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
Kick off fall at Apple Fest (Oct. 5 – 6): The 37th annual Lincoln Square Ravenswood Apple Fest features plenty of apple-centric food and drinks to celebrate the start of autumn in Chicago.
Honor Chicago’s house music legacy (Oct. 5): Celebrate the birthplace of house music at The Warehouse Landmark Dedication Block Party with live DJ sets, food trucks, and more.
Celebrate LGBTQ+ voices at the Reeling Film Festival (through Oct. 6): This year is the 42nd edition of the Reeling: The Chicago LGBTQ+ International Film Festival, the second longest-running film festival of its kind.
Attend the inaugural Chicago Fashion Week (Oct. 9 – 20): The first-ever Chicago Fashion Week is a multi-day event featuring various panels, runway events, social panels, markets, exhibitions, and much more.
Step back in time on the Historic Pullman House Tours (Oct. 12 – 13): Enjoy exclusive interior access to the historic area’s well-preserved homes during this 51st edition of Chicago’s longest-running house tour series.
Cheer on the runners at the Chicago Marathon (Oct. 13): There’s something special about marathon weekend in Chicago, and one of the best ways to support for the thousands of runners is to show up and cheer along the 26.2-mile route.
Catch a film at the Chicago International Film Festival (Oct. 16 – 27): The 60th annual edition of North America’s longest-running competitive film festival presents hundreds of movies and short films to Chicago film lovers.
Visit Spooky Zoo at Lincoln Park Zoo (Oct. 19): Who wouldn’t want to trick-or-treat on the zoo grounds? Lincoln Park Zoo hosts a free, one-day trick-or-treating extravaganza for all ages, including family-friendly entertainment.
Be mesmerized by Arts in the Dark (Oct. 19): This year is the 10th annual Arts in the Dark parade that takes over downtown State Street every Halloween season. The family-friendly parade features music, dance, spooky floats, puppets, and so much more.
Go behind the scenes during Open House Chicago (Oct. 19 – 20): This one-of-a-kind free architecture festival takes you inside the city’s most unique buildings, skyscrapers, and landmarks.
Catch a show during the Chicago International Latino Theater Festival (through October): Discover emerging voices in the local Latino theatre community during this multifaceted fest.
Don’t miss the 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.
Learn about Day of the Dead customs (through October): See an artistic take on Día de Muertos traditions at this annual exhibit by the National Museum of Mexican Art.
More events in Chicago this October
Expand your mind at the Chicago Humanities Festival (through October): This season’s conversations include events and performances from icons like Connie Chung, Joan Baez, Ta-Nehisi Coates, and so much more.
Enjoy a family-friendly Oktoberfest at The Northman (Oct. 1– 2): The German festivities head to the Chicago Riverwalk, including live music performances from a German folk-pop group.
Attend the Little Village farmers market (Oct. 5): It’s the last market of the season at this colorful neighborhood plaza. Afterward, explore the abundance of local shopping options in the area.
Surround yourself with art during Chicago Exhibition Weekend (Oct. 3 – 6): More than 50 galleries, institutions, and artist-run spaces will present exhibitions, unique programs, and extended hours.
Enjoy the West Town Art Walk (Oct. 4 – 6): The West Town area is hosting a special community art walk, featuring Chicago artists at various galleries and a self-guided public art walking tour.
Celebrate Hispanic Heritage Month with Canto Latino (Oct. 5): The annual outdoor concert festival is back in Senka Park. Singers from youth neighborhood choir programs will perform different genres of South American music, from the samba, to morenada, joropo and more.
Sip fall flavors at the Cider and Ale Festival (Oct. 5): Sample hard ciders and seasonal beers with a backdrop of fall foliage at the Morton Arboretum. Over 30 local breweries and cideries will beshowcased across three different walking paths at the arboretum.
Check out Boo at the Zoo (Oct. 5 – 20): Every weekend, Brookfield Zoo showcases a variety of Halloween-themed activities, including from photo spots, corn mazes, creepy carousels, and zoo chats. All attendees will also get a sweet treat as you exit.
Head to the Chicago Beer Festival (Oct. 5): Visit the Field Museum for a one-of-a-kind beer festival featuring 65 breweries showcasing their favorite fall seasonal beers, all-the-while having a select few of the museum’s exhibits open to attendees.
Sample wines at the Lincoln Park Wine Festival (Oct. 4 – 6): This annual wine fest transforms Jonquil Park into an open-air market featuring food and wine sample galore.
Celebrate Oktoberfest in North Center (Oct. 4 – 6): Oktoberfest celebrations are plentiful throughout the month, and this family-friendly mainstay promises plenty of German fun, including inspired music, food, drinks, and carnival games and rides.
