Our weekend guide
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. Read the guide →
12:00 AM
DePaul Blue Demons Mens Basketball vs. Notre Dame Fighting Irish Mens Basketball
Wintrust Arena Tickets
12:00 AM
The Chicago Theatre Tour Experience
The Chicago Theatre Tour Experience Tickets
12:00 AM
Chicago Architecture Center River Cruise Aboard First Lady
Chicago Architecture Center - First Lady Tickets
11:00 AM
Vip Stadium Tour
Soldier Field Tickets
12:00 PM
Yousuke Yukimatsu
The Fields Studios Tickets
5:00 PM
***OFF-SITE*** Beatles & BBQ w/ Phil Angotti & Friends at Cheney Mansion!
FITZGERALDS NIGHTCLUB $68
5:30 PM
HAPPY HOUR in the SIDEBAR: KATHRYN & CHRIS!
FITZGERALDS SIDEBAR Free
5:30 PM
Happy Hour in the Sidebar with THE SCOVILLES!
FITZGERALDS SIDEBAR Free
6:00 PM
This Wild Life w/ Nate Bergman
Chop Shop - IL Tickets
7:00 PM
The Book of Mormon (Chicago)
Cadillac Palace Tickets
7:00 PM
Rebecca Black - Exhibitionism on Tour
House of Blues Chicago Tickets
7:00 PM
The Winter's Tale
Chicago Shakespeare Theater Tickets
7:00 PM
Bassvictim
Cermak Hall Tickets
7:00 PM
Chicago Steel vs. Youngstown Phantoms
USG Arena at Blackhawks Ice Center Tickets
7:00 PM
Chicago Blackhawks vs. Montreal Canadiens
United Center Tickets
7:00 PM
This Wild Life
Chop Shop Tickets
7:00 PM
Lil Ed & The Blues Imperials/Nora Jean Wallace Blues Band
Kingston Mines - Chicago Blues Center $23
7:00 PM
Adam Ray: WHO IS ME Tour
Athenaeum Theatre Tickets
7:00 PM
Adam Ray
Athenaeum Theatre Tickets
7:00 PM
Randy Feltface
Vic Theatre Tickets
7:00 PM
BRAD ARENA / THE LONG GOODBYE
Cubby Bear $13
7:00 PM
Chicago Stars FC vs. Houston Dash
Martin Stadium Tickets
7:00 PM
Ian Bagg
Chicago Improv $33
7:00 PM
LAKEVIEW - WRECK MY NIGHT TOUR
Hobart Art Theater Tickets
7:30 PM
Tedeschi Trucks Band: Future Soul 2026 Tour
The Chicago Theatre Tickets
7:30 PM
Music Theater Works Presents: Escape to Margaritaville
North Theatre at North Shore Center for the Performing Arts Tickets
8:00 PM
Gilla Band
Bottom Lounge Tickets
8:00 PM
Maggie Rose
Garcia's Chicago Tickets
8:00 PM
William Elliott Whitmore, Meg & the Wheelers
Reggies Rock Club Tickets
8:00 PM
Silvis, Everyday Fantastic, Om In Gold
Reggies Bananna's Shack Tickets
8:00 PM
Gilla Band, Piss
Bottom Lounge $32
8:00 PM
*SOLD OUT* PLAYGRND SERIES CHICAGO
Thalia Hall Free
8:00 PM
Sammy Rae & The Friends - the GET DOWN!
The Salt Shed Indoors (Shed) Tickets
8:00 PM
Austin Snell - Colors Tour 2026
Joe's on Weed Street $14
8:00 PM
Austin Snell (21+ Event)
Joe's on Weed Street Chicago Tickets
8:00 PM
Hablando Huevadas - US Tour 2026
Copernicus Center Tickets
8:00 PM
Vincent Neil Emerson w. Dax Lindholm
SPACE $34
8:00 PM
Menudo 50
Rosemont Theatre Tickets
8:00 PM
La Diosa
George Van Dusen Theatre at North Shore Center Tickets
8:00 PM
Matt Mathews: Not What I Ordered World Tour
The Venue at Horseshoe Casino Tickets
8:00 PM
Matt Mathews | Official Caesars Ticket + Hotel Packages
The Venue at Horseshoe Casino Tickets
8:30 PM
THE BONO BROS BAND w/ special guests Chris Neville and Nick Kitsos return to FITZGERALDS Historic Nightclub to raise awareness and funds for NAMI (National Alliance on Mental Illness)
FITZGERALDS NIGHTCLUB $24
8:30 PM
FRIDAY Night in the SIDEBAR w/ RIGHTEOUS ROOSTER!
FITZGERALDS SIDEBAR Free
8:30 PM
The Ron Burgundy's
Joe's Live Rosemont $17
9:00 PM
MJT the Band, Desmond Jones, When We Was Kids
Reggies Music Joint Tickets
9:00 PM
¥ØU$UK ¥UK1MAT$U: Autumn 2026 Tour
Aragon Ballroom Tickets
9:30 PM
Vinny Guadagnino
The Den Theatre Tickets
9:30 PM
The Messengers
Carol's Pub $8
10:00 PM
Grabbitz
Outset Tickets
10:00 PM
In the Mix
Three Top Lounge Free
12:00 AM
Northwestern vs Rutgers and The Great Chicago Food Festival
Ryan Field Tickets
11:00 AM
FITZGERALDS FALL FAIR 5!
