The best things to do in Chicago in the fall 2026. From fall foliage and fun fall-themed activities and events, these are the top things to do in late September, October and November in the city and suburbs.
I suggest bookmarking this blog post as I will be updating it regularly with new events and activities.
Chicago in the Fall
Fall is my favorite season and one of the best times to visit Chicago. It has the best weather (not too hot or too cold) which makes it a perfect time to be outdoors.
There are many fun activities and events that take place in Chicago in the fall. September brings the start of unique fall activities like apple picking, visiting pumpkin patches and corn mazes. October brings beautiful fall colors and fun Halloween themed activities, while November brings the start of Christmas holiday events and activities and Thanksgiving.
Best Chicago Fall Activities in 2026
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Whether you live in the Chicagoland area or are planning a visit, here are the best things to do in and around Chicago in the fall including the best Chicago fall 2026 events.
Take an Architecture Cruise
Taking an architecture river cruise is a must when visiting Chicago. Fall is the best season for a river cruise as they tend to be less crowded and the weather tends to be more pleasant.
Take a Lake Cruise
Early fall is your last chance for a lake cruise before it gets too cold and lake cruises stop running (usually end of October). While you don’t get to see the buildings up close like on a architecture river cruise, you do get to enjoy skyline views. Lake cruises depart from Navy Pier or the Michigan Avenue bridge.
If your time is short, consider a combination river and lake cruise.
Tip: It is breezy and much colder on water than on land (especially in the evening) so bring a scarf and sweater even if the weather is warm.
Take a Ghost Tour
Explore Chicago while learning about its haunted past and visiting the sites of some of the most gruesome disasters and murders in Chicago’s history.
If you enjoy guided tours, this haunted history walking tour is a fun fall themed tour.
This ghosts and gangsters tour is available year round and also covers Chicago’s history of organized crime.
Drunk Dracula
Step into a darkly enchanting adult-only adventure at Drunk Dracula where laughter, tipsy thrills, and the legend of Dracula collide. Each 90-minute session invites you to sip, shiver, and revel in the mischievous antics of a vampire gone delightfully rogue. Mingle with fellow thrill-seekers in a mysterious, adult-only setting. Must be 21+ with valid ID.
When: September 17 – November 7, 2026
Where: 182 North Wabash Avenue, Chicago, IL 60601
Cost: Prices start at $29 per person. Click here to purchase tickets.
Enjoy the Views from 360 CHICAGO Observation Deck
360 CHICAGO, the observatory on the 94th floor of the former John Hancock Building, has one of the best views of the Chicago skyline and Lake Michigan. October and November are great months to visit as you can see fall colors from above.
(Click here to buy a skip the line ticket).
Where: 875 North Michigan Avenue, 94th floor, Chicago, IL 60611
Enjoy the Views from the Ferris Wheel at Navy Pier
A ride on the large Ferris wheel offers paranoramic skyline views of Chicago and is a great way to see fall colors from above. (Click here to purchase a fast pass ticket and skip the long line).
Check out the new Flyover Chicago, an immersive flyover experience.
Other fun attractions at Navy Pier include rides and games, restaurants, shops and the Chicago Children’s Museum making it a must do if you are visiting Chicago with toddlers or kids. Navy Pier is also the starting point for many boat rides and lake cruises.
Enjoy the Views From the Chicago Riverwalk
The Chicago Riverwalk is one of the best spots in Chicago for people watching and there are also restaurants, bars, shops and places to sit along the way. Fall is a great time to relax at the Riverwalk as it is less crowded than the summer and you can also enjoy the fall colors.
Where: Along the south bank of the Chicago River in downtown Chicago from Lake Michigan to west of Franklin Street. You can see a map here.
Hours: Open daily from 6 a.m. to 11 p.m.
Watch Digital Art at Art on theMart
Looking for a unique thing to do at night? Check out Art on theMART, the largest permanent digital art projection in the world, projecting contemporary artwork across the 2.5-acre river-façade of theMART. Spectators can watch the show from the jetty section of the Chicago Riverwalk on Wacker Drive between Wells Street and Franklin Street.
When: Free 30-minute program of projections will be shown from Thursday to Sunday.
Look for Street Art
Fall is a great time to walk around Chicago looking for street art while also enjoying the beautiful full colors.
One of the most well known Chicago murals is “Moose Bubblegum Bubble” by Jacob Watts which located at 33 E. Congress (South Wall). This famous mural is part of the Wabash Arts Corridor and is walking distance to Millennium Park, The Art Institute of Chicago and other tourist attractions.
Another famous mural is the Greetings From Chicago Mural at 2226 N Milwaukee Ave. You can see this mural and other street art on this street art tour.
