#1
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
Things to Do in Downtown, the Loop & West Loop on Columbus Day Monday, Oct 12
40 picks
The 10 best things to do in Downtown, the Loop & West Loop on Columbus Day Monday, Oct 12
- 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
- Play On! — Chicago Shakespeare Theater — September 11–October 18; selected performances · Downtown
- Kowalski — September 15 – October 25 · Downtown
- Emma Stebbins: Carving Out History — October 9 – April 18, 2027 · Adults $23 · Downtown
- Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour — Sep 18–Oct 17, 2026 · Downtown
- Indigenous People’s Day at Chicago Children’s Museum — Monday, October 12 10 AM–3 PM · Downtown
- Tangible Sound: Arrival to a Higher Ground — Apr 25–Oct 18, 2026 · Free · Downtown
- Faust with Live Score by ten thousand lakes — Monday 7pm · Downtown
Broadway Playhouse at Water Tower Place, Downtown, the Loop & West Loop#1Oct 2, 2026–Oct 18, 2026 · Limited Run
Broadway Playhouse at Water Tower Place, Downtown, the Loop & West Loop#2
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
#2Open this weekend — recently opened · Limited Run
F1 Arcade, River North, Downtown, the Loop & West Loop#3
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
#3October 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 calendar#4
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
#4September 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#5
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
#5September 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#6
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
#6October 9, 2026 – April 18, 2027 · Limited Run
Richard H. Driehaus Museum, River North, Downtown, the Loop & West Loop#7
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
#7Sep 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#8
Chicago Children’s Museum, Navy Pier, Downtown, the Loop & West LoopMonday, October 12, 2026 · 10 AM–3 PMMuseum admission applies
Indigenous People’s Day at Chicago Children’s Museum
Downtown, the Loop & West Loop
A story lounge and native Illinois seed-ball activity mark Indigenous People’s Day.
One Day Only
#8Monday, October 12, 2026 · 10 AM–3 PM · One Day Only
Chicago Children’s Museum, Navy Pier, Downtown, the Loop & West LoopIndigenous People’s Day at Chicago Children’s Museum
A story lounge and native Illinois seed-ball activity mark Indigenous People’s Day.
Add to calendar#9
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
#9Apr 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#10
Gene Siskel Film Center, Downtown, the Loop & West LoopMrschimpf · CC BY-SA 4.0 · Wikimedia CommonsMonday 7pm
Faust with Live Score by ten thousand lakes
Downtown, the Loop & West Loop
The Gene Siskel Film Center screens Faust with a live score by ten thousand lakes.
One Day Only
#10Monday 7pm · One Day Only
Gene Siskel Film Center, Downtown, the Loop & West LoopMrschimpf · CC BY-SA 4.0 · Wikimedia CommonsFaust with Live Score by ten thousand lakes
The Gene Siskel Film Center screens Faust with a live score by ten thousand lakes.
Add to calendarMore on Columbus Day Monday
#11
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
#11Sep 18, 2026–Oct 18, 2026 · Limited Run
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West Loop#12
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
#12Thursdays 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#13
American Writers Museum, Downtown, the Loop & West LoopSep 18, 2026–Oct 18, 2026
American Prophets: Writers, Religion, and Culture
Downtown, the Loop & West Loop
American Prophets: Writers, Religion and Culture is listed for Chicago this weekend.
ArtLimited Run
#13Sep 18, 2026–Oct 18, 2026 · Limited Run
American Writers Museum, Downtown, the Loop & West LoopAmerican Prophets: Writers, Religion, and Culture
American Prophets: Writers, Religion and Culture is listed for Chicago this weekend.
Add to calendar#14
Chicago Architecture Center, Downtown, the Loop & West LoopSep 18, 2026–Oct 18, 2026
Flyway City: Architecture for a Flourishing Ecosystem
Downtown, the Loop & West Loop
Flyway City: Architecture for a Flourishing Ecosystem is listed for Chicago this weekend.
Limited Run
#14Sep 18, 2026–Oct 18, 2026 · Limited Run
Chicago Architecture Center, Downtown, the Loop & West LoopFlyway City: Architecture for a Flourishing Ecosystem
Flyway City: Architecture for a Flourishing Ecosystem is listed for Chicago this weekend.
Add to calendarThe whole weekend, in one email.
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#15
The Comedy Bar, Downtown, the Loop & West LoopMon, Oct 12, 2026 · 7:00pm$25 – $30
Late Nite Mic w/ Vik Pandya at The Comedy Bar
Downtown, the Loop & West Loop
Late Nite Mic w/ Vik Pandya at The Comedy Bar has enough weekend energy to earn a spot on the board.
