Where To Do Holiday Stuff Around Chicago

From hot chocolate to ice skating, it’s time to get into the holiday spirit (whether you like it or not).

It’s that magical time of year when the chill in the air feels invigorating, the snow is charming and freshly driven, and winter has yet to wrap its icy grip around our throats and not let go until April. So, it’s time to take advantage. Whether you want to drink mulled wine under twinkle lights, watch holiday movies, or throw an ax and go ice skating (please not at the same time), here are 16 bars, pop-ups, and special events where this will be possible.

The Stuff

Jack Frost Winter Walk

When you think of “holiday stuff”, Jack Frost is what you’re imagining—even if you don’t realize it. It’s a large, outdoor holiday event in Goose Island with an ice skating rink, photo booth, ax throwing, holiday music, twinkle lights, and Christmas trees for sale. Tickets start at $23, and you can get them here. It’s open until January 2nd.

Christkindlmarket imageoverride image


Even if your only experience with Christmas in Chicago was a layover at O’hare, you probably already know about Christkindlmarket. But it was canceled last year, so we consider it our duty to remind you about the European holiday market at Daley Plaza in the Loop. It’s full of food stands, unbearably cute ornaments, all sorts of decorations, music, spiced wine, and roasted nuts. In case you forgot, there’s another Christkindlmarket in Wrigleyville.

Hotel Zachary

There’s a lot of cute winter stuff happening at Hotel Zachary at Gallagher Way in Wrigleyville. This is where you’ll find the second outpost of Christkindlmarket (which includes all the stuff we mentioned above) plus ice skating, curling, and ice bumper cars. And Friday through Sundays until December 19th, you can take pictures with Santa—and thankfully you can bring your pets.

Fairmont Hotel

Fairmount Hotel off of Millenium Park has a winter-themed lounge they’re calling Fairmont Chicago Lodge. There are indoor fire pits, holiday decorations, Happy Hours, and holiday movie screenings. And if you’re just having so much fun you decide you want to live inside the holiday universe forever, they’re also offering overnight packages. Check here for details.

Jojo's Shake Bar imageoverride image

Jojo's Shake Bar

As usual, JoJo’s has you covered if you want to do cute seasonal sh*t, and post pictures of it. Their Winter Wonderland pop-up takes place in a heated tent, and includes a massive Christmas tree, oversized presents, private igloos, and a red vintage pick up truck. They also have milkshakes, hot chocolate, and dishes like pot pie and a “snowflake” grilled cheese.

The Sixth imageoverride image

The Sixth

This cocktail bar in Lincoln Square has a half-Hanukkah/half-Christmas pop-up bar called “OY To The World.” It goes through January 9th, and has specialty drinks,bar snacks, and holiday decorations. They have it set up with a dividing line down the middle of the bar that splits the space into its respective themes. They have things like a Hanukkah disco party, the “Mistletoe Makeout Corner”, Elf On The Shelf, and Mensch On A Bench. You can make reservations here.

The Graystone Tavern imageoverride image

The Graystone Tavern

“8 Crazy Nights” is a Hanukkah-themed pop-up bar at The Graystone Tavern in Wrigleyville. And folks, there’s a lot going on here. From now until January 2nd, you can drink inside a bar full of over 14,000 blue and white twinkle lights and Hanukkah decorations. There will also be themed cocktails, latkes, matzo ball soup, and brisket.

The Pink Squirrel review image

The Pink Squirrel

    Perfect for
  • Big Groups
  • Birthdays
  • Drinks & A Light Bite

This retro bar in Logan Square recently reopened after being closed since the beginning of the pandemic. To commemorate, The Pink Squirrel has turned into a holiday pop-up bar. This means seasonal decorations and lots of colorful twinkling lights. And more importantly: they still have duckpin bowling, which is basically like regular bowling only smaller (and you don’t have to wear someone’s old shoes).

