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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 StreetFestivals, 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
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 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 StFestivals, 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,…
Sunday, October 5thThe Harris Theater for Music and Dance
205 East Randolph StreetFestivals, Fairs & Special Events
Wolff’s Flea Market Opening Day
Wolff’s Flea Market announces opening day April 20, 2025. Join us for our 34th season outdoors at the Allstate Arena, Rosemont. Sundays 6am-2pm through October…
Sunday, October 5th
6:00 a.m. – 2:00 p.m.Wolff’s Flea Market
6920 N Mannheim RdFestivals, 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.
Sunday, October 5th
7:00 a.m. – 12:00 p.m.30 W. Division St.
30 W. Division St.Festivals, Fairs & Special Events
Glenwood Sunday Market in Rogers Park
The nonprofit Rogers Park Business Alliance (RPBA) announces 23 local vendors for the 16th anniversary season of the Glenwood Sunday Market, which will operate every…
Festivals, Fairs & Special Events
Maxwell Street Market
Visitors to the Maxwell Street Market will experience an eclectic mix of foods and finds—including handmade crafts, resale housewares, clothing, and much more.
Sunday, October 5th
10:00 a.m. – 3:00 p.m.Maxwell Street Market
800 S. Desplaines St.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,…
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…
Sunday, October 5th
11:30 a.m. – 10:00 p.m.Simone’s bar Simone’s Bar 960 W 18th Street, Chicago, IL 60608
960 W 18th StreetFestivals, Fairs & Special Events, Music & Comedy
Crossing Borders // La Caccina // Holocene
Ear Taxi Festival presents an ear taxi concert. Celebrate contemporary music with powerful performances from Crossing Borders Music, La Caccina, and Holocene. Crossing Borders’ program…
Sunday, October 5th
2:00 p.m. – 5:00 p.m.PianoForte Chicago
1335 South Michigan AvenueFestivals, Fairs & Special Events, Theatre & Performing Arts
FashionBar The Shows: October 2025 – Modest, Formal, Evening Wear
The closing runway of October 2025, this event presents modest fashion alongside formal and evening wear collections, bringing elegance, refinement, and cultural expression to the…
Sunday, October 5th
2:00 p.m. – 6:00 p.m.Water Tower Place
835 N Michigan AveFestivals, 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,…
Monday, October 6thThe Harris Theater for Music and Dance
205 East Randolph StreetFestivals, 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.
Monday, October 6th
7:00 a.m. – 12:00 p.m.30 W. Division St.
30 W. Division St.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,…
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,…
Tuesday, October 7thThe Harris Theater for Music and Dance
205 East Randolph StreetFestivals, 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.
Tuesday, October 7th
7:00 a.m. – 12:00 p.m.30 W. Division St.
30 W. Division St.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,…
Tuesday, October 7th
10:00 a.m. – 5:00 p.m.Brookfield Zoo Chicago
3300 Golf RdFestivals, Fairs & Special Events
JBF Greens Chicago x Kayao
Join JBF Greens for vibrant Peruvian flavors in Old Town. Opened in June 2024 by Éxodo Hospitality Group, Kayao showcases the culinary vision of chefs…
Tuesday, October 7th
6:00 p.m. – 8:30 p.m.Kayao
1252 N Wells StFestivals, 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,…
Wednesday, October 8thThe Harris Theater for Music and Dance
205 East Randolph Street

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