#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
Things to do tonight in Chicago on Monday, Nov 2
16 picks
The 10 best things to do in Chicago on Monday, Nov 2 night
- Monday Night PlayGround — Monday Nov 2 · Free · Logan Square
- Chicago Blackhawks vs. Colorado Avalanche — Monday Nov 2 · Pilsen
- Jerker, or The Helping Hand — Monday Nov 2 · $30.00 · Open Space Arts
- Design Graveyard: An Exhibition of Unbuilt Chicago Design — Monday Nov 2 · Free · 135 S LaSalle St
- jackzebra - Ages 17+ — Monday Nov 2 · Logan Square
- Lady — Monday Nov 2 · Downtown
- LATE NITE MIC WITH VIK PANDYA — Monday Nov 2 · Downtown
- Best of The Second City — Monday Nov 2 · Lincoln Park
- Fjord — Monday Nov 2 · Downtown
- DePaul Blue Demons Men's Basketball vs. West Georgia Wolves — Monday Nov 2 · Downtown
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
United Center, Pilsen, West Town & the West SideMonday · Nov 2
Chicago Blackhawks vs. Colorado Avalanche
Pilsen, West Town & the West Side
Program at United Center November 2 at 7 PM. Listed on United Center's official calendar.
SportsOne Day Only
#2Monday · Nov 2 · One Day Only
United Center, Pilsen, West Town & the West SideChicago Blackhawks vs. Colorado Avalanche
Program at United Center November 2 at 7 PM. Listed on United Center's official calendar.
Add to calendar#3
Open Space ArtsMonday · Nov 2$30.00
Jerker, or The Helping Hand
Open Space Arts
Two gay men move from anonymous phone fantasy toward tenderness as the AIDS crisis closes around them.
TheaterLGBTQ+Drama
#3Monday · Nov 2 · One Day Only
Open Space ArtsJerker, or The Helping Hand
Two gay men move from anonymous phone fantasy toward tenderness as the AIDS crisis closes around them.
Add to calendar#4
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
#4Monday · 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#5
Subterranean, 2011 North Ave, Logan Square, Wicker Park & BucktownMonday · Nov 2
jackzebra - Ages 17+
Logan Square, Wicker Park & Bucktown
Concert at Subterranean November 2 at 8 PM. Listed on Subterranean's official calendar.
MusicLimited Run
#5Monday · Nov 2 · Limited Run
Subterranean, 2011 North Ave, Logan Square, Wicker Park & Bucktownjackzebra - Ages 17+
Concert at Subterranean November 2 at 8 PM. Listed on Subterranean's official calendar.
Add to calendar#6
Gene Siskel Film Center, Downtown, the Loop & West LoopMonday · Nov 2
Lady
Downtown, the Loop & West Loop
Sian Clifford leads Samuel P. Abrahams's 95-minute absurdist comedy in an exclusive Siskel run.
FilmComedyLate Night
#6Monday · Nov 2 · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West LoopLady
Sian Clifford leads Samuel P. Abrahams's 95-minute absurdist comedy in an exclusive Siskel run.
Add to calendar#7
The Comedy Bar, Downtown, the Loop & West LoopMonday · Nov 2
LATE NITE MIC WITH VIK PANDYA
Downtown, the Loop & West Loop
Comedy show at The Comedy Bar November 2 at 7 PM. Listed on The Comedy Bar's official calendar.
ComedyLimited Run
#7Monday · Nov 2 · Limited Run
The Comedy Bar, Downtown, the Loop & West LoopLATE NITE MIC WITH VIK PANDYA
Comedy show at The Comedy Bar November 2 at 7 PM. Listed on The Comedy Bar's official calendar.
Add to calendar#8
The Second City, Lincoln Park, Lakeview & WrigleyvilleMonday · Nov 2
Best of The Second City
Lincoln Park, Lakeview & Wrigleyville
Comedy show at The Second City November 2 at 7 PM. Listed on The Second City's official calendar.
