#1
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
Things to Do in Downtown, the Loop & West Loop Saturday Night, Halloween Weekend 2026
13 picks
The 10 best things to do in Downtown, the Loop & West Loop on Saturday night, Oct 31
- Theater of the Mind — Fri, Nov 13 · Tickets from $69 · Downtown
- Drunk Shakespeare: Drunk Dracula (21+ Event) — Fri, Nov 6 7:00pm · 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
- ART on THE Mart — Thursdays through Sundays, 7:30–8:00 PM · Free · Downtown
- The Winter's Tale — Sat, Nov 7 7:00pm · Downtown
- Akeem Ali – The Texture Tour — Sat, Oct 31 7:00pm · Downtown
- Haunted House Party at Shedd Aquarium — Sat, Oct 31 7:00pm · Downtown
- Swmrs, North By North, Repent — Sat, Oct 31 9:00pm · Downtown
- Skalloween Ft. Noskalgia, Local Legends, Rude Echos — Sat, Oct 31 8:00pm · Downtown
- City Cruises Chicago Seadog Haunted River Tour — Fri, Oct 30 3:00pm · $37 – $60 · Downtown
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West Loop#1Fri, Nov 13, 2026 · Limited Run
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West Loop#2
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
#2Fri, 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#3
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
#3Fri, 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#4
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
#4Thursdays 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#5
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
#5Sat, Nov 7, 2026 · 7:00pm · Limited Run
Chicago Shakespeare Theater, 800 East Grand Avenue on Navy Pier, Downtown, the Loop & West Loop#6
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
#6Sat, Oct 31, 2026 · 7:00pm · One Day Only
House of Blues, River North, Downtown, the Loop & West Loop#7
Shedd Aquarium, Downtown, the Loop & West LoopSat, Oct 31, 2026 · 7:00pm
Haunted House Party at Shedd Aquarium
Downtown, the Loop & West Loop
Haunted House Party at Shedd Aquarium at Shedd Aquarium.
One Day Only
#7Sat, Oct 31, 2026 · 7:00pm · One Day Only
Shedd Aquarium, Downtown, the Loop & West LoopHaunted House Party at Shedd Aquarium
Haunted House Party at Shedd Aquarium at Shedd Aquarium.
Add to calendar#8
Reggies Rock Club, 2109 South State Street, Downtown, the Loop & West LoopSat, Oct 31, 2026 · 9:00pm
Swmrs, North By North, Repent
Downtown, the Loop & West Loop
SWMRS, North By North, Repent at Reggies Rock Club.
Limited Run
#8Sat, Oct 31, 2026 · 9:00pm · Limited Run
Reggies Rock Club, 2109 South State Street, Downtown, the Loop & West Loop#9
Reggies Bananna's Shack, 2105 South State Street, Downtown, the Loop & West LoopSat, Oct 31, 2026 · 8:00pm
Skalloween Ft. Noskalgia, Local Legends, Rude Echos
Downtown, the Loop & West Loop
Skalloween Ft. Noskalgia, Local Legends, Rude Echos at Reggies Bananna's Shack.
Limited Run
#9Sat, Oct 31, 2026 · 8:00pm · Limited Run
Reggies Bananna's Shack, 2105 South State Street, Downtown, the Loop & West LoopSkalloween Ft. Noskalgia, Local Legends, Rude Echos
Skalloween Ft. Noskalgia, Local Legends, Rude Echos at Reggies Bananna's Shack.
Add to calendar#10
City Cruises Chicago – Navy Pier, Downtown, the Loop & West LoopFri, Oct 30, 2026 · 3:00pm$37 – $60
City Cruises Chicago Seadog Haunted River Tour
Downtown, the Loop & West Loop
City Cruises Chicago Seadog Haunted River Tour at City Cruises Chicago – Navy Pier.
Limited Run
#10Fri, Oct 30, 2026 · 3:00pm · Limited Run
City Cruises Chicago – Navy Pier, Downtown, the Loop & West LoopCity Cruises Chicago Seadog Haunted River Tour
City Cruises Chicago Seadog Haunted River Tour at City Cruises Chicago – Navy Pier.
Add to calendarMore on Saturday night
#11
Garcia's Chicago, 1001 W Washington Blvd, Downtown, the Loop & West LoopSat, Oct 31, 2026 · 8:00pm
Dumpstaphunk
Downtown, the Loop & West Loop
Dumpstaphunk at Garcia's Chicago.
Limited Run
#11Sat, Oct 31, 2026 · 8:00pm · Limited Run
Garcia's Chicago, 1001 W Washington Blvd, Downtown, the Loop & West Loop#12
Foundation Room at House of Blues Chicago, 329 N Dearborn St, Downtown, the Loop & West LoopSat, Oct 31, 2026 · 6:30pm
Witches & Wizards Ball
Downtown, the Loop & West Loop
WITCHES & WIZARDS BALL at Foundation Room at House of Blues Chicago.
Limited Run
#12Sat, Oct 31, 2026 · 6:30pm · Limited Run
Foundation Room at House of Blues Chicago, 329 N Dearborn St, Downtown, the Loop & West LoopWitches & Wizards Ball
WITCHES & WIZARDS BALL at Foundation Room at House of Blues Chicago.
Add to calendar#13
Moe's Cantina - River North, River NorthSat, Oct 31, 2026 · 5pm–12am$10
Nightmare On Kinzie Street
Moe's Cantina - River North, River North
A 21+ Halloween bar crawl through three River North venues. Start at Moe’s Cantina from 5–7pm, continue to Tunnel from 7–9pm and finish at Tree House from 9pm–midnight for a Hocus Pocus-themed finale.
From the organizerOne Day Only
#13Sat, Oct 31, 2026 · 5pm–12am · One Day Only
Moe's Cantina - River North, River NorthNightmare On Kinzie Street
A 21+ Halloween bar crawl through three River North venues. Start at Moe’s Cantina from 5–7pm, continue to Tunnel from 7–9pm and finish at Tree House from 9pm–midnight for a Hocus Pocus-themed finale.
Add to calendarAbout this list
Stumblday's hand-checked ranking of the best things to do in Downtown, the Loop & West Loop on Saturday night of Halloween weekend, Oct 31: 13 picks.
