Welcome autumn in Chicago with festivals, leaf-peeping, and more!
Looking for the best fall activities this year in Chicago?
You’re in for a treat!
As the summer heat fades and cool breezes blow, the Windy City comes alive with vibrant colors and festive events.
From leaf peeping to Halloween and city tours, there's an autumn adventure for everyone.
So put on your seasonal best, grab a pumpkin spice latte, and start planning fall 2024 in Chicago!
Leaf peeping
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One of the best things about autumn in Chicago is the leaves turning a medley of red and orange.
Whether enjoying yourself at a park or strolling through a leaf-strewn neighborhood, you really start to feel the timeless love song Autumn Leaves.
Here are the best places for leaf peeping in Chicago -
Lincoln Park: Stroll along the waterfront and enjoy the vibrant fall colors in Chicago, especially around the North Pond and South Pond.
Jackson Park: Head to the Wooded Island and Osaka Garden for a peaceful escape filled with vibrant autumn fall hues.
Garfield Park Conservatory: The outdoor gardens here explode with color in the fall, making it a must-see.
Lakefront Trail: Whether biking or walking, this 18-mile trail gives you a front-row seat to the changing leaves along the lake.
Morton Arboretum (Lisle): One of the best places for leaf peeping in the Chicago suburbs, with thousands of trees. A short train ride from Chicago.
Busse Woods (Schaumburg): Perfect for a fall day out. Enjoy the trails, maybe even spot some elk while you're there.
Halloween
Halloween in the Windy City is nothing short of legendary. The top October attraction in Chicago.
The city transforms into a spooky playground filled with haunted houses, costume parades, and eerie tours.
Whether you're into family-friendly fun or spine-chilling scares, there's something for you, including…
Northalsted Halloween Parade: Known for its vibrant costumes and lively atmosphere, this parade is a must-see. It’s free to watch, making it one of the best free fall events in Chicago.
Nightmare on Clark Street: Fancy yourself as a daredevil? See if you can make your way through this seasonal haunted house!
Howl-o-ween at Lincoln Park Zoo: Searching for a Halloween for grown-ups? Check out Howl-o-ween at Lincoln Park Zoo with music, free rides, bars, and a haunted trail.
For the kids, there’s Spooky Zoo with trick-or-treating and family-friendly entertainment.
Halloween Season At Navy Pier: Navy Pier gets a festive makeover with thousands of pumpkins, light displays, and Halloween-themed activities.
Chicago Ghost Tours: Discover the haunted history of Chicago with guided tours that take you through the city’s most haunted locations. Perfect for history buffs and thrill-seekers alike.
Día de los Muertos (a.k.a. Day of the Dead)
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This Mexican-origin holiday honors deceased loved ones with colorful altars, traditional music, and lively parades.
Here are some must-see events:
National Museum of Mexican Art: Experience authentic Mexican culture through events like the Love Never Dies Ball and the Día de Muertos exhibit.
Pilsen's Day of the Dead Parade: Join the community in this lively parade featuring elaborate costumes, face painting, and traditional dances.
Oktoberfest
Get ready to don your dirndls and lederhosen, because Oktoberfest in Chicago is a celebration you won't want to miss.
The city transforms into a Bavarian wonderland, filled with traditional German food, lively music, and plenty of beer.
The iconic and traditional Oktoberfest event in Lincoln Square is one of the best September activities in Chicago. Enjoy authentic German food, beer, wine, music, and carnival games!
For a family-friendly event, head for the West Loop Bavarian Block Party— the city's first sober-friendly Oktoberfest. It offers a vibrant mix of Oompah music, delicious brats and pretzels, and other activities.
City tours
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Chicago's history and architecture turn even more stunning against the backdrop of cool weather and amazing fall foliage.
Making city tours one of the best things to do in Chicago throughout September, October, and November.
Here are some of the best options:
Chicago Architecture Foundation Center River Cruise: Climb aboard Chicago’s First Lady and marvel at the skyline as you glide down the Chicago River. Enjoy interesting tidbits from expert guides.
Chicago History Museum Tours: Delve the city's past with guided tours that take you through pivotal moments in Chicago's history.
Chicago Food Planet Tours: Combine sightseeing with delicious eats. Have your fill of culinary excellence while learning about the city’s diverse neighborhoods.
Bike and Roll Chicago: Take a bike or segway tour along the lakefront and through Chicago's parks. It’s an active and fun way to enjoy the fall scenery.
Ghost Tours: Discover the eerie side of Chicago with ghost tours that delve into the city’s haunted history.
Farms and Pumpkin Patches
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Apple picking, corn mazes, and pumpkin patches offer the perfect escape from everyday city life.
This makes them some of the best activities to look forward to during September & October in Chicago.
Jack's Pumpkin Pop-Up: An urban pumpkin patch experience with corn mazes and seasonal treats, right in the heart of Chicago.