ComedyOne Day Only
#8Monday · Nov 2 · One Day Only
The Second City, Lincoln Park, Lakeview & WrigleyvilleBest of The Second City
Comedy show at The Second City November 2 at 7 PM. Listed on The Second City's official calendar.
Add to calendar#9
Gene Siskel Film Center, Downtown, the Loop & West LoopMonday · Nov 2
Fjord
Downtown, the Loop & West Loop
Cristian Mungiu's multilingual 146-minute drama gets a late digital screening at the Siskel.
FilmInternationalSubtitled
#9Monday · Nov 2 · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West LoopFjord
Cristian Mungiu's multilingual 146-minute drama gets a late digital screening at the Siskel.
Add to calendar#10
Wintrust Arena, 200 E Cermak Road, Downtown, the Loop & West LoopMonday · Nov 2
DePaul Blue Demons Men's Basketball vs. West Georgia Wolves
Downtown, the Loop & West Loop
DePaul opens a Monday evening at Wintrust Arena against the West Georgia Wolves.
BasketballCollege Sports
#10Monday · Nov 2 · Limited Run
Wintrust Arena, 200 E Cermak Road, Downtown, the Loop & West LoopDePaul Blue Demons Men's Basketball vs. West Georgia Wolves
DePaul opens a Monday evening at Wintrust Arena against the West Georgia Wolves.
Add to calendarMore on Mon, Nov 2
#11
Welsh Ryan Arena / McGaw Hall, 1501 Central St, Evanston & Oak ParkMonday · Nov 2
Northwestern Wildcats Men's Basketball vs. Binghamton Bearcats
1501 Central St, Evanston & Oak Park
Northwestern hosts Binghamton in a 7 PM men's basketball game at Welsh-Ryan Arena.
BasketballEvanston
#11Monday · Nov 2 · Limited Run
Welsh Ryan Arena / McGaw Hall, 1501 Central St, Evanston & Oak ParkNorthwestern Wildcats Men's Basketball vs. Binghamton Bearcats
Northwestern hosts Binghamton in a 7 PM men's basketball game at Welsh-Ryan Arena.
Add to calendarAlso open Mon, Nov 2 — check hours
#12
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
#12Runs 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#13
Aguijón TheaterRuns through Nov 15, 2026
I.A. Inteligencia Actoral – Destinos: 9th Chicago International Latino Theater Festival
Aguijón Theater
I.A. Inteligencia Actoral – Destinos: 9th Chicago International Latino Theater Festival at Aguijón.
Limited Run
#13Runs through Nov 15, 2026 · Limited Run
Aguijón TheaterI.A. Inteligencia Actoral – Destinos: 9th Chicago International Latino Theater Festival
I.A. Inteligencia Actoral – Destinos: 9th Chicago International Latino Theater Festival at Aguijón.
Add to calendar#14
KermessRuns through Nov 15, 2026
Premonitions Inc. at Kermess
Kermess
Premonitions Inc. at Kermess at Kermess.
Limited Run
#14Runs through Nov 15, 2026 · Limited Run
KermessThe whole weekend, in one email.
Friday at 5pm, one email. Unsubscribe anytime.
#15
Raven Theatre, Edgewater, Andersonville, Uptown & Lincoln SquareOctober 8 – November 8, 2026Tickets via Raven Theatre
A Strange Loop
Andersonville, Uptown & Lincoln Square
A Strange Loop is listed for Chicago this weekend.
Limited Run
#15October 8 – November 8, 2026 · Limited Run
Raven Theatre, Edgewater, Andersonville, Uptown & Lincoln Square#16
Stolp Island Theatre, Aurora, Far SuburbsOctober 7, 2026 – January 3, 2027$87 in person
Million Dollar Quartet
Aurora, Far Suburbs
Million Dollar Quartet is listed for Chicago this weekend.
Limited Run
#16October 7, 2026 – January 3, 2027 · Limited Run
Stolp Island Theatre, Aurora, Far SuburbsAbout 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.