October is a fun-filled time in Chicago, with endless Halloween events and fall-themed celebrations happening all month long.
Start filling up your calendar with mystical evening parades, spooky ghost tours, food festivals, architecture events, and more — there are seemingly endless ways to celebrate the start of the fall season in Chicago. Here are a few of the events and activities we’re most excited about this month.
Top events in Chicago this October
Lincoln Square Ravenswood Apple Fest (Oct. 3 – 5): The 38th annual Apple Fest is one of the most beloved traditions to mark the arrival of fall, with plenty of apple-focused food and drink vendors.
Maxwell Street Market (Oct. 4): Browse an eclectic array of handmade crafts, live music, and street food vendors at this Chicago’s oldest outdoor market.
World Music Festival Chicago (through Oct. 5): Celebrate global sounds with free concerts across the city, featuring artists from 16 countries performing at venues throughout Chicago.
Chicago Fashion Week (Oct. 9 – 19): The second annual Chicago Fashion Week features exciting panels, runway events, markets, exhibitions, and much more.
Historic Pullman House Tour (Oct. 11 – 12): Step back in time during the Historic Pullman House Tour, offering rare access to stately mansions and charming workers’ cottages in this landmark neighborhood.
Bank of America Chicago Marathon (Oct. 12): Runners from around the world travel to Chicago for this iconic marathon course, which winds through 29 of the city’s neighborhoods.
Chicago International Film Festival (Oct. 15 – 26): The 61st annual film festival is North America’s longest-running competitive film festival, presenting screenings of buzzy movies, documentaries, and short films.
Arts in the Dark (Oct. 18): The 11th annual Arts in the Dark Halloween parade takes over a stretch of downtown State Street with music, dance, spooky floats, puppets, and so much more.
Open House Chicago (Oct. 18 – 19): This free city-wide architecture festival gives you inside access to the city’s most jaw-dropping landmarks, private clubs, skyscrapers, and more.
Yoko Ono: Music of the Mind at the Museum of Contemporary Art (opens Oct. 18): Yoko Ono’s impressive artistic career is on full display at this new retrospective during its only U.S. tour stop.
Chicago International Latino Theater Festival (Oct. 1 – Nov. 2): Explore bold new performances and rising talent at this month-long showcase of the city’s vibrant Latino theatre community.
Día de los Muertos Xicágo (Oct. 23): Explore an artistic take on Día de Muertos traditions at this annual event hosted by the National Museum of Mexican Art in Pilsen.
Chicago Architecture Biennial (through October): Experience the future of architecture at this ground-breaking event, the largest free architecture and design exhibition in North America.
Haunted Halsted Halloween Parade (Oct. 31): This spooktacular evening includes fun and themed performances, a costume contest with an awards ceremony, and an aftershow with a dance party.
More events in Chicago this October
West Town Art Walk (Oct. 3 – 5): The West Town neighborhood and local businesses are opening their doors for a special community art walk, showcasing Chicago artists at various galleries and along neighborhood streets.
St. Benedict Oktoberfest (Oct. 3 – 5) The family-friendly Oktoberfest event at St. Ben’s in North Center promises plenty of German fun for all ages.
Fall Taste of Northalsted (Oct. 4): Sample seasonal bites and drinks from 20 local bars and restaurants while strolling through the vibrant Northalsted neighborhood at this one-day fall tasting event.
Cider and Ale Festival (Oct. 4): Sip hard ciders and seasonal beers with a backdrop of beauty at the Morton Arboretum. Over 30 local breweries and cideries will be bringing samples to taste across three different walking paths at the arboretum.
Chicago Beer Festival (Oct. 4): Sample seasonal brews from over 60 local breweries, all while exploring inside the historic Field Museum.
Boo at the Zoo (Oct. 4 – 31): Brookfield Zoo showcases a variety of Halloween-themed activities, including photo spots, corn mazes, creepy carousels, and zookeeper chats.
