#1
Gene Siskel Film Center, Downtown, the Loop & West LoopMonday · Nov 2
WILD RIVER
Downtown, the Loop & West Loop
Screening at Gene Siskel Film Center November 2 at 6 PM. Listed on Gene Siskel Film Center's official calendar.
FilmLimited Run
Date night in Chicago on Monday, Nov 2
12 picks
The 7 best date night in Chicago on Monday, Nov 2
- WILD RIVER — Monday Nov 2 · Downtown
- Monday Night PlayGround — Monday Nov 2 · Free · Logan Square
- Jerker, or The Helping Hand — Monday Nov 2 · $30.00 · Open Space Arts
- 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
Gene Siskel Film Center, Downtown, the Loop & West Loop#1Monday · Nov 2 · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West LoopWILD RIVER
Screening at Gene Siskel Film Center November 2 at 6 PM. Listed on Gene Siskel Film Center's official calendar.
Add to calendar#2
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
#2Monday · 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#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
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
#4Monday · 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#5
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
#5Monday · 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#6
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
#6Monday · 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#7
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
#7Monday · 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 calendarAlso open Mon, Nov 2 — check hours
#8
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
#8Runs 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#9
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
#9Runs 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#10
KermessRuns through Nov 15, 2026
Premonitions Inc. at Kermess
Kermess
Premonitions Inc. at Kermess at Kermess.
Limited Run
#10Runs through Nov 15, 2026 · Limited Run
Kermess#11
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
#11October 8 – November 8, 2026 · Limited Run
Raven Theatre, Edgewater, Andersonville, Uptown & Lincoln Square#12
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
#12October 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.