Things to do in Chicago in the fall

Chicago has something to offer every season of the year, but fall is particularly magical. The leaves turn golden in Millennium Park, a crisp breeze blows near the lake, and the city boasts tons of cool activities and events.

Fall is also one of the best times to visit for culture lovers, when the city is filled with film festivals, exciting theatrical premieres, blockbuster museum exhibits, architecture events, and so much more.

Top Halloween events

Chicago celebrates Halloween with its own unique style — you’ll find artistic evening spectacles, glowing pumpkin displays, spooky tours of haunted places, family-friendly festivals, and beyond.

Discover a few of the Halloween events we’re most excited about this year:

• Arts in the Dark (Oct. 24, 2026): This artistic evening parade takes over downtown with  artists, performers, musicians, puppeteers, dancers, and more.
• Haunted Halsted Halloween Parade (Oct. 31, 2026): In the historic Northalsted neighborhood, this over-the-top nighttime spectacle is a beloved Halloween tradition.
• Spooky Zoo (Oct. 17, 2026): This family-friendly celebration at Lincoln Park Zoo includes a pumpkin patch, trick-or-treating, and more kid-approved Halloween activities.
• Upside Down Halloween Parade (Oct. 31, 2026): This all-ages daytime event encourages families to don costumes and join the spectacular procession through Washington Park.

Explore more: Check out our guide to Halloween events and activities across Chicago.

Haunted history and ghost tours

Chicago is home to plenty of haunting history, from the Great Chicago Fire to the sinking of the SS Eastland. These events have led to more than a few urban legends and countless supernatural sightings. Step into the shadows on these haunted ghost tours and uncover the chilling truth for yourself.

Book a spot on these top Chicago ghost tours: 

• Embers of the Windy City: Chilling Chicago Ghost Tours by Windy City Ghosts (various dates): Get ready to uncover the city’s spine-tingling secrets on this nighttime tour, hosted year-round.
• The Devil in the White City Bus Tour by American Ghost Walks (select Saturdays): Hear the chilling true story of America’s first serial killer on this in-depth bus tour.
• Chicago Booze and Boos Tour by Nightly Spirits (Thursday through Sunday): Visit haunted pubs, taverns, and historic Chicago buildings, while enjoying a pint or two along the way.

Explore more: See our full guide to haunted Chicago tours. Or create your own DIY walking tour with our list of Chicago’s most haunted places.

Fall food festivals

The cooler weather brings an exciting blend of fall food and drink festivals to Chicago, including one of the city’s most anticipated culinary events — Chicago Gourmet. Foodies can get their fix at these upcoming events celebrating the city’s food, beer, and wine scenes.

Chicago’s signature fall food festival:

• Chicago Gourmet (Sept. 24 – 27, 2026): This upscale food festival includes a celebratory brunch, a burger competition, and an elevated tasting experience in downtown Millennium Park.

More fall food and drink festivals in Chicago:

• St. Al’s Oktoberfest (Sept. 25 – 27, 2026): Get a big dose of German cuisine, heritage, and beer at this favorite neighborhood festival.
• Lincoln Square Apple Fest (Oct. 2 – 4, 2026): Celebrate the fall harvest in Ravenswood with apple pie, apple cider, and other autumnal treats.
• Cider and Ale Festival (Oct. 3, 2026): Taste an array of seasonal sips at the scenic Morton Arboretum just outside Chicago.
• Lincoln Park Wine Festival (Oct. 9 – 11, 2026): Sip wine while strolling an open-air market of sommeliers, food vendors, and live music.
• Zoo Brews: Howls and Growls (Oct. 23 – 24, 2026): This adults-only Halloween event features craft beer and cider tasting stations throughout Lincoln Park Zoo.
• Festival of Wood and Barrel-Aged Beer (Nov. 13 – 14, 2026): Explore a curated selection of rare aged beer, mead, and cider at this prestigious competition.

Explore more: Check out more festivals and events in Chicago this fall.

Fall colors in Chicago

This city is gorgeous year-round, but it really shines in the fall. Whether you’re wandering a lakefront park or just meandering the leaf-strewn streets of a charming neighborhood, you’ll find pops of fall foliage everywhere you go.

Top places to see fall colors in and around Chicago:

• Lincoln Park: Enjoy the stunning foliage at this lakefront park, particularly the area around North Pond and South Pond.
• Jackson Park: Home to an ornate Japanese garden, Jackson Park is equal parts historic and naturally stunning.
• Lakefront Trail: Take a stroll along this paved pedestrian trail, featuring a sparkling waterfront and skyline views.
• Humboldt Park: This sprawling neighborhood park is known for its meandering lagoons and native plants.
• Morton Arboretum: A tree-filled oasis, this massive natural area is just a short train ride away.

Explore more: Read the full fall colors guide to Chicagoland.

Film festivals

Fall in Chicago is an excellent time for movie lovers. In October, the city hosts the longest-running competitive film festival in North America, along with a variety of niche festivals that feature everything from hard-to-find indie picks to spine-tingling horror films.

Chicago’s signature fall film festival:

• Chicago International Film Festival (Oct. 14 – 25, 2026): Now in its 62nd year, this international event is North America’s longest-running competitive film festival.

