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Love it or hate it, Black Wednesday and Black Friday have become unconventional holidays. Even bars and restaurants are jumping on the "big deals" bandwagon. So check out our list of knock out food and drink specials around Chicago if you plan to head out for America's new favorite pastime.

Umbria
Caffe Umbria kicks off Free Drink Fridays on Black Friday.

Free Drink Fridays at Caffè Umbria

  • Friday, November 27

In recognition of Black Friday, the recently opened Caffè Umbria (346 N. Clark St.) will launch their Free Drink Friday promotion. Every Friday beginning November 25, guests who purchase a bag of any of their fresh roasted coffee blends ($11.50 each) will receive a complimentary coffee of their choice. This includes both traditional Italian espresso drinks like Americano and Cappuccino, and specialty drinks like Caffe Assisi (espresso, Italian chocolate sauce, cinnamon, whipped cream), and Espresso Shakerato (espresso shaken over ice, served neat in a sugar rimmed martini glass).

Black Wednesday Specials at Commonwealth

  • Wednesday, November 25

Guests who visit Commonwealth Tavern in Roscoe Village (2000 W. Roscoe St.) on Black Wednesday will enjoy $5 seasonal draft beers, $5 well drinks, and half-price appetizers from 4 p.m. to 7 p.m. including items like Soft Pretzel (served with beer cheese and mustard sauce; regularly $6), Queso Fundido (roasted poblano, chorizo, chihuahua cheese; regularly $10), and wings (buffalo, celery, carrot OR bbq, served with bread and butter pickles; regularly $10).

Compass Bar
The beer-centric bar will have $5 Stout and Black IPA's on Black Wednesday.

Compass Bar Black Wednesday & Black Friday Specials

  • Wednesday, November 25 and Friday, November 27

Guests who visit Compass Bar in Lincoln Park (433 W. Diversey) on Black Wednesday will enjoy specials including $5 Stout and Black IPA's and $5 Jager shots. On Black Friday, Compass Bar will open at 3 p.m. and show the Blackhawks vs. Ducks game at 4 p.m. Specials will include Happy Hour from 4 p.m. to 6 p.m. featuring $5 well drinks.

Black Wednesday Specials & Black Friday Benefit at Flagship

  • Wednesday, November 25 and Friday, November 27

Guests who visit Flagship (1622 W. Belmont Ave.) on Black Wednesday will enjoy Trivia Night from 7 p.m. to 9 p.m. as well as specials including $3 Blue Moon drafts, $3 Blue Moon seasonal bottles and $4 Fireball shots.

On Black Friday, November 27, Flagship will offer their Friday Happy Hour package from 6 p.m. to 9 p.m. Options include a $25 package (well drinks and domestic drafts plus one food item) or a $30 package (call drinks, domestic drafts and bottles and one food item).

Additionally, patrons who bring a non-perishable food item anytime during the month of November will receive $5 off the happy hour package price. Donations will benefit the Lakeview Food Pantry.

Kanela
Kanela is giving out complimentary Julius Meinl coffee with food purchase on Black Friday, if you can prove you were shopping.

Black Friday Special at Kanela Breakfast Club

  • Friday, November 27

Shoppers who visit Kanela's Lakeview, Old Town, Wicker Park or Streeterville location on Black Friday will receive a complimentary Julius Meinl coffee with any food purchase when they show their receipt from shopping that day.

Win a Free Lunch at MAK on Black Friday

  • Friday, November 27

Guests who dine in at MAK (1924 W. Division) on Friday, November 27 while shopping in Wicker Park for Black Friday can enter to win a lunch for up to 12 guests by dropping off a business card at the restaurant.

Black Wednesday & Black Friday Specials at Municipal Bar

  • Wednesday, November 25 and Friday, November 27

On Black Wednesday, Municipal Bar (216 W. Ohio) will feature half-price bottle service, $5 Moscow Mules, $5 Jack Daniels shots, and a DJ at 9 p.m. On Black Friday, Municipal will open at 11 a.m. and show the Chicago Blackhawks vs. Anaheim Ducks game at 4 p.m.

PTG
This marks the fifth year of Pioneer Tavern Group's Black Out Black Wednesday Trolley Crawl.

5th Annual Black Wednesday Trolley Crawl

  • Wednesday, November 25
  • Trolley runs every 30-minutes between each location

Guests can celebrate Black Wednesday with Pioneer Tavern Group as they host the 5th annual Black Wednesday Trolley Crawl that features a complimentary trolley 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.

The trolley launch point begins at Lottie's at 7 p.m. and heads to The Pony, which will feature a Chicago Blackhawks vs. San Jose Sharks official roadwatch party beginning at 9 p.m. with Blackhawks ticket giveaways. The trolley also makes a stop at Frontier which will have a "Barn Party" featuring a campfire, music, S'mores, spiced wine, hot cocktails, smoked turkey legs, and free screen printed t-shirts (while supplies last).

To guarantee a spot on the trolley, guests can sign up at the bar or email freetrolley@pioneertaverngroup.com.

Phil Stefani's 437 Rush Black Wednesday & Black Friday Specials

  • Wednesday, November 25 and Friday, November 27

Chicagoans who visit Phil Stefani's 437 Rush (437 N. Rush St.) on Black Wednesday will enjoy half-price wine all day (excluding reserve selection. On Black Friday, 437 Rush will offer half-price appetizers from 4:37 p.m. to 7 p.m., $5 house wine by the glass, $4 craft beer, and $3 Bud or Miller Lite, available all day.

Black Wednesday and Black Friday at Stretch

  • Wednesday, November 25 and Friday, November 27

Guests who visit Stretch in Wrigleyville (3485 N. Clark St.) on Wednesday, November 25 will enjoy specials including $3 Miller and Coors, and $4 Tijuana Sweet Tea shots.

On Black Friday, November 27, Stretch will open at 2 p.m. for a "Black Friday Sale". Guests will enjoy two-for-one bombs all day, half-off cocktails from 2 p.m. to 6 p.m., and Stretch's $20 Happy Hour package from 6 p.m. to 10 p.m. which includes a cheeseburger and fries or appetizer of choice, domestic bottles, well drinks, and $5 Jameson shots. Guests can upgrade to call drinks for $25. They will also show the Blackhawks vs. Ducks game at 4 p.m.

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