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There are so many fall activities in Chicago that visitors and locals can take advantage of during the spooky season, such as ghost tours, fall colors, and seasonal events.
Living in the Windy City gives me the chance to experience it all year round, and it is my privilege to share what life is like during autumn so that you can plan your time here wisely.
You may also like our 3-Day Chicago itinerary, and you can read all of my Illinois guides here.
Best Fall Things to Do in Chicago
Take a Ghost Tour
Get familiar with the ghosts and spirits in the area!
You’ll need a local guide to introduce you to the popular ghosts and haunted buildings; luckily, we can recommend a few amazing tours in Chicago.
The Gangsters and Ghosts Walking Tour is a two-hour tour around the Loop District, the center of downtown Chicago.
This Wind and Souls Adults Only Ghost Tour is a truly frightening walking tour of some of the most chilling sites and stories from Chicago’s past.
Any of these iconic tours will feature the most intriguing ghosts and gangsters from the darkest parts of Chicago’s history.
Stroll Through the (Spooky) Rosehill Cemetery
Visit the 350 acres of Rosehill Cemetery (5800 N Ravenswood Ave), which has served the city since the mid-1800s, and wander among the historic grounds of the largest cemetery in Chicago.
Rosehill is known for its elegant architecture, ornate marble monuments and sculptures, and rolling hills; it was featured in.
While this is an off-the-beaten-path fall activity, there are many other unique things to do in Chicago.
Open House Chicago
Every fall, the Chicago Architecture Center (111 E Wacker St) hosts Open House Chicago, a free public event that allows anybody to take a self-guided architecture tour through the most iconic buildings in the city.
Architecture enthusiasts will have the chance to access the inner workings of some of the area’s most significant sites.
Take an adventure through architecture and history trails, attend talks and programming by experts, and get incredible behind-the-scenes access to amazing buildings.
Do you still want more architectural goodness?
Check out this 2.5-hour architecture boat tour for an exciting overview of the best architecture along the Chicago River!
Check Out the City’s Skyline at Night
As gorgeous and breathtaking as the city can be during the day, one of the best activities in the fall is riding downtown at night when sunset occurs a little earlier than in summer.
Bundle up and climb aboard the Big Bus Open-Top Panoramic Night Tour.
You’ll travel from the iconic Magnificent Mile down Michigan Ave, with a tour guide explaining every beautiful sight.
There’s almost nothing like watching the Buckingham Fountain’s impressive spray at night.
You’ll also see the spectacular Chicago Theatre (175 North St) lit up just like it was during its glory days, one of the more historic yet fun things to do in October in Chicago.
Explore the Downtown Area
While the city’s busiest times are spring and summer, you can still visit the historic downtown area in the fall, and fewer crowds will make for a refreshing trip.
One of the best ways to learn about the city is to follow a local around their favorite spots; the History, Culture, and Architecture Walking Tour visits parks, iconic landmarks, and statues and shares facts and stories only locals know.
This tour also includes some snacks.
Art Institute of Chicago
Want a little behind-the-scenes look at the Art Institute of Chicago (111 S Michigan Ave) without the lines and crowds?
You can enter the museum 30 minutes before it opens and take a Guided Tour Led by an Art Expert.
Check out the events schedule for seasonal sessions this autumn.
Fall in Love With Chicago’s Food Scene
Did you know that there are over 20 Michelin-starred restaurants in the city?
It is known for its amazing food and was even voted the Best Restaurant City of the Year in 2017, and its restaurants, like Alinea, continue to win awards every year.
Get a taste of Chicago in the fall with three of the best food tours in the city, exploring traditional and seasonal produce.
The Chicago Food Tour: 2.5 Hour Guided Walking Tour will allow you to sample all the classic fare while being led around the city by an expert guide.
The Taste of Chinatown Food Walking Tour will introduce you to the city’s most exciting Asian cultures and food inspirations.
Finally, the Chicago Underground Donut Tour will take you to four donut shops around the city to give you a taste of the city’s most delicious treats.
No matter which tour you choose, you can rest assured that you’ll get an authentic taste of the city’s best food.
Corn Mazes In Chicago
Jack’s Pumpkin Pop-Up (1267 W Le Moyne St) is the city’s largest.
While it is aimed at all ages, the bars serve seasonal cocktails.
Konow’s Corn Maze (16849 S Cedar Rd, Homer Glen) offers maze trails ranging from 0.4 miles to 3.4 miles, live music, and snacks.
Pumpkin Patches In Chicago
J4K Pumpkins (3539 E 95th St) runs throughout October and is a fun day out for big kids.
Along with pumpkin picking, there are inflatables for wee ones, too.
Visit Farmers’ Markets Across the City
Did you know there are 49 farmers’ markets across Chicago?
Almost all the markets go through September, and many are ongoing for most of October.
Some even go into November for all the late-fall visitors.
Stock up on fall vegetables, dried flowers and garlic, and specialty items like honey and granola.
Check out the city’s markets, such as The Lincoln Park Farmers Market; the perfect spot for a fall date day, too?
