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Festivals, Fairs & Special Events, Music & Comedy
The 26th Anniversary Englewood Jazz Festival
The 26th Annual Englewood Jazz Festival, presented by Live the Spirit Residency, returns to Chicago’s historic Hamilton Park on September 18–20, 2025, marking a powerful…
Festivals, Fairs & Special Events, Theatre & Performing Arts
Czech Heritage Week 2025
A vibrant celebration of Czech culture in Chicago! From September 20 to 28, 2025, a wide variety of Czech-themed events will take place across the…
Theatre & Performing Arts
Chicago Danztheatre Ensemble Presents Full Circle Festival
Chicago Danztheatre Ensemble (CDE) is pleased to announce the plays and artists featured in the reimagined “Full Circle Festival,” September 19-28, at Chicago Danztheatre, 1650…
Festivals, Fairs & Special Events, Music & Comedy, Tours & Attractions
Logan Square Preservation’s 35th Biennial House Walk
Logan Square Preservation is proud to present the 35th Biennial House Walk on Saturday, September 20th 2025, from 10 AM to 5 PM. This beloved…
Saturday, September 20th
10:00 a.m. – 5:00 p.m.Old Holy Resurrection Serbian Orthodox Church
3062 W Palmer Square BlvdFestivals, Fairs & Special Events, Music & Comedy
Summer’s Last Dance Music & Arts Festival
🔥🎶 AFTERLIFE ENTERTAINMENT PRESENTS: 🎶🔥 🌞🎨 SUMMER’S LAST DANCE MUSIC & ARTS FESTIVAL 2025 🎨🌞 The ultimate farewell to festival season in Chicago! We’re BACK for Year 2 of Summer’s Last Dance—the…
Saturday, September 20th
11:00 a.m. – 11:00 p.m.Summer’s Last Dance Festival Grounds
7337 W 100th Pl,Theatre & Performing Arts
Angels in America, Part One: Millennium Approaches
Part One of Tony Kushner’s two-part, Pulitzer Prize-winning expansive, poetic, and politically charged look at the ‘80s in America. In the midst of the AIDS…
Saturday, September 20th
12:00 p.m. – 3:00 p.m.Windy City Playhouse
3014 W. Irving Park Rd.Theatre & Performing Arts
Boudoir Bingo
“Lucky cards and sultry stars!” Boudoir Bingo is Chicago’s favorite bingo and variety show. Your hosts, The Bingo B*tch & The Card Kween will guide…
Saturday, September 20th
3:00 p.m. – 5:00 p.m.The Newport Theater
956 West Newport AvenueTheatre & Performing Arts
Imaginarium: An improv show for kids 4 and up!
Imaginarium is the magical improv show where kids take center stage! In the first half, kids jump up to play fast, funny, and interactive improv…
Saturday, September 20th
4:00 p.m. – 5:00 p.m.iO Theater
1501 N. Kingsbury St.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, September 20th
5:00 p.m. – 6:00 p.m.The Den Theatre
1331 North Milwaukee AvenueTheatre & Performing Arts
Redtwist Theatre’s “How To Transcend a Happy Marriage”
Award-winning Redtwist Theatre launches its 21st season, “Defiant Femmes,” with How to Transcend a Happy Marriage, by Sarah Ruhl, directed by Elizabeth Swanson and movement…
Saturday, September 20th
5:00 p.m. – 7:00 p.m.Redtwist Theatre
1044 W. Bryn Mawr AveMusic & 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, September 20th
6:00 p.m. – 7:30 p.m.Malarkey Comedy Company
1501 N Kingsbury StMusic & Comedy, Theatre & Performing Arts
The Dinner Detective True Crime Murder Mystery Dinner Show
The Dinner Detective is an interactive true crime mystery show set in the present day and based on real cold cases. Feast on a fantastic…
Saturday, September 20th
6:00 p.m. – 9:00 p.m.Courtyard by Marriott Chicago Downtown
165 E. Ontario StMusic & Comedy, Theatre & Performing Arts
Symphony Ball: Joyce DiDonato & the Chicago Symphony Orchestra
