OCT
01
2026
7:00 PM
THU
Ali Macofsky
Zanies Comedy Club Chicago · 200 seats
1548 North Wells St, Chicago, IL
Avg. price ~ $52
From $47
OCT
01
2026
7:15 PM
THU
Chad Daniels
The Den Theatre
1333 N Milwaukee Ave, Chicago, IL
Avg. price ~ $65
From $63
OCT
01
2026
7:30 PM
THU
Jazmyn W
City Winery - Chicago · 300 seats
1200 West Randolph Street, Chicago, IL
Avg. price ~ $85
From $49
OCT
01
2026
8:00 PM
THU
The Second City Mainstage 114th Revue
Second City Chicago - Mainstage · 290 seats
1616 N Wells St, Chicago, IL
Avg. price ~ $128
From $111
OCT
02
2026
7:00 PM
FRI
Ali Macofsky (21+ Event)
Zanies Comedy Club Chicago · 200 seats
1548 North Wells St, Chicago, IL
Avg. price ~ $54
From $56
OCT
02
2026
7:00 PM
FRI
Dauood Naimyar
The Comedy Bar - Chicago Main Stage
162 E Superior St, Chicago, IL
Avg. price ~ $147
From $52
OCT
02
2026
7:30 PM
FRI
Bill Burr
Chicago Theatre · 3,600 seats
175 N. State Street, Chicago, IL
Avg. price ~ $163
From $82
OCT
02
2026
8:00 PM
FRI
Polski Stand-Up
Copernicus Center · 1,890 seats
5216 W Lawrence Ave, Chicago, IL
Avg. price ~ $224
From $72
OCT
02
2026
9:15 PM
FRI
Ali Macofsky (21+ Event)
Zanies Comedy Club Chicago · 200 seats
1548 North Wells St, Chicago, IL
Avg. price ~ $54
From $56
OCT
02
2026
10:00 PM
FRI
The Second City Mainstage 114th Revue
Second City Chicago - Mainstage · 290 seats
1616 N Wells St, Chicago, IL
Avg. price ~ $140
From $116
OCT
03
2026
7:00 PM
SAT
Bill Burr
Chicago Theatre · 3,600 seats
175 N. State Street, Chicago, IL
Avg. price ~ $179
From $73
OCT
03
2026
7:00 PM
SAT
The Second City Mainstage 114th Revue
Second City Chicago - Mainstage · 290 seats
1616 N Wells St, Chicago, IL
Avg. price ~ $147
From $119
OCT
03
2026
7:00 PM
SAT
Ali Macofsky
Zanies Comedy Club Chicago · 200 seats
1548 North Wells St, Chicago, IL
Avg. price ~ $54
From $56
OCT
03
2026
7:00 PM
SAT
Dauood Naimyar
The Comedy Bar - Chicago Main Stage
162 E Superior St, Chicago, IL
Avg. price ~ $147
From $52
OCT
03
2026
7:30 PM
SAT
KevOnStage
Athenaeum Center · 984 seats
2936 N. Southport Ave., Chicago, IL
Avg. price ~ $206
From $123
OCT
03
2026
8:00 PM
SAT
Kyle Gordon
Subterranean - Upstairs · 400 seats
2011 North Ave, Chicago, IL
Avg. price ~ $46
From $35
OCT
03
2026
9:15 PM
SAT
Ali Macofsky
Zanies Comedy Club Chicago · 200 seats
1548 North Wells St, Chicago, IL
Avg. price ~ $68
From $56
OCT
03
2026
10:00 PM
SAT
Bill Burr
Chicago Theatre · 3,600 seats
175 N. State Street, Chicago, IL
Avg. price ~ $128
From $40
OCT
03
2026
10:00 PM
SAT
The Second City Mainstage 114th Revue
Second City Chicago - Mainstage · 290 seats
1616 N Wells St, Chicago, IL
Avg. price ~ $141
From $102
OCT
04
2026
6:00 PM
SUN
Kevin Williams
The Comedy Bar - Chicago Main Stage
162 E Superior St, Chicago, IL
Avg. price ~ $100
From $100
OCT
04
2026
6:00 PM
SUN
Dr. Fix Me
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL
Avg. price ~ $67
From $67
OCT
04
2026
7:00 PM
SUN
The Second City Mainstage 114th Revue
Second City Chicago - Mainstage · 290 seats
1616 N Wells St, Chicago, IL
Avg. price ~ $128
From $102
OCT
04
2026
7:00 PM
SUN
Emil Wakim
Zanies Comedy Club Chicago · 200 seats
1548 North Wells St, Chicago, IL
Avg. price ~ $54
From $56
OCT
04
2026
7:15 PM
SUN
Jenny Tian
The Den Theatre
1333 N Milwaukee Ave, Chicago, IL
Avg. price ~ $66
From $70
OCT
04
2026
7:30 PM
SUN
Skyler Higley
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL
Avg. price ~ $47
From $47
OCT
04
2026
8:00 PM
SUN
Justin Whitehead
The Comedy Bar - Chicago Main Stage
162 E Superior St, Chicago, IL
Avg. price ~ $71
From $57
OCT
05
2026
7:00 PM
MON
Emil Wakim
Zanies Comedy Club Chicago · 200 seats
1548 North Wells St, Chicago, IL
Avg. price ~ $54
From $56
OCT
05
2026
8:00 PM
MON
Best of The Second City
Second City Chicago - UP Comedy Club
230 W North Ave, Chicago, IL
Avg. price ~ $123
From $103
OCT
06
2026
7:00 PM
TUE
Emil Wakim
Zanies Comedy Club Chicago · 200 seats
1548 North Wells St, Chicago, IL
Avg. price ~ $54
From $56
OCT
06
2026
7:00 PM
TUE
Tomato Throw Show
The Comedy Bar - Chicago Main Stage
