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Upcoming Chicago Events

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Improvised Shakespeare
Oct3
Music & Comedy, Theatre & Performing Arts

Improvised Shakespeare

Critically-acclaimed improvised comedy featuring the language and themes of William Shakespeare

Friday, October 3rd
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
The Witcher Live in Concert
Oct3
Music & Comedy

The Witcher Live in Concert

The Witcher in Concert is coming to celebrate the 10th anniversary of the critically acclaimed The Witcher 3: Wild Hunt! Witness the open-world RPG’s timeless…

Friday, October 3rd
7:30 p.m.9:30 p.m.
Auditorium Theatre
50 East Ida B. Wells Drive
Ear Taxi Festival and Bella Voce present “Lost Objects”
Oct3
Festivals, Fairs & Special Events, Music & Comedy

Ear Taxi Festival and Bella Voce present “Lost Objects”

Bella Voce opens the 2025 Ear Taxi Festival with Lost Objects, a genre-defying oratorio by Bang on a Can founders Gordon, Wolfe, and Lang. Combining…

Friday, October 3rd
7:30 p.m.9:30 p.m.
Reva and David – Logan Center for the Arts
915 E 60th St
Devil’s Daughter
Oct3
Music & Comedy

Devil’s Daughter

The hottest show in town Devil’s Daughter features a cast of seasoned comedians who have performed together in Chicago and around the country for over a decade.…

Friday, October 3rd
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Missed Call Sketch Comedy Show
Oct3
Music & Comedy, Theatre & Performing Arts

Missed Call Sketch Comedy Show

Missed Call is a premier Chicago comedy group that writes and performs an entirely new sketch show every Friday — inspired by the audience’s suggestion!

Friday, October 3rd
8:00 p.m.9:00 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Natan Badalov: Chosen Fam
Oct3
Music & Comedy, Theatre & Performing Arts

Natan Badalov: Chosen Fam

Coming off the success of his first solo show, Connect The Dots (New York Comedy Festival, Y’all Comedy Fest), Natan Badalov performs Chosen Fam, his…

Friday, October 3rd
8:00 p.m.9:30 p.m.
Red Room Comedy Club
7442 N. Western Ave.
AFI: 2025 Tour
Oct3
Music & Comedy

AFI: 2025 Tour

Award-winning rockers AFI will perform live at The Salt Shed Indoors on Oct. 3, 2025 /w special guest TR/ST.

Friday, October 3rd
8:00 p.m.11:00 p.m.
The Salt Shed
1357 N Elston Ave, Chicago, IL
Lowkey Funny Comedy Show
Oct3
Music & Comedy, Theatre & Performing Arts

Lowkey Funny Comedy Show

This monthly show will shine light on some of Chicago’s emerging talent in stand-up, improv/ sketch comedy, and up and coming music artists. Break away…

Friday, October 3rd
8:30 p.m.11:00 p.m.
Laugh Factory, 3175 N. Broadway St, Chicago, IL 60657
3175 N. Broadway St
Trapped in a Musical – an improvised musical
Oct3
Music & Comedy, Theatre & Performing Arts

Trapped in a Musical – an improvised musical

Trapped in a Musical is a completely improvised Broadway-style show created before your very eyes. It’s the opening and closing night of a brand new…

Friday, October 3rd
9:00 p.m.10:00 p.m.
Ahamed Weinberg at The Comedy Bar
Oct3
Music & Comedy

Ahamed Weinberg at The Comedy Bar

2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Ahamed Weinberg is a Los Angeles-based…

Friday, October 3rd
9:00 p.m.10:30 p.m.
The Comedy Bar
500 N. LaSalle St.
Voila: The Improvised Musical
Oct3
Music & Comedy, Theatre & Performing Arts

Voila: The Improvised Musical

iO Chicago presents: a fully made-up, off-off-off Broadway style musical every Friday at 10pm in the Fremont Theater. Spend your Friday night with us. See…

Friday, October 3rd
10:00 p.m.11:30 p.m.
The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,
The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,
Hitch*Cocktails
Oct3
Music & Comedy, Theatre & Performing Arts

Hitch*Cocktails

A Chicago based improv comedy show and drinking game based on the works of Alfred Hitchcock. Based on an audience suggestion, the cast weave together…

Friday, October 3rd
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Ear Taxi Festival
Oct4
Festivals, Fairs & Special Events

Ear Taxi Festival

The Ear Taxi Festival 2025, themed “The Composer’s Voice,” is a landmark event showcasing contemporary concert music across Chicagoland from October 3 through November 2,…

Saturday, October 4th
Division Street Farmers Market
Oct4
Festivals, Fairs & Special Events

Division Street Farmers Market

Fresh seasonal produce, flowers, prepared foods, unique Chicago-made products and rare finds are available at the Division Street Farmers Market.

