Whether you like parades, movies, parties or old-school trick-or-treating, there are lots of free and cheap Halloween events to explore all over Chicago. Check out everything from boat rides to shopping and fall fests in our roundup below. Chicago Halloween Cruises Float along … [Read more...] about Chicago Free and Cheap Halloween Events
fall events
Free Slightly Spooky October at Navy Pier
Spend the spooky season watching movies, creating fun projects and trick-or-treating at Navy Pier. Enjoy interactive art and performances during Slightly Spooky October at Navy Pier on Saturdays throughout the month on October 17, 24 and 31, 2026. Dive into fun and watch movies like … [Read more...] about Free Slightly Spooky October at Navy Pier
Free National Museum of Mexican Art Dia de los Muertos Chicago
Celebrate the Mexican tradition of Día de los Muertos or Day of the Dead, with the free "Día de Los Muertos Xicago" event organized by the National Museum of Mexican Art on October 24, 2026, in the Pilsen community. Honoring loved ones who have passed away with ofrendas or altars filled with … [Read more...] about Free National Museum of Mexican Art Dia de los Muertos Chicago
Ravenswood Costume Crawl
Dive into the joy of the season with a visit to the Ravenswood Costume Crawl, filled with Halloween-themed fun, seasonal goods, treats and drinks on October 28, 2026. This thrill-filled event will transform Ravenswood's Montrose Avenue of shops and restaurants into a spooky space for sipping, … [Read more...] about Ravenswood Costume Crawl
Free Festival del Arte Popular at National Museum of Mexican Art
Start your holiday shopping early by checking out the masterful work of Mexican artisans at the annual Festival del Arte Popular at the National Museum of Mexican Art on October 13-18, 2026. Witness live demonstrations of intricate Mexican folk art and meet artists from all over Mexico at … [Read more...] about Free Festival del Arte Popular at National Museum of Mexican Art
Chicago Fashion Week
The cultural and stylistic diversity of the Windy City will take the stage with the return of Chicago Fashion Week, from October 8-18, 2026. Runway shows, activations, exhibits and events will highlight Chicago's design and fashion history in neighborhoods across the city. The thrilling … [Read more...] about Chicago Fashion Week
Open House Chicago
Explore the architectural and cultural treasures that Chicago is famous for during the annual Open House Chicago events. Visit over 200 sites in more than 20 neighborhoods across the city during the in-person activities on October 17-18, 2026. Go behind the scenes in members-only clubs, … [Read more...] about Open House Chicago
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
Arts in the Dark Halloween Parade
Head to State Street to celebrate Halloween as the "artist's holiday" with an evening of wonder and creativity at the Arts in the Dark Halloween Parade on October 24, 2026, in the Loop. Recognized as one of the top six Halloween events in the world, the tenth annual Arts in the Dark parade … [Read more...] about Arts in the Dark 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
West Town Art Walk
Enjoy visual art, music, and fashion while browsing restaurants and shops along Chicago Avenue in the bustling West Town neighborhood during the 16th annual West Town Art Walk on October 2-4, 2026. The West Town neighborhood bubbles with color, food and art in all forms during this popular … [Read more...] about West Town Art Walk
Oktoberfestiversary
Dovetail Brewery and Begyle Brewing serve up their annual fall street festival with Oktoberfestiversary on October 10-11, 2026, in the Ravenswood neighborhood. Enjoy brews, live music and food in the spirit of the season. Sip on special tapings from Beglye and Dovetail while munching on … [Read more...] about Oktoberfestiversary