162 E Superior St, Chicago, IL
Avg. price ~ $75
From $75
OCT
06
2026
7:30 PM
TUE
Chris Klemens - Chris vs. The People
City Winery - Chicago · 300 seats
1200 West Randolph Street, Chicago, IL
Avg. price ~ $94
From $67
OCT
06
2026
8:00 PM
TUE
The Second City Mainstage 114th Revue
Second City Chicago - Mainstage · 290 seats
1616 N Wells St, Chicago, IL
Avg. price ~ $128
From $102
OCT
07
2026
7:00 PM
WED
Starbomb
Aragon Ballroom · 4,500 seats
1106 W Lawrence Ave, Chicago, IL
Avg. price ~ $77
From $41
OCT
07
2026
7:00 PM
WED
Robby Hoffman
Vic Theatre · 1,400 seats
3145 N Sheffield Ave, Chicago, IL
Avg. price ~ $135
From $54
OCT
07
2026
7:00 PM
WED
Vidura Bandara Rajapaksa
Zanies Comedy Club Chicago · 200 seats
1548 North Wells St, Chicago, IL
Avg. price ~ $170
From $170
OCT
07
2026
7:00 PM
WED
Crowd Work Wednesday
The Comedy Bar - Chicago Main Stage
162 E Superior St, Chicago, IL
Avg. price ~ $75
From $75
OCT
07
2026
7:00 PM
WED
Damn Near Famous Comedy Show
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL
Avg. price ~ $83
From $83
OCT
07
2026
8:00 PM
WED
The Second City Mainstage 114th Revue
Second City Chicago - Mainstage · 290 seats
1616 N Wells St, Chicago, IL
Avg. price ~ $128
From $102
OCT
08
2026
8:00 PM
THU
The Second City Mainstage 114th Revue
Second City Chicago - Mainstage · 290 seats
1616 N Wells St, Chicago, IL
Avg. price ~ $128
From $102
OCT
09
2026
7:00 PM
FRI
Jerry Seinfeld
Chicago Theatre · 3,600 seats
175 N. State Street, Chicago, IL
Avg. price ~ $167
From $82
OCT
09
2026
7:00 PM
FRI
Robby Hoffman
Vic Theatre · 1,400 seats
3145 N Sheffield Ave, Chicago, IL
Avg. price ~ $130
From $99
OCT
09
2026
7:00 PM
FRI
The Second City Mainstage 114th Revue
Second City Chicago - Mainstage · 290 seats
1616 N Wells St, Chicago, IL
Avg. price ~ $135
From $102
OCT
09
2026
7:00 PM
FRI
Paul Elia
The Comedy Bar - Chicago Main Stage
162 E Superior St, Chicago, IL
Avg. price ~ $147
From $52
OCT
09
2026
7:30 PM
FRI
The ReUp - A Monthly Comedy Show
Stars and Garters Theater
3914 N Clark St, Chicago, IL
Avg. price ~ $36
From $34
OCT
09
2026
9:30 PM
FRI
Robby Hoffman
Vic Theatre · 1,400 seats
3145 N Sheffield Ave, Chicago, IL
Avg. price ~ $98
From $29
OCT
09
2026
10:00 PM
FRI
The Second City Mainstage 114th Revue
Second City Chicago - Mainstage · 290 seats
1616 N Wells St, Chicago, IL
Avg. price ~ $135
From $102
OCT
10
2026
3:00 PM
SAT
Best of The Second City
Second City Chicago - UP Comedy Club
230 W North Ave, Chicago, IL
Avg. price ~ $152
From $132
OCT
10
2026
5:00 PM
SAT
Jerry Seinfeld
Chicago Theatre · 3,600 seats
175 N. State Street, Chicago, IL
Avg. price ~ $172
From $94
OCT
10
2026
6:00 PM
SAT
Hunter Hill
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL
Avg. price ~ $72
From $61
OCT
10
2026
7:00 PM
SAT
The Second City Mainstage 114th Revue
Second City Chicago - Mainstage · 290 seats
1616 N Wells St, Chicago, IL
Avg. price ~ $161
From $142
OCT
10
2026
7:00 PM
SAT
Paul Elia
The Comedy Bar - Chicago Main Stage
162 E Superior St, Chicago, IL
Avg. price ~ $76
From $52
OCT
10
2026
7:00 PM
SAT
Laugh Candy RX
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL
Avg. price ~ $61
From $61
OCT
10
2026
7:30 PM
SAT
Jordan Jensen
Vic Theatre · 1,400 seats
3145 N Sheffield Ave, Chicago, IL
Avg. price ~ $101
From $46
OCT
10
2026
8:00 PM
SAT
Jerry Seinfeld
Chicago Theatre · 3,600 seats
175 N. State Street, Chicago, IL
Avg. price ~ $209
From $104
OCT
10
2026
9:00 PM
SAT
Paul Elia
The Comedy Bar - Chicago Main Stage
162 E Superior St, Chicago, IL
Avg. price ~ $147
From $52
OCT
10
2026
10:00 PM
SAT
The Second City Mainstage 114th Revue
Second City Chicago - Mainstage · 290 seats
1616 N Wells St, Chicago, IL
Avg. price ~ $161
From $142
OCT
11
2026
6:00 PM
SUN
Mike Falzone
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL
Avg. price ~ $72
From $61
OCT
11
2026
7:00 PM
SUN
Kanan Gill
Park West · 900 seats
322 W. Armitage, Chicago, IL
Avg. price ~ $65
From $57
OCT
11
2026
7:00 PM
SUN
Jordan Jensen
Vic Theatre · 1,400 seats
3145 N Sheffield Ave, Chicago, IL
Avg. price ~ $52
From $34