Cleveland Comedy Shows in May 2027

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

  • Updated: November 7, 2026
  • 2 Comedy Venues

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

  • 6 Comedy Shows
  • May 13 Next Show
  • $54 Lowest Price
  • $94 Average Price
  • Next Comedy Show:
  • Usama Siddiquee
  • May 13 · 7:00 PM · Hilarities 4th Street Theatre At Pickwick & Frolic
  • View Tickets
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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: 6
  • May 13, 2027, 7:00 PM Thu — COMEDY, Best Value: Usama Siddiquee at Hilarities 4th Street Theatre At Pickwick & Frolic, 2035 East 4th Street, Cleveland, OH 44115. From $54, Avg. price ~ $89, Tickets Remaining: 20. View Tickets
  • May 13, 2027, 7:00 PM Thu — COMEDY, High Demand, Pay Later Available: Modi at Mimi Ohio Theatre At Playhouse Square • 1,000 seats, 1511 Euclid Avenue, Cleveland, OH 44115. From $108, Avg. price ~ $183, Tickets Remaining: 5. View Tickets
  • May 14, 2027, 7:00 PM Fri — COMEDY, Best Value: Usama Siddiquee at Hilarities 4th Street Theatre At Pickwick & Frolic, 2035 East 4th Street, Cleveland, OH 44115. From $54, Avg. price ~ $94, Tickets Remaining: 20. View Tickets
  • May 14, 2027, 9:45 PM Fri — COMEDY, Best Value: Usama Siddiquee at Hilarities 4th Street Theatre At Pickwick & Frolic, 2035 East 4th Street, Cleveland, OH 44115. From $54, Avg. price ~ $94, Tickets Remaining: 20. View Tickets
  • May 15, 2027, 7:00 PM Sat — COMEDY, Best Value, Weekend Event: Usama Siddiquee at Hilarities 4th Street Theatre At Pickwick & Frolic, 2035 East 4th Street, Cleveland, OH 44115. From $54, Avg. price ~ $94, Tickets Remaining: 20. View Tickets
  • May 15, 2027, 9:45 PM Sat — COMEDY, Best Value, Weekend Event: Usama Siddiquee at Hilarities 4th Street Theatre At Pickwick & Frolic, 2035 East 4th Street, Cleveland, OH 44115. From $54, Avg. price ~ $94, Tickets Remaining: 20. View Tickets

About Comedy Shows in May

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


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