#1
Jack's Pumpkin Pop-Up, Downtown Chicago, Downtown, the Loop & West LoopRunning through November 1Adult entry with corn maze fr…
Jack's Pumpkin Pop-Up
Downtown, the Loop & West Loop
Jack's Pumpkin Pop-Up at Jack's Pumpkin Pop-Up.
Limited Run
Things to Do in Downtown, the Loop & West Loop on Sunday, Halloween Weekend 2026
44 picks
The 10 best things to do in Downtown, the Loop & West Loop on Sunday, Nov 1
- Jack's Pumpkin Pop-Up — Running through November 1 · Downtown
- American Prophets: Writers, Religion, and Culture — Fri, Nov 13 10:00am · Adults $14 online or $16 at t… · Downtown
- Theater of the Mind — Fri, Nov 13 · Tickets from $69 · Downtown
- Drunk Shakespeare: Drunk Dracula (21+ Event) — Fri, Nov 6 7:00pm · Downtown
- Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour — Fri, Nov 13 4:00pm · Downtown
- Bruce Liu — Sun, Nov 1 3:00pm · Downtown
- Día de los Muertos at Navy Pier — Sun, Nov 1 1:00pm · Free · Downtown
- Hot Chocolate Run Chicago — Sun, Nov 1 race times on official site · Downtown
- Death By Disco: Chicago's Biggest Halloween Pop-Up — Fri, Oct 30, 8pm–2am; Sat, Oct 31, 8pm–1am · City Hall and Morgan MFG
- If Emmett Till Lived: Freedom on American Ground — September 10–December 19 · Free · Downtown
Jack's Pumpkin Pop-Up, Downtown Chicago, Downtown, the Loop & West Loop#1Running through November 1 · Limited Run
Jack's Pumpkin Pop-Up, Downtown Chicago, Downtown, the Loop & West Loop#2
American Writers Museum, Downtown, the Loop & West LoopFri, Nov 13, 2026 · 10:00amAdults $14 online or $16 at t…
American Prophets: Writers, Religion, and Culture
Downtown, the Loop & West Loop
American Prophets: Writers, Religion and Culture at American Writers Museum.
ArtLimited Run
#2Fri, Nov 13, 2026 · 10:00am · Limited Run
American Writers Museum, Downtown, the Loop & West LoopAmerican Prophets: Writers, Religion, and Culture
American Prophets: Writers, Religion and Culture at American Writers Museum.
Add to calendar#3
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West LoopFri, Nov 13, 2026Tickets from $69
Theater of the Mind
Downtown, the Loop & West Loop
Theater of the Mind at Reid Murdoch Building – 333 N LaSalle.
Limited Run
#3Fri, Nov 13, 2026 · Limited Run
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West Loop#4
The Lion Theatre, 182 N Wabash Ave, Downtown, the Loop & West LoopFri, Nov 6, 2026 · 7:00pm
Drunk Shakespeare: Drunk Dracula (21+ Event)
Downtown, the Loop & West Loop
Drunk Shakespeare: Drunk Dracula (21+ Event) at The Lion Theatre.
Limited Run
#4Fri, Nov 6, 2026 · 7:00pm · Limited Run
The Lion Theatre, 182 N Wabash Ave, Downtown, the Loop & West LoopDrunk Shakespeare: Drunk Dracula (21+ Event)
Drunk Shakespeare: Drunk Dracula (21+ Event) at The Lion Theatre.
Add to calendar#5
Inside Chicago Walking Tours, Downtown, the Loop & West LoopFri, Nov 13, 2026 · 4:00pm
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 at Inside Chicago Walking.
Limited Run
#5Fri, Nov 13, 2026 · 4:00pm · 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 at Inside Chicago Walking.
Add to calendar#6
Orchestra Hall, Symphony Center, Downtown, the Loop & West LoopSun, Nov 1, 2026 · 3:00pm
Bruce Liu
Downtown, the Loop & West Loop
Bruce Liu at Orchestra Hall, Symphony Center.
One Day Only
#6Sun, Nov 1, 2026 · 3:00pm · One Day Only
Orchestra Hall, Symphony Center, Downtown, the Loop & West Loop#7
Navy Pier, Downtown, the Loop & West LoopSun, Nov 1, 2026 · 1:00pmFree
Día de los Muertos at Navy Pier
Downtown, the Loop & West Loop
Día de los Muertos at Navy Pier at Navy Pier.
FreeOne Day Only
#7Sun, Nov 1, 2026 · 1:00pm · One Day Only
Navy Pier, Downtown, the Loop & West Loop#8
Grant Park, Downtown, the Loop & West LoopSun, Nov 1, 2026 · race times on official site
Hot Chocolate Run Chicago
Downtown, the Loop & West Loop
Chicago's chocolate-themed race returns to Grant Park with 5K, 10K, 15K and two-mile routes.