Overview Kick off the new season in style! Superstar mezzo-soprano and 2025/26 CSO Artist-in-Residence Joyce DiDonato joins Nikolaj Szeps-Znaider and the CSO for a celebratory…
Saturday, September 20th
6:30 p.m. – 8:00 p.m.Chicago Symphony Center
220 S Michigan AveMusic & Comedy, Theatre & Performing Arts
The Infinite Wrench
Don’t miss the longest running late-night show in Chicago! At The Infinite Wrench you’ll see 30 original plays in 60 minutes written and performed by…
Saturday, September 20th
7:00 p.m. – 8:00 p.m.The Neo-Futurist Theater
5153 N. Ashland Ave.Theatre & Performing Arts
Abby Paj Tries to Stay Alive
Abby Paj Tries to Stay Alive is a solo show written and performed by Neo-Futurist Ensemble Member, Abby Pajakowksi. THE DOOMSDAY CLOCK TICKS 89 SECONDS…
Saturday, September 20th
7:00 p.m. – 8:30 p.m.The Neo-Futurist Theater
5153 N. Ashland Ave.Music & Comedy
Darren Fleet at The Comedy Bar
DARREN FLEET has been shaking up pop culture and championing diversity, especially within the LGBTQ+ community, since 2014. Best known for his recurring role on…
Saturday, September 20th
7:00 p.m. – 8:30 p.m.The Comedy Bar
500 N. LaSalle St.Music & Comedy
Across The Waters: Song of Memory and Migration
Àkójọpọ̀ and Hearing in Color welcome you to Across the Waters: Songs of Memory and Migration, a vocal chamber concert that explores the historical and cultural…
Saturday, September 20th
7:00 p.m. – 9:00 p.m.2330 West Sunnyside Avenue Chicago, Illinois 60625Music & Comedy, Theatre & Performing Arts
Teatro Zinzanni
Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…
Saturday, September 20th
7:00 p.m. – 10:00 p.m.Spiegeltent – Cambria Hotel
32 W. RandolphMusic & Comedy
Ethel Cain- The Willoughby Tucker Forever Tour
Florida-born singer, songwriter, producer, and model Ethel Cain will perform live at The Salt Shed Outdoors on Sep. 20, 2025.
Saturday, September 20th
7:00 p.m. – 10:00 p.m.The Salt Shed
1357 N Elston Ave, Chicago, ILTheatre & Performing Arts
Angels in America, Part Two: Perestroika
Part Two of Tony Kushner’s two-part, Pulitzer Prize-winning expansive, poetic, and politically charged look at the ‘80s in America. In the midst of the AIDS…
Saturday, September 20th
7:00 p.m. – 10:00 p.m.Windy City Playhouse
3014 W. Irving Park Rd.Music & Comedy
Atif Aslam – Borderless Tour
Get ready for an unforgettable musical journey as the sensational Atif Aslam embarks on his highly anticipated North America Tour this September to October 2025!…
Saturday, September 20th
7:00 p.m. – 10:00 p.m.Arie Crown Theater
2301 S. Jean Baptiste Point DuSable, S Lake Shore DrMusic & Comedy, Theatre & Performing Arts
Baby Wants Candy! The Original Completely Improvised Musical
“CRITICS’ PICK. TRULY AMAZING!” – New York Times “BEST VISITING IMPROV COMEDY!”– TimeOut NY “HIGHLY RECOMMENDED!” – The Onion “★★★★★” THEY ARE AN ENTERTAINMENT PHENOMENON AND I…
Saturday, September 20th
7:30 p.m. – 8:30 p.m.The Second City
1616 N. Wells St.Music & Comedy, Theatre & Performing Arts
Clued In
After getting a single suggestion, the cast of six professional comedians asks the audience to choose a detective. Enjoy as they invent a tale of…
Saturday, September 20th
7:30 p.m. – 8:30 p.m.The Second City
1616 N. Wells St., Theater on the Second FloorTheatre & Performing Arts
Tom & Eliza
Tom & Eliza is a dual meditation on the choices we make (and those we don’t) in a world that spins relentlessly into the future. Performed…
Saturday, September 20th
7:30 p.m. – 8:40 p.m.TUTA Theatre
4670 N. Manor Avenue

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