#1
Fri, Oct 9, 2026 · 7pm; Sat, Oct 10 · 5pm and 8pmTicket required
Jerry Seinfeld Live!
Downtown, the Loop & West Loop
The stand-up legend does a live set at the Chicago Theatre, one night only.
One Weekend Only
Things to Do in West Loop, Chicago Saturday Night, Columbus Day Weekend 2026
22 picks
The 10 best things to do in West Loop, Chicago on Saturday night, Oct 10
- Jerry Seinfeld Live! — Fri, Oct 9 7pm; Sat, Oct 10 · 5pm and 8pm · Downtown
- Beck – Ride Lonesome Tour — Fri, Oct 9 8:00pm · Downtown
- Chicago Fire FC vs. New York City FC — Saturday, October 10, 1:30 PM · Downtown
- Chicago Art Fair — October 7–10 Wed 5–8 PM; Thu–Fri 11 AM–8 PM · Downtown
- Operation Mincemeat: A New Musical — Through Oct 11 · Downtown
- Jekyll& Hyde — Oct 2–Oct 18, 2026 · Downtown
- Play On! — Chicago Shakespeare Theater — September 11–October 18; selected performances · Downtown
- Kowalski — September 15 – October 25 · Downtown
- Symphony Ball with Klaus Mäkelä — Sat, Oct 10 6:30pm · Downtown
- Switchfoot with special guest Anberlin - Forever Now Tour — Sat, Oct 10 7:00pm · Downtown
#1Fri, Oct 9, 2026 · 7pm; Sat, Oct 10 · 5pm and 8pm · One Weekend Only
Jerry Seinfeld Live!
The stand-up legend does a live set at the Chicago Theatre, one night only.
Add to calendar#2
Fri, Oct 9, 2026 · 8:00pm
Beck – Ride Lonesome Tour
Downtown, the Loop & West Loop
Beck opens two nights at the Auditorium on a new 25-date North American tour.
One Weekend Only
#2Fri, Oct 9, 2026 · 8:00pm · One Weekend Only
Beck – Ride Lonesome Tour
Beck opens two nights at the Auditorium on a new 25-date North American tour.
Add to calendar#3
Saturday, October 10, 2026, 1:30 PM
Chicago Fire FC vs. New York City FC
Downtown, the Loop & West Loop
The Fire take on New York City FC in an afternoon MLS match at Soldier Field.
One Day Only
#3Saturday, October 10, 2026, 1:30 PM · One Day Only
Chicago Fire FC vs. New York City FC
The Fire take on New York City FC in an afternoon MLS match at Soldier Field.
Add to calendar#4
THE MART, River North, Downtown, the Loop & West LoopDavid Wilson from Oak Park, Illinois, USA · CC BY 2.0 · Wikimedia CommonsOctober 7–10, 2026 · Wed 5–8 PM; Thu–Fri 11 AM–8 PM; Sat 11 AM–6 PMTickets via the fair's website
Chicago Art Fair
Downtown, the Loop & West Loop
Galleries at every price point fill THE MART, with guidance for first-time buyers and collectors.
ArtOne Weekend Only
#4October 7–10, 2026 · Wed 5–8 PM; Thu–Fri 11 AM–8 PM; Sat 11 AM–6 PM · One Weekend Only
THE MART, River North, Downtown, the Loop & West LoopDavid Wilson from Oak Park, Illinois, USA · CC BY 2.0 · Wikimedia CommonsChicago Art Fair
Galleries at every price point fill THE MART, with guidance for first-time buyers and collectors.
Add to calendar#5
CIBC Theatre, Downtown, the Loop & West LoopOnasill - Bill Badzo - 144 Million Views from Canada · Public domain · Wikimedia CommonsThrough Oct 11, 2026
Operation Mincemeat: A New Musical
Downtown, the Loop & West Loop
The Olivier-winning musical about a WWII deception plot built around a dead body.
One Weekend Only
#5Through Oct 11, 2026 · One Weekend Only
CIBC Theatre, Downtown, the Loop & West LoopOnasill - Bill Badzo - 144 Million Views from Canada · Public domain · Wikimedia CommonsOperation Mincemeat: A New Musical
The Olivier-winning musical about a WWII deception plot built around a dead body.
Add to calendar#6
Broadway Playhouse at Water Tower Place, Downtown, the Loop & West LoopOct 2, 2026–Oct 18, 2026
Jekyll& Hyde
Downtown, the Loop & West Loop
Jekyll& Hyde is listed for Chicago this weekend.
Limited Run
#6Oct 2, 2026–Oct 18, 2026 · Limited Run
Broadway Playhouse at Water Tower Place, Downtown, the Loop & West Loop#7
The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopSeptember 11–October 18, 2026; selected performances
Play On! — Chicago Shakespeare Theater
Downtown, the Loop & West Loop
A new play runs select dates at Chicago Shakespeare's Navy Pier stage.