Marvel at a Glass Pumpkin Patch (Oct. 11 – 13) This annual art event at the Morton Arboretum features a dazzling array of handblown glass transformed into molten pumpkin masterpieces.
Brunch your heart out at the Lincoln Brunch Fest (Oct. 12): West Lakeview is hoting this one-day Brunch Festival, when beloved local restaurants will show off their best brunch menu items.
Head to Navy Pier for the Slow & Low Festival (Oct. 12): Chicago’s lowrider festival returns to Navy Pier for this year’s cultural celebration and exhibition of the lowrider community.
Sing along to Sabrina Carpenter at the United Center (Oct. 13): The Espresso singer is coming to Chicago during her first stadium tour to promote her Short n’ Sweet album.
Shop the Chicago Artisan Market (Oct. 13): Head to the West Loop to shop this fall artisan market, welcoming hundreds of food, jewelry, art, home, and art vendors.
Celebrate Indigenous People’s Day (Oct. 14): The Field Museum invited guests to enjoy a special cultural performance by Danza Azteca and explore Native Truths: Our Voices, Our Stories, which was created in-part with Indigenous local collaborators.
Celebrate fall at Jack’s Pumpkin Pop-Up (through October): With pumpkins galore, this over-the-top experience also includes a corn maze, axe throwing, food trucks, carnival games, fortune tellers, and more.
Check out the Night of 1,000 Jack-o’-Lanterns (Oct. 16 – 27): The Chicago Botanic Garden will display over 1,000 intricately hand-carved pumpkins, plus live carving demos and seasonal treats.
Catch a short film at the Study Abroad Film Festival (Oct. 17): This year is the tenth celebration of the IES Study Abroad Film Festival, which showcases works from young filmmakers highlighting their experiences around the world.
Enjoy a beer stroll in Roscoe Village (Oct. 19): Stroll through the Lakeview and Roscoe Village neighborhoods while tasting craft beer samples and tasty bites from local breweries along three different routes, totaling 30 local participating businesses and restaurants.
Bring the family to BOO-Palooza (Oct. 19): With live music, a kids costume parade, pumpkin patch, and more, this family-friendly fall festival takes over Wicker Park for a neighborhood celebration of all things fall.
Race through Rosehill Cemetery (Oct. 19): The Rosehill Cemetery Crypt 5K RUn adn Walk is back, offering participants the chance to run through the cemetery at night via candlelight.
Do yoga surrounded by plants (Oct. 23): Get zen while surrounded by abundant greenery during this yoga class at the Garfield Park Conservatory.
Check out the Upside Down Parade in Washington Park (Oct. 26): The fifth 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.
Eat your heart out at the Great Food Expo (Oct. 26 – 27): The Great Food Expo is headed to nearby Rosemont for a two-day, food lovers conference, featuring endless samples, shopping, panels from celebrity chefs, and so much more.
Find the best deals at Maxwell Street Market (Oct. 27): The historic Maxwell Street Market is a Chicago tradition filled with live music, family activities, plenty of shopping from local artisan vendors, and lots of food, drink, and fun.
Run past fall colors at Morton Arboretum (Oct. 26): The Fall Color 5K is a great way to see the fall foliage, while also getting plenty of steps. The Morton Arboretum will host this magical morning of running or walking, followed by post-race live music, food, and a complimentary beer.
Meet creepy creatures at the conservatory (Oct. 26): The Garfield Park Conservatory is hosting Creatures of the Night, where kids and families can get up close and personal with live creatures and carnivorous plants.
Attend Fall Fest at the zoo (through Oct. 27): Visit Lincoln Park Zoo during its annual Fall Fest. This family-friendly celebration will offer fun fall activities including a pumpkin patch, kid-friendly rides, professional pumpkin carvers, musical entertainment, story times, and more.
Catch a film at the Rooftop Cinema Club (through October): This West Loop rooftop hosts regular movie screenings, including seasonal options and fan favorites like Hocus Pocus, Mamma Mia, Practical Magic, American Psycho, and more.
Browse the goods at a giant flea market (through October): Every Sunday, head to the parking lot of Allstate Arena for a specialty flea market showcasing hundreds of small businesses with treasures to discover.
Celebrate spooky season at the Music Box Theatre (through October): This year’s annual horror-themed film festival features 24 hours of spooky movie favorites and also will include special guests, giveaways, vendors, and more.
Snag a ticket for Harry Potter and the Cursed Child (through October): Straight from Broadway on its first North American Tour, the magic of Hogwarts returns to the stage with Harry Potter and the Cursed Child for a limited run at the Nederlander Theatre.
