Weekend guide · October 23–25, 2026
Things to Do in Chicago This Weekend: October 23–25, 2026
Friday is packed with live music, comedy, theater, and sports—plenty of ways to kick off the weekend in Chicago.
By Weekend Owl · Published October 22, 2026
This weekend in Chicago, Friday is the standout with a full slate of concerts, comedy, theater, and sports. You can catch the Tedeschi Trucks Band at The Chicago Theatre or Menudo 50 at the Rosemont Theatre, both on Friday night. If you’re in the mood for laughs, Adam Ray and Vinny Guadagnino take the stage for stand-up. There’s also hockey action with the Chicago Steel and a classic play at Chicago Shakespeare Theater. Saturday and Sunday are quieter, so Friday is your night to get out.
Tedeschi Trucks Band: Future Soul 2026 Tour
The Tedeschi Trucks Band: Future Soul 2026 Tour brings a night of rock music to The Chicago Theatre on Friday at 7:30 PM. If you’re looking for a classic concert outing to start your weekend, this show could be for you. The venue is at 175 N State St, right in the heart of downtown, making it easy to pair with dinner or drinks before or after.
Menudo 50
Menudo 50 is a Latin music concert happening Friday at 8:00 PM at Rosemont Theatre, 5400 North River Road. It’s a good pick if you’re up for a night of live music with a different flavor. With its later start time, this could be a fun way to cap off your Friday evening.
Vinny Guadagnino
Vinny Guadagnino brings his comedy to The Den Theatre on Friday at 9:30 PM. This is a late option for anyone who wants to keep the night going with some laughs. The Den Theatre is at 1331 N Milwaukee Ave, so it’s convenient if you want to grab a bite in the area beforehand.
Adam Ray: WHO IS ME Tour
Adam Ray’s WHO IS ME Tour stops at Athenaeum Theatre on Friday at 7:00 PM. If you’re looking for a stand-up comedy show to start your weekend, this is an early evening pick. The Athenaeum is at 2936 North Southport Avenue, making it easy to get to from many neighborhoods.
The Chicago Theatre Tour Experience
The Chicago Theatre Tour Experience offers a behind-the-scenes look at one of the city’s iconic venues on Friday. The start time isn’t announced, so if you’re interested, consider planning your day flexibly around this. The tour meets at 175 N State St, the same address as The Chicago Theatre.
The Winter's Tale
The Winter's Tale is on stage at Chicago Shakespeare Theater on Friday at 7:00 PM. If you’re in the mood for classic theater, this performance art event on Navy Pier (800 East Grand Avenue) makes for a cultured night out. Arrive a bit early if you want to enjoy the pier before the show.
Chicago Steel vs. Youngstown Phantoms
Chicago Steel faces the Youngstown Phantoms in a hockey matchup at USG Arena at Blackhawks Ice Center, Friday at 7:00 PM. For sports fans, this is a straightforward way to catch some live action and kick off the weekend. The arena is at 1801 W Jackson Blvd.
DePaul Blue Demons Mens Basketball vs. Notre Dame Fighting Irish Mens Basketball
DePaul Blue Demons take on Notre Dame Fighting Irish in men’s basketball at Wintrust Arena on Friday. The start time isn’t listed, but it’s a chance to see two college teams compete at 200 E Cermak Road. If you’re planning to go, keep your evening open for this matchup.
A plan for the weekend
Friday is the busiest night, so you might start with Adam Ray’s comedy at 7:00 PM, then head to Vinny Guadagnino at 9:30 PM if you’re up for more laughs. If music or sports is more your style, catch the Tedeschi Trucks Band at 7:30 PM or the Chicago Steel hockey game at 7:00 PM. Saturday and Sunday have no events on this list, so Friday is your best bet for a night out. Whichever you choose, there’s plenty happening to start your weekend.
How this guide is made: each week we pick one event from each kind of event listed in Chicago (music, comedy and theatre, the arts, sports, food and drink, family, community, wellness), favouring named acts and the bigger nights. The write-up is drafted with AI from those listings and nothing else. Times and prices come from the ticket sellers, and plans change, so confirm with the organizer before you go.
Other cities this weekend: Brampton · Buffalo · Calgary · Edmonton · Halifax · Hamilton · Las Vegas · Mississauga · Montreal · Nashville · New York · Orange County · Ottawa · Pittsburgh · Salt Lake City · Toronto · Vancouver · Winnipeg