12 Exciting Things To Eat & Do In December guide image


12 Exciting Things To Eat & Do In December

From hot chocolate to ice skating, it’s time to get into the holiday spirit.

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 11 bars, pop-ups, and special events where this will be possible.


La Josie

La Josie has three full bars and a rooftop deck, and is one of our favorite places for a fun Mexican meal in the West Loop. And during the month of December, they'll have tamales as a special on the menu for the holiday. The varieties include rajas con queso, verdes with chicken, and pork with chile arbol. They're available for dine-in or takeout, and you can place an order here.

Jack Frost Winterfest

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, tubing, bumper cars, ax throwing, holiday music, twinkle lights, and Christmas trees for sale. Tickets start at $10, and you can get them here. It’s open until January 1st.


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. It's also where Smoke Daddy is located, which is turning into a winter cabin pop-up called "Lumberjack Lodge."

Pilsen Gourmet

Pilsen Fest is a food festival that takes place on Friday, December 16th, at Apollo's 2000. It features local and celebrity Latino chefs, with food from over 25 Chicago restaurants (like 5 Rabanitos and Amaru. Tickets are $40, and include unlimited food along with mezcal, tequila, beer, and music. More info, here.

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 domes, and a red vintage pickup truck. They also have milkshakes, hot chocolate, and dishes like pot pie and a “snowflake” grilled cheese.

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 9th, 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 has turned into a holiday pop-up bar. This means seasonal decorations and lots of colorful twinkling lights. And more importantly: they have duckpin bowling, which is basically like regular bowling only smaller (and you don’t have to wear someone’s old shoes).

Amaze Light Festival

The Amaze Light Festival is in Tinley Park at Odyssey Fun World. As the name implies, the deal here is tons of twinkly light displays. There are also lots of other winter festival-type activities like tubing, a holiday market, food and drinks, and a little train that goes around the festival. The festival runs through January 8th, and you can purchase tickets here.

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.

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.

Revival Food Hall

On December 1st-16th Revival Food Hall is hosting a holiday market Mondays through Fridays from 3-7pm. There will be curated gift baskets from local chefs, along with food and drinks you can give yourself while you’re shopping around. Check here for more info.

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12 Exciting Things To Eat & Do In December guide image