Richardson Adventure Farm: In Spring Grove, featuring the world's largest corn maze and a plethora of pumpkins.
Bengtson’s Pumpkin Fest: A Homer Glen favorite, famous for its rides, petting zoo, and wide variety of pumpkins.
Sonny Acres Farm: Located in West Chicago, with classic fall fun with hayrides, haunted barns, and pumpkin picking.
Food festivals
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Fall in Chicago isn't just about stunning foliage and spooky fun—it's also a feast for your taste buds!
The food festivals are a must-visit, offering everything from savory delights to sweet treats.
Here are some of the top fall food festival ideas to mark on your calendar:
Chicago Gourmet: This high-end food festival in Millennium Park showcases the best of the city’s culinary scene with gourmet tastings, chef demos, and wine pairings.
Taste of Chicago: While traditionally a summer event, the fall edition brings a unique twist with seasonal dishes and local favorites.
Lincoln Square Apple Fest: Celebrate the quintessential fall fruit at this charming festival. Enjoy everything apple—from pies and ciders to crafts and live music. One of the best October events in Chicago.
Taco Fest: Head to Lakeview for a fiesta of flavors. This festival features some of the best tacos in town, along with live music, dancing, and plenty of margaritas.
Chi Food Truck Fest: Head to Daley Plaza for some of Chicago’s best food truck grub. On select dates throughout September and early October.
You should also check out our blog post on Chicago’s best food festivals for more ideas.
Film festivals
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Lights, camera, action!
Enjoy the magic of cinema under the autumn sky.
Whether you're a film buff or just looking for a cozy date night, Chicago's fall film festivals are something to look forward to.
Chicago International Film Festival: As North America's longest-running competitive film festival, this event showcases a diverse array of films from around the globe.
Reeling—The Chicago LGBTQ+ International Film Festival: The US’ second oldest LGBTQ+ film festival, celebrating LGBTQ+ stories and voices.
Black Harvest Film Festival: Held at the Gene Siskel Film Center, this festival highlights the best in contemporary independent films that explore the Black experience.
Music Box of Horrors: This 24-hour marathon at the historic Music Box Theatre is a must-visit for horror aficionados.
Escape rooms
Looking to bond with family and friends during the fall?
Escape rooms offer an exhilarating way to challenge your problem-solving skills while creating unforgettable memories.
Fox in a Box (that’s us): We offer four different themes including The Bank, The Prison, The Bunker, and Zodiac (scary, a good choice for Halloween). We were voted the #1 escape room in Chicago (not kidding!)
PanIQ Escape Room: Situated in Fulton Market and Logan Square, PanIQ offers a variety of themes such as Insane Asylum, Voodoo Spirits, and Mob Boss.
Escape Artistry: Known as Chicago’s original escape room, it offers handcrafted games with custom puzzles. With locations in Wicker Park, you can try missions like Roaring Dan’s Pirate Dungeon and Detective vs. Dillinger.
The Great Escape Room: This venue features several themed rooms like Mountain Top Murders and Escape the Colosseum, offering a mix of mystery and adventure for groups of all sizes.
Fall activities in the Chicago suburbs
- Deer Grove Forest Preserve: Follow a network of trails through hardwood forests, ideal for catching the autumn colors. Check out this cool web map which shows the best fall color hotspots.
- Jack O'Lantern World: Held at The Forge in Lemont, this event features thousands of artisan-carved pumpkins along a trail. It runs throughout October on select evenings.
- Goebbert’s Pumpkin Farm: One of the best fall family activities—especially the kids and young at heart! Try everything from a corn stalk maze to a duck derby. Visit the pumpkin-eating dinosaur and make it through the haunted house.
- Highwood Pumpkin Fest: With ‘zillions of jack-o-lanterns’, this is a real treat! With all-you-can-carve pumpkin stations, nightly lightings of pumpkin-filled walls, and costume contests, there’s a lot to look forward to!
The best fall activities in Chicago—FAQs
What kind of weather will it be during fall 2024?
In fall 2024, Chicago is expected to experience cooler-than-normal temperatures with above-average precipitation.
You can expect occasional rain showers, so it's wise to keep an umbrella handy while enjoying the vibrant fall foliage and festive events throughout the city.
What’s the best free activity to enjoy during fall in Chicago?
One of the best free activities to enjoy during fall in Chicago is the Fall Fest at Lincoln Park Zoo.
This family-friendly event offers live professional pumpkin carving, festive photo ops, animal viewing, and more—all without paying a dime.
Started planning for fall yet?
With so many incredible activities, Chicago in the fall is an experience you won't want to miss.
Whether you're leaf-peeping, enjoying a spooky Halloween, or solving puzzles in an escape room, there's something for everyone.
So start planning your autumn adventures now and make the most of this vibrant season!
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