Saturday, October 4th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Boo! at the Zoo
Oct4
Festivals, Fairs & Special Events

Boo! at the Zoo

Get ready for a fang-tastic time at BOO! at the Zoo, Brookfield Zoo Chicago’s family-friendly Halloween celebration. This event is packed with not-so-scary thrills, festive decorations,…

Saturday, October 4th
10:00 a.m.5:00 p.m.
Brookfield Zoo Chicago
3300 Golf Rd
Ninth Annual Lincoln Park Wine Fest
Oct4
Festivals, Fairs & Special Events

Ninth Annual Lincoln Park Wine Fest

Wines from Around the World Featured at 9thAnnual Lincoln Park Wine Fest in Jonquil Park October 3-5 Wine tastings, a food and beverage market, sommeliers on hand…

Saturday, October 4th
11:00 a.m.10:00 p.m.
Jonquil Park
1001 W. Wrightwood Avenue
Simone’s Bar Sweet 16 Anniversary Celebration and 1st Annual Block Party
Oct4
Festivals, Fairs & Special Events

Simone’s Bar Sweet 16 Anniversary Celebration and 1st Annual Block Party

Event Name:Simone’s Sweet 16 Block Party Admission:Free Description (Event Overview):Celebrate 16 years of community, music, and culture at Simone’s Sweet 16 Block Party in Chicago’s…

Saturday, October 4th
11:30 a.m.10:00 p.m.
Simone’s bar Simone’s Bar 960 W 18th Street, Chicago, IL 60608
960 W 18th Street
Oktoberfest on Division Street Festival: Prost in the Gold Coast
Oct4
Festivals, Fairs & Special Events

Oktoberfest on Division Street Festival: Prost in the Gold Coast

Raise a stein at Prost in the Gold Coast Oktoberfest on Division Street! Dust off your lederhosen and celebrate Oktoberfest as Division Street transforms into a lively…

Saturday, October 4th
12:00 p.m.10:00 p.m.
Lodge Tavern
21 W Divsion st
Kate McKinnon: Secrets of the Purple Pearl
Oct4
Festivals, Fairs & Special Events

Kate McKinnon: Secrets of the Purple Pearl

Saturday Night Live icon Kate McKinnon returns to Chicago Humanities to discuss Secrets of the Purple Pearl, the highly anticipated sequel to her #1 New…

Saturday, October 4th
2:00 p.m.3:00 p.m.
Apollo’s 2000
2875 W. Cermak Road
Chicago Composers Consortium // Caroline Jesalva // Shannon McGinnis & Corrine Costello // Constellation Men’s Ensemble
Oct4
Festivals, Fairs & Special Events, Music & Comedy

Chicago Composers Consortium // Caroline Jesalva // Shannon McGinnis & Corrine Costello // Constellation Men’s Ensemble

Ear Taxi Festival presents an ear taxi concert. A dynamic afternoon of new music featuring bold performances and thought-provoking works. Baritone Brad Jungwirth joins the…

Saturday, October 4th
2:00 p.m.5:00 p.m.
Logan Center Penthouse
915 E 60th St
Disability Advocate and Online Creative Molly Burke: Unseen
Oct4
Festivals, Fairs & Special Events

Disability Advocate and Online Creative Molly Burke: Unseen

Multi-hyphenate creative, advocate, and social media star Molly Burke was diagnosed with retinitis pigmentosa, a rare degenerative eye disease that leads to eventual blindness, at…

Saturday, October 4th
3:30 p.m.4:30 p.m.
Illinois Institute of Technology – Hermann Hall
3241 S Federal St
FashionBar The Shows: October 2025 – Next Gen, Urban & Streetwear
Oct4
Festivals, Fairs & Special Events, Theatre & Performing Arts

FashionBar The Shows: October 2025 – Next Gen, Urban & Streetwear

Step into the pulse of street culture and fresh talent at the Next Gen, Urban & Streetwear runway. This show brings forward-thinking designs that embody…

Saturday, October 4th
4:00 p.m.8:00 p.m.
Water Tower Place
835 N Michigan Ave
Tikka Masala
Oct4
Music & Comedy, Theatre & Performing Arts

Tikka Masala

Tikka Masala: The Indian Improv Comedy Game Show. Get ready for a laugh-out-loud night of unscripted chaos, cultural flavor, and spicy twists! Tikka Masala is…

Saturday, October 4th
5:00 p.m.6:00 p.m.
The Den Theatre
1331 North Milwaukee Avenue
ComedySportz Chicago
Oct4
Music & Comedy, Theatre & Performing Arts

ComedySportz Chicago

Chicago’s longest running and best interactive improv comedy experience. ComedySportz is comedy played as a sport, not comedy ABOUT sports (whew). Refs, fouls, points, games…

Saturday, October 4th
6:00 p.m.7:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
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