One Weekend Only
#8Sun, Nov 1, 2026 · race times on official site · One Weekend Only
Grant Park, Downtown, the Loop & West LoopHot Chocolate Run Chicago
Chicago's chocolate-themed race returns to Grant Park with 5K, 10K, 15K and two-mile routes.
Add to calendar#9
Recess, City Hall and Morgan MFG, West LoopFri, Oct 30, 8pm–2am; Sat, Oct 31, 8pm–1am
Death By Disco: Chicago's Biggest Halloween Pop-Up
City Hall and Morgan MFG, West Loop
A two-night Halloween pop-up takes over three West Loop venues with DJs, performers and interactive rooms.
One Weekend Only
#9Fri, Oct 30, 8pm–2am; Sat, Oct 31, 8pm–1am · One Weekend Only
Recess, City Hall and Morgan MFG, West LoopDeath By Disco: Chicago's Biggest Halloween Pop-Up
A two-night Halloween pop-up takes over three West Loop venues with DJs, performers and interactive rooms.
Add to calendar#10
Museum of Contemporary Photography, South Loop, Downtown, the Loop & West LoopViselippi · CC BY-SA 4.0 · Wikimedia CommonsSeptember 10–December 19, 2026; Mon–Wed and Fri–Sat 10 a.m.–5 p.m., Thu 10 a.m.–8 p.m.; Sun closedFree
If Emmett Till Lived: Freedom on American Ground
Downtown, the Loop & West Loop
Imagine the life Emmett Till was denied through a free MoCP exhibition drawing on photographs by more than 110 artists.
FreeArt
#10September 10–December 19, 2026; Mon–Wed and Fri–Sat 10 a.m.–5 p.m., Thu 10 a.m.–8 p.m.; Sun closed · Limited Run
Museum of Contemporary Photography, South Loop, Downtown, the Loop & West LoopViselippi · CC BY-SA 4.0 · Wikimedia CommonsIf Emmett Till Lived: Freedom on American Ground
Imagine the life Emmett Till was denied through a free MoCP exhibition drawing on photographs by more than 110 artists.
Add to calendarMore on Sunday
#11
Chicago Children’s Museum, Downtown, the Loop & West LoopMusikAnimal · CC BY-SA 4.0 · Wikimedia CommonsFri, Nov 13, 2026 · 10:00am
Castle
Downtown, the Loop & West Loop
Castle at Chicago Children’s Museum.
Limited Run
#11Fri, Nov 13, 2026 · 10:00am · Limited Run
Chicago Children’s Museum, Downtown, the Loop & West LoopMusikAnimal · CC BY-SA 4.0 · Wikimedia Commons#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
Inside Chicago Walking Tours, Downtown, the Loop & West LoopSaturdays through Nov 14, 2026
All That Glam: Chicago’s Art Deco Masterpieces Walking Tour
Downtown, the Loop & West Loop
All That Glam: Chicago’s Art Deco Masterpieces Walking Tour at Inside Chicago Walking Tours.
Limited Run
#13Saturdays through Nov 14, 2026 · Limited Run
Inside Chicago Walking Tours, Downtown, the Loop & West LoopAll That Glam: Chicago’s Art Deco Masterpieces Walking Tour
All That Glam: Chicago’s Art Deco Masterpieces Walking Tour at Inside Chicago Walking Tours.
Add to calendar#14
Field Museum, Museum Campus, Downtown, the Loop & West LoopJoe Ravi · CC BY-SA 3.0 · Wikimedia CommonsOn view May 22, 2026 – April 11, 2027Requires an add-on ticket
Pokémon Fossil Museum
Downtown, the Loop & West Loop
Pokémon Fossil Museum is listed for Chicago this weekend.
ArtLimited Run
#14On view May 22, 2026 – April 11, 2027 · Limited Run
Field Museum, Museum Campus, Downtown, the Loop & West LoopJoe Ravi · CC BY-SA 3.0 · Wikimedia CommonsThe whole weekend, in one email.
Friday at 5pm, one email. Unsubscribe anytime.
#15
Chicago Architecture Center, Downtown, the Loop & West LoopFri, Nov 13, 2026 · 10:00am
Flyway City: Architecture for a Flourishing Ecosystem
Downtown, the Loop & West Loop
Flyway City: Architecture for a Flourishing Ecosystem at Chicago Architecture Center.
Limited Run
#15Fri, Nov 13, 2026 · 10:00am · Limited Run
Chicago Architecture Center, Downtown, the Loop & West LoopFlyway City: Architecture for a Flourishing Ecosystem
Flyway City: Architecture for a Flourishing Ecosystem at Chicago Architecture Center.
