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Last Updated On: December 20, 2018

One of my absolute favorite things to do in Chicago during the holiday season is finding the best places to go for holiday cocktails. Pretty much all of December,  I’m on a mission to find the best holiday cocktails. I enjoy both loungy places that have a yummy hot toddy or a good glass of mulled wine as well as the fun, kitschy, over-the-top holiday bar with usually over-priced drinks. But hey, it’s the holidays and you’ve got to go out and have fun during this season. After all, it only happens once a year.

The Best Places to go for Holiday Cocktails in Chicago

Christkindlmarket Chicago

Christkindlmarket is a holiday MUST in Chicago. It’s also one of the best holiday markets to go to in Chicago and probably in the U.S.


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Holiday Cocktails: Hot mulled wine (make sure you pay extra to get the souvenir mug!)
Location: Daley Plaza in The Loop

Lost Lake

When the coolest Hawaiian tiki bar becomes Jingle Bell Square during the month of December. Last year, I couldn’t wait to enjoy a Santa cocktail at Lost Lake and it did not disappoint! It’s such a fun vibe and the drinks were really great too. Get there as soon as they open to avoid the line.


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Holiday Cocktails: Anything in a Santa mug
Location: 3154 W. Diversey Avenue

Paradise Park Chicago

If you love Christmas decorations and pizza (and really, who doesn’t?) you need to celebrate the holiday season with your friends at Paradise Park.


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Holiday Cocktails:  Pink Flamingo, The Hooch, or the Dixie Cup
Location: 1913 W. North Avenue

Fox Bar Chicago

From now to New Years get festive at Fox Bar on the 2nd Floor of Soho House Chicago. They will be serving festive drinks all season long in cute little mugs.


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Holiday Cocktails: TBA
Location: 113-125 N. Green Street

Parson’s Chicken & Fish

During the summer months, Parson’s has one of the coolest and most popular patios in the city but don’t let the cold stop you from coming here to enjoy some good fried chicken and maybe a hot toddy or two.


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Holiday Cocktails: A hot toddy in a festive holiday mug
Location: 2952 W. Armitage Avenue

Drawl Chicago

Looking for a cozy neighborhood spot where you can sit by the fire and enjoy a cocktail? Head to Drawl Chicago! Did you know this spot is also a whiskey bar?


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Holiday Cocktails: A hot toddy (by the fire of course)
Location: 2423 N. Clark Street

Gibson Italia

Gibson Italia is the perfect romantic spot to enjoy a few holiday-inspired cocktails as you glaze out over the Chicago River.


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Holiday Cocktails: Apple Brandy Smash, Spiced Pear Cobbler
Location: 233 N. Canal Street

The Walnut Room

The Walnut Room at Macy’s (but really, it’s always going to be Marshall Field’s to us Chicagoans) has been a magical place to celebrate the holidays since I was a little girl. There’s nothing like seeing that gigantic tree. Here’s a little tip, go there for lunch during the week at the beginning of December. Not only is there not much of a wait you might also get a table right next to the tree.


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Holiday Cocktails: Poinsettia, Eggnog Brandy Alexander, The Kris Kringle (You can also get a holiday mug to take home)
Location: 111 N. State Street

CH Distillery

Celebrate the holidays with holiday cocktails and food, inspired by everyone’s all-time favorite Christmas movie “A Christmas Story!” CH Distillery will be all decked out with Leg Lamps, tacky decorations, and of course cocktails in holiday mugs.


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Holiday Cocktails: Frozen Eggnog, the Sweater Weather
Location: 1564 W. Randolph Street

Frosty’s Christmas Bar

Last year Frosty’s Christmas Bar was such a hit, that they brought it back again. Tickets went quickly last year and lines were still long. Hopefully, that won’t be the case this year, but it’s really just part of what we do to have fun during one of the best times of the year.


