#1
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 at Jack's Pumpkin Pop-Up.
Limited Run
Things to Do in Downtown, the Loop & West Loop the Weekend of Oct 30–Nov 1, 2026
60 picks
The 10 best things to do in Downtown, the Loop & West Loop the weekend of Oct 30 – Nov 1
- Jack's Pumpkin Pop-Up — Running through November 1 · Downtown
- American Prophets: Writers, Religion, and Culture — Fri, Oct 30 10:00am · Downtown
- Theater of the Mind — Fri, Oct 30 · Downtown
- Kokandy Productions Jekyll & Hyde (Chicago) — Fri, Oct 30 7:00pm · Downtown
- Drunk Shakespeare: Drunk Dracula (21+ Event) — Fri, Oct 30 5:00pm · Downtown
- Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour — Fri, Oct 30 4:00pm · Downtown
- NoMI Gallery — Fri, Oct 30 · 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
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, Oct 30, 2026 · 10:00amIncluded with general admissi…
American Prophets: Writers, Religion, and Culture
Downtown, the Loop & West Loop
American Prophets: Writers, Religion and Culture at American Writers Museum.
ArtLimited Run
#2Fri, Oct 30, 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, Oct 30, 2026
Theater of the Mind
Downtown, the Loop & West Loop
Theater of the Mind at Reid Murdoch Building – 333 N LaSalle.
Limited Run
#3Fri, Oct 30, 2026 · Limited Run
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West Loop#4
Broadway Playhouse at Water Tower Place, 175 E. Chestnut St, Downtown, the Loop & West LoopFri, Oct 30, 2026 · 7:00pm
Kokandy Productions Jekyll & Hyde (Chicago)
Downtown, the Loop & West Loop
Kokandy Productions Jekyll & Hyde (Chicago) at Broadway Playhouse at Water Tower Place.
Limited Run
#4Fri, Oct 30, 2026 · 7:00pm · Limited Run
Broadway Playhouse at Water Tower Place, 175 E. Chestnut St, Downtown, the Loop & West LoopKokandy Productions Jekyll & Hyde (Chicago)
Kokandy Productions Jekyll & Hyde (Chicago) at Broadway Playhouse at Water Tower Place.
Add to calendar#5
The Lion Theatre, 182 N Wabash Ave, Downtown, the Loop & West LoopFri, Oct 30, 2026 · 5:00pm
Drunk Shakespeare: Drunk Dracula (21+ Event)
Downtown, the Loop & West Loop
Drunk Shakespeare: Drunk Dracula (21+ Event) at The Lion Theatre.
Limited Run
#5Fri, Oct 30, 2026 · 5:00pm · 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#6
Inside Chicago Walking Tours, Downtown, the Loop & West LoopFri, Oct 30, 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
#6Fri, Oct 30, 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#7
NoMI, Downtown, the Loop & West LoopFri, Oct 30, 2026
NoMI Gallery
Downtown, the Loop & West Loop
NoMI Gallery | Everything is Bright. All Things are Beautiful. at NoMI.
ArtLimited Run
#7Fri, Oct 30, 2026 · Limited Run
NoMI, Downtown, the Loop & West Loop#8
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
#8Sun, Nov 1, 2026 · 3:00pm · One Day Only
Orchestra Hall, Symphony Center, Downtown, the Loop & West Loop#9
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
#9Sun, Nov 1, 2026 · 1:00pm · One Day Only
Navy Pier, Downtown, the Loop & West Loop#10
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
#10Sun, 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 calendarMore picks for Oct 30–Nov 1, 2026
#11
Orchestra Hall, Symphony Center, 220 S. Michigan Ave., Downtown, the Loop & West LoopFri, Oct 30, 2026 · 1:30pm
Brahms Requiem
Downtown, the Loop & West Loop
Brahms Requiem at Orchestra Hall, Symphony Center.
One Weekend Only
#11Fri, Oct 30, 2026 · 1:30pm · One Weekend Only
Orchestra Hall, Symphony Center, 220 S. Michigan Ave., Downtown, the Loop & West Loop#12
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
#12Fri, 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#13
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
#13September 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 calendar#14
Chicago Children’s Museum, Downtown, the Loop & West LoopFri, Oct 30, 2026 · 10:00am
Castle
Downtown, the Loop & West Loop
Castle at Chicago Children’s Museum.
Limited Run
#14Fri, Oct 30, 2026 · 10:00am · Limited Run
Chicago Children’s Museum, Downtown, the Loop & West LoopPlanning ahead for Oct 30–Nov 1, 2026?
It lands the Friday before, plus every Friday until then. Unsubscribe anytime.
#15
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
#15Thursdays 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#16
Inside Chicago Walking Tours, Downtown, the Loop & West LoopSat, Oct 31, 2026 · 10:30am
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
#16Sat, Oct 31, 2026 · 10:30am · 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#17
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
#17On 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 Commons#18
Chicago Architecture Center, Downtown, the Loop & West LoopFri, Oct 30, 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
#18Fri, Oct 30, 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#19
Chicago Shakespeare Theater, 800 East Grand Avenue on Navy Pier, Downtown, the Loop & West LoopFri, Oct 30, 2026 · 7:00pm
The Winter's Tale
Downtown, the Loop & West Loop
The Winter's Tale at Chicago Shakespeare Theater.
Limited Run
#19Fri, Oct 30, 2026 · 7:00pm · Limited Run
Chicago Shakespeare Theater, 800 East Grand Avenue on Navy Pier, Downtown, the Loop & West Loop#20
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
#20October 9, 2026 – April 18, 2027 · Limited Run
Richard H. Driehaus Museum, River North, Downtown, the Loop & West Loop#21
House of Blues, River North, Downtown, the Loop & West LoopSat, Oct 31, 2026 · 7:00pm
Akeem Ali – The Texture Tour
Downtown, the Loop & West Loop
Akeem Ali – The Texture Tour at House of Blues.
One Day Only
#21Sat, Oct 31, 2026 · 7:00pm · One Day Only
House of Blues, River North, Downtown, the Loop & West Loop#22
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
#22On 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#23
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
#23On 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#24
Radius, 640 West Cermak Rd, Downtown, the Loop & West LoopFri, Oct 30, 2026 · 10:00pm
ATLiens (18 and Over with Valid Government ID)
Downtown, the Loop & West Loop
ATLiens (18 and Over with Valid Government ID) at Radius - Chicago.
Limited Run
#24Fri, Oct 30, 2026 · 10:00pm · Limited Run
Radius, 640 West Cermak Rd, Downtown, the Loop & West LoopATLiens (18 and Over with Valid Government ID)
ATLiens (18 and Over with Valid Government ID) at Radius - Chicago.
Add to calendarAbout this list
Stumblday's hand-checked ranking of the best things to do in Downtown, the Loop & West Loop the weekend of Oct 30–Nov 1, 2026: 60 picks, refreshed weekly.
