15 Great Things to Do in Chicago This Weekend

Warm up with Chicago Restaurant Week, puppets and a drag queen bagel class

January 19, 2024 9:17 am
Eataly cheese variety
Eat all the cheese you can in Chicago this weekend.
Eataly Chicago

Avoid the mid-January blues this weekend with events that make trudging out in the freezing cold 100% worth it. Think things like a music festival, a cheese class and a party celebrating all things pop punk. Here are 15 things to do in Chicago this weekend.

Friday, January 19 

Chicago Restaurant Week 

For Chicago-based foodies, Restaurant Week is like the Oscars, the Super Bowl and Lollapalooza opening day all rolled into one. The event actually extends from January 19 through February 4 and features 400+ participating restaurants offering specials and deals. Get your OpenTable login ready. 

Blair Thomas holding puppet
Blair Thomas
Saverio Truglia

Chicago International Puppet Theater Festival 

Expand your understanding of the puppetry arts beyond Muppet Treasure Island this weekend with the largest event dedicated to the art form in America. The Chicago International Puppet Theater Festival features 100+ activities with artists from around the world. Ticket prices vary per show with free events offered throughout the festival. 

Band playing on a stage in front of a large crowd in black & white
Tomorrow Never Knows Festival
Tomorrow Never Knows

Tomorrow Never Knows Festival

The team at Lincoln Hall and Schubas are hosting their annual music and comedy festival this weekend, with a line-up that will make even your impossible-to-impress teenage niece jealous. Check out rising local artists, as well as musicians and comedians with a national platform. Most shows start around $20 per ticket. 

Rosanne Cash posing for photo with guitar
Rosanne Cash
Rosanne Cash

Rosanne Cash at Old Town School of Folk Music 

Singer-songwriter legend Rosanne Cash is celebrating the 30th anniversary of her album The Wheel this weekend at the Old Town School of Folk Music, with shows both Friday and Saturday night. Tickets to the general public are available for $85 with a slight discount for Old Town School of Folk Music members. 

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Brett Goldstein at The Chicago Theater

Actor, director, comedian and everyone’s crush from Ted Lasso Brett Goldstein (aka Roy Kent) is taking his stand-up tour “The Second Best Night of Your Life” to Chicago this weekend, with three shows at the Chicago Theater. Tickets start at $170.

Chicago Blackhawks vs New York Islanders at the United Center 

Escape the Chicago freeze this Friday and retreat to a slightly less cold ice hockey rink — it’s worth the chill to catch the Blackhawks take on the New York Islanders. (And why not use the cold as an excuse to treat yourself to a cup of Mindy’s famous hot chocolate and homemade marshmallows at United Center Section 212.) 300-level seats start at $59. 

Saturday, January 20 

Polar Adventure Days at Big Marsh Park

Celebrate all things winter at Big Marsh Park this weekend, with demonstrations by husky teams, guided bird hikes, winter crafts, an outdoor bonfire and live music. Admission is free and so is the chance to remember how great Chicago is, even when the temperature is in the single digits.  

Riot! At The Disco: A Pop Punk Party at Subterranean 

Spend the night dancing to the music of Green Day, Blink-182, Fall Out Boy, Jimmy Eat World and more bands from your Myspace days at this pop punk party at Subterranean. Making a pre-show Hot Topic run is encouraged but not required. Tickets are $20. 

Cheese 101: Guided Cheese Tasting at Eataly

Can’t tell your Asiago from your Havarti? Eataly has you covered with this course on Cheese 101, highlighting different styles and techniques. Sample six cheeses paired with condiments and three Italian wines, and gain the knowledge to wow your friends with your next charcuterie board. Tickets are $70. 

Stan’s Donut Festival at Stan’s Donuts River North

Sure, one donut is great, but wouldn’t your Saturday afternoon be a whole lot better with 12? Celebrate Stan’s 10th anniversary this weekend with Stan’s Donut Festival, where you can enjoy a dozen donut tastings, drinks and more. GA tickets are $20 and VIP tickets (which include two drinks) are $30. 

The Official Onesie Bar Crawl 

Dreams really do come true this weekend at the Official Onesie Bar Crawl, when wearing your pajamas to the bar is actually encouraged. Join 250+ onesie-wearing partiers at six Chicago venues, with specials, events and selfie opportunities galore. Tickets start at $20. 

Jazz, Art and Whiskey at The Green Living Room 

Spend a refined night on the town this weekend at the Jazz, Art and Whiskey event at The Green Living Room, with live musical performances, a whiskey tasting, an art exhibit and light refreshments. Tickets are available for $25. 

Sunday, January 21 

Bagel Making Drag Queen Brunch at Get In The Kitchen 

It’s a cooking class! It’s a drag show! It’s a party! It’s all of the above! Sip on a complimentary strawberry Mimosa while you learn how to make bagels, frittatas and flavored cream cheeses, followed by a fun-filled drag show. Tickets to the class are $69. 

Yoga Class at Midwest Coast Brewing 

Finally, yoga the way it was meant to be taught — with a craft beer or seltzer served afterwards. Class will be held inside the Midwest Coast Brewing taproom and is open to all skill levels. Attendees should bring their own mats, and tickets are $20. 

Ginger Minj With Gidget Galore at the Mercury Theater

Drag Race superstar Ginger Minj, alongside the famed Gidget Galore, take their hit Provincetown comedy and music show to Chicago this weekend, with performances running until February 14. Tickets start at just $40. 


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