Add to calendar#16
Chicago Shakespeare Theater, 800 East Grand Avenue on Navy Pier, Downtown, the Loop & West LoopSat, Nov 7, 2026 · 7:00pm
The Winter's Tale
Downtown, the Loop & West Loop
The Winter's Tale at Chicago Shakespeare Theater.
Limited Run
#16Sat, Nov 7, 2026 · 7:00pm · Limited Run
Chicago Shakespeare Theater, 800 East Grand Avenue on Navy Pier, Downtown, the Loop & West Loop#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
Art Institute of Chicago, Gallery 283, Downtown, the Loop & West LoopOn view through Jan 25, 2027
Abigail Lucien: Blood of the Earth
Downtown, the Loop & West Loop
Abigail Lucien: Blood of the Earth at Art Institute of Chicago.
ArtLimited Run
#18On view through Jan 25, 2027 · Limited Run
Art Institute of Chicago, Gallery 283, Downtown, the Loop & West LoopAbigail Lucien: Blood of the Earth
Abigail Lucien: Blood of the Earth at Art Institute of Chicago.
Add to calendar#19
Art Institute of Chicago, 111 S Michigan Ave, Downtown, the Loop & West LoopOn view through Jan 25, 2027
Embroidered Traditions
Downtown, the Loop & West Loop
Embroidered Traditions from Morocco to Afghanistan at Art Institute of Chicago.
ArtLimited Run
#19On view through Jan 25, 2027 · Limited Run
Art Institute of Chicago, 111 S Michigan Ave, Downtown, the Loop & West LoopEmbroidered Traditions
Embroidered Traditions from Morocco to Afghanistan at Art Institute of Chicago.
Add to calendar#20
Art Institute of Chicago, Gallery 186, Downtown, the Loop & West LoopOn view through Dec 11, 2026
Karimah Ashadu: Machine Boys
Downtown, the Loop & West Loop
Karimah Ashadu: Machine Boys at Art Institute of Chicago.
ArtLimited Run
#20On view through Dec 11, 2026 · Limited Run
Art Institute of Chicago, Gallery 186, Downtown, the Loop & West LoopKarimah Ashadu: Machine Boys
Karimah Ashadu: Machine Boys at Art Institute of Chicago.
Add to calendar#21
Museum of Contemporary Art Chicago, Downtown, the Loop & West LoopUser:JeremyA · CC BY-SA 2.5 · Wikimedia CommonsOn view through Jun 20, 2027
Atrium Project: Celeste Rapone
Downtown, the Loop & West Loop
Atrium Project: Celeste Rapone at Museum of Contemporary Art Chicago.
ArtLimited Run
#21On view through Jun 20, 2027 · Limited Run
Museum of Contemporary Art Chicago, Downtown, the Loop & West LoopUser:JeremyA · CC BY-SA 2.5 · Wikimedia CommonsAtrium Project: Celeste Rapone
Atrium Project: Celeste Rapone at Museum of Contemporary Art Chicago.
Add to calendar#22
Museum of Contemporary Art Chicago, Downtown, the Loop & West LoopOn view through Jan 31, 2027
Kenzi Shiokava
Downtown, the Loop & West Loop
Kenzi Shiokava at Museum of Contemporary Art Chicago.
ArtLimited Run
#22On view through Jan 31, 2027 · Limited Run
Museum of Contemporary Art Chicago, Downtown, the Loop & West Loop#23
Art Institute of Chicago, 111 S Michigan Ave, Downtown, the Loop & West LoopOn view through Dec 31, 2027
Double Feature with Short Subject
Downtown, the Loop & West Loop
Double Feature with Short Subject at Art Institute of Chicago.
ArtLimited Run
#23On view through Dec 31, 2027 · Limited Run
Art Institute of Chicago, 111 S Michigan Ave, Downtown, the Loop & West LoopDouble Feature with Short Subject
Double Feature with Short Subject at Art Institute of Chicago.
Add to calendar#24
Art Institute of Chicago, Gallery 289, Downtown, the Loop & West LoopOn view through Jan 18, 2027
Jill Mulleady: The Passenger
Downtown, the Loop & West Loop
Jill Mulleady: The Passenger at Art Institute of Chicago.
ArtLimited Run
#24On view through Jan 18, 2027 · Limited Run
Art Institute of Chicago, Gallery 289, Downtown, the Loop & West LoopJill Mulleady: The Passenger
Jill Mulleady: The Passenger at Art Institute of Chicago.
Add to calendarAbout this list
Stumblday's hand-checked ranking of the best things to do in Downtown, the Loop & West Loop on Sunday of Halloween weekend, Nov 1: 44 picks.
