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

Dia de los Muertos at the National Museum of Mexican Art
Dia de los Muertos at the National Museum of Mexican Art

Hear global beats at World Music Festival (Oct. 1): Wrap up this year’s edition of the World Music Festival Chicago with Madalitso Band at The Hideout.

Attend the inaugural Chicago Exhibition Weekend (Sept. 29 – Oct. 1): More than 50 galleries, institutions, and artist-run spaces will present exhibitions, unique programs, and extended hours.

Step back in time on the Historic Pullman House Tours (Oct. 8): Enjoy exclusive interior access to the area’s well-preserved historic homes during this 50th annual event.

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.

Visit the Chicago Architecture Biennial (through October): Experience the future of architecture at this ground-breaking event, the largest architecture and design exhibition in North America.

Catch a film at the Reeling Film Festival(through Oct. 8): This year is the 41st edition of the Reeling Film Festival, which showcases a variety of LGBTQ-centered stories.

Cheer on the runners at the Chicago Marathon (Oct. 8): There’s something special about marathon weekend in Chicago, when runners from around the world complete 26.2 miles through the city’s neighborhoods.

Hear Native American musicians on Indigenous People’s Day (Oct. 8 – 9): This free two-day festival, now in its fifth year, will be a showcase of musicians from Native American and Indigenous communities

Catch a screening at the Chicago International Film Festival (Oct. 11 – 22): North America’s longest-running competitive film festival presents hundreds of movies and short films to Chicago film lovers.

Visit the Fine Arts Building for an anniversary celebration (Oct. 13): This historic space in the Loop will be celebrating 125 years with a free concert, artist demos, and more.

Check out the Night of 1,000 Jack-o’-Lanterns (Oct. 11 – 22): The Chicago Botanic Garden will display over 1,000 hand-carved pumpkins, plus live carving demos and seasonal treats.

Watch Ballet Folklorico at the Field Museum (Oct. 14): Celebrate National Hispanic Heritage Month with this traditional performance by local dancers.

Go behind the scenes during Open House Chicago (Oct. 14 – 15): 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.

Be mesmerized by Arts in the Dark (Oct. 21): This whimsical evening parade celebrates Halloween as the artist’s holiday, with creative puppets, floats, and performances on downtown State Street.

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.

More things to do this October

Jacks Pumpkin Pop-up
Jacks Pumpkin Pop-up

Celebrate Oktoberfest in Lakeview (Sept. 29 – Oct. 1): Lakeview East will be hosting its first Oktoberfest event with live music, food, drinks, and activities for the whole family. 

Get a dose of culture from Chicago Humanities (through October): The fall festival brings a range of performances and conversations from today’s top cultural figures. 

Try fall treats at Apple Fest (Sept. 30 – Oct. 1): The 36th annual Apple Fest in Lincoln Square is a tradition to mark the arrival of fall and will include plenty of apple-focused food and drink vendors.

Enjoy a family-friendly Oktoberfest at The Northman (through Oct. 2): The German festivities head to the Riverwalk, with live music and kid-approved activities. 

Grab tickets for Holy Ghost Bingo(starts Oct. 6): The Greenhouse Theatre Center is home to Holy Ghost Bingo, hosted by a former nun, which will include a night of Halloween trivia, a costume contest, and more. 

Sip wine at the Lincoln Park Wine Festival (Oct. 6 – 8): This year is the seventh annual wine fest that transforms Jonquil Park into an open-air market featuring food and wine samples galore. 

Enjoy Oktoberfest at Time Out Market(Oct. 7): Time Out Market has a day full of Oktoberfest activities, including live music, a stein hoisting contest, German band performances and storytime, face-painting, and more.

Cheers to the Chicago Beer Festival(Oct. 7): Visit the Field Museum for a one-of-a-kind beer festival featuring 65 breweries showcasing their favorite seasonal brews and select museum exhibits.

See Bob Dylan at the United Center (Oct. 7 – 8): The iconic Bob Dylan headlines the United Center for a two-day show of his Rough and Rowdy Tour.

Check out Boo at the Zoo (Oct. 7 – 22): On weekends this month, Brookfield Zoo showcases a variety of Halloween-themed activities with photo opps, corn mazes, creepy carousels, and zoo chats. 

