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Craigslist Playdate Improv: Award Season Tickets

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On the schedule

Craigslist Playdate Improv: Award Season Tour Dates & Tickets

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Inside the performance

Sound, stage & company

Onstage company

Documented collaborators

Craigslist Playdate Improv: Award Season is a Chicago-based ensemble redefining the sketch and improv landscape with a distinctive deconstructed format. Formed by a group of improv students from The Second City and guided by director David Montgomery, Award Season has quickly become a staple of the city’s vibrant comedy scene. They’re known for collaborative, high-energy performances that mix spontaneity with thoughtful structure, delivering fresh takes on familiar formats.

The live experience

What reaches the room

Recognized by the Chicago Reader as the Best Sketch/Improv Troupe in 2024, Award Season continues to tour and perform regularly at top venues across Chicago and beyond. If you’re looking for accessible, engaging, and reliably entertaining improv, this is the group to watch.

The live experience

What reaches the room

Upcoming performances keep expanding the troupe’s footprint. Look for early 2025 tour dates at Io Theater and 2025 appearances such as Third Coast Improv Fest in Nashville on November 8, 2025, and a Chicago stop at The Den Theatre on December 12, 2025. You can expect dynamic sets at familiar Chicago spaces like Bughouse Theater, Second City, The Den Theatre, Cornservatory, ComedyPlex, Logan Square Improv, and iO Theater.

The essentials

Quick Facts About Craigslist Playdate Improv: Award Season

  • Genre/style: deconstruction improv format (improv with a unique, deconstructed approach).
  • Award: Chicago Reader 'Best Sketch/Improv Troupe' in 2024.
  • Origin/leadership: formed by a group of improv students from Second City, led by director David Montgomery.
  • Venues: regularly perform at Bughouse Theater, Second City, The Den Theatre, Cornservatory, ComedyPlex, Logan Square Improv, iO Theater.
  • 2025 notable appearances: Third Coast Improv Fest in Nashville (Nov 8, 2025) and The Den Theatre in Chicago (Dec 12, 2025).
  • Early 2025 tour/ticketing: listed for an April 27, 2025 show at Io Theater (Award Season).

Biography

Craigslist Playdate Improv: Award Season emerged from a cohort of aspiring writers and performers trained in improv fundamentals at The Second City. Under the direction of veteran improv educator and director David Montgomery, the troupe developed a deconstructionist approach that breaks traditional formats down to their essential components, creating a playful and unpredictable live experience. The core philosophy centers on collaboration, rapid scene construction, and clever commentary that resonates with both hardcore improv fans and casual audiences.

Discography Highlights

  • Live show recordings featuring signature deconstructed formats – available through select venue archives and official show reels.
  • Festival showcases and collaborative pieces with Chicago’s improv community, capturing the troupe’s improv approach across multiple formats.
  • Digital shorts and episodic clips highlighting on-stage chemistry and quick-witted interplay among the performers.

Upcoming Tour & Shows

  • Io Theater – April 27, 2025 (Address: 1515 W Foster Ave, Chicago) Ticket details and seating information will appear at booking time.
  • Third Coast Improv Fest – Nashville, TN – November 8, 2025
  • The Den Theatre – Chicago, IL – December 12, 2025

Where to See Them

Regularly performing at notable Chicago venues, Award Season brings its deconstructed improv to Bughouse Theater, Second City, The Den Theatre, Cornservatory, ComedyPlex, Logan Square Improv, and iO Theater. These venues offer intimate to mid-size stages with robust indie and experimental comedy scenes that pair well with Award Season’s bold format.

Social & Media

Social media channels provide updates and behind-the-scenes looks at rehearsals, show concepts, and tour news. Follow official channels for the latest releases and show announcements. Note: Social handles are not publicly listed in current sources, but their content often appears across Chicago’s improv community pages and venue event calendars.

Notes for Fans

For the most current schedule and to secure your seats, check venue calendars and the troupe’s official booking pages. As always with City-based improv, show times and venues are subject to change, so we recommend confirming the date and location before planning your visit.

Official Links

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