Chicago, Unknown, November 1, 2025 — Chicago’s celebrated 312 Comedy Festival is set to make a triumphant return this November, promising a week filled with laughter, creativity, and community spirit. Now in its third year, the festival has rapidly become a cornerstone of the city’s entertainment calendar, drawing acclaimed comedians and enthusiastic audiences from across the region. From 4 to 9 November, six of Chicago’s most iconic venues will host twenty-four shows, each designed to showcase the vibrant diversity and innovation that define contemporary comedy.
The festival’s organisers, Outback Presents and Jam Productions, have curated an impressive roster of talent for 2025, blending household names with emerging voices. The Chicago Theatre, renowned for its grandeur and history, will anchor the festival’s biggest events. Audiences can look forward to Fortune Feimster’s “Taking Care of Biscuits” tour, which brings her signature warmth and wit to the stage on 8 November. The night before, Ralph Barbosa will perform two shows as part of his “Bean Without a Cause” tour, offering a fresh perspective that has resonated with fans nationwide.
Podcasts have become a powerful force in the comedy world, and the festival embraces this trend with live performances from “My Favorite Murder” and “Smosh Reads Reddit Stories Live!” Both events are scheduled for the Chicago Theatre, providing fans with the unique opportunity to experience their favourite digital personalities in a dynamic, interactive setting.
Beyond the marquee acts, the festival’s commitment to inclusivity and variety is evident in its programming across other venues. The Vic Theatre will host comic magician Justin Willman, whose blend of humour and illusion has captivated audiences, alongside Dusty Slay, a comic whose relatable storytelling bridges cultural divides. Legendary performer Earthquake will also take the Vic stage, bringing decades of experience and a distinctive voice to the festival.
At Park West, audiences can enjoy the darkly comedic music of Honestav and family-friendly routines from Derrick Stroup, ensuring that festival-goers of all ages and tastes find something to enjoy. Zanies, both downtown and in Rosemont, remains a vital partner in the festival’s success, offering intimate settings for rising stars and established favourites alike. The club’s monthly Roast Battle Chicago, a highlight since the festival’s inception, returns with local comics facing off in rapid-fire contests judged by celebrity panels. This event has become a beloved tradition, fostering camaraderie and spotlighting Chicago’s homegrown talent.
Pete Holmes, a festival headliner with deep ties to the city, exemplifies the nurturing environment that Chicago provides for comedians. Having launched his career at local open mics, Holmes joins a distinguished group of alumni who have gone on to national acclaim. His return to the festival underscores the city’s enduring role as an incubator for comedic innovation.
The festival’s organisers have emphasised the importance of community and positivity in their approach. Andrew Farwell, Vice President of Outback Presents, noted that Chicago’s diverse population and rich cultural landscape make it an ideal setting for a comedy festival of this scale. By partnering with local venues and clubs, the festival not only brings world-class entertainment to the city but also supports the ongoing development of the local comedy scene.
In addition to headline performances, the festival features interactive events designed to engage audiences and foster new connections. Stand Up Throw Down: Millennials vs Gen X, hosted at Zanies Rosemont, invites comedians from different generations to share perspectives and bridge gaps through humour. Other events, such as Stand Up on the Spot and live podcast tapings, encourage spontaneity and audience participation, creating memorable experiences for all involved.
The festival’s organisers have also prioritised accessibility and inclusion, offering both in-person and virtual ticket options. This hybrid approach ensures that comedy lovers across Chicago and beyond can participate, regardless of location or circumstance. Attendees can choose from comprehensive packages that include access to all sessions, networking opportunities, and recordings of every performance, reflecting a commitment to broadening the festival’s reach and impact.
As the festival approaches, anticipation is building among performers and audiences alike. The 312 Comedy Festival stands as a testament to Chicago’s resilience, creativity, and unwavering love of laughter. By bringing together a diverse array of voices and styles, the festival not only entertains but also strengthens the bonds of community and celebrates the city’s unique spirit.
With a star-studded lineup, innovative programming, and a focus on positivity and progress, the 312 Comedy Festival is poised to deliver an unforgettable week of entertainment. Chicago’s stages will once again echo with laughter, affirming the city’s status as a national hub for comedic excellence and cultural vitality.
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