In honor of the fall season, Chicago's signature open-air market, the Randolph Street Market, is hosting its fall market with vintage treasures, live bands, food and fun on September 27-28, 2025, in the West Loop. Celebrating 22 years, the Randolph Street Market Festival features an … [Read more...] about Randolph Street Market
live music
Lakeview East Art Festival
The 20th annual Lakeview East Festival of the Arts showcases an exciting range of visual arts and live music on two stages in the Lakeview neighborhood on September 13-14, 2025. Explore a line-up of 150 juried artists from around the country displaying everything from paintings, … [Read more...] about Lakeview East Art Festival
St. Alphonsus Oktoberfest Chicago
It's that time of year when Chicagoans welcome the autumn season with polka, lederhosen and lots and lots of beer. St. Alphonsus Church celebrates its 21st annual Oktoberfest Chicago in the west Lakeview neighborhood with Bavarian food, live music and craft beer tasting on September 26-28, … [Read more...] about St. Alphonsus Oktoberfest Chicago
West Loop Art Fest
Stroll into the trendy West Loop neighborhood for five blocks of eye-catching art for the fifth annual West Loop Music & Art Fest on September 20-21, 2025. The free event supplies a full weekend of fun in the Fulton Market district. Browse through art displays from over … [Read more...] about West Loop Art Fest
Chicago Live! at Navy Pier
Witness the excitement of Chicago's extensive performing arts scene during the fifth annual Chicago Live! festival on September 20-21, 2025. Navy Pier will host free, non-stop performances featuring Chicago dance, theater, music and more during the two-day event. The breadth of Chicago's … [Read more...] about Chicago Live! at Navy Pier
Free World Music Wednesday Concerts
The new season for World Music Wednesday has been announced! Every Wednesday, through December 3, 2025, at 8:00 pm, the Old Town School of Folk Music will host a free concert series, World Music Wednesdays, featuring musicians from all around the world. Culture and countries represented … [Read more...] about Free World Music Wednesday Concerts
Englewood Jazz Fest
The 26th annual Englewood Jazz Festival presents an exciting line-up of established and emerging Chicago musicians for three days in the Englewood community on September 18-20, 2025. Live the Spirit Residency at Hamilton Cultural Center educates and mentors the next generation of … [Read more...] about Englewood Jazz Fest
Free Thirsty Ears Classical Music Fest
Enjoy the beautiful melodies, cultural traditions and welcoming community of Chicago's only classical music festival, the Thirsty Ears Festival on August 23-24, 2025. The 10th annual event supplies two days of classical music, food vendors, craft beer and kids' activities in the … [Read more...] about Free Thirsty Ears Classical Music Fest
Ravenswood ArtWalk
The Ravenswood Corridor community celebrates 21 years of the annual Ravenswood ArtWalk on September 13-14, 2025. The area's artists, manufacturers and brewers will welcome visitors during the ArtWalk for the first time in two years, with a host of fun and interactive … [Read more...] about Ravenswood ArtWalk
Free Chicago World Music Festival
The 25th annual World Music Festival Chicago is a city-wide, multi-venue festival presenting over 30 artists and ensembles from 22 countries around the globe, presented for free over 10 days from September 26 to October 5, 2025. Dance to the rhythms and melodies of musicians from all … [Read more...] about Free Chicago World Music Festival
Hyde Park Jazz Festival
Venues across the Hyde Park, Kenwood and Washington Park neighborhoods will come alive with live jazz during the 18th annual Hyde Park Jazz Festival on September 27-28, 2025. Music lovers will enjoy 34 free performances of local, national and international artists at a varied assortment of … [Read more...] about Hyde Park Jazz Festival
Harper Court Summer Music Series
Hyde Park sizzles in the summer and the neighborhood will get even more energized during the Harper Court Summer Music Series, set for August 7 and September 4, 2025. A summer tradition since 2015, the free outdoor concerts feature local musicians and bring a festive sense of community … [Read more...] about Harper Court Summer Music Series
