15 Great Things to Do in Chicago This Weekend

Spend your weekend enjoying comedy, 90s-themed Whirlyball and bottomless hot chocolate

January 12, 2024 6:43 am
Spread of bottles and cups
Here's everything you should do in Chicago this weekend.
NA Day

Winter may finally be here in full force (hello, negative temperatures), but don’t let that stop you from throwing on your bulkiest coat and enjoying the best that Chicago has to offer this weekend, including stand-up comedy, live music and the chance to swap travel stories with Rick Steves himself. Here are 15 great things to do in Chicago this long weekend. 

Friday, January 12 

Get your 2024 resolutions off to a good start (assuming your resolution was to consume as many cups of hot chocolate as possible). Tickets to this sugar-filled fever dream start at $15 and include bottomless hot chocolate and cookie samples from a wide range of bakeries. 

Hasan Minhaj at the Chicago Theater 

The Daily Show correspondent, former host of the Patriot Act and Celebrity Jeopardy participant Hasan Minhaj is in town this weekend, with back-to-back Friday night shows at the Chicago Theater. Tickets start at $70. 

Chicago Cubs Convention at the Sheraton Grand Chicago

Now’s your chance to share your surefire outfield strategy with the Cubs coaching squad — or at least your chance to meet Cubs legends, watch panel discussions and start emotionally preparing for the 2024 season. The convention kicks off on Friday, and weekend passes start at $125. (Keep your eye on the Chicago Cubs’ website for information about single day tickets, which will be released as available.) 

Saturday, January 13 

Packed crowds and booths at the Travel and Adventure show
Travel and Adventure show
Sofia Negron Photography

Chicago Travel and Adventure Show at the Donald E. Stephens Convention Center

Whether your 2024 travel plans include scaling Mount Kilimanjaro or just finally making your way to the end of the Brown Line, the Chicago Travel and Adventure Show is worth a stop. Learn about the latest travel trends, book your next trip and swap stories with travel celebrities Rick Steves and Phil Rosenthal themselves. Single-day admission is $13.  

Rebirth Brass Band at Thalia Hall

New Orleans legends the Rebirth Brass Band are taking the stage at Thalia Hall this weekend. Founded 35 years ago, the band has played alongside everyone from the Grateful Dead to Ani DiFranco. General admission tickets are $30. 

The 8 Best Hotels in Downtown Chicago
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Founders Day at the Peggy Notebaert Nature Museum 

Get an inside peek at the Peggy Notebaert Nature Museum this Saturday at Founders Day, where attendees can meet with the collections team, oggle rare specimens, make nature journals and learn more about getting involved. Tickets are $15 for Illinois adult residents, which includes access to the event and the museum. 

Woman pouring nitrogen into a cup
Drink mocktails and have all the fun of enjoying a cocktail — but without the hangover
Chicago AF

NA Day 2024 at Loft on Lake

Modeled after a traditional craft beer fair or wine festival, you’ll have the chance to sample a wide range of non-alcoholic spirits, wine and beer at this event — without the brutal Sunday hangover. Tickets are $25. 

Handmade Market at the Empty Bottle

Holidays, shmolidays — it’s time to buy yourself some presents. Meet with local artisans at the Handmade Market, which is free to attend. (But don’t blame us if you end up buying one of everything available.) 

Earliana McLaurin, participant in the 27th Annual Fillet of Solo Festival
Earliana McLaurin, participant in the 27th Annual Fillet of Solo Festival
Fillet of Solo Festival

Fillet of Solo Festival at Multiple Venues 

Dive headfirst into Chicago’s vibrant storytelling and live lit scene with the Fillet of Solo Festival, featuring a wide range of powerful performances. The festival runs from January 13 until Jan. 22, with tickets starting at $12 per show. 

Sunday, January 14

20×2 Chicago: Do You Remember? at Gman Tavern

Join 20 of Chicago’s most creative people from all walks of life who each get two minutes to answer the show’s Question of the Day however they’d like. Tickets are $20. 

Totally 90s: Whirlyball’s 30th Anniversary at Multiple Locations 

Dust off your overalls and freshen up your Rachel haircut — Whirlyball is celebrating their birthday this weekend with a 90s-themed party at their Chicago, Naperville and Vernon Hills locations. The event features a buffet based on the original 1993 menu, themed drinks, movies, music, Cosmic Bowling, laser tag and rounds of Whirlyball. Tickets are $15. 

Thank You for Smoking: A Celebration of Smoked Beer at Dovetail Brewing

Get your fill of smoky beers with an open bar from Dovetail Brewing and an all-you-can-eat Frühschoppen (a German-style beer brunch) from 10 a.m. to 1 p.m. If brats and spaetzle aren’t your thing, pop in after 1 p.m. when the celebration continues with guest beers, smoky snacks and more. 

Monday, January 15 

Stories for Peace: A Celebration of MLK Day at SPACE

Join Story Jam as they commemorate Martin Luther King Jr. Day with true, personal stories and original music, all celebrating the spirit and courage of Dr. King. Tickets start at $18. 

Midnight Sun Presents a Tribute to Stevie Wonder at City Winery

Chicago R&B Legends the Midnight Sun play a tribute to Stevie Wonder this Monday, with three-part harmony, a full horn section and percussion. Can’t tell your “Superstition” from your “Isn’t She Lovely”? Midnight Sun will also play at City Winery on Sunday with a Blaxploitation Mixtape show. Tickets range from $28 to $48.

PULSE: An Annual MLK Tribute Concert at the Auditorium Theater

The Chicago Sinfonietta honors Dr. Martin Luther King Jr. this weekend with their annual MLK Tribute Concert, featuring the music of Scott Joplin, Xavier Dubois Foley and Margaret Bonds. Tickets start at $25.


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