Everything Fun You Can Do in Chicago This Weekend

These are all your local must-hit music and food festivals, events, movies, markets, deals, and concerts to help you make the most of your weekend.

When your weekends don’t include a Monster Trucks glow party, a mac & cheese bar crawl, and a Dungeons & Dragons drinking performance, you gotta be asking yourself what sort of wrong turn you have taken in life. Luckily, you don’t have to ask yourself such silly questions. Here’s everything fun you can do in Chicago this weekend.

Friday, January 27
Sure, anyone can buy art. But isn’t it more fun to watch the art being created live? Such is the idea behind this event in which artists each have 20 minutes to turn blank canvases into works of art over three rounds, with audience votes determining the winner. Don’t worry, you can still buy the art after via silent auction.
Cost: $17 - $25

Friday, January 27 - Saturday, January 28
City Winery
Veteran comic/actor/author Kevin Nealon brings his stand-up act to Chicago for three shows over two nights. It’s January in Chicago. You could use a laugh.
Cost: $40 - $65 per show

Saturday, January 28
Various Wrigleyville locations
Combining mac & cheese with the almighty bar crawl isn’t some far-flung fantasy created in Caligula’s workshop. It’s an actual thing happening this weekend featuring seven mac & cheese servings, drink specials at nine Wrigleyville bars, and giveaways.
Cost: $10 - $20

Saturday, January 28
Argyle & Winthrop
This Uptown community tradition dates back 40 years and features 20+ local community groups, cultural institutions, dancers, and performers plus family friendly-activities and pop-ups in celebration of the Year of the Rabbit.
Cost: Free

Saturday, January 28
Coats and hats are great and all. But whiskey is better. Especially when said whiskey is being poured over the course of 2-3.5 hours with live music, food/drink specials, brand ambassadors, and more.
Cost: $0 - $400

Saturday, January 28 – Sunday, January 29
NOW Arena
If you’re wondering if those hallucinogens you “mistakenly” took in college have finally kicked in, don’t worry. Like it or not, there really is a mashup of Monster Trucks and a glow party happening before your very eyes. Actually, three of them.
Cost: $13 - $76+ per show

Sunday, January 29
Wentworth & Cermak
Celebrate year 4721 of the Chinese New Year with traditional lion and dragon dancing teams, colorful floats, marching bands, local groups and more. And yes, Chinatown restos are open for business.
Cost: Free

Sunday, January 29
Den Theatre
Alcohol makes any Dungeons and Dragons experience more entertaining, as this event by Rough Magic so clearly demonstrates. Bring your adventuring party of up to six people as professional “dungeon masters” lead you in a D&D One Shot Adventure.
Cost: $33

Now through Sunday, February 5
Various locations
In Chicago, a week is 17 days. At least when that week is Chicago Restaurant Week, continuing this weekend with special deals and events from 300+ local restos. If you can’t find something new to get excited about, you aren’t trying hard enough.
Cost: $25 for lunch/brunch, $42 - $59 for dinner

Now through Sunday, January 29
Various locations
More than 100 live puppetry performances and events take place in venues across the city, transforming Chicago into the puppet capital of the world for one final weekend. Do yourself a favor and get weird while you still can.
Cost: Varies

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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.