Limited Run
#7September 11–October 18, 2026; selected performances · Limited Run
The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopPlay On! — Chicago Shakespeare Theater
A new play runs select dates at Chicago Shakespeare's Navy Pier stage.
Add to calendar#8
Lookingglass Theatre, The Joan and Paul Theatre, Streeterville, Downtown, the Loop & West LoopChris Rycroft · CC BY 2.0 · Wikimedia CommonsSeptember 15 – October 25, 2026Ticketed via Lookingglass The…
Kowalski
Downtown, the Loop & West Loop
Johnny Galecki stars in this limited engagement about Williams meeting Brando.
Limited Run
#8September 15 – October 25, 2026 · Limited Run
Lookingglass Theatre, The Joan and Paul Theatre, Streeterville, Downtown, the Loop & West LoopChris Rycroft · CC BY 2.0 · Wikimedia CommonsKowalski
Johnny Galecki stars in this limited engagement about Williams meeting Brando.
Add to calendar#9
Orchestra Hall, Symphony Center, Downtown, the Loop & West LoopI'm nonpartisan · CC BY-SA 3.0 · Wikimedia CommonsSat, Oct 10, 2026 · 6:30pm
Symphony Ball with Klaus Mäkelä
Downtown, the Loop & West Loop
The CSO's season gala: Mäkelä conducts Walton's Babylon cantata with baritone Thomas Hampson.
One Day Only
#9Sat, Oct 10, 2026 · 6:30pm · One Day Only
Orchestra Hall, Symphony Center, Downtown, the Loop & West LoopI'm nonpartisan · CC BY-SA 3.0 · Wikimedia CommonsSymphony Ball with Klaus Mäkelä
The CSO's season gala: Mäkelä conducts Walton's Babylon cantata with baritone Thomas Hampson.
Add to calendar#10
Sat, Oct 10, 2026 · 7:00pm
Switchfoot with special guest Anberlin - Forever Now Tour
Downtown, the Loop & West Loop
Switchfoot brings the Forever Now Tour to House of Blues Chicago with guest Anberlin.
One Day Only
#10Sat, Oct 10, 2026 · 7:00pm · One Day Only
Switchfoot with special guest Anberlin - Forever Now Tour
Switchfoot brings the Forever Now Tour to House of Blues Chicago with guest Anberlin.
Add to calendarMore on Saturday night
#11
THE MART, River North, Downtown, the Loop & West LoopOctober 7–10, 2026 · Wed 5–8 PM; Thu–Fri 11 AM–8 PM; Sat 11 AM–6 PMTicketed
Spectrum Chicago
Downtown, the Loop & West Loop
Spectrum spotlights independent artists and gallery programs at THE MART.
ArtOne Weekend Only
#11October 7–10, 2026 · Wed 5–8 PM; Thu–Fri 11 AM–8 PM; Sat 11 AM–6 PM · One Weekend Only
THE MART, River North, Downtown, the Loop & West LoopSpectrum Chicago
Spectrum spotlights independent artists and gallery programs at THE MART.
Add to calendar#12
Radius Chicago, East Pilsen, Downtown, the Loop & West LoopSaturday, October 10, 2026 · Doors 10 PMTicketed
Hamdi FC vs. Chicago
Downtown, the Loop & West Loop
Hamdi’s bass tour lands at Radius with Taiki Nulight and a three-DJ back-to-back set.
Limited Run
#12Saturday, October 10, 2026 · Doors 10 PM · Limited Run
Radius Chicago, East Pilsen, Downtown, the Loop & West LoopHamdi FC vs. Chicago
Hamdi’s bass tour lands at Radius with Taiki Nulight and a three-DJ back-to-back set.
Add to calendar#13
Inside Chicago Walking Tours, Downtown, the Loop & West LoopSep 18, 2026–Oct 17, 2026
Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour
Downtown, the Loop & West Loop
Haunted by Our Dark Side: Chicago Ghosts, Gangsters and True Crime Tour is listed for Chicago.
Limited Run
#13Sep 18, 2026–Oct 17, 2026 · Limited Run
Inside Chicago Walking Tours, Downtown, the Loop & West LoopHaunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour
Haunted by Our Dark Side: Chicago Ghosts, Gangsters and True Crime Tour is listed for Chicago.
Add to calendar#14
The Comedy Bar, Downtown, the Loop & West LoopFri, Oct 9, 2026 · 7:00pm$25 – $35
Paul Elia at The Comedy Bar
Downtown, the Loop & West Loop
Paul Elia at The Comedy Bar has enough weekend energy to earn a spot on the board.
One Weekend Only
#14Fri, Oct 9, 2026 · 7:00pm · One Weekend Only
The Comedy Bar, Downtown, the Loop & West LoopPaul Elia at The Comedy Bar
Paul Elia at The Comedy Bar has enough weekend energy to earn a spot on the board.