Check out Cinema of Screams(Oct. 10): The American Writers Museum is hosting a one-night Halloween deep-dive into the world of our favorite horror films, which will include a costume contest, movie trivia bingo, arts and crafts, and specialty cocktails to boot.

Explore the Field Museum’s Boo with Sue(Oct. 13): Come in costume to the Field Museum for an after-hours, family-friendly exploration of the museum’s exhibits. 

Dress up for the Chicago Vampire Ball(Oct. 13): The Tip Top Tap Ballroom at the Warwick Allerton Hotel transforms for a night to welcome the Chicago Vampire Ball with costume prizes, live music, tarot card readings, and more.

Head to the Morton Arboretum for the Glass Pumpkin Patch(Oct. 13 – 15) The annual glass pumpkin patch features various exhibits, showcasing artists that turn bits of glass into molten pumpkin masterpieces. 

Eat your heart out at the Great Food Expo(Oct. 14 – 15): The Great Food Expo is headed to the Donald E. Stephens Convention Center for a two-day, food lovers conference, featuring endless samples, shopping, panels from celebrity chefs, and so much more.

Shop the Chicago Artisan Market (Oct. 15): Morgan Manufacturing in Fulton Market is home to the fall Artisan Market, welcoming hundreds of food, jewelry, art, home, and art vendors.

Snag tickets for Hamilton(through October): The beloved Broadway musical is back in Chicago, telling the story of Founding Father Alexander Hamilton, and his epic legacy.

Watch live Ballet 5:8 performances (Oct. 18 – 21): The premier dance company is performing at the Athenaeum Center, telling an enthralling, thought-provoking story through ballet.

Run a 5K race through Rosehill Cemetery(Oct. 21): The ever-popular Rosehill Cemetery Crypt 5K is back, featuring a run through the cemetery at night via candlelight. There’s a post-race party at Fireside Tavern.

Watch Art on The Mart (through October): Catch the new fall program of this evening lights display debuting this month, featuring exciting new collaborations. 

Check out BOO-Palooza at Wicker Park(Oct. 21): This family-friendly fall festival takes over Wicker Park for a neighborhood celebration of all things fall.

Sip seasonal drinks at Cider and Ale Fest (Oct. 21): Enjoy hard ciders and seasonal beers from 30 different vendors with a backdrop of natural beauty at the Morton Arboretum. 

Get spooked at the Music Box of Horrors (through October): The annual horror-themed film festival features 24 hours of spooky film favorites and also will include special guests, giveaways, vendors, and more. 

Celebrate fall at Jack’s Pumpkin Patch Pop-Up (through October): With pumpkins galore, this family-friendly, autumnal pop-up also includes a corn maze, axe throwing, food trucks, carnival games, fortune tellers, and more. 

Head to Navy Pier for the Slow & Low Festival(Oct. 21): Chicago’s lowrider festival returns to Navy Pier for this year’s cultural celebration and exhibition of the lowrider artistic community. 

Check out Nightmare on Clark Street(through October): Deuce’s Sports Bar in Wrigley transforms into an immersive, creepy, and over-the-top haunted house experience throughout October.

Visit Spooky Zoo at Lincoln Park Zoo(Oct. 21): 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.

Trick or treat at Navy Pier’s Spooky Saturday (Oct. 28): Come in your Halloween best to Navy Pier for a family-fun day of trick or treating with the waves of Lake Michigan as your backdrop.

Snag your tickets for the Haunted Halloween Ball(Oct. 28): The annual Halloween Ball takes over the Congress Plaza Hotel for a night of spooky fun, including a costume contest, live DJ music, food, drink, and more.

Find the best deals at Maxwell Street Market (through October): The weekly 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.

Watch a movie at the Rooftop Cinema Club (through October): The Emily Hotel is home to this rooftop movie series including everything from classics to new releases.

Celebrate the start of autumn at Fall Fest (through Oct. 29): From pumpkin carving to a harvest maze, various rides, and more, this family-friendly free event at Lincoln Park Zoo is the perfect way to kick off a new fall season.