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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 AvenueMuseums, Galleries & Exhibitions, Sports & Recreation, Tours & Attractions
Ferris Bueller Movie Tour in the Art Institute of Chicago
Calling art enthusiasts and Ferris Bueller fans! Get ready to step into the iconic world of Ferris Bueller’s Day Off on our popular 90-minute guided walking tour…
Saturday, October 4th
11:30 a.m. – 1:00 p.m.Art Institute of Chicago
111 S. Michigan Ave.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 StreetSports & Recreation, Tours & Attractions
Rappel In Northwest Chicago
Conquer your limits at 168 feet up and rappel down the Westin Chicago Northwest in Itasca Illinois. Professional equipment provided and no experience needed. Trained…
Saturday, October 4th
12:00 p.m. – 3:00 p.m.Westin Chicago Northwest
400 Park Blvd.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…
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 RoadFestivals, 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 StFestivals, Fairs & Special Events, Tours & Attractions
Discover HH Holmes for Halloween: The Devil in the White City Bus Tour by American Ghost Walks
Join American Ghost Walks for an immersive 3-hour experience on The Devil in the White City Bus Tour in Chicago. Uncover the chilling tale of…
Saturday, October 4th
2:00 p.m. – 5:00 p.m.Meeting Point: Inside the bar at the Congress Plaza Hotel
520 S Michigan Ave.Festivals, Fairs & Special Events
Chicago Chinatown Moon Festival 2025
The Mid-Autumn Festival, second only to Lunar New Year in cultural importance, is a beloved celebration of the full moon and family reunion. This year’s…
Saturday, October 4th
3:00 p.m. – 9:00 p.m.Chinatown Square Plaza
2130 S. Archer AveFestivals, 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 StFestivals, 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 AveMusic & 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 AvenueMusic & 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 StMusic & Comedy
The Dinner Detective True Crime Murder Mystery Dinner Show – Chicago, IL
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, October 4th
6:00 p.m. – 9:00 p.m.Courtyard by Marriott Chicago Downtown Magnificent Mile
165 E Ontario StMusic & 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, October 4th
7:00 p.m. – 8:00 p.m.The Neo-Futurist Theater
5153 N. Ashland Ave.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…
Music & 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, October 4th
7:00 p.m. – 10:00 p.m.Spiegeltent – Cambria Hotel
32 W. RandolphFestivals, Fairs & Special Events, Tours & Attractions
Halloween Chicago Hauntings Ghost Tour: Explore Paranormal Activity with American Ghost Walks
Join the acclaimed Original Chicago Hauntings Ghost Tour by American Ghost Walks. Discover the city’s most haunted sites, including the tragic Eastland disaster location and…
Saturday, October 4th
7:00 p.m. – 10:00 p.m.Meeting Point: Inside the bar at the Congress Plaza Hotel
520 S Michigan Ave.Music & 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…
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, October 4th
7:30 p.m. – 8:30 p.m.The Second City
1616 N. Wells St., Theater on the Second FloorSaturday, October 4th
7:30 p.m. – 9:00 p.m.Soldier Field
1410 Special Olympics DriveMusic & Comedy, Theatre & Performing Arts
Improvised Shakespeare
Critically-acclaimed improvised comedy featuring the language and themes of William Shakespeare
Music & Comedy, Theatre & Performing Arts
Chicago Symphony Orchestra: Piccolo Play & Adagio for Strings
Overview Pergolesi’s sacred masterpiece, the Stabat Mater, is filled with gorgeous, spine-tingling music that explores the nature of grief, hope and healing. These emotions also course…
Saturday, October 4th
7:30 p.m. – 9:30 p.m.Chicago Symphony Center
220 S Michigan AveFestivals, Fairs & Special Events, Music & Comedy
Composer Showcase Featuring Quintet Attacca
Ear Taxi Festival presents a Composer Showcase. Join us as Quintet Attacca premiers new works by Shane Scott Cook, Marybeth Kurnat, John Dorhauer, Gillian Rae…
Saturday, October 4th
7:30 p.m. – 9:30 p.m.Logan Center Penthouse
915 E 60th St

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