11 Actually Fun Things to Do in Chicago This Weekend

Charity runs, ugly sweater parties, and all things holiday shopping.

What do a cannabis convention, Speedo run, magic show, and beer fest have to do with holiday spirit? Only one way to find out. Here’s everything fun you can do in Chicago this weekend.

Thursday, December 2 - Sunday, December 5
Merchandise Mart
Celebrate the 20th year of this independent holiday market showcasing indie arts, goods, media, food, fashion, jewelry, glass, and more from 400 artists. In other words, it’s kind of like a real-life Etsy.
Cost: Admission runs $10 per person; vendor prices vary

Friday, December 3
Derno’s
Raise money for local youth at this ugly sweater party complete with an ugly sweater contest (obvi), Jello shots, wine pulls, a holiday photo booth, and homemade holiday cookies.
Cost: Tickets start at $55 per person

Friday, December 3 - Sunday, December 5
Clark & Catalpa
Swedish vendors line the streets of Andersonville as you stroll from shop to shop with the help of glogg from Simon’s, a drag queen-led story time, photos with Santa, and the lighting of the Andersonville menorah.
Cost: No cover; vendor prices vary

Friday, December 3 - Sunday, January 2
360 N. State Street
A Houdini chamber, bullet catch, and magic bar are just a few of the “cavalcade of wonders” that await visitors at this new immersive magic experience spread out across 300,000-cubic-feet of illusions. Hint: It’s a lot.
Cost: Tickets start at $45 per person

Thursday, December 2 - Sunday, December 5
The Bamboo Room at Three Dots and a Dash
The creative geniuses behind award-winning subterranean cocktail denThree Dots and a Dash from Lettuce Entertain You are once again unveiling their stellar bar-within-a-bar concept, The Bamboo Room, this weekend. The intimate 22-seat rum haven is the brainchild of LEYE beverage director Kevin Beary and promises a wealth of tropical libations to get you through the winter woes. Snag a reservation via Tock.
Cost: No cover; menu prices vary

Saturday, December 4
Soldier Field
If running around Soldier Field in a Santa suit is your kind of thing, this event is for you. And if that’s not quite enough exercise for you, hit another festive race on Sunday at Runstreet Art Run Chicago Holiday 5K in Uptown.
Cost: Santa Hustle registration starts at $50 per person; Registration for Runstreet Art Run runs $35 per person

Saturday, December 4
Delilah’s
This 23rd annual Christmas beer fest features more than 100 brews in what is claimed to be “the most comprehensive tasting of Christmas and winter beers held anywhere in the world.” We’re not sure about that, but we’re sure you won’t want to miss it.
Cost: Tickets run $20 per person

Saturday, December 4
Sidetrack
Run around Sidetrack in a Christmas Speedo along a one-mile course through Lakeview East—complete with an afterparty featuring awards, entertainment, games, caroling, and door prizes—at this benefit for Center on Halsted.
Cost: $35

Saturday, December 4 - Sunday, December 5
Hilton Chicago
The first cannabis convention focused exclusively on the Illinois market takes over the Hilton Chicago this weekend with panels, discussions, exhibitors, and more. Keep the party going on Sunday when the Dispensary 33-curated Windy City Smoke Up pops up in a secret location.
Cost: Convention tickets start at $25 per person; Smoke Up tickets start at $55 per person

Sunday, December 5
Sleeping Village
This Krampus-themed party features live music from White Mystery and “a sardonic holiday release record” from Wild Earp & the Free For Alls, plus a costume contest, puppet show, and meat and veggie sausages.
Cost: Tickets start at $12 per person; additional prices vary

Sunday, December 5
Salvage One
This annual holiday pop-up showcases wares from 70+ artists and vendors centered around recycled art and wellness with food and drink, a hand pan concert, charity creations, and “generally awesome things.”
Cost: No cover; vendor prices vary

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Jay Gentile is an award-winning freelance journalist specializing in travel, food & drink, culture, events and entertainment stories. In addition to Thrillist, you can find his work in The Washington Post, The Guardian, CNN Travel, Chicago Tribune, Lonely Planet, VICE, Outside Magazine and more. Follow @thejaygentile.