Searching for what to do in Chicago this October? Here are the best things to do in Chicago in October 2025 (from a local) – from the best October events and festivals to fun fall and Halloween themed activities.
Chicago in October
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October is a great month to visit Chicago. Temperatures are typically pleasant but popular attractions are less crowded than they are in the summer. October also brings beautiful fall foliage as well as new fall and Halloween themed activities like visiting pumpkin patches and corn mazes.
For out of town visitors, please note that the weather in Chicago in October is very unpredictable and temperatures can vary greatly. Be prepared for fall, winter, or summer like temperatures (sometimes all in one day!) as well as rain. Make sure to pack a travel umbrella, layers and check the weather right before your visit to know what to expect.
I suggest bookmarking this blog post as I will be updating it regularly with new events and activities.
Best Things to Do in Chicago in October 2025
Take an Architecture Cruise
Taking an architecture river cruise is a must when visiting Chicago. While you can go on an architecture cruise most of the year (except when the water is frozen in the winter), they tend to be less crowded and the weather tends to be more pleasant in October. If the temperature is still warm, you might enjoy a combination river and lake cruise.
Look for Street Art
October is a great month to walk around Chicago looking for street art while also enjoