October is a jam-packed time in Chicago, with tons of Halloween events and fall-themed celebrations happening all month long.
Start filling up your calendar with mystical evening parades, spooky ghost tours, fall 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
Maxwell Street Market (Oct. 4): Browse an eclectic array of handmade crafts, live music, and street food vendors at this long-running Sunday market, with roots dating back over a century. The last market of the season, this edition will have a block party theme.
World Music Festival (through Oct. 4): The final stretch of Chicago’s annual World Music Festival brings the sounds of artists from around the world to venues across the city. The finale will be the outdoor Global Peace Picnic in Humboldt Park.
Chicago Fashion Week (Oct. 8 – 18): Now in its third year, Chicago Fashion Week showcases the city’s creativity, culture, and couture. Expect runway shows, industry panels, pop-up markets, exhibitions, and more.
Historic Pullman House Tour (Oct. 10 – 11): For more than 50 years, the annual Historic Pullman House Tour has offered a rare opportunity to step inside the stately mansions and well-preserved workers’ cottages that surround the Pullman National Historical Park.
Destinos: Chicago International Latino Theater Festival (through Oct. 11): This month-long celebration of Latino theatre showcases bold new performances, rising talent, and established companies from across Chicago, the U.S., and Latin America.
Bank of America Chicago Marathon (Oct. 11): Chicago is famous for its fast and flat marathon course — which means spectators have the opportunity to watch world records get broken. The 26.2-mile course starts and ends in lakefront Grant Park.
Chicago International Film Festival (Oct. 14 – 25): The longest-running competitive film festival in North America, the Chicago International Film Festival brings hundreds of feature films, documentaries, and short films from around the world to screens across Chicago.
Open House Chicago (Oct. 17 – 18): This free, citywide architecture festival offers behind-the-scenes access to some of Chicago’s most extraordinary buildings, from iconic skyscrapers and historic landmarks to private clubs and residential buildings normally closed to the public.
Arts in the Dark (Oct. 24): This free event is a uniquely Chicago Halloween tradition. Arts in the Dark is a magical evening procession that features giant puppets, live music, dance performances, and costumed participants marching through the heart of downtown Chicago.
Día de los Muertos Xicágo (Oct. 24): In Pilsen, the National Museum of Mexican Art hosts this annual community gathering to honor Day of the Dead. Enjoy live music and performances, art activities, and a stunning illuminated ofrenda.
Upside Down Parade (Oct. 31): This all-ages daytime event encourages families to don costumes and join the spectacular Halloween procession through Washington Park. The event is free and kids will receive free goodie bags.
Haunted Halsted Halloween Parade (Oct. 31): The famous Northalsted neighborhood goes all-out for Halloween with the city’s most spectacular celebrations. This annual costume parade is free to attend and features creative, elaborate, and outrageous costumes. This year’s event also features a daytime street festival.
More events in Chicago in October
Lincoln Square Ravenswood Apple Fest (Oct. 2 – 4): Apple Fest marks the arrival of fall with plenty of apple-centric treats, including fresh-picked apples, ciders, apple cider donuts, apple pies, and more in a festive and family-friendly atmosphere.
West Town Art Walk (Oct. 2 – 4): This vibrant arts district invites locals and visitors to pop into the many galleries, design shops, and restaurants throughout the neighborhood. There will also be guided public art walking tours.
St. Benedict Oktoberfest (Oct. 2 – 4): St. Ben’s beloved annual Oktoberfest is back for another year of family-friendly German fun, complete with live music, traditional food and drink, carnival games, and rides for the little ones in the heart of the North Center neighborhood.
TEDxChicago (Oct. 3): TEDxChicago returns to the Harris Theater with bold ideas, inspiring speakers, and the kind of thought-provoking conversations that stay with you long after you leave the auditorium.
Boo at the Zoo (starting Oct. 3): Brookfield Zoo gets into the Halloween spirit with themed activities, including photo spots, a corn maze, a creepy carousel, zoo chats, and a sweet treat for all attendees on the way out.
Chicago Art Fair (Oct. 7 – 10): The Chicago Art Fair brings together local, national, and international artists for a multi-day celebration of contemporary art in the heart of Chicago. The event at The Mart will feature painting, photography, sculpture, mixed media, and more.
Lincoln Park Wine Fest (Oct. 9– 11): The 10th annual Lincoln Park Wine Fest is a can’t-miss event for wine lovers, with wine tastings, local food vendors, and stunning fall vibes.
Mocktoberfest (Oct. 10): Enjoy a zero-proof Oktoberfest at this fun event dedicated to alcohol-free living. Tickets include unlimited samples of N/A beers and mocktails, live music, a stein-holding contest with prizes, tarot reading, and lawn games.
Lincoln Brunch Fest (Oct. 10): Brunch lovers should head to Lincoln Avenue for this one-day festival, bringing together some of the neighborhood’s best-loved local restaurants to showcase their most indulgent brunch offerings.
Oktoberfestiversary (Oct. 10 – 11): Two local breweries join forces for their annual fall celebration, bringing together food trucks, live music, and a stellar lineup of Oktoberfest-style beers.
Operation Mincemeat (through Oct. 11): This acclaimed new musical, fresh off a celebrated run in London’s West End and on Broadway, brings one of World War II’s most audacious true stories to the stage at the CIBC Theatre.
Spooky Zoo at Lincoln Park Zoo (Oct. 17): Lincoln Park Zoo hosts this free trick-or-treating extravaganza for kids of all ages, with costumed characters, family-friendly entertainment, and candy stations winding through the zoo grounds.
Howl-O-Ween Canine Cruise (Oct. 17 – 25): Dog parents, this one’s for you! This canine-friendly cruise along the lake and river is the perfect outing for you and your furry best friend. Costumes are encouraged for dogs and humans alike.
The Night of 1,000 Jack-o’-Lanterns (through October): The Chicago Botanic Garden transforms its stunning grounds with over 1,000 hand-carved pumpkins, illuminated for a magical nighttime experience.
Jack’s Pumpkin Pop-Up (through October): Chicago’s most over-the-top Halloween experience is back, and it’s bigger than ever. Jack’s Pumpkin Pop-Up features a giant corn maze, carnival games, axe throwing, photo opportunities, bars, food trucks, and an abundance of pumpkin-themed fun.
Pokémon Fossil Museum (through October): Making its U.S. debut at Chicago’s Field Museum, this buzzy new exhibition invites visitors to compare fossil Pokémon, like Tyrantrum and Archeops, and real-world prehistoric fossils.
