Chicago Comedy Shows May 2026

Browse the schedule of all comedy shows and stand-up comedians this month.
Get ready, get set, and laugh as you discover the best comedy shows and comedians this season. People can enjoy various comedy shows, from stand-up to sitcom to sketch comedy. Some popular comedy venues in the city include UP Comedy Club, etc. Theater, Mainstage at Second City, and more. There are many comedians that people can enjoy watching live someday. People love to laugh. Thanks to the talented artists who make laughter the best medicine. Don’t miss the best comedy shows this month. Find the best seats, buy comedy tickets today, and save!

Start Date
May 1, 2026
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End Date
May 6, 2026
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Events Calendar
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Schedule & Tickets
List Of Shows
Comedy Venues
All Theatre Shows

Comedy Tickets

Comedy Shows: 39
Shows in May
  • Pat Tomasulo
    May
    01
    2026
    7:00 PM
    Fri
    Zanies Comedy Club - Rosemont
    60018, 5437 Park Pl, Rosemont, IL, US
    Event Info
  • Chicago Theater Shows
    May
    01
    2026
    7:15 PM
    Fri
    Rayna Greenberg
    Heath Mainstage At The Den Theatre | Capacity: 302
    60622, 1331 N. Milwaukee Ave, Chicago, IL, US
    Event Info
  • Steven Ho
    May
    01
    2026
    8:00 PM
    Fri
    Historic Main Stage at Athenaeum Center - IL | Capacity: 984
    60657, 2936 North Southport Avenue, Chicago, IL, US
    Event Info
  • Matteo Lane
    May
    02
    2026
    7:00 PM
    Sat
    The Chicago Theatre | Capacity: 3600
    60601, 175 North State Street, Chicago, IL, US
    Event Info
  • Katt Williams
    May
    02
    2026
    8:00 PM
    Sat
    Katt Williams VIP Experience Available
    United Center | Capacity: 23500
    60612, 1901 West Madison Street, Chicago, IL, US
    Event Info
  • Chicago Theater Shows
    May
    03
    2026
    7:00 PM
    Sun
    Joe Sib
    Zanies Comedy Club - Chicago
    60610, 1548 North Wells Street, Chicago, IL, US
    Event Info
  • Chicago Theater Shows
    May
    03
    2026
    7:30 PM
    Sun
    House Guest Live ft. Scott Evans
    City Winery - Chicago
    60607, 1200 W. Randolph St., Chicago, IL, US
    Event Info
  • Doug Benson
    May
    04
    2026
    7:30 PM
    Mon
    Zanies Comedy Club - Chicago
    60610, 1548 North Wells Street, Chicago, IL, US
    Event Info
  • Doug Loves Movies
    May
    05
    2026
    7:30 PM
    Tue
    Zanies Comedy Club - Rosemont
    60018, 5437 Park Pl, Rosemont, IL, US
    Event Info
  • Will Burkart
    May
    07
    2026
    7:00 PM
    Thu
    Zanies Comedy Club - Chicago
    60610, 1548 North Wells Street, Chicago, IL, US
    Event Info
  • Sooshi Mango
    May
    07
    2026
    8:00 PM
    Thu
    Historic Main Stage at Athenaeum Center - IL | Capacity: 984
    60657, 2936 North Southport Avenue, Chicago, IL, US
    Event Info
  • Will Burkart
    May
    08
    2026
    7:00 PM
    Fri
    Zanies Comedy Club - Chicago
    60610, 1548 North Wells Street, Chicago, IL, US
    Event Info
  • Chicago Theater Shows
    May
    08
    2026
    7:00 PM
    Fri
    Gus Constantellis
    The Comedy Bar - Chicago
    60611, 162 E Superior Street, Chicago, IL, US
    Event Info
  • Chicago Theater Shows
    May
    08
    2026
    7:30 PM
    Fri
    Tasha K
    City Winery - Chicago
    60607, 1200 W. Randolph St., Chicago, IL, US
    Event Info
  • Chicago Theater Shows
    May
    08
    2026
    7:30 PM
    Fri
    Vic Theatre | Capacity: 1400
    60657, 3145 N Sheffield, Chicago, IL, US
    Event Info
  • Chicago Theater Shows
    May
    08
    2026
    8:00 PM
    Fri
    Harland Williams
    Park West | Capacity: 900
    60614, 322 W. Armitage, Chicago, IL, US
    Event Info
  • Chicago Theater Shows
    May
    08
    2026
    9:00 PM
    Fri
    Gus Constantellis
    The Comedy Bar - Chicago
    60611, 162 E Superior Street, Chicago, IL, US
    Event Info
  • Will Burkart
    May
    08
    2026
    9:15 PM
    Fri
    Zanies Comedy Club - Chicago
    60610, 1548 North Wells Street, Chicago, IL, US
    Event Info
  • Will Burkart
    May
    09
    2026
    7:00 PM
    Sat
    Zanies Comedy Club - Chicago
    60610, 1548 North Wells Street, Chicago, IL, US
    Event Info
  • Chicago Theater Shows
    May
    09
    2026
    7:00 PM
    Sat
    Gus Constantellis
    The Comedy Bar - Chicago
    60611, 162 E Superior Street, Chicago, IL, US
    Event Info
  • Chicago Theater Shows
    May
    09
    2026
    9:00 PM
    Sat
    Gus Constantellis
    The Comedy Bar - Chicago
    60611, 162 E Superior Street, Chicago, IL, US
    Event Info
  • Will Burkart
    May
    09
    2026
    9:15 PM
    Sat
    Zanies Comedy Club - Chicago
    60610, 1548 North Wells Street, Chicago, IL, US
    Event Info
  • Ryan Long
    May
    12
    2026
    7:00 PM
    Tue
    Zanies Comedy Club - Chicago
    60610, 1548 North Wells Street, Chicago, IL, US
    Event Info
  • Ryan Long
    May
    13
    2026
    7:00 PM
    Wed
    Zanies Comedy Club - Chicago
    60610, 1548 North Wells Street, Chicago, IL, US
    Event Info
  • Ryan Long
    May
    14
    2026
    7:00 PM
    Thu
    Zanies Comedy Club - Chicago
    60610, 1548 North Wells Street, Chicago, IL, US
    Event Info
  • Emma Willmann
    May
    15
    2026
    7:00 PM
    Fri
    Zanies Comedy Club - Chicago
    60610, 1548 North Wells Street, Chicago, IL, US
    Event Info
  • Chicago Theater Shows
    May
    15
    2026
    7:30 PM
    Fri
    Davide De Pierro
    City Winery - Chicago
    60607, 1200 W. Randolph St., Chicago, IL, US
    Event Info
  • Emma Willmann
    May
    15
    2026
    9:15 PM
    Fri
    Zanies Comedy Club - Chicago
    60610, 1548 North Wells Street, Chicago, IL, US
    Event Info
  • Matt McCusker
    May
    16
    2026
    7:00 PM
    Sat
    Riviera Theatre - IL | Capacity: 2500
    60640, 4746 North Racine Avenue, Chicago, IL, US
    Event Info
  • Emma Willmann
    May
    16
    2026
    7:00 PM
    Sat
    Zanies Comedy Club - Chicago
    60610, 1548 North Wells Street, Chicago, IL, US
    Event Info
Show More