Houndstooth Saloon

Hours: THURSDAY5:00PM to 2:00AM

Houndstooth Saloon in Lincoln Park has the “Griswold’s at Houndstooth” Christmas pop-up from now until February 8th. It’s inspired by National Lampoon’s Christmas Vacation, and the bar will be decorated like different scenes from the film. There will also be movie-themed dishes like the Christmas Bonus (a triple decker PB& J with fig jelly), drinks like mulled wine, and special events. There’s a $5 cover charge, which goes towards Toys for Tots.

Fatpour Tap Works

This is another holiday movie pop-up, and it’s at Fatpour in Wicker Park. The theme here is A Christmas Story, and the bar has a ton of lights, ornaments, and a 24-foot Christmas tree that sparkles from blocks away. It goes through December 26th, and you can get more information here.

We normally go to Woodies because of their fantastic chicken wings, but from now until the end of the month this sports bar is hosting a Winter Wonderland Luau pop-up. The space will be full of decorated palm trees, Christmas lights, ornaments, a six-foot Elvis cutout, and one of those inflatable beach santas. Check out their site for the full lineup of events and to make reservations.

Good Measure

Bar Food in River North

    Perfect for
  • Casual Weeknight Dinner
  • Dining Solo
  • Drinking Good Cocktails
  • Drinks & A Light Bite
  • Eating At The Bar
  • First/Early in the Game Dates
  • Late Night Eats
  • Walk-Ins

Good Measure in River North has turned itself into the “Holiday Cheers Bar”. This means the entire bar is covered in seasonal decorations and there are cocktails like hot toddies and a persimmon mule and agua fresca. Every Wednesday during the month of December they’re hosting holiday movie marathons, starting at 7pm. This might be a good time to mention that Good Measure also has incredible food.

Santa Baby Christmas Bar imageoverride image

Santa Baby Christmas Bar

If Mariah Carey was a pop-up bar, she’d be Santa Baby. It’s a giant, multi-story holiday pop-up in Wrigleyville at Deuces. Along with a ton of decorations, there are themed cocktails, shots, milkshakes, snacks, and you can also rent a heated cabana. Which is what Mariah would do if she deigned to show up. Which she wouldn’t.

Parson’s Chicken & Fish imageoverride image

Parson's Chicken & Fish

American in Humboldt Park


Get Directions  |   773-384-3333  |  Website

Hours: THURSDAY10:00AM to 2:00AM
    Perfect for
  • Big Groups
  • Day Drinking
  • Dogs
  • Drinking Good Cocktails
  • Eating At The Bar
  • Impressing Out of Towners
  • Outdoor/Patio Situation
  • People Watching

On December 11th, the Logan Square location of Parson’s is hosting the “World’s Tiniest Tree Lot” from 3pm-11pm. The event is in support of the Love Fridge, and you can swing by and get a free mini Christmas tree. There will also be photos with Santa, mini ornament decorating, negroni slushies, fried chicken, and the rest of their menu, too.

Tack Room imageoverride image

Tack Room

Unlike that apartment across the hall, this piano bar in Thalia Hall in Pilsen is tastefully decorated for the holidays. So if you want to listen to music while looking at garland, Christmas trees, and twinkle lights, come here. They also have seasonal cocktails and live music every night they’re open. Click here for details.

Saint Lou’s Assembly imageoverride image

Saint Lou's Backyard

American in Fulton Market

Hours: THURSDAY5:00PM to 10:00PM
    Perfect for
  • Brunch
  • Casual Weeknight Dinner
  • Day Drinking
  • Drinking Good Cocktails
  • Eating At The Bar
  • Lunch
  • Outdoor/Patio Situation

Lou’s Backyard is another bar that’s decorated for the holidays. This West Loop pop-up is called Lou’s Lights, and it’s free to enter. There are a ton of decorations, fire pits, and things like ’s’mores pie and boozy hot chocolate. Reservations can be made here.

Revival Food Hall

On December 10th and 11th Revival Food Hall is hosting a night market on saturday, and a day market on Saturday. There will be curated gift baskets from from local chefs, along with food and drinks you can give yourself while you’re shopping around. Check here for more info.

Suggested by writer