Celebrate the spooky season with a fun-filled Haunted Halloween Night Lake Cruise along Lake Michigan that combines costumes, dancing and drinks with views of the iconic Chicago skyline. 312 Cruises offers cruises as cheap as $30 on October 30 and 31, 2026. Hop aboard a three-story, 140-foot … [Read more...] about Chicago Halloween Cruises from $30
Music
Haunted Halsted Halloween Parade
The ultimate Chicago Halloween celebration kicks off with the 30th Annual Haunted Halsted Halloween Parade and costume contest on October 31, 2026. Throw together your most creative, witty costume for the dramatic spectacle of the Haunted Halsted Halloween Parade. Prepare to see … [Read more...] about Haunted Halsted Halloween Parade
Chicago Free and Cheap Fall Events
After the close of the beloved Summertime Chicago season, the fun continues with a hearty lineup of activities that celebrate the flavors, scents and visions of fall. As the red and gold foliage reflects off the lake, the city vibrates with autumn fests, apple-picking events, Oktoberfest and artisan … [Read more...] about Chicago Free and Cheap Fall Events
Free World Music Wednesday Concerts
The new season for World Music Wednesday has been announced! Every Wednesday, through December 9, 2026, 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
Riverwalk Fall Fest
Experience the beauty of the fall season with the Chicago River as the backdrop at the Island Party Hut Fall Fest on the Chicago Riverwalk on Saturdays, September 19- October 31, 2026. Enjoy autumn festivities like hay rides on the river, pumpkin patches and eating apple cider donuts along … [Read more...] about Riverwalk Fall Fest
Jazz in the Court
The Hyde Park neighborhood celebrates South Side jazz traditions with free outdoor concerts in Harper Court on the first Fridays of the summer months. Enjoy free live music in the heart of the historic community This year's dates are June 5, 2026. July 10, 2026, August 7, 2026, and September … [Read more...] about Jazz in the Court
Free Time Out Market Fifth Anniversary Party
Join the all-day celebration for five years of food, drinks and events during the Fifth Anniversary Celebration of Time Out Market, on November 16, 2024. Enjoy food and drink specials and live DJs in the West Loop neighborhood. Head to Time Out Market for festivities filled … [Read more...] about Free Time Out Market Fifth Anniversary Party
Autumn Fest at Gallagher Way
The pleasures of the season will fill the field around Wrigley Stadium in celebration of the cooler temperatures and bright foliage, Autumn Fest at Gallagher Way will run from October to November 2024. The Autumn Fest includes activities and offerings like seasonally themed food and drinks, … [Read more...] about Autumn Fest at Gallagher Way
Chicago Lowrider Festival
Celebrate Hispanic Heritage Month with a visit to the Latine cultural event that showcases the Lowrider movement at the 13th annual Slow & Low: Chicago Lowrider Festival on October 12, 2024, at Navy Pier. At the festival, you can view more than 250 elaborately customized cars, as well … [Read more...] about Chicago Lowrider Festival
Beverly Art Walk
Explore the vibrant arts community of the historic Beverly/Morgan Park neighborhood at the 11th annual Beverly Art Walk on September 28, 2024. Hosted by the Beverly Arts Alliance, the Beverly Art Walk is a free, family-friendly event that spotlights local art and music. … [Read more...] about Beverly Art Walk
Chicago Jazz Fest at Elastic Arts Foundation
The internationally acclaimed Chicago Jazz Fest draws music fans from all over the globe for the Millenium Park event but the fest also sponsors free neighborhood concerts, including the Elastic Arts Foundation on August 25, 27 and 28, 2024. Head to the Logan Square neighborhood to enjoy an … [Read more...] about Chicago Jazz Fest at Elastic Arts Foundation
Latinxt Music Festival
Chicago's diverse Latinx community comes together to celebrate contemporary Latin music and arts during the fifth annual LatiNXT Music Festival on August 24 -25, 2024. This free, two-day festival showcases all the sounds and arts scenes that Chicago's Latinx community has inspired. Navy … [Read more...] about Latinxt Music Festival