Lincoln Brunch Fest (Oct. 11) Lincoln Avenue is hosting a one-day Brunch Festival, when local restaurants will showcase their brunch favorites, alongside plenty of family-friendly activities for the kids.
Glass Pumpkin Patch at the Morton Arboretum (Oct. 10 – 12) The annual glass pumpkin patch features a dazzling array of artwork, including live glassblowing demonstrations and hands-on activities.
Slow & Low Festival (Oct. 11): Chicago’s lowrider festival returns to Navy Pier with over 250 meticulously customized cars from local clubs.
Oktoberfestiversary (Oct. 11 – 12): Begyle Brewing and Dovetail Brewery are teaming up for their annual fall celebration with food trucks, live music, and plenty of Oktoberfest-style beers.
Indigenous People’s Day at the Field Museum (Oct. 13): The Field Museum invites guests to enjoy special cultural performances and explore Native Truths: Our Voices, Our Stories, an exhibit created with local Indigenous collaborators.
Rare Map, Book, and Autograph Fair (Oct. 17 – 18): Shop unique items from leading map, book, and autograph dealers from across the country at the Newberry Library.
Spooky Zoo at Lincoln Park Zoo (Oct. 18): Who wouldn’t want to trick-or-treat on the zoo grounds? Lincoln Park Zoo hosts a free, trick-or-treating extravaganza for all ages, including family-friendly entertainment.
BOO-Palooza at Wicker Park (Oct. 18): With live music, a kids costume parade, a pumpkin patch, and more, this family-friendly fall festival takes over Wicker Park for a neighborhood celebration of all things fall.
Chicago Artisan Market (Oct. 19): Morgan Manufacturing in Fulton Market is home to the annual Artisan Market, welcoming hundreds of food, jewelry, art, home, and art vendors for your fall shopping needs.
37th Annual Edgar Allan Poe Readings (Oct. 25): Actors from Lifeline Theatre present readings of Poe’s classic, haunting tales at the historic Glessner House Museum.
Upside Down Parade (Oct. 25): The annual “reverse” Halloween event lets Chicago families and kiddos become the parade as they march past musical groups and performances, acrobats, sports mascots, and more in Washington Park.
Fall Fest at the Zoo (through Oct. 26): This family-friendly celebration at Lincoln Park Zoo will offer fun fall activities, including a pumpkin patch, kid-friendly rides, professional pumpkin carvers, musical entertainment, and more.
Trick or Treat on Southport (Oct. 27): Bring the kids to Southport Corridor for a festive celebration of costumes, candy, and fun. There will be family-friendly activities like a pumpkin patch, crafts, inflatables, and plenty of trick-or-treating fun.
Night of 1,000 Jack-o’-Lanterns (through October): The Chicago Botanic Garden will showcase more than 1,000 intricately hand-carved pumpkins at this Halloween event.
Chicago Humanities Festival (through October): Expand your mind with fascinating conversations with luminaries like Kate McKinnon, Nick Offerman, Roxanne Gay, Samin Nosrat, and more.
Rooftop Cinema Club (through October): Catch seasonal favorites like Practical Magic, Scream, Hocus Pocus, and The Nightmare Before Christmas, on the rooftop of The Emily Hotel in Fulton Market.
Music Box of Horrors at the Music Box Theatre (through October): This annual horror-themed film festival at the historic Music Box Theatre features 24 hours of spooky film favorites, plus special guests, giveaways, vendors, and more.
Jack’s Pumpkin Pop-Up (through October): This over-the-top Halloween pop-up includes a giant corn maze, carnival games, photo opportunities, axe throwing, bars, food trucks, and tons of pumpkin-packed fun.
Escape the Museum at the Museum of Science & Industry (through October): Step into an escape room experience inside the the largest science museum in the Western Hemisphere, where puzzles and challenges guide you through the museum after-hours.
Pigmented Black Fine Art Faire (Oct. 31 – Nov. 2): This celebration of Black art will include artist talks, a youth exhibition, collectible fine art, and more at the Zhou B Art Center.