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#15
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West LoopSep 18, 2026–Oct 18, 2026
Theater of the Mind
Downtown, the Loop & West Loop
Theater of the Mind is listed for Chicago this weekend.
Limited Run
#15Sep 18, 2026–Oct 18, 2026 · Limited Run
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West Loop#16
Sat, Oct 10, 2026 · 7:00pm
Alice Smith
Downtown, the Loop & West Loop
Alice Smith plays a show at Garcia's Chicago.
One Day Only
#16Sat, Oct 10, 2026 · 7:00pm · One Day Only
#17
Northwestern University Chicago Campus – Abbott Hall Wirtz Theatre, Downtown, the Loop & West LoopFri, Oct 9, 2026 · 7:30pm
(dark) Toilet Fire (matter(s))
Downtown, the Loop & West Loop
(dark) Toilet Fire (matter(s)) has enough weekend energy to earn a spot on the board.
One Weekend Only
#17Fri, Oct 9, 2026 · 7:30pm · One Weekend Only
Northwestern University Chicago Campus – Abbott Hall Wirtz Theatre, Downtown, the Loop & West Loop(dark) Toilet Fire (matter(s))
(dark) Toilet Fire (matter(s)) has enough weekend energy to earn a spot on the board.
Add to calendar#18
Chicago Riverwalk (Wells St. to Franklin St.), River North, Downtown, the Loop & West LoopChris Rycroft from Madison, Wisconsin, United States · CC BY 2.0 · Wikimedia CommonsThursdays through Sundays, 7:30–8:00 PM, through Nov 15, 2026Free and open to the public
ART on THE Mart
Downtown, the Loop & West Loop
ART on THE Mart is listed for Chicago this weekend.
FreeArt
#18Thursdays through Sundays, 7:30–8:00 PM, through Nov 15, 2026 · Limited Run
Chicago Riverwalk (Wells St. to Franklin St.), River North, Downtown, the Loop & West LoopChris Rycroft from Madison, Wisconsin, United States · CC BY 2.0 · Wikimedia Commons#19
Gene Siskel Film Center, Downtown, the Loop & West LoopSaturday 7pm
The Scout
Downtown, the Loop & West Loop
The Scout has enough weekend energy to earn a spot on the board.
One Day Only
#19Saturday 7pm · One Day Only
Gene Siskel Film Center, Downtown, the Loop & West Loop#20
Reggies Bananna's Shack, 2105 South State Street, Downtown, the Loop & West LoopSat, Oct 10, 2026 · 8:30pm
Lily Vakili & Her Band, Mighty Joe Castro and the Gravamen, Greystone
Downtown, the Loop & West Loop
Lily Vakili & Her Band, Mighty Joe Castro and the Gravamen, Greystone has enough weekend energy to earn a spot on the board.
One Day Only
#20Sat, Oct 10, 2026 · 8:30pm · One Day Only
Reggies Bananna's Shack, 2105 South State Street, Downtown, the Loop & West LoopLily Vakili & Her Band, Mighty Joe Castro and the Gravamen, Greystone
Lily Vakili & Her Band, Mighty Joe Castro and the Gravamen, Greystone has enough weekend energy to earn a spot on the board.
Add to calendar#21
Foundation Room at House of Blues Chicago, 329 N Dearborn St, Downtown, the Loop & West LoopSat, Oct 10, 2026 · 5:00pm
Next Showcase presents Mark Hubbard's 60th Birthday Celebration
Downtown, the Loop & West Loop
Next Showcase marks Mark Hubbard's 60th birthday in House of Blues' Foundation Room.
One Day Only
#21Sat, Oct 10, 2026 · 5:00pm · One Day Only
Foundation Room at House of Blues Chicago, 329 N Dearborn St, Downtown, the Loop & West LoopNext Showcase presents Mark Hubbard's 60th Birthday Celebration
Next Showcase marks Mark Hubbard's 60th birthday in House of Blues' Foundation Room.
Add to calendar#22
Reggies Music Joint, 2105 South State Street, Downtown, the Loop & West LoopSat, Oct 10, 2026 · 9:00pm
Orange Dog Club, Tba
Downtown, the Loop & West Loop
Orange Dog Club, Tba has enough weekend energy to earn a spot on the board.
One Day Only
#22Sat, Oct 10, 2026 · 9:00pm · One Day Only
Reggies Music Joint, 2105 South State Street, Downtown, the Loop & West LoopOrange Dog Club, Tba
Orange Dog Club, Tba has enough weekend energy to earn a spot on the board.
Add to calendarAbout this list
Stumblday's hand-checked ranking of the best things to do in West Loop, Chicago on Saturday night of Columbus Day weekend, Oct 10: 22 picks.
