Thanksgiving is right around the corner and with it, Black Wednesday. Before you stuff yourself full of turkey and pie, start the holidays off with a drink (or two) at one of the following spots. They'll be hosting parties or offering other food and drink specials to celebrate one of the biggest bar nights of the year. Just don't blame us if Thursday morning is a bit rough.
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14 Places to Celebrate Black Wednesday

Headquarters Beercade
Show off your Mario Kart skills at Headquarter’s tournament on Black Wednesday for a chance at winning a $500 grand prize HQ gift certificate. There will also be drink deals tailored to every taste with $5 craft cans, infusion shots, cocktails and more.
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Henry's Swing Club
Enjoy a free show by the Get Up with the Get Downs, the best funk soul dance party in town on Black Wednesday. Holiday-themed shots and carbonated draft cocktails will get you in the mood, and parties of up to 8 can reserve a table for $100 and get unlimited sliders all night. 10% of all food sales for the night will be matched by DMK restaurants and donated to the Chicago Food Depository.
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The Dawson
The Dawson will be teaming up with Hennessy to throw a Black Party, where Clint Rogers and guest bartender Thomas Mooneyham will be crafting Hennessy Black cocktails as well as serving Hennessy V.S (Very Special) punch. The event will feature complimentary appetizers, bartender games and live music from DJ Intel from 7 p.m. to 10 p.m. on the second floor. Guests are encourage to wear black.
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Lottie's Pub
Pioneer Tavern Group will host the 4th Annual Black Wednesday Trolley Crawl running all night between Lottie’s, The Pony and Frontier. Each location will feature drink specials including $5 Jameson Black, $5 Black and Stormys, $4 Strongbow, $4 Heineken and more. Guests can guarantee a spot on the trolley by signing up at the bar or emailing freetrolley@pioneertaverngroup.com
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Osteria Langhe
Gather your friends and family and head to Osteria Langhe for a four-course, pre-Thanksgiving dinner. The menu will feature items such as Brussel sprout Caesar and quail egg panino; king crab cake and crisp pancetta insalata; osso bucco risotto; and panettone bread pudding. Libations will include The Gobbler, a cranberry-infused cocktail created for the evening. The cost is $30 per person.
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Timothy O'Toole's Chicago
Timothy O’Toole’s will hold its 5th Annual Turkey Testicles Festival on Black Wednesday. The contest will commence at 9 p.m., with the winner receiving a whole frozen turkey. Then at 11 p.m., the pub will hold a pumpkin pie eating contest with the winner taking home a $25 gift certificate.
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Start Thanksgiving weekend with a special Black Wednesday Unbridled. Happy Misgiving will feature daring burlesque, devilish dances and Old Forester cocktails for a fun and freaky time. It’s a feast for the senses and you can register for the event online.
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SHAY
SHAY will be paying homage to Truman Capote’s “Party of the Century” by hosting a Black and White Masked Ball. The festivities kick off at 9 p.m. and will continue at Cuvee beginning at 11 p.m. Come dressed to impress and don’t forget your mask.
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Nacional 27
Learn some new moves on Black Wednesday as dance instructor Rickey Spivey will lead complimentary salsa lessons from 7:30 p.m. to 8:30 p.m. After class, show off your skills on the dance floor as DJ X spins hot Latin beats until 2 a.m. (no cover). If you need liquid courage, Nacional 27’s Rum Punch cocktail ($8 per glass, $30 per 52 oz. fishbowl) will do the trick.
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American Junkie
Stop by American Junkie on Black Wednesday for a special appearance by a guest DJ upstairs. Guests can also enjoy the new menu featuring items like winter vegetable tater tots, meatball pizza and chicken pot pie.
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MAX'S Wine Dive Chicago
Drink up on some fine wines and save 15% off regular retail price on Black Wednesday. Stop in for happy hour between 4 p.m. and 7 p.m. and nosh on snack-sized portions of classic menu items including pork-stuffed piquillo peppers, Nacho Mama’s Oysters, a bowl of five wings served naked or tossed in sauce, and more.
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High Noon Saloon
Party it up to a lineup of live DJs from 8 p.m. to 2 a.m. Drink specials include $4 Shiner Holiday Cheer drafts, $3 Jameson shots and $3 Cazadores tequila shots.
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Chicago Q
Chicago q will offer a special Bourbon flight featuring three Wild Turkey Bourbons: Rare Breed, Russell’s Reserve and Russell’s Reserve Rye for $18.
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Division Ale House
Division Ale House will celebrate Black Wednesday with live entertainment from DJ Rob and specials such as $5 chicken tender w/fries, $4 Goose Island drafts and $3 Jameson shots.
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