Riddles Comedy Club Events

Buy tickets online TO GUARANTEE YOUR SEATS 
or pay cash @ the door.
WALK INS WELCOME BUT SEATS ARE NOT GUARANTEED.
Every Monday Night
Open Mic Mondays, Hosted by Smitty Smith & Said Moore

8:00 PM

  • 2 Beverage Minimum During the Show

  • CASH VENUE ONLY (ATM ON PREMISES)

  • Free Parking

  • Must be 21 to enter with a photo ID

Sign Up @ 7:00 PM
Showtime @ 8:00PM

Starting November 11th
Every Tuesday Night
Karaoke Night Every Tuesday

7:00 PM

  • 2 Beverage Minimum During the Show

  • CASH VENUE ONLY (ATM ON PREMISES)

  • Free Parking

  • Must be 21 to enter with a photo ID

Doors open @ 7:00 PM

DECEMBER SHOWS

December 18th
ISSA CELEBRATION!!!!

7:30 pm

  • 2 Beverage minimum during the Event

  • CASH VENUE ONLY (ATM ON PREMISES)

  • Free Parking

  • Must be 21 to enter with a photo ID

7:30PM
Doors open @ 7:30 PM

Buy Tickets
December 19th & 20th
Built 2 Destroy Presents Comedy Holiday Weekend!

7:30 PM & 10:00 PM

  • 2 Beverage minimum during the Event

  • CASH VENUE ONLY (ATM ON PREMISES)

  • Free Parking

  • Must be 21 to enter with a photo ID

  • $25 Cash Cover

7:30 pm & 10:00 pm
Doors open @ 6:30 PM

BUY TICKETS
December 26th & 27th
Built 2 Destroy Presents XMAS Customer Appreciation Weekend!

7:30 PM & 10:00 Pm

  • 2 Beverage minimum during the Event

  • CASH VENUE ONLY (ATM ON PREMISES)

  • Free Parking

  • Must be 21 to enter with a photo ID

7:30 pm & 10:00 pm
Doors open @ 7:00 PM

BUY TICKETS
December 31st
Broke But Famous Presents NYE All Black Affair Stick & Just Nesh!

8:00 PM

  • 2 Beverage minimum during the Event

  • CASH VENUE ONLY (ATM ON PREMISES)

  • Free Parking

  • Must be 21 to enter with a photo ID

Doors open @ 8:00 PM

BUY TICKETS
December 18th
ISSA CELEBRATION!!!!

7:30 pm

  • 2 Beverage minimum during the Event

  • CASH VENUE ONLY (ATM ON PREMISES)

  • Free Parking

  • Must be 21 to enter with a photo ID

7:30PM
Doors open @ 7:30 PM

Buy Tickets
December 19th & 20th
The legendary Gerald Kelly and Son live at Riddles Comedy Club doing four shows over the weekend. Laughter will be passed out in bundles.

7:30 PM & 10:00 PM

  • 2 Beverage minimum during the Event

  • CASH VENUE ONLY (ATM ON PREMISES)

  • Free Parking

  • Must be 21 to enter with a photo ID

  • $25 Cash Cover

7:30 pm & 10:00 pm
Doors open @ 7:00 PM

BUY TICKETS

JANUARY SHOWS 2026

January  2nd & 3rd
Chicago Hottest House Music DJ's and Four Funny Comedians takeover Riddles Comedy Club!

8:00 pm

  • 2 Beverage minimum during the Event

  • CASH VENUE ONLY (ATM ON PREMISES)

  • Free Parking

  • Must be 21 to enter with a photo ID

8:00 pm
Doors open @ 7:30 PM

Buy Tickets
January 11th
Join us for Healing in Laughter, a fun live event where good vibes and laughs boost your soul and mood!

Skip Clark is one funny and talented Comedian. He was the talent coordinator for BET's/ComicView-Hosted by Comedian Ricky Smiley. He appeared on Just Kickin it-STARZtv -West Coast Comedy-H...More

Skip Clark is one funny and talented Comedian. He was the talent coordinator for BET's/ComicView-Hosted by Comedian Ricky Smiley. He appeared on Just Kickin it-STARZtv -West Coast Comedy-Hulu Network and Comedy Time. He has also appeared in the film Two Degrees and Recruitment Day.

His Featuring sidekick Ellis Wynne is one of the funniest comics I've seen on stage. Ellis has a great stage presence and will have you laughing till it hurts. With his real stories of his life and his clever approach to stand up comedy. He is refreshing to the stage and the world of comedy. He has been in the movie Natural Born Killers and a finalist on Last Comic Standing.

Less

5:00 PM

  • 2 Beverage minimum during the Event

  • CASH VENUE ONLY (ATM ON PREMISES)

  • Free Parking

  • Must be 21 to enter with a photo ID

  • $25 Cash Cover

5:00 pm
Doors open @ 4:30 PM

BUY TICKETS
January 11th
R&B BiNGO CHICAGO! TRAP Vs R&B BiNGO W/ Comedian THANK YOU CHRIS!

7:00 PM

  • 2 Beverage minimum during the Event

  • CASH VENUE ONLY (ATM ON PREMISES)

  • Free Parking

  • Must be 21 to enter with a photo ID

Doors open @ 7:00 PM

BUY TICKETS
January  15th
Living The Dream Comedy Show!

8:00 pm

  • 2 Beverage minimum during the Event

  • CASH VENUE ONLY (ATM ON PREMISES)

  • Free Parking

  • Must be 21 to enter with a photo ID

8:00 pm
Doors open @ 7:30 PM

Buy Tickets
January 16th & 17th
Damon Williams Capricorn Birthday Weekend!