One Day Only
#15Mon, Oct 12, 2026 · 7:00pm · One Day Only
The Comedy Bar, Downtown, the Loop & West LoopLate Nite Mic w/ Vik Pandya at The Comedy Bar
Late Nite Mic w/ Vik Pandya at The Comedy Bar has enough weekend energy to earn a spot on the board.
Add to calendar#16
Nan Xiang Soup Dumplings, River North, Downtown, the Loop & West LoopOpen this weekend — recently opened
Nan Xiang Soup Dumplings
Downtown, the Loop & West Loop
Nan Xiang Soup Dumplings is listed for Chicago this weekend.
Limited Run
#16Open this weekend — recently opened · Limited Run
Nan Xiang Soup Dumplings, River North, Downtown, the Loop & West Loop#17
Tarra, River North, Downtown, the Loop & West LoopOpen this weekend — recently opened
Tarra
Downtown, the Loop & West Loop
Tarra is listed for Chicago this weekend.
Limited Run
#17Open this weekend — recently opened · Limited Run
Tarra, River North, Downtown, the Loop & West Loop#18
Jack's Pumpkin Pop-Up, Downtown Chicago, Downtown, the Loop & West LoopRunning through November 1
Jack's Pumpkin Pop-Up
Downtown, the Loop & West Loop
Jack's Pumpkin Pop-Up is listed for Chicago this weekend.
Limited Run
#18Running through November 1 · Limited Run
Jack's Pumpkin Pop-Up, Downtown Chicago, Downtown, the Loop & West Loop#19
Vietnam Veteran’s Memorial, Downtown, the Loop & West LoopSep 18, 2026–Oct 18, 2026FREE
Chicago Greeter Riverwalk InstaGreeter Walk
Downtown, the Loop & West Loop
Chicago Greeter Riverwalk InstaGreeter Walk is listed for Chicago this weekend.
FreeLimited Run
#19Sep 18, 2026–Oct 18, 2026 · Limited Run
Vietnam Veteran’s Memorial, Downtown, the Loop & West LoopChicago Greeter Riverwalk InstaGreeter Walk
Chicago Greeter Riverwalk InstaGreeter Walk is listed for Chicago this weekend.
Add to calendar#20
Chicago Children’s Museum, Downtown, the Loop & West LoopSep 18, 2026–Oct 18, 2026
Castle
Downtown, the Loop & West Loop
Castle is listed for Chicago this weekend.
Limited Run
#20Sep 18, 2026–Oct 18, 2026 · Limited Run
Chicago Children’s Museum, Downtown, the Loop & West Loop#21
Chicago Children’s Museum, Downtown, the Loop & West LoopOct 2, 2026–Oct 18, 2026
Mini Zoom Room
Downtown, the Loop & West Loop
Mini Zoom Room is listed for Chicago this weekend.
ArtLimited Run
#21Oct 2, 2026–Oct 18, 2026 · Limited Run
Chicago Children’s Museum, Downtown, the Loop & West Loop#22
Chicago Cultural Center, Downtown, the Loop & West LoopSep 18, 2026–Oct 18, 2026FREE
Chicago Greeter – Loop InstaGreeter
Downtown, the Loop & West Loop
Chicago Greeter – Loop InstaGreeter is listed for Chicago this weekend.
FreeLimited Run
#22Sep 18, 2026–Oct 18, 2026 · Limited Run
Chicago Cultural Center, Downtown, the Loop & West LoopChicago Greeter – Loop InstaGreeter
Chicago Greeter – Loop InstaGreeter is listed for Chicago this weekend.
Add to calendar#23
Pitch And Pour Supper Club, West LoopOpen this weekend — recently opened
Pitch And Pour Supper Club
Pitch And Pour Supper Club, West Loop
Pitch And Pour Supper Club is listed for Chicago this weekend.
Limited Run
#23Open this weekend — recently opened · Limited Run
Pitch And Pour Supper Club, West LoopPitch And Pour Supper Club
Pitch And Pour Supper Club is listed for Chicago this weekend.
Add to calendar#24
Con Azucar Cafe, South Loop, Downtown, the Loop & West LoopOpen this weekend — recently opened
Con Azucar Cafe
Downtown, the Loop & West Loop
Con Azucar Cafe is listed for Chicago this weekend.
Limited Run
#24Open this weekend — recently opened · Limited Run
Con Azucar Cafe, South Loop, 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 Columbus Day Monday, Oct 12: 40 picks, refreshed weekly.