More fall film festivals around Chicago:

• Reeling Film Festival (Sept. 17 – 27, 2026): The second-oldest LGBTQ+ film festival in the country, featuring a diverse selection of works.
• Chicago Underground Film Festival (Sept. 23 – 27, 2026): The longest-running event of its kind, highlighting genre-defying works from independent artists.
• Music Box of Horrors (Oct. 24, 2026): This cult favorite event brings 24 hours of horror movie madness to the historic Music Box Theatre.
• Black Harvest Film Festival (Nov. 6 – 15, 2026): Celebrate Black storytelling in cinema during this fest, spotlighting rising voices and acclaimed filmmakers.

Architecture events

Architecture fans will love fall in Chicago. The city’s autumn architecture events take you inside of some of the city’s most historic, innovative, and iconic spaces — so you can experience Chicago’s groundbreaking architecture up close.

Fall architecture events in Chicago:

• Historic Pullman House Tour (Oct. 10 – 11, 2026): A favorite for more than 50 years, this event offers an exclusive look at homes in the Pullman National Historical Park, an 1880s industrial town known for its unique residential architecture.
• Open House Chicago (Oct. 17 – 18, 2026): This annual event is one of the largest architecture festivals in the world. Go behind the scenes of the greatest spaces and places in Chicago, including soaring skyscrapers, historic spaces, members-only clubs, and other areas not normally open to the public.

Fall festivals and pop-ups

It’s not fall until you visit a pumpkin patch. And you don’t even need to leave the Chicago area to do it. Our seasonal fall festivals and pop-up events bring all the classic fall fun to the city, from bonfires and pumpkin patches to corn mazes and jack-o-lanterns.

Check out these top fall festivals and pop-ups around Chicago:

• Jack’s Pumpkin Pop-up (Sept. 19 – Nov. 1, 2026): Jack’s takes over Goose Island with tons of fun seasonal activities, including axe throwing, carnival games, food vendors, and the city’s largest corn maze.
• Fall Fest at Lincoln Park Zoo (Sept. 25 – Nov. 1, 2026): Fall Fest returns to Lincoln Park Zoo, a family-friendly favorite with a pumpkin patch, pumpkin carvers, live music, and more.
• Night of 1,000 Jack-o’-Lanterns (Oct. 7 – 25, 2026): This spectacular event transforms the Chicago Botanic Garden into a glowing wonderland, with hundreds of artist-carved pumpkins.
• Glass Pumpkin Patch (Oct. 9 – 11, 2026): The Morton Arboretum hosts this beloved artistic tradition, featuring more than 8,000 dazzling blown-glass pumpkins.

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Day of the Dead celebrations

Día de los Muertos, or Day of the Dead, is a time to remember and honor loved ones who have passed. Experience authentic traditions, cultural celebrations, art exhibits, and more throughout Chicago.

Top Day of the Dead celebrations in Chicago:

• Where Memory Lives: 40 Years of Día de Muertos (Sept. 25 – Nov. 29, 2026): The National Museum of Mexican Art hosts this annual exhibition, celebrating the history and culture of Day of the Dead through the perspective of Mexican artists.

Keep an eye out for more Day of the Dead celebrations, like the annual Day of the Dead event in Pilsen’s Harrison Park and the fundraising Día de los Muertos: Love Never Dies Ball at the National Museum of Mexican Art.

Fall boat cruises

It’s not too late to get out on the water! Many of Chicago’s boat tours are still setting sail through autumn, and many offer indoor and climate-controlled options so you can stay comfortable no matter the weather. Grab your tickets today.

Fall boat cruises in Chicago:

• Chicago Line Cruises (through Nov. 1): Learn about the history, impact and legacy of Chicago’s renowned architecture with this family-run tour company.
• Chicago Seadog Lakefront Speedboat Tours (through Nov. 3): Feel the unbeatable thrill of these exhilarating speedboat rides along the Lake Michigan shoreline.
• Shoreline Sightseeing (through Nov. 8): Explore the Chicago lakefront or all three branches of the Chicago River with these classic skyline tours.
• Chicago Architecture Center River Cruise (through Nov. 22): Led by expert docents, these popular tours include the fascinating stories that make up Chicago’s iconic skyline.

Explore more: Check out all of Chicago’s lake and river cruise options.

Theatre and performing arts

Nothing compares to the thrill of live theatre. And the curtain is rising this fall on Chicago’s dynamic theatre scene, from our stunning downtown venues to intimate neighborhood storefronts.

Top shows to catch in Chicago this fall:

• Jekyll & Hyde (Sept. 8 – Oct. 25, 2026): This acclaimed musical comes to the Broadway Playhouse after last year’s sold-out run.
• Destinos: Chicago International Latino Theater Festival (Sept. 14 – Oct. 11, 2026): This acclaimed multi-week fest spotlights Latino theatre artists in venues across the city.
• Operation Mincemeat (Sept. 29 – Oct. 11, 2026): This exciting new production, currently on a world tour, was nominated for four Tony Awards in 2025.
• Vape! The Grease Parody (through Jan. 3, 2027): The Apollo Theater hosts this hilarious revamp of the classic film, featuring a campy modern take.

Explore more: Find your next show with our fall theatre guide.