FITZGERALDS PATIO Free
12:00 PM
Bluegrass Brunch in the NIGHTCLUB with The BOX BAND!
FITZGERALDS NIGHTCLUB Free
2:00 PM
The Winter's Tale
The Yard at Chicago Shakespeare Tickets
3:00 PM
The Best of The Second City
Second City-Chicago: Mainstage Tickets
4:00 PM
The Wrecks - Finally : OUTSIDE Tour
House of Blues Chicago Tickets
5:00 PM
SIDEBAR CLOSED for Private Event
FITZGERALDS SIDEBAR Tickets
6:00 PM
Nice as F**k - (EARLY SHOW)
Outset Tickets
6:00 PM
Soul Jam Featuring Russell Thompkins Jr. & the New Stylistics
Hard Rock Live Northern Indiana Tickets
6:30 PM
Badluv, Dan Vallejo, KR!S Cortez, Freshman
Reggies Bananna's Shack Tickets
Tomorrow Friday, Oct 23
11:00 AM
Vip Stadium Tour
Soldier Field Tickets
12:00 PM
Yousuke Yukimatsu
The Fields Studios Tickets
5:00 PM
***OFF-SITE*** Beatles & BBQ w/ Phil Angotti & Friends at Cheney Mansion!
FITZGERALDS NIGHTCLUB $68
5:30 PM
HAPPY HOUR in the SIDEBAR: KATHRYN & CHRIS!
FITZGERALDS SIDEBAR Free
5:30 PM
Happy Hour in the Sidebar with THE SCOVILLES!
FITZGERALDS SIDEBAR Free
6:00 PM
This Wild Life w/ Nate Bergman
Chop Shop - IL Tickets
7:00 PM
The Winter's Tale
Chicago Shakespeare Theater Tickets
7:00 PM
This Wild Life
Chop Shop Tickets
7:00 PM
Lil Ed & The Blues Imperials/Nora Jean Wallace Blues Band
Kingston Mines - Chicago Blues Center $23
7:00 PM
BRAD ARENA / THE LONG GOODBYE
Cubby Bear $13
7:30 PM
Tedeschi Trucks Band: Future Soul 2026 Tour
The Chicago Theatre Tickets
8:00 PM
Gilla Band
Bottom Lounge Tickets
8:00 PM
William Elliott Whitmore, Meg & the Wheelers
Reggies Rock Club Tickets
8:00 PM
Silvis, Everyday Fantastic, Om In Gold
Reggies Bananna's Shack Tickets
8:00 PM
Gilla Band, Piss
Bottom Lounge $32
8:00 PM
*SOLD OUT* PLAYGRND SERIES CHICAGO
Thalia Hall Free
8:00 PM
Matt Mathews: Not What I Ordered World Tour
The Venue at Horseshoe Casino Tickets
8:00 PM
Matt Mathews | Official Caesars Ticket + Hotel Packages
The Venue at Horseshoe Casino Tickets
8:30 PM
THE BONO BROS BAND w/ special guests Chris Neville and Nick Kitsos return to FITZGERALDS Historic Nightclub to raise awareness and funds for NAMI (National Alliance on Mental Illness)
FITZGERALDS NIGHTCLUB $24
8:30 PM
FRIDAY Night in the SIDEBAR w/ RIGHTEOUS ROOSTER!
FITZGERALDS SIDEBAR Free
8:30 PM
The Ron Burgundy's
Joe's Live Rosemont $17
9:00 PM
MJT the Band, Desmond Jones, When We Was Kids
Reggies Music Joint Tickets
9:00 PM
¥ØU$UK ¥UK1MAT$U: Autumn 2026 Tour
Aragon Ballroom Tickets
9:30 PM
The Messengers
Carol's Pub $8
10:00 PM
Grabbitz
Outset Tickets
10:00 PM
In the Mix
Three Top Lounge Free
Saturday, Oct 24
11:00 AM
FITZGERALDS FALL FAIR 5!
FITZGERALDS PATIO Free
12:00 PM
Bluegrass Brunch in the NIGHTCLUB with The BOX BAND!
FITZGERALDS NIGHTCLUB Free
2:00 PM
The Winter's Tale
The Yard at Chicago Shakespeare Tickets
3:00 PM
The Best of The Second City
Second City-Chicago: Mainstage Tickets
5:00 PM
SIDEBAR CLOSED for Private Event
FITZGERALDS SIDEBAR Tickets
6:00 PM
Soul Jam Featuring Russell Thompkins Jr. & the New Stylistics
Hard Rock Live Northern Indiana Tickets
6:30 PM
Badluv, Dan Vallejo, KR!S Cortez, Freshman
Reggies Bananna's Shack Tickets
Other cities
Toronto this weekend
Mississauga this weekend
Brampton this weekend
Ottawa this weekend
Hamilton this weekend
Halifax this weekend
Oshawa this weekend
Winnipeg this weekend
Calgary this weekend
Edmonton this weekend
Vancouver this weekend
Montreal this weekend
Buffalo this weekend
Pittsburgh this weekend
Salt Lake City this weekend
Las Vegas this weekend
New York this weekend
Orange County this weekend
Nashville this weekend
FAQ
What's happening in Chicago this weekend?
There are 103 events in Chicago this weekend, from live music and festivals to comedy and family activities. Browse the full list above.