What’s Funny Comedy Festival Brings Comedy, Culture and Chicago Together

Chicago spent the week laughing as the What’s Funny Comedy Festival brought together comedians, and entertainers for a citywide celebration of comedy.

With events ranging from live showcases and podcasts to special appearances, the festival created plenty of opportunities to experience comedy on all levels.

Culture Loft attended two of the festival’s standout events: Honors Night, celebrating Bill Bellamy, and the Still 400 Podcast featuring Lil Rel Howery.

A Night Honoring Bill Bellamy

Honors Night was one of the festival’s biggest moments, with Bill Bellamy receiving the 2026 Icon Award.

The evening recognized Bellamy’s place in comedy while also shining a light on Chicago talent. The event included recognition of Chicago’s Top 15 Comedy Legends,

celebrating comedians whose work has helped shape the city’s comedy culture.

The celebration continued with the What’s Funny Today Show Podcast, with Knowledge Beckon, Lil Rel Howery, Bill Bellamy, and Shawn Morgan bringing live conversation and comedy together in one room.

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The Still 400 Podcast

This event was lit! The festival continued with the Still 400 Podcast, hosted by Juvenile and Mannie Fresh featuring Lil Rel Howery in a live Chicago appearance.

There was a surprise performance by Chicago’s own rap group, Do or Die. This was in true Chicago fashion. Good conversation, comedy, old school hip hop, and good vibes is a recipe for a great night!

More Than a Comedy Festival

Across the week, What’s Funny offered showcases, podcasts, special events and opportunities to connect with iconic comedians and creatives from Chicago and beyond.

But for us those moments stood out: honoring the people who helped build comedy and creating space for today’s voices to connect with audiences.

Comedy has always been part of Chicago culture. What’s Funny Comedy Festival gave Chicago a full week to celebrate it.

This weeks events were definitely worth your time and a moment Chicago will remember and always look forward to.