#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 on Saturday, Columbus Day Weekend 2026
59 picks
The 10 best things to do in West Loop, Chicago on Saturday, Oct 10
- Jerry Seinfeld Live! — Fri, Oct 9 7pm; Sat, Oct 10 · 5pm and 8pm · Downtown
- Abbott Health & Fitness Expo — Thursday, October 8 – Saturday, October 10 · Free · 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
- Golden Boy Promotions Pres: Schofield vs Bahdi — Sat, Oct 10 3:15pm · Downtown
- Jekyll& Hyde — Oct 2–Oct 18, 2026 · Downtown
- F1 Arcade — Open this weekend — recently opened · Downtown
- Chicago Fashion Week — October 8–18; events at venues across the city · 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
McCormick Place, North Building, Hall B1, Near South Side, Downtown, the Loop & West LoopWarren LeMay from Chicago, IL, United States · CC BY-SA 2.0 · Wikimedia CommonsThursday, October 8 – Saturday, October 10, 2026Free and open to the public
Abbott Health & Fitness Expo
Downtown, the Loop & West Loop
Free and open to anyone: marathon bib pickup and the whole race-weekend trade floor.
FreeOne Weekend Only
#2Thursday, October 8 – Saturday, October 10, 2026 · One Weekend Only
McCormick Place, North Building, Hall B1, Near South Side, Downtown, the Loop & West LoopWarren LeMay from Chicago, IL, United States · CC BY-SA 2.0 · Wikimedia CommonsAbbott Health & Fitness Expo
Free and open to anyone: marathon bib pickup and the whole race-weekend trade floor.
Add to calendar#3
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
#3Fri, 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#4
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
#4Saturday, 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#5
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
#5October 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#6
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
#6Through 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#7
Wintrust Arena, 200 E Cermak Road, Downtown, the Loop & West LoopSat, Oct 10, 2026 · 3:15pm
Golden Boy Promotions Pres: Schofield vs Bahdi
Downtown, the Loop & West Loop
A WBA lightweight world title is on the line in an in-city arena boxing card.
One Day Only
#7Sat, Oct 10, 2026 · 3:15pm · One Day Only
Wintrust Arena, 200 E Cermak Road, Downtown, the Loop & West LoopGolden Boy Promotions Pres: Schofield vs Bahdi
A WBA lightweight world title is on the line in an in-city arena boxing card.
Add to calendar#8
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
#8Oct 2, 2026–Oct 18, 2026 · Limited Run
Broadway Playhouse at Water Tower Place, Downtown, the Loop & West Loop#9
F1 Arcade, River North, Downtown, the Loop & West LoopOpen this weekend — recently opened
F1 Arcade
Downtown, the Loop & West Loop
F1 Arcade is listed for Chicago this weekend.
Limited Run
#9Open this weekend — recently opened · Limited Run
F1 Arcade, River North, Downtown, the Loop & West Loop#10
Venues across Chicago, Citywide, Downtown, the Loop & West LoopMatt Reeves / Darkroom Demons · CC0 · Wikimedia CommonsOctober 8–18, 2026; events at venues across the city
Chicago Fashion Week
Downtown, the Loop & West Loop
The citywide fashion calendar spans markets, runway shows and store events.
Limited Run
#10October 8–18, 2026; events at venues across the city · Limited Run
Venues across Chicago, Citywide, Downtown, the Loop & West LoopMatt Reeves / Darkroom Demons · CC0 · Wikimedia CommonsChicago Fashion Week
The citywide fashion calendar spans markets, runway shows and store events.
Add to calendarMore on Saturday
#11
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
#11September 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#12
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
#12September 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#13
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
#13Sat, 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#14
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
#14Sat, 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 calendarThe whole weekend, in one email.
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#15
Navy Pier, 600 E. Grand Ave., Downtown, the Loop & West LoopSat, Oct 10, 2026 · 12:00pm
TenderFest @ East End Plaza at Navy Pier
Downtown, the Loop & West Loop
TenderFest @ East End Plaza at Navy Pier
One Day Only
#15Sat, Oct 10, 2026 · 12:00pm · One Day Only
Navy Pier, 600 E. Grand Ave., Downtown, the Loop & West Loop#16
Museum of Contemporary Art Chicago, Streeterville, Downtown, the Loop & West LoopSaturday, October 10, 2026 · 11 AM–3 PMFREE for Family Day attendees
Family Day | Warmups
Downtown, the Loop & West Loop
Free museum admission, artmaking and ASL interpretation open the MCA family season.
FreeOne Day Only
#16Saturday, October 10, 2026 · 11 AM–3 PM · One Day Only
Museum of Contemporary Art Chicago, Streeterville, Downtown, the Loop & West LoopFamily Day | Warmups
Free museum admission, artmaking and ASL interpretation open the MCA family season.
Add to calendar#17
Richard H. Driehaus Museum, River North, Downtown, the Loop & West LoopOctober 9, 2026 – April 18, 2027Adults $23
Emma Stebbins: Carving Out History
Downtown, the Loop & West Loop
Emma Stebbins: Carving Out History
ArtLimited Run
#17October 9, 2026 – April 18, 2027 · Limited Run
Richard H. Driehaus Museum, River North, Downtown, the Loop & West Loop#18
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
#18October 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#19
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
#19Saturday, 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#20
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
#20Sep 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#21
McCormick Bridgehouse & Chicago River Museum, Riverwalk, Downtown, the Loop & West LoopSaturday, October 10, 2026 · 9:30–10:30 AM$15 per person
Bridge Lift Viewing
Downtown, the Loop & West Loop
Watch the DuSable Bridge gears move from inside the Bridgehouse Museum.
One Day Only
#21Saturday, October 10, 2026 · 9:30–10:30 AM · One Day Only
McCormick Bridgehouse & Chicago River Museum, Riverwalk, Downtown, the Loop & West LoopBridge Lift Viewing
Watch the DuSable Bridge gears move from inside the Bridgehouse Museum.
Add to calendar#22
Chicago Cultural Center, Downtown, the Loop & West LoopGrant Henninger · CC BY-SA 4.0 · Wikimedia CommonsApr 25, 2026–Oct 18, 2026Free
Tangible Sound: Arrival to a Higher Ground
Downtown, the Loop & West Loop
Tangible Sound: Arrival to a Higher Ground is listed for Chicago this weekend.
FreeLimited Run
#22Apr 25, 2026–Oct 18, 2026 · Limited Run
Chicago Cultural Center, Downtown, the Loop & West LoopGrant Henninger · CC BY-SA 4.0 · Wikimedia CommonsTangible Sound: Arrival to a Higher Ground
Tangible Sound: Arrival to a Higher Ground is listed for Chicago this weekend.
Add to calendar#23
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
#23Fri, 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.
Add to calendar#24
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
#24Sep 18, 2026–Oct 18, 2026 · Limited Run
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West LoopAbout this list
Stumblday's hand-checked ranking of the best things to do in West Loop, Chicago on Saturday of Columbus Day weekend, Oct 10: 59 picks, refreshed weekly.
