View the thrills and chills of classic Hollywood monster movies at a discount. Check out Monster Mash, the classic Halloween film series at the 400 Theater in the Rogers Park neighborhood through November 5, 2026. Travel back to the classic Hollywood era of the '1930s, '1940s and '1950s, when … [Read more...] about Cheap Halloween Film Series at 400 Theater
Entertainment
Regal Cinemas hosts ’31 Screams on Screen’ series with $7.99 tickets every day in October
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
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
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
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
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
Jack’s Pumpkin Pop Up
Wander through pumpkin patches and corn mazes while you enjoy the season at Chicago's largest fall festival, Jack's Pumpkin Pop Up, located near Goose Island, from September 19 to November 1, 2026. The large number of all-ages festivities make Jack's one of the most popular fall excursions. … [Read more...] about Jack’s Pumpkin Pop Up
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
