Somewhere along the way, being cheap somehow became a bad thing. Sure, it’s one thing if you’re buying fake Prada purses and trying to pass them off as the real thing on your sister’s birthday. But when it comes to eating and drinking in bars, you’re getting the same quality product -- so why not save a little cash in the process? In the end, it will enable you to drink more. And who could fault you for that? Here’s everywhere you need to drink during happy hour in Chicago.
Old Town Pour House
Old TownWhen: 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.
The Globe Pub
North CenterWhen: 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.
Brando’s Speakeasy
South LoopWhen: 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.
Hutch American Kitchen & Bar
AndersonvilleWhen: 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.
GMan Tavern
WrigleyvilleWhen: 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.
Late Bar
AvondaleWhen: 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.
Duck Inn
BridgeportWhen: 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).
The Bristol
BucktownWhen: 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.
Cold Storage
Fulton MarketWhen: 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.
Doc B’s
Gold CoastWhen: 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.
Sparrow
Lincoln ParkWhen: 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.
The Bad Apple
Lincoln SquareWhen: 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.
The Walk In
Logan SquareWhen: 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.
McCormick & Schmick’s
LoopWhen: 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.
Frontier
Noble SquareWhen: 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.
Union Sushi + Barbecue Bar
River NorthWhen: 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.
Ravenswood Tavern
RavenswoodWhen: 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.
Rogers Park Social
Rogers ParkWhen: 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.
Drumbar
StreetervilleWhen: 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.
Funkenhausen
Ukrainian VillageWhen: 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.
El Nuevo Mexicano
LakeviewWhen: 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.
Fat Cat
UptownWhen: 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.
The Promontory
Hyde ParkWhen: 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.
Sepia
West LoopWhen: 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.
Easy Bar
Wicker ParkWhen: 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.
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