December 21st is going to be the longest night of the year (literally, it's the Winter solstice). Here to help you ensure it also doubles as the Best Night of Your Life, we've got a list of the best happy hour spots in Chicago to kick if off -- because no good/great/best/average/kinda aight night is complete without one of them. Check out our picks below (which celebrate eight establishments that skirt Illinois' system of oppression with incredible deals on food and booze), and make sure to fully map out a perfect evening with our itinerary builder.
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Union Sushi + Barbecue Bar
River North
This two-story sushi house is home to arguably one of the best happy hour deals in Chi-town: $1 oysters, $2 beef fillet skewers, and $4 shrimp tempura rolls Monday through Saturday from 5-630p. Tack on a glass of sake, and you have all your major food groups for $20.
Cafe Ba-ba-reeba
Lincoln Park
This bacon-wrapped-dates-equipped tapas spot offers $1 pinchos and $3 small plates Mon-Thurs 4-6p and Fri-Sat, 10p-midnight. Assuming you're not gassed from yelling at the TV with FC Barcelona on, you can also take down half-priced signature cocktails on Mondays, and bottles of Spanish wine on Tuesdays.
Matchbox
River West
There’s a reason this tavern touts the title, “Chicago’s Most Intimate Bar”: on any given night, this 460sqft'er is packed wall-to-wall with thirsty bar-goers. Try one of their legendary gimlets or margaritas made with fresh ingredients and quality spirits, and check their Facebook page for the latest specials.
Howell’s & Hood
Streeterville
This epic Downtown beer hall offers 114 domestic and international beers on tap, and upscale bar fare like tomato powder-crusted venison. Plus, their weekly “Hump Day Hops” leans on one awesome beer special.
Barcito
Near North Side
Brought to you by the folks behind Tavernita and Mercadito, this Spanish-y hotspot is the answer to your pork belly slider and cheeky craft cocktail needs. Thanks to their daily Tapas Time, guests who order a boozy beverage (might we suggest the Booty Collins?) between 5-7p will receive a small plate special.
Sunda
Near North Side
This highly trafficked New Asian-haven offers 50% off select appetizers, like lemongrass beef lollipops and sushi from 4-6p during their Sunda Social Hour. Also worth putting on your iCal: between 6-7p on the last Monday of every month, $25'll buy you a maki-making lesson with Executive Chef Jess DeGuzman—sushi and sake included.
The Beer Bistro
Lincoln Park
All December long, this Lincoln Park fixture is running its annual 12 Beers of Xmas challenge. Imbibe 12 diverse Christmas-style brews (not at once, you've got a whole month) and win a t-shirt with the logos of every beer you just drank.
High Noon Saloon
Wicker Park
This Old West-inspired tequila bar and eatery serves Tex-Mex brunch Saturdays and Sundays from 11a-2p, complete with breakfast burritos and “huevos benedictos”. For $25, you can snag an entrée and bottomless Bloody Marys or mimosas.
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1. Union Sushi & Barbeque Bar
230 W Erie St, Chicago -
2. Café Ba-Ba-Reeba
2024 N Halsted St, Chicago -
3. The Matchbox
770 N Milwaukee Ave, Chicago -
4. Howells & Hood
435 N Michigan Ave, Chicago -
5. Barcito
151 W Erie St, Chicago -
6. Sunda
110 W Illinois St, Chicago -
7. Beer Bistro North
1415 W Fullerton, Chicago -
8. High Noon Saloon
1560 N Milwaukee Ave, Chicago
A towering two-level sushi bar with graffiti-covered concrete walls and a custom-made Robata grill, Union's Sushi-Wabi-vet chef's using said flame to work up prosciutto-wrapped scallops and garlic-soy lamb, while also kicking out noodle creations.
This tapas joint is satiating Chicago with their small plates, like bacon wrapped dates (warrants a second date, for sure), goat cheese in a tomato sauce w/ garlic toast, and pitchers (after pitcher) of sangria. Call ahead to make a reservation and thank us later.
As the self-proclaimed "most intimate bar in Chicago" at only 460sqft, The Matchbox is not for those who require substantial personal space. It is, however, for folks who enjoy high-quality cocktails like fresh lime juice gimlets and Manhattans garnished with tasty french cherries, paired with emphatic conversation with friends and strangers at very close range. Having stood at the corner of Ogden and Milwaukee for over 75 years, the divey hallway-eqsue space is a Chicago staple, with red tin ceilings, a dark-wooded bar, and ever-present rows of christmas light dangling above shelves crammed with liquor. The place serves a handful of bar snacks -- panko-crusted mozzarella, bacon-wrapped-scallops, wings -- and in the warmer months, there is side walk seating available (with far more space and far less character than the joint's interior).
From the folks behind Old Town Pour House and Sweetwater, Howells & Hood is an epic beer hall in the Trib Tower, equipped with 114 beers on tap springing from 360 draft faucets spread across the 23,000sqft venue. With copper-topped bars and inscriptions on the travertine-tiled walls, the restaurant replicates the epic neo-Gothic design of the landmark space credited to John Howells and Raymond Hood, who thankfully weren't name Lipschitz and McDingleberry.
Barcito is serving up a rambunctious, awesome happy hour deal, as well as specialties like artichoke salad and something called a Booty-Collins (get it).
Toeing the line between swanky hotspot and sophisticated dining destination, this Asian fusion concept from Rockit Ranch Productions is a worthy choice for an undeniably hip meal out in River North. The menu offers some seriously interesting eats (duck breast kimchi, oxtail pot stickers) and includes sushi, sashimi, and plenty of wok dishes. The beer list is heavy on the Asian pours, and there are sake and speciality cocktails as well. Sunda's decor feels just as sleek as the menu with polished black bamboo and high wooden tables.
The former Small Bar Fullerton has changed hands, but will remain craft-centric now that it's BB North, a second location for the West Loop bar that flaunts more than 160 taps, and sports a menu aided by the kitchen's smoker, which'll flavor up everything from ribs to wings.
Are you a fan of Tombstone? The 1993 film, not the popular frozen pizza brand. Because you can get an Old West feel and stop eating from the freezer section thanks to High Noon Saloon, a Tex-Mex tequila bar sporting a spur-scuffed hickory floor, olde-tyme photography, butcher block tables, and fringed leather stools.