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
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Free and cheap perks on National Coffee Day 2026
Cream and sugar, please? Everyone will definitely be buzzin’ with excitement (and caffeine!) on National Coffee Day, Sept. 29, 2026, thanks to these cheap perks for coffee lovers and bargain hunters alike. To stir things up for the day, many coffee shops are celebrating the day with freebies and … [Read more...] about Free and cheap perks on National Coffee Day 2026
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 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 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
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
Reeling International Film Fest
The second-oldest LBTGQ+ film festival in the country kicks off with an exciting line-up of international features, documentaries and shorts with the 44th annual Reeling International Film Festival on September 17-27, 2026. The rich diversity of the queer community is showcased during the … [Read more...] about Reeling International Film Fest
Chicago Fall Market for Makers
Celebrate the work of independent artists and makers specializing in home decor, fashion, art, design, food and more at the Chicago Fall Market for Makers on October 24- 25, 2026, in the Ravenswood neighborhood. Score one-of-a-kind deals and support small businesses at this market, which … [Read more...] about Chicago Fall Market for Makers
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
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
Lincoln Square Ravenswood Apple Fest
Enjoy Fall fun with apple-inspired food, drinks and artisan goods at the beloved Lincoln Square Ravenswood Apple Fest, October 2-4, 2026. Celebrate the new season with a bounty of edible goodness. Midwest farms will be serving up fresh apples and related dishes and local restaurants and … [Read more...] about Lincoln Square Ravenswood Apple Fest
First Lady Fall Cruises
One of Chicago's most iconic experiences is sailing on the scenic Chicago Architecture Center (CAC) River Cruise aboard First Lady and absorbing the city's stunning skyline while learning about its design history. The fun continues through the fall, with cruises floating along the shore … [Read more...] about First Lady Fall Cruises
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 24th annual Oktoberfest Chicago in the West Lakeview neighborhood with Bavarian food, live music and craft beer tasting on September 25-27, … [Read more...] about St. Alphonsus Oktoberfest Chicago
Enjoy free Chicken Shack Sandwich or Lettuce Wrap at Shake Shack every week
Shake Shack is definitely known for its juicy burgers and creamy shakes, but there is also a delicious option for chicken sandwich fans on the menu. And, for a limited time, customers can enjoy big savings on a Chicken Shack Sandwich or Chicken Shack Lettuce Wrap every week at the popular … [Read more...] about Enjoy free Chicken Shack Sandwich or Lettuce Wrap at Shake Shack every week
Destinos Chicago Latino Theater Festival
Celebrate Hispanic Heritage Month along with Latino theater and dramatic creativity at the ninth annual Destinos: Chicago International Latino Theater Festival for three weeks from September 14 to October 11, 2026, at theaters across the city. The Chicago Latino Theater Alliance … [Read more...] about Destinos Chicago Latino Theater Festival
