Pittsburgh Comedy Shows in May 2027

Stand-up comedians, comedy clubs, touring acts, and performances in Pittsburgh and nearby areas.

Updated: October 17, 2026
3 Comedy Venues

Browse upcoming comedy shows in Pittsburgh during May 2027. Explore stand-up performances, comedy club events, touring comedians, special appearances, venue information, and ticket options updated regularly.

5
Comedy Shows
May 1
Next Show
$56
Lowest Price
$82
Average Price
Next Comedy Show:
Caitlin Peluffo
May 1 · 6:30 PM · Homestead, PA
View Tickets
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Comedy Shows Schedule
Featured Comedy Shows
Popular Comedy Venues
About Comedy Shows
Comedy Shows by Month

Comedy Shows by Date

Popular comedians, touring acts, and upcoming comedy performances this month.

Comedy Shows Schedule — May 2027

Upcoming comedy performances, club shows, and touring comedians.
Upcoming Comedy Shows: 5
  • May
    01
    2027
    6:30 PM
    Sat
    COMEDY
    Best Value
    Weekend Event
    Caitlin Peluffo
    Pittsburgh Improv
    Pittsburgh Improv
    location166 E Bridge St, Homestead, PA 15120location166 E Bridge St, Homestead, PA 15120
    From $56Avg. price ~ $82Tickets Remaining: 18
    View Tickets
  • May
    01
    2027
    9:00 PM
    Sat
    COMEDY
    Best Value
    Weekend Event
    Caitlin Peluffo
    Pittsburgh Improv
    Pittsburgh Improv
    location166 E Bridge St, Homestead, PA 15120location166 E Bridge St, Homestead, PA 15120
    From $56Avg. price ~ $82Tickets Remaining: 18
    View Tickets
  • May
    14
    2027
    7:00 PM
    Fri
    COMEDY
    High Demand
    Taylor Tomlinson
    Benedum Center • 2,800 seats
    Benedum Center
    location237 7th Street, Pittsburgh, PA 15222location237 7th Street, Pittsburgh, PA 15222
    From $85Avg. price ~ $261Tickets Available: 155
    View Tickets
  • May
    20
    2027
    8:00 PM
    Thu
    COMEDY
    Tom Segura
    Rivers Casino Event Center at The Rivers Casino - Pittsburgh
    Rivers Casino Event Center at The Rivers Casino - Pittsburgh
    location777 Casino Dr, Pittsburgh, PA 15212location777 Casino Dr, Pittsburgh, PA 15212
    From $128Avg. price ~ $201Tickets Available: 416
    View Tickets
  • May
    21
    2027
    8:00 PM
    Fri
    COMEDY
    Tom Segura
    Rivers Casino Event Center at The Rivers Casino - Pittsburgh
    Rivers Casino Event Center at The Rivers Casino - Pittsburgh
    location777 Casino Dr, Pittsburgh, PA 15212location777 Casino Dr, Pittsburgh, PA 15212
    From $128Avg. price ~ $239Tickets Available: 315
    View Tickets

Featured Comedy Shows in May 2027

Popular comedians, touring acts, and upcoming comedy performances this month
Caitlin Peluffo
Caitlin Peluffo
Pittsburgh Improv
Homestead, PA
Upcoming Events 6
Next Event: May 01, 2027 6:30 PM
View Tickets
Taylor Tomlinson
Taylor Tomlinson
Benedum Center
Pittsburgh, PA
Upcoming Events 6
Next Event: May 14, 2027 7:00 PM
View Tickets
Tom Segura
Tom Segura
Rivers Casino Event Center at The Rivers Casino - Pittsburgh
Pittsburgh, PA
Upcoming Events 10
Next Event: May 20, 2027 8:00 PM
View Tickets

Popular Comedy Venues in Pittsburgh

Comedy clubs, theaters, casinos, and entertainment venues in Pittsburgh and nearby areas.
Benedum Center
Pittsburgh, PA
Arena
Upcoming Comedy Shows: 1
Next Event: May 14, 2027
→
Pittsburgh Improv
Homestead, PA
Comedy Club
Upcoming Comedy Shows: 2
Next Event: May 01, 2027
→
Rivers Casino Event Center at The Rivers Casino - Pittsburgh
Pittsburgh, PA
Casino / Entertainment
Upcoming Comedy Shows: 2
Next Event: May 20, 2027
→
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About Comedy Shows in May

Stand-up comedy, touring comedians, improv shows, and live entertainment.

Comedy events in Pittsburgh during May 2027 may include stand-up comedy, improv performances, touring comedians, comedy festivals, podcast tours, and live entertainment across venues throughout the region.

Comedy Shows by Month

Browse comedy shows scheduled throughout the year.
January
Comedy Shows in January 2027
11 Upcoming Comedy Shows
February
Comedy Shows in February 2027
9 Upcoming Comedy Shows
March
Comedy Shows in March 2027
15 Upcoming Comedy Shows
April
Comedy Shows in April 2027
14 Upcoming Comedy Shows
May
Comedy Shows in May 2027
5 Upcoming Comedy Shows
June
Comedy Shows in June 2027
Comedy Shows Coming Soon
July
Comedy Shows in July 2027
4 Upcoming Comedy Shows
August
Comedy Shows in August 2027
Comedy Shows Coming Soon
September
Comedy Shows in September 2027
5 Upcoming Comedy Shows
October
This Month
Comedy Shows in October 2026
16 Upcoming Comedy Shows
November
Comedy Shows in November 2026
37 Upcoming Comedy Shows
December
Comedy Shows in December 2026
25 Upcoming Comedy Shows