Double Header Comedy

Two headliners. One stage. Zero filler.

Two of Chicago's top headliners are performing at the colorful, intimate showspace found at Hotel Indigo on Friday, February 27. Join us for a night of nonstop laughs and great vibes in an eclectic venue just east of downtown Madison.

Tyler Fowler is a nationally touring comedian who expertly weaves relatable anecdotes about marriages, kids, and jobs - none of which he has - to create a show you won't want to miss. His debut album Friends With 401(k) Benefits premiered #1 on iTunes and Top 10 on the Billboard Comedy Charts and was followed by a 30 minute special with Drybar Comedy titled Little Spoon and an hour special with Comedy Dynamics titled My Mom Said I Can’t Go. Based in Chicago Tyler can be seen regularly at The Laugh Factory and Zanies Comedy Clubs.

Chris Trani is a favorite of the Chicago comedy scene and the producer of The House of Blues stand-up comedy show on Thursday nights in Chicago. He’s also a regular at Zanies, The Laugh Factory, The Funny Bone, and more. Chris has opened for Ken Flores, Jon Lovitz, and regularly opens for David Koechner of The Office & Anchorman. He’s also shared the stage with Ari Shaffir, Roy Wood Jr., and Pat McGann. Chris integrates all forms of comedy into his act: stand-up, storytelling, crowd work, one-liners; and if need be, can do it all in Spanish too.

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Friday, February 27, 2026

Doors at 6:30pm

Show at 7pm

Hotel Indigo

901 E Washington Ave

Madison, WI

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Tickets are $15 in advance, $20 day of show. Purchase tickets online to guarantee seating.

https://www.eventbrite.com/e/double-header-comedy-tickets-1980781031386

SPECIAL DISCOUNT FOR STUDENTS (CASH ONLY): $5 at the door with a student ID!

RSVP on Facebook:

https://www.facebook.com/events/1236856644971390

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Recommended for ages 18+. Lineup subject to change.

Seating is first come, first served, so we suggest arriving thirty minutes prior to showtime when doors open to have your pick of seats.

We do not offer refunds, but if you purchase a ticket and are unable to attend, please contact Cheshire Cat Comedy at cheshirecatcomedyco@gmail.com to redeem for free admission to a future show of your choice. Refunds will be issued automatically in the event of a show's cancellation.