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Holiday Cocktails: TBA
Location: 809 W. Evergreen Avenue

Santa Baby Bar

Last year it was all about Frosty’s Christmas Bar but this year it’s all about the new Instagramable spot, Santa Baby Bar in Wrigleyville. This new pop-up has wall-to-wall Christmas decor, multiple bars, and even Santa! Relax with a beer in Alpine Village, enjoy a cocktail in the Winter Wonderland, or hang out with the elves in “Rudolph’s”, the local elf dive bar. Sounds like a whole lotta Christmas!


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Holiday Cocktails: Spiked hot chocolate & cider, Rumchata-nog, the Elf Fashioned, and the Rum Bull Rudolph
Location: 3505 N. Clark Street


Yay for another over-the-top holiday bar! Come to Happy’s for cocktails, warm vibes, holiday sounds, and as many twinkling lights as possible. After, head to Cindy’s rooftop to see the beautiful holiday lights around the city.


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Holiday Cocktails: Varies holiday cocktails
Location: 12 S. Michigan Avenue (Chicago Athletic Association)

Public House

OMG! The Grinchmas Cake Shake! This spiked shake at Public House is definitely Instagram worthy!


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Holiday Cocktails: The Grinchmas Cake Shake
Location: 400 N. State Street

River Roast

River Roast is a cozy spot, overlooking the river, so come for brunch or lunch and maybe even enjoy a spiked hot chocolate?


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Holiday Cocktails: Smoky hot cocoa
Location: 315 N. Lasalle Street

Margeaux Brasserie/Petit Margeaux

This is another great brunch spot, especially if you love French cuisine. Stop by Margeaux Brasserie for brunch and their featured holiday cocktail, the Enlightened Holiday Trixter. On Saturday and Sundays, you can also stop by Petit Margeaux and enjoy a glass of mulled wine at this outdoor holiday pop-up market.


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Holiday Cocktails: The Enlightened Holiday Trixter
Location: 11 East Walton (Waldorf Astoria Chicago)

Sable Kitchen & Bar

When I lived downtown, Sable Kitchen & Bar was one of my go-to bars so I’m so looking forward to going to their Miracle Christmas Pop-up this holiday season.


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Holiday Cocktails: Christmas Carol Barrel, Yippie Ki Ya Mother, Run Run Roldoph
Location: 505 N. State Street

Cerise Rooftop

Cerise Rooftop is turning into Cousin Eddie’s Bar during most weekends in December. Cousin Eddie’s bar, of course, has floor-to-ceiling Christmas lights, holiday-themed cocktails inspired by favorite holiday movie, Christmas Vacation.


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Holiday Cocktails: TBA
Location: 203 N. Wabash Avenue

Upstairs at The Gwen

Come for Curling and Cocktails at Upstairs at The Gwen. Enjoy lots of fireplaces and fireplaces, play a few games of curling, and order a hot teapot of mulled wine.


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Holiday Cocktails: A hot teapot of mulled wine
Location: 521 N. Rush Street

BAITA at Eataly

The newest winter restaurant at Eataly, BAITA is now open and features food and drink perfect for the chilly ski slopes and cozy fireplaces. Featured menu items include melted cheese, warming reds, seasonal cocktails, and more). BAITA will be open through the entire winter season.


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Holiday Cocktails: A variety of wines and seasonal cocktails
Location: 43 E. Ohio Street

Elf’d Up Holiday Pop-Up Bar

In honor of the holiday movie Elf Stretch Bar & Grill is decorated from floor to ceiling with over 200 elves, a 10-foot Christmas tree, an upside down Christmas tree, wreath chandeliers, strands of colored lights, a snow machine, and more. The bar will also have featured cocktails inspired by the movie.


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Holiday Cocktails: Mr. Narwhal Vodka Cocktail, The World’s Best Cup of Naughty Coffee
Location: 3485 N. Clark Street

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Happy Holidays! xo

The Best Places to go for Holiday Cocktails in Chicago

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