Enjoy all that's jolly and bright during the festive season at the beloved Winter Wonderfest at Navy Pier. Slide, skate, ride and soak up holiday fun at this indoor fest from November 27, 2026, to January 3, 2027. Head to Navy Pier's Festival Hall and take in the 420-foot holiday … [Read more...] about Winter WonderFest at Navy Pier
Entertainment
Black Harvest Film Fest
Celebrate Chicago's significant role in Black filmmaking and visit the 32nd annual Black Harvest Film Festival showcase of Black film across the Diaspora from November 6-15, 2026, at the Gene Siskel Film Center. View an exciting range of films, from shorts, features, documentaries, dramas and … [Read more...] about Black Harvest Film Fest
ZooLights at Lincoln Park Zoo $7 plus free nights
Lincoln Park Zoo's annual Zoo Lights is the highlight of Chicago's holiday season, with hundreds of lights twinkling across the grounds. Tickets are on sale now for the event, which opens on November 20, 2026. Stroll through the zoo and enjoy an illuminated holiday wonderland of animal … [Read more...] about ZooLights at Lincoln Park Zoo $7 plus free nights
Chicago Magnificent Mile Lights Festival
Chicago's iconic Michigan Avenue will shine even brighter during the 35th annual Magnificent Mile Lights Festival on November 21, 2026. This beloved holiday tradition combines a parade, lights, music, tree lighting and family activities for joy-filled holiday fun. The event kicks off at … [Read more...] about Chicago Magnificent Mile Lights Festival
Chicago Thanksgiving Parade
The Chicago holiday season roars into gear with the 92nd annual Chicago Thanksgiving Parade, which marches down the heart of downtown on State Street on November 26, 2026. This free family-friendly event is highly anticipated because of the exciting showcase of talented performers from … [Read more...] about Chicago Thanksgiving 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
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
New Greektown Public Art Exhibit
Chicago's historic Greektown neighborhood will introduce a new public art exhibit, "We The People," on June 9, 2026, along Halsted Street between Madison and Van Buren Streets. Celebrating the 250th anniversary of the Declaration of Independence, 'We The People: Life, Liberty and the … [Read more...] about New Greektown Public Art Exhibit
New Flyover in Chicago Attraction
Chicago's iconic skyline and skyscrapers got a little closer since the opening of the Flyover in Chicago immersive flying experience at Navy Pier. This exciting attraction that soars over downtown Chicago just added another experience: Call of the Canadian Rockies. Leave the city and fly … [Read more...] about New Flyover in Chicago Attraction
Guide to Chicago Water Taxis
Guide to Chicago Water Taxis. The Chicago water taxis are a fun and relaxing transit alternative that gets you from A to B while gliding along our waterways. It's also a more relaxing way to travel and avoid street traffic. Take a cheap tour of our lake and river They're also … [Read more...] about Guide to Chicago Water Taxis
Light up the Lake at Navy Pier
Chicago's largest indoor light experience is a family fun tradition. Light Up The Lake returns to Navy Pier from November 29 to January 5, 2025, for lots of interactive activities. Dive into twinkling holiday magic with Light Up The Lakes light displays, games, visits with Santa and more. This … [Read more...] about Light up the Lake at Navy Pier




















Chicago on the Cheap is a member of Living on the Cheap, a network of websites published by frugalistas, journalists and consumer advocates. Find practical advice on saving money on groceries, travel and shopping, plus tips from our experts on how to live the good life for less at 