#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 Downtown, the Loop & West Loop on Saturday, Columbus Day Weekend 2026
59 picks
The 10 best things to do in Downtown, the Loop & West Loop 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 Downtown, the Loop & West Loop on Saturday of Columbus Day weekend, Oct 10: 59 picks.