Visit Lincoln Park Zoo During Fall Fest
Visit Lincoln Park Zoo during its annual Fall Fest. This family-friendly celebration will offer free fun fall activities including a pumpkin patch, professional pumpkin carvers, free musical entertainment, story times and more. Every weekend will offer something new.
Address: 2400 N. Cannon Drive
Cost: Admission to the zoo is FREE but some fall fest attractions are paid.
Enjoy Fall Foliage
There are many places in and near Chicago to admire the beautiful autumn leaves. The peak time for the best fall foliage in Chicago is usually mid October. For exact dates, this weekly fall color report keeps track of fall foliage times across Illinois and this fall foliage map by weather.com shows the progress of fall foliage in all of the United States.
You can see fall colors at some of Chicago’s most popular attractions including Cloud Gate (aka “The Bean”) in Millennium Park, Lurie Garden, Chicago Riverwalk and Lincoln Park.
If you are willing to leave the city, you can find even more spectacular fall foliage in the suburbs of Chicago. Some of the best spots to see fall colors in the suburbs include:
• Morton Arboretum (in Lisle about 26 miles west of downtown) is home to more than 4,000 different types of trees among 1,700 acres. They publish a weekly fall color report on their website. The arboretum hosts fall events and activities including the Cider and Ale Festival, Annual Glass Pumpkin Patch and Fall Color 5K Run and Walk.
• The Chicago Botanic Garden (in suburban Glencoe about 24 miles north of downtown) is one of the world’s great living museums and conservation science centers with 27 gardens and four natural areas, situated on 385 acres on and around nine islands, with six miles of lake shoreline. Their website has a recommended fall color-tree walk for the best viewing. Every October, they host the Night of 1,000 Pumpkins which is very popular event. Tickets are now on sale and sell out quickly.
Visit Local Farmers Markets
You can find many farmers markets around Chicago until the end of October. These markets are a great place to buy healthy farm-fresh foods from local farms.
Two of the best farmers markets in Chicago include the Green City Market in Lincoln Park and the Logan Square Farmers Market.
You can see the list and schedule of all Chicago farmers markets here.
Visit a Pumpkin Patch
Looking for a fun fall themed activity? There are many pumpkin patches you can visit in Chicago and the suburbs.
Pumpkin patches usually open to the public sometime in September and stay open until the end of October. Here is a list of the best pumpkin patches in and near Chicago.
Get Lost in a Corn Maze
There are many corn mazes in the Chicago area – from large intricate mazes perfect for adults and older children to small kid-friendly corn mazes. Most mazes open sometime in September until the end of October.
Richardson Adventure Farm located in Spring Grove, Illinois (about an hour north of the city) claims to be world’s largest most intricate corn maze. Here are more corn mazes near Chicago to visit this fall.
Go Apple Picking
You might not associate apple picking with a big city like Chicago, but there are many apple orchards located nearby. The closest apple orchards are located in the Chicago suburbs about an hour or less from downtown.
Some apple orchards are small and only offer apple picking for an affordable price while other farms offer fresh apple cider donuts and kid friendly attractions and activities like pumpkin patches, corn mazes, kid farms, animals, playgrounds and more.
Apple picking season starts mid to late August and lasts until mid to end of October but different types of apples are available for picking throughout the season. Here is a list of apple orchards near Chicago for apple picking with locations, dates, hours, prices and all the information you need to plan your visit.
Best Chicago Fall 2026 Events
Open House Chicago
The Chicago Architecture Center hosts Open House Chicago – a free event which gives you behind-the-scenes access into hundreds of buildings across Chicago every year in October.
Lincoln Square Ravenswood Apple Fest
Usher in the fall with the Lincoln Square Ravenswood Chamber of Commerce’s Annual Apple Fest. Apple Fest is a long standing tradition in Lincoln Square, bringing the neighborhood together to celebrate the beginning of autumn. Enjoy on ciders and apple inspired dishes and stock up on your fall essentials from local vendors while listening to local musicians.
More Chicago Fall 2026 Events
In addition to the activities mentioned above, other Chicago fall 2026 events include: Chicago Gourmet (September 24-27, 2026), Oktoberfest at St. Alphonsus (September 25-27, 2026), Hyde Park Jazz Festival (September 26-27, 2026), World Music Festival (late September/early October), Lincoln Park Wine Fest (October 9-11, 2026), Bank of America Chicago Marathon (October 11, 2026), Chicago Fashion Week (TBD), Arts in the Dark Halloween Parade (TBD), Upside Down Parade (TBD), Carrera de los Muertos® / Race of the Dead (October 31, 2026) and Haunted Halsted Halloween Parade & Costume Contest (October 31, 2026).
These are some of the best things to do in Chicago during the fall.
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