Are you afraid of the dark? Face your fears this October with 31 Screams on Screen at Regal Cinemas. The theater chain will show a different classic horror movie on the big screen each day, so fans can relive the thrills of their favorites or experience new scares they haven’t encountered … [Read more...] about Regal Cinemas hosts ’31 Screams on Screen’ series with $7.99 tickets every day in October
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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
Chicago Halloween Cruises from $30
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
Lincoln Park Blues and Gangster Tour
Chicago boasts a reputation for a lot of great things--architecture, food and a stunning skyline. The city's claim as the home of the blues is another great accolade but Chicago is also recognized for its extensive gangster history. Take the Lincoln Park Guns, Guitars & Gangsters Tour … [Read more...] about Lincoln Park Blues and Gangster Tour
Free and cheap things to do this weekend in Chicago
Looking for something fun to do this weekend in Chicago? There are tons of free and cheap events in the city. Here’s our list of the top free events, discounts, and deals to have fun around town on your Friday, Saturday, and Sunday. There are many diverse events, so choose your favorite. … [Read more...] about Free and cheap things to do this weekend in Chicago
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
Shake Shack celebrates Halloween season with 3 free sandwiches in October
Ding-dong! Trick-or-burger! Shake Shack is shaking up the spooky season with three juicy deals for a FREE sandwich in October. The chain’s burgers are made with a custom 100% Angus beef blend, never frozen, no hormones or antibiotics ever, humanely raised and grazed in the U.S. Fans and hungry … [Read more...] about Shake Shack celebrates Halloween season with 3 free sandwiches in October
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 International Film Festival Free Events
As North America's longest-running competitive film festival, the Chicago International Film Festival showcases movies from all over the world as well as tributes, special programs and celebrity guests. This year's 62nd Chicago International Film Festival runs from October 14-25, … [Read more...] about Chicago International Film Festival Free Events
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
