From 5 p.m. to 7 p.m. every day of the week, this karaoke lounge serves up $5 Carlsberg and Elijah Craig boilermakers, $5 Bulleit Rye old fashioneds, $4 Absolut Moscow mules and half-priced Revolution beer, all of which can be paired with $4 flatbreads, $3 small pizzas or $6 to $8 meat and cheese trays.

A relatively new addition to Chicago’s historic River North neighborhood, Bernie’s Lunch and Supper has quickly ingratiated itself to the area with killer food and drink specials that last from 5 p.m. to 7 p.m. every weekday and from 4 p.m. to 6 p.m. on the weekends.

The happy hour menu includes $5 drafts, $4 Miller High Life beers, $7 wine glasses, $8 mules and $9 mojitos. It also includes bar bites ranging from $5 garlic fries to the $11 Bernie’s cheeseburger.

If it’s seafood you’re after, swim across the north branch of the Chicago River to Cold Storage, which stands out amongst Fulton Market’s crowded restaurant scene by offering $1 oysters and $3 draft beers from 3 p.m. to 6 p.m. every weekday.

North and West Side Savings

Happy Hour at Longman & Eagle.
Happy Hour at Longman & Eagle.

Logan Square’s hipsterish bar/restaurant/bed-and-breakfast Longman & Eagle has earned rave reviews (and occasionally interminable lines) for serving up creative dishes that use every part of the animal — from the pork jowl with barley risotto to the bone marrow topped with bacon jam and scallion chimichurri.

To offset their expensive and exotic menu items, Longman & Eagle also offers a delightfully cheap domestic drink deal — from 3 p.m. to 5 p.m. on Monday through Friday, customers can snag $1 cans of PBR, as well as a weekly rotating $4 draft beer.

Head a bit further south down Milwaukee Avenue and you’ll hit The Owl, a late night haunt that nonetheless offers its best deals from 6 p.m. to 8 p.m. on weekdays, when beers and cocktails are all half-off. Spendthrifts with refined palates can also enjoy $2 and $3 craft beers every Tuesday night.

The iconic “six corners” intersection in Wicker Park has become pretty pricy real estate, but legendary 4 a.m. bar Estelle’s still keeps things cheap on weekdays by offering half-off deals on all beer, cider, wine and cocktails from 5 7 p.m., as well as daily food and drink specials.

Chicago is far from a college town, but there are a few bars near DePaul University that cater to the “broke student” market.

And even if you’ve long-since graduated from eating ramen for every meal, you’re never too old to pay $2.50 for all drafts and bottles, which is the special every Sunday through Wednesday at Hook and Ladder. Every drink at H&L is also just $2.50 from 5 p.m. to 8 p.m. on Thursdays, and $3 from 4 p.m. to 8 p.m. on Fridays.

If your bar crawl takes you as far north as Edgewater, you can locate uncommonly decent prices at Uncommon Ground. This eco-conscious bar is home to the first certified organic rooftop farm in the United States. From 4 p.m. to 6:30 p.m. on weekdays, it offers $4 Greenstar drafts, $5 well craft cocktails and tasty $6 uncommon appetizers.

South Side Sippers

Located just a couple blocks north of Guaranteed Rate Field, Turtle’s Bar and Grill is one of Armour Square’s coziest neighborhood dives.

Turtle’s attracts locals by offering a weeknight happy hour from 4 p.m. to 6 p.m. that includes 20% off all appetizers, $1 off tap beers and domestic bottles for $2.50 (there’s one catch: those offers aren’t valid during White Sox home games).

The hippest spot in Bridgeport right now is Maria’s Packaged Goods & Community Bar, and it’s easy to see why: this booze-and-Korean-Polish-street-food joint gives customers a good reason to stop by every Monday through Thursday from 4 p.m. to 7 p.m., when the bartenders pour delicious $5 draft cocktails.

Chef Matthias Merges’ A10 is considered by some to be the jewel of Hyde Park. The restaurant’s happy hour menu is available from 5 p.m. to 7 p.m. on Tuesdays through Fridays, and features $6 glasses of wine, $3.50 Schlitz tallboys and $3.50 Revolution Anti-Hero IPA cans. It also includes good eats that range from $8 northern bean bruschetta to a $13 fried chicken sandwich.

From Wrigleyville to Hyde Park, there are plenty of bars all over Chicago that have taken advantage of the city’s recently liberalized happy hour laws.

Why not check them out?

Patrick Grieve is a tight-fisted skinflint who can typically be found scrounging around in dive bars, empty baseball stadiums and second-run movie theaters. He’s also a writer, so The Penny Hoarder just felt like a natural fit for him.