7:30 PM - 10:00 pm

  • 2 Beverage minimum during the Event

  • CASH VENUE ONLY (ATM ON PREMISES)

  • Free Parking

  • Must be 21 to enter with a photo ID

7:30 PM - 10:00 pm
Doors open @ 7:00 PM

BUY TICKETS
January 11th
Join us for Healing in Laughter, a fun live event where good vibes and laughs boost your soul and mood!

Skip Clark is one funny and talented Comedian. He was the talent coordinator for BET's/ComicView-Hosted by Comedian Ricky Smiley. He appeared on Just Kickin it-STARZtv -West Coast Comedy-H...More

Skip Clark is one funny and talented Comedian. He was the talent coordinator for BET's/ComicView-Hosted by Comedian Ricky Smiley. He appeared on Just Kickin it-STARZtv -West Coast Comedy-Hulu Network and Comedy Time. He has also appeared in the film Two Degrees and Recruitment Day.

His Featuring sidekick Ellis Wynne is one of the funniest comics I've seen on stage. Ellis has a great stage presence and will have you laughing till it hurts. With his real stories of his life and his clever approach to stand up comedy. He is refreshing to the stage and the world of comedy. He has been in the movie Natural Born Killers and a finalist on Last Comic Standing.

Less

5:00 PM

  • 2 Beverage minimum during the Event

  • CASH VENUE ONLY (ATM ON PREMISES)

  • Free Parking

  • Must be 21 to enter with a photo ID

  • $25 Cash Cover

5:00 pm
Doors open @ 4:30 PM

BUY TICKETS

february SHOWS 2026

February 6th & 7th
8th Annual T K Takeover

7:30 PM - 10:00 pm

  • 2 Beverage minimum during the Event

  • CASH VENUE ONLY (ATM ON PREMISES)

  • Free Parking

  • Must be 21 to enter with a photo ID

7:30 PM - 10:00 pm
Doors open @ 7:00 PM

BUY TICKETS
December 7th
Mr. Bankshot Live @ Riddles Comedy Club!

7:30 PM & 10:00 pm

  • 2 Beverage minimum during the Event

  • CASH VENUE ONLY (ATM ON PREMISES)

  • Free Parking

  • Must be 21 to enter with a photo ID

7:30PM - 10:00PM
Doors open @ 7:00 PM

Buy Tickets
December 12th &13th
Skip Clark Live, you won't leave without tears in your eyes from laughing so hard!

Skip Clark is one funny and talented Comedian. He was the talent coordinator for BET's/ComicView-Hosted by Comedian Ricky Smiley. He appeared on Just Kickin it-STARZtv -West Coast Comedy-H...More

Skip Clark is one funny and talented Comedian. He was the talent coordinator for BET's/ComicView-Hosted by Comedian Ricky Smiley. He appeared on Just Kickin it-STARZtv -West Coast Comedy-Hulu Network and Comedy Time. He has also appeared in the film Two Degrees and Recruitment Day.

His Featuring sidekick Ellis Wynne is one of the funniest comics I've seen on stage. Ellis has a great stage presence and will have you laughing till it hurts. With his real stories of his life and his clever approach to stand up comedy. He is refreshing to the stage and the world of comedy. He has been in the movie Natural Born Killers and a finalist on Last Comic Standing.

Less

7:30 PM & 10:00 PM

  • 2 Beverage minimum during the Event

  • CASH VENUE ONLY (ATM ON PREMISES)

  • Free Parking

  • Must be 21 to enter with a photo ID

  • $25 Cash Cover

7:30 pm & 10:00 PM
Doors open @ 7:00 PM

BUY TICKETS

march SHOWS 2026

March 26th
Missta LaCraig Live — He Finna Snap!

7:30 PM

  • 2 Beverage minimum during the Event

  • CASH VENUE ONLY (ATM ON PREMISES)

  • Free Parking

  • Must be 21 to enter with a photo ID

7:30 PM
Doors open @ 7:00 PM

BUY TICKETS
December 7th
Mr. Bankshot Live @ Riddles Comedy Club!

7:30 PM & 10:00 pm

  • 2 Beverage minimum during the Event

  • CASH VENUE ONLY (ATM ON PREMISES)

  • Free Parking

  • Must be 21 to enter with a photo ID

7:30PM - 10:00PM
Doors open @ 7:00 PM

Buy Tickets
December 12th &13th
Skip Clark Live, you won't leave without tears in your eyes from laughing so hard!

Skip Clark is one funny and talented Comedian. He was the talent coordinator for BET's/ComicView-Hosted by Comedian Ricky Smiley. He appeared on Just Kickin it-STARZtv -West Coast Comedy-H...More

Skip Clark is one funny and talented Comedian. He was the talent coordinator for BET's/ComicView-Hosted by Comedian Ricky Smiley. He appeared on Just Kickin it-STARZtv -West Coast Comedy-Hulu Network and Comedy Time. He has also appeared in the film Two Degrees and Recruitment Day.

His Featuring sidekick Ellis Wynne is one of the funniest comics I've seen on stage. Ellis has a great stage presence and will have you laughing till it hurts. With his real stories of his life and his clever approach to stand up comedy. He is refreshing to the stage and the world of comedy. He has been in the movie Natural Born Killers and a finalist on Last Comic Standing.

Less

7:30 PM & 10:00 PM

  • 2 Beverage minimum during the Event

  • CASH VENUE ONLY (ATM ON PREMISES)

  • Free Parking

  • Must be 21 to enter with a photo ID

  • $25 Cash Cover

7:30 pm & 10:00 PM
Doors open @ 7:00 PM

BUY TICKETS

Stand Up Comedy Open Mic Night

Every Monday

COMEDY SHOW FOLLOWED BY OPEN MIC @ 8:00 PM

21 to Enter, 7 pm sign-up 2 drink minimum $0 admission