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.
OITNB's Jackie Cruz Takes 6 Shots, Gets Tipsy, Talks About Dream Role
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.