#1
The Den Theatre, Logan Square, Wicker Park & BucktownMonday · Nov 2Free
Monday Night PlayGround
Logan Square, Wicker Park & Bucktown
Performance at The Den Theatre November 2 at 7 PM. Listed on The Den Theatre's official calendar.
FreeTheater
Free things to do in Chicago on Monday, Nov 2
6 picks
The 3 best free things to do in Chicago on Monday, Nov 2
- Monday Night PlayGround — Monday Nov 2 · Free · Logan Square
- Design Graveyard: An Exhibition of Unbuilt Chicago Design — Monday Nov 2 · Free · 135 S LaSalle St
- LeRoy Neiman: A Keen Observer of Style — Monday Nov 2 · Free · School of the Art Institute
The Den Theatre, Logan Square, Wicker Park & Bucktown#1Monday · Nov 2 · One Day Only
The Den Theatre, Logan Square, Wicker Park & BucktownMonday Night PlayGround
Performance at The Den Theatre November 2 at 7 PM. Listed on The Den Theatre's official calendar.
Add to calendar#2
135 S LaSalle StMonday · Nov 2Free
Design Graveyard: An Exhibition of Unbuilt Chicago Design
135 S LaSalle St
Rejected pitches and abandoned Chicago design ideas finally leave the studio in this free exhibition.
FreeArtDesign
#2Monday · Nov 2 · One Day Only
135 S LaSalle StDesign Graveyard: An Exhibition of Unbuilt Chicago Design
Rejected pitches and abandoned Chicago design ideas finally leave the studio in this free exhibition.
Add to calendar#3
School of the Art InstituteMonday · Nov 2Free
LeRoy Neiman: A Keen Observer of Style
School of the Art Institute
Eighty works connect LeRoy Neiman's Chicago fashion training to his vivid later images of people and sport.
FreeArtFashion
#3Monday · Nov 2 · One Day Only
School of the Art InstituteLeRoy Neiman: A Keen Observer of Style
Eighty works connect LeRoy Neiman's Chicago fashion training to his vivid later images of people and sport.
Add to calendarAlso open Mon, Nov 2 — check hours
#4
Harold Washington Library CenterOn view through Nov 15, 2026Free
“Pulitzer on the Road: Prize-Winning Works That Inform, Empower & Inspire”
Harold Washington Library Center
“Pulitzer on the Road: Prize-Winning Works That Inform, Empower & Inspire” at Harold Washington.
FreeArt
#4On view through Nov 15, 2026 · Limited Run
Harold Washington Library Center“Pulitzer on the Road: Prize-Winning Works That Inform, Empower & Inspire”
“Pulitzer on the Road: Prize-Winning Works That Inform, Empower & Inspire” at Harold Washington.
Add to calendar#5
Annoyance Theatre & BarRuns through Nov 13, 2026Free
Comedy Hour at Annoyance Theatre
Annoyance Theatre & Bar
Comedy Hour at Annoyance Theatre at Annoyance Theatre & Bar.
FreeLimited Run
#5Runs through Nov 13, 2026 · Limited Run
Annoyance Theatre & BarComedy Hour at Annoyance Theatre
Comedy Hour at Annoyance Theatre at Annoyance Theatre & Bar.
Add to calendar#6
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
#6September 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 calendarAbout this list
Stumblday's ranked list of the best things to do in Chicago on Monday, November 2: 15 events, led by WILD RIVER, Monday Night PlayGround and Chicago Blackhawks vs. Colorado Avalanche — each one checked against the organizer's own page. Below them, 24 exhibitions and shows running through the day.