Fall Events Chicago
Pier Pumpkin Lights, Navy Pier
You won’t want to miss Pier Pumpkin Lights on Navy Pier (600 E Grand Ave), a fantastic display of Halloween spirit in the fall in Chicago.
Wander among almost 1,000 jack-o-lanterns throughout October.
Throughout the month, you’ll experience pumpkin-themed pop-ups, pier-specific deals and sales, and general Halloween-themed festivities.
Check out their website closer to October for more details!
Chicago Food Truck Fall Festival
Food trucks are a staple in the Chicago food scene.
One of the best ways to appreciate the city’s variety and abundance of food truck options is to check out the Chicago Food Truck Fall Festival (LaBagh Woods).
Every fall, the Food Truck Festival brings together all the corners of the globe to serve you classic and unique dishes straight from the trucks’ windows.
Oktoberfest
If you love German beer, food, and culture (or are curious to learn more), check out Chicago Oktoberfest (Lincoln Square)!
Oktoberfest usually occurs in mid-September, but check the website for any date changes or updates.
Submerge yourself in German culture under two hospitality tents all weekend long.
Sip on beer, taste unique food, and listen to live bands playing throughout the day and night.
Check out our guide to the best Oktoberfests in the US.
Where to See Fall Colors in Chicago
Did you know the Chicago Park District manages almost 9,000 acres of green space, making it the largest municipal park manager in the nation?
If you’re hoping to enjoy the fall colors in Chicago, you’ll be able to see them at every corner!
Plus, there is a public park in every neighborhood throughout the city, so no matter where you are, you can stroll through incredible changing leaves throughout the fall season.
Check out the Illinois Fall Color Report for a day-by-day update on the best fall colors in Chicago.
Check out our comprehensive guide for even more free things to do in Chicago!
Lincoln Park
Lincoln Park is a community area on the North Side that features the city’s largest park, Lincoln Park.
During fall, the leaves change with the skyline in the background.
It has 1,188.62 acres that can be explored on foot, and some of the park is located by the lakefront.
The park has several Chicago attractions, including the Chicago History Museum, the Peggy Notebaert Nature Museum, the Alfred Caldwell Lily Pool, and the North Pond Nature Sanctuary.
Grant Park
The famous Buckingham Fountain is located at the center of Gran Park and has enjoyed this pride of place since the 1920s.
During fall, the fountain pops against the orange trees of the park.
Garfield Park Conservatory
Visit Chicago’s “landscape art under glass” at the Garfield Park Conservatory (300 N Central Park Ave) during fall to see the trees change in one of the largest botanical conservatories in the US.
With 184 acres to explore, you can easily spend half a day here.
The park includes a swimming pool, fishing lagoon, athletic fields, and tennis courts.
Humboldt Park
Humboldt Park (1400 North Sacramento Ave) is located on the city’s west side and boasts 207 acres.
The park was named after the German naturalist and botanist Alexander von Humboldt.
It is also home to the National Museum of Puerto Rican Arts and Culture.
You can learn more about the park during this free audio tour.
Fall Activities Near Chicago
Night of 1,000 Jack-o-Lanterns, Glencoe
Ready to head out of the city to enjoy the fall weather?
The Chicago Botanical Garden (1000 Lake Cook Rd) hosts a Night of 1,000 Jack-o-Lanterns every year in October over the weekends.
Just a 20-minute drive from the city, the Garden boasts an incredible collection of 1,000 hand-carved pumpkins, some weighing up to 150 pounds!
Wander around the paved path, enjoy light fare and drinks, and greet the costumed professionals there to entertain the kids.
Check the website before you visit for updates, parking passes, and official event dates.
Apple Picking Near Chicago
Why not visit a farm near Chicago for fall activities?
Work for your food at Heinz Orchard (1050 Crest Rd, Libertyville).
This family-run orchard invites visitors to pick apple varieties, including Empire, McIntosh, and Jonathan.
Walk or Bike Along the Illinois Prairie Path, DuPage County
Prairie ecosystems are threatened by urban and suburban development, but the Illinois Prairie Path has set out to protect them and help people develop a deep appreciation for them.
One big bonus: you enjoy these incredible landscapes just a 40-minute drive west of the city.
Walk or bike through the area and enjoy the incredible fall colors while they last!
Take a Fall Camping Trip, South Holland
Some of the best, quietest camping takes place in the fall.
If you don’t mind the cooler weather and are ready to avoid the summer camping crowds, take a 40-minute drive south to South Holland to stay at Camp Shabbona Woods (15810 S Torrance Ave).
Part of the Forest Preserves of Cook County, you can enjoy protected outdoor spaces while staying in a cabin or your tent.
Enjoy the fall colors and the beauty of nature, all while staying close to Chicago.
Crabtree Nature Preserve in Illinois
Crabtree (3 Stover Rd, Barrington Hills) is a nature preserve on 112 acres of woodlands and wetlands.
It is open all year round but boasts of fall colors in autumn.