List Of Comedy Shows

Pat Tomasulo
Pat Tomasulo
Comedy Shows: 1
Zanies Comedy Club - Rosemont
May 1, 2026 7:00 PM
Rayna Greenberg
Rayna Greenberg
Comedy Shows: 1
Heath Mainstage At The Den Theatre
May 1, 2026 7:15 PM
Steven Ho
Steven Ho
Comedy Shows: 1
Historic Main Stage at Athenaeum Center - IL
May 1, 2026 8:00 PM
Matteo Lane
Matteo Lane
Comedy Shows: 1
The Chicago Theatre
May 2, 2026 7:00 PM
Katt Williams
Katt Williams
Comedy Shows: 1
United Center
May 2, 2026 8:00 PM
Joe Sib
Joe Sib
Comedy Shows: 1
Zanies Comedy Club - Chicago
May 3, 2026 7:00 PM
Scott Evans
Scott Evans
Comedy Shows: 1
City Winery - Chicago
May 3, 2026 7:30 PM
Doug Benson
Doug Benson
Comedy Shows: 1
Zanies Comedy Club - Chicago
May 4, 2026 7:30 PM
Doug Loves Movies
Doug Loves Movies
Comedy Shows: 1
Zanies Comedy Club - Rosemont
May 5, 2026 7:30 PM
Will Burkart
Will Burkart
Comedy Shows: 5
Zanies Comedy Club - Chicago
May 7, 2026 7:00 PM
Sooshi Mango
Sooshi Mango
Comedy Shows: 1
Historic Main Stage at Athenaeum Center - IL
May 7, 2026 8:00 PM
Gus Constantellis
Gus Constantellis
Comedy Shows: 4
The Comedy Bar - Chicago
May 8, 2026 7:00 PM
Tasha K
Tasha K
Comedy Shows: 1
City Winery - Chicago
May 8, 2026 7:30 PM
Naomi Watanabe
Naomi Watanabe
Comedy Shows: 1
Vic Theatre
May 8, 2026 7:30 PM
Harland Williams
Harland Williams
Comedy Shows: 1
Park West
May 8, 2026 8:00 PM
Ryan Long
Ryan Long
Comedy Shows: 3
Zanies Comedy Club - Chicago
May 12, 2026 7:00 PM
Emma Willmann
Emma Willmann
Comedy Shows: 5
Zanies Comedy Club - Chicago
May 15, 2026 7:00 PM
Davide De Pierro
Davide De Pierro
Comedy Shows: 1
City Winery - Chicago
May 15, 2026 7:30 PM
Matt McCusker
Matt McCusker
Comedy Shows: 1
Riviera Theatre - IL
May 16, 2026 7:00 PM
David Sedaris
David Sedaris
Comedy Shows: 1
Auditorium Theatre - IL
May 17, 2026 2:00 PM
Roast Battle Chicago
Roast Battle Chicago
Comedy Shows: 1
Zanies Comedy Club - Chicago
May 21, 2026 9:30 PM
Kerwin Claiborne
Kerwin Claiborne
Comedy Shows: 4
The Comedy Bar - Chicago
May 29, 2026 7:00 PM
Roast Battle
Roast Battle
Comedy Shows: 1
Zanies Comedy Club - Rosemont
May 31, 2026 8:30 PM

Comedy Venues

A-Z List Of All Comedy Clubs and Theaters in City and Chicago Area
Allstate Arena
location 60018, 6920 Mannheim Road, Rosemont, IL, US
Comedy Shows: 1
Arie Crown Theater
location 60616, 2301 Lake Shore Dr At Mccormick Place, Chicago, IL, US
Comedy Shows: 1
Auditorium Theatre - IL
location 60605, 50 East Congress Parkway, Chicago, IL, US
Comedy Shows: 1
Beat Kitchen
location 60618, 2100 W. Belmont, Chicago, IL, US
Comedy Shows: 3
City Winery - Chicago
location 60607, 1200 W. Randolph St., Chicago, IL, US
Comedy Shows: 12
Copernicus Center
location 60630, 5216 West Lawrence Avenue, Chicago, IL, US
Comedy Shows: 1
Des Plaines Theatre
location 60016, 1476 Miner St, Des Plaines, IL, US
Comedy Shows: 2
Garcias Chicago
location 60607, 1001 W Washington Blvd, Chicago, IL, US
Comedy Shows: 1
George Van Dusen Theatre At North Shore Center For The Performing Arts
location 60077, 9501 North Skokie Boulevard
Comedy Shows: 7
Harris Theater
location 60601, 205 E. Randolph, Chicago, IL, US
Comedy Shows: 1
Heath Mainstage At The Den Theatre
location 60622, 1331 N. Milwaukee Ave, Chicago, IL, US
Comedy Shows: 42
Historic Main Stage at Athenaeum Center - IL
location 60657, 2936 North Southport Avenue
Comedy Shows: 2
House Of Blues - Chicago
location 60654, 329 N Dearborn St, Chicago, IL, US
Comedy Shows: 2
Park West
location 60614, 322 W. Armitage, Chicago, IL, US
Comedy Shows: 7
Riviera Theatre - IL
location 60640, 4746 North Racine Avenue, Chicago, IL, US
Comedy Shows: 8
Rosemont Theatre
location 60018, 5400 North River Road, Rosemont, IL, US
Comedy Shows: 1
Subterranean
location 60647, 2011 West North Ave, Chicago, IL, US
Comedy Shows: 1
Thalia Hall
location 60608, 1807 S Allport St, Chicago, IL, US
Comedy Shows: 2
The Chicago Theatre
location 60601, 175 North State Street, Chicago, IL, US
Comedy Shows: 25
The Comedy Bar - Chicago
location 60611, 162 E Superior Street, Chicago, IL, US
Comedy Shows: 31
The Laugh Factory - Chicago
location 60657, 3175 North Broadway, Chicago, IL, US
Comedy Shows: 31
Theatre 2A At The Den Theatre
location 60622, 1331 N. Milwaukee Ave, Chicago, IL, US
Comedy Shows: 13
United Center
location 60612, 1901 West Madison Street, Chicago, IL, US
Comedy Shows: 5
Vic Theatre
location 60657, 3145 N Sheffield, Chicago, IL, US
Comedy Shows: 13
Wintrust Arena
location 60616, 200 E Cermak Rd., Chicago, IL, US
Comedy Shows: 1
Wrigley Field
location 60613, 1060 West Addison Street, Chicago, IL, US
Comedy Shows: 1
Zanies Comedy Club - Chicago
location 60610, 1548 North Wells Street, Chicago, IL, US
Comedy Shows: 135
Zanies Comedy Club - Rosemont
location 60018, 5437 Park Pl, Rosemont, IL, US
Comedy Shows: 60
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