Many people like myself prefer to avoid the holiday peak and get our celebrations out of the way ahead of time. Or, you might want to have a Friendsgiving before the big weekend so you can dedicate all your time and attention to your families when the time comes. Either way, we know there’s one thing you’d want: good deals. For anybody thinking of an early celebration, here are 5+ Black Wednesday specials in Chicago this year.

Image Credit: Frontier


1072 N Milwaukee Ave, Chicago, IL 60642

Frontier will host their annual Whiskey & Wine Fest beginning at 8 PM on Wednesday, November 23rd. Celebrate Black Wednesday with whiskey and wine samplings from 8-10 PM, with over 60 samplings available! Explore whiskey profiles with brand ambassadors while also enjoying small bites & appetizers. Tickets are only $35 each and can be purchased via Tock.

Ina Mae Tavern

1415 North Wood St, Chicago, IL 60622

Looking for unique Black Wednesday fun in Chicago? Come to Ina Mae’s Drag Bingo on Wednesday, November 23rd starting at 7 PM. Specials will include $5 High Noons, $8 Crystal Head Voodoo Punch, $8 Jim Beam Spiced Highballs, $5 Lilith Towers Shots, and $35 Skull Punch Bowls. Guests can also enjoy Ayce Fried Chicken served with a biscuit and coleslaw for only $25/person. Prizes for winning bingo include $100 gift cards to Ina Mae Tavern, Frontier & Lottie’s Pub! Additional prizes will be Chicago Bulls tickets, a ‘staycation’ at Ina Mae Tavern’s Airbnb (Wednesday or Thursday), and a $100 gift card to Ina Mae Tavern included!


Lottie’s Pub

925 W Cortland St, Chicago, IL 60622


For those who plan on pregaming the Thanksgiving festivities, attend Lottie’s Pub for Black Wednesday specials on Wednesday, November 23rd from 6-9 PM. Offerings include: $4 Rhinegeist Cloud Harvests, $5 Wild Turkey Shots, $5 Pumpkin Pie Shots, $7 Titos & Cranberries, $8 Turkey Burgers, and $10 Pumpkin Spice Old Fashioneds. For those ready to keep the celebrations going, Lottie’s Pub will also be open on Thanksgiving Day! With their doors opening at 6 PM, come cheer on the New England Patriots and Minnesota Vikings at 9:20 PM, with plenty of food and drink options ready to enjoy!

To reserve a table, please email ; walk-ins are also welcome.



2683 N. Halsted St. Chicago, IL 60614

Chicagoans can kick off the Thanksgiving holiday with aliveOne’s half-price everything happy hour from 5 p.m. to 7 p.m. on Black Wednesday, followed by FREE live music at 9 p.m. in the back room with Drew N Friends. Additional drink specials available all evening will include $6 Half Acre brews $6 aliveOne house cocktails like the Copernicus with Crown Royal, Pimms, simple syrup, lemon juice and ginger beer and the Light My Fire with Cazadores Reposado, Del Maguey Vida Mezcal and demerara sugar.

Central Park Bar

2924 N. Central Park Ave. Chicago, IL 60618

Chicagoans staying in town for Thanksgiving can kick off the holiday weekend at Central Park Bar in Avondale on Black Wednesday. The evening will feature half-price happy hour from 4 p.m. to 7 p.m., and $9 beer and shot combos all night. Guests can also partake in Bring Your Own Board Game Night and either bring their own or choose from a variety of games the bar has in-house like Connect 4, Guess Who, Uno and more. To celebrate the season, Central Park Bar is serving a $10 Frozen Spiced Latte featuring Misunderstood Ginger Spiced Whiskey, Maplewood Coffee Liqueur, oat milk, cookie syrup, and a cinnamon stick.

Easy Bar

1944 W. Division St. Chicago, IL 60622

Easy Bar will kick off Black Wednesday with their popular half-price happy hour from 5 p.m. to 7 p.m. Later in the evening, guests can enjoy “Easy Laughs”, a late-night open mic comedy show with hosts Shannon Baccus and George Howington. Sign up is at 10 p.m. and the show begins at 10:30 p.m. Along with FREE POOL, other all night specials include $4 Malort shots, $5 hard seltzers, and a $9 beer and shot combo.


2013 W. North Ave. Chicago, IL 60647

Chicagoans looking for a casual spot to kick off the long Thanksgiving weekend can head to Estelle’s for a half-price happy hour from 5 p.m. to 7 p.m. on Black Wednesday.House cocktails will be on special for $8 all night, including new seasonal drinks like the Cofresi’s Brewty with Mr. Black Cold Brew Coffee Liqueur, Ron Zacapa 23 Rum, and BroVo Boomerang. For late-night bites, Estelle’s kitchen is open until 4 a.m. with specials like $8 Party Pockets.

Cody’s Public House

1658 W. Barry Ave. Chicago, IL 60618

Always dog-friendly inside and out, Cody’s Public House in West Lakeview will be open at 4 p.m. on Wednesday, November 23 for Black Wednesday. Weather permitting, guests are invited to “Bring Your Own Meat” (BYOM) and use the grills in Cody’s beer garden to grill up all their dinner favorites. Cody’s beer garden features TVs, darts and bean bags while the indoor game room offers darts, Golden Tee, Big Buck
Hunter and more.


169 W. Kinzie St. Chicago, IL 60654

A staple for lunch, happy hour and dinner throughout the week, Highline offers upscale bar fare and a FREE arcade with classic games. Come here on Wednesday, Nov. 25th between 4 to 6 p.m and enjoy $6 cocktails and specialty 4C drinks, half-priced draft beers, and half-priced bottles of wines. Don’t forget to try your luck at Highline’s game lounge, Hi-Point, featuring arcade games like Skee-Ball, NBA Jam and Donkey Kong.


1510 N. Wells St. Chicago, IL 60610

Benchmark is a lively sports bar in the heart of Old Town with over 40 TV’s and a menu of shareable snacks, burgers, pizza, beer and signature cocktails. But, if you need more reason why Benchmark is the perfect for a gathering this month, check out their Black Wednesday specials. Join the festivities early with Benchmark’s Happy Hour from 5 to 8 p.m. on Wednesday, Nov. 25th, indulge on $5 specialty drinks and cocktails and $5 fries & tater tots.

Featured Image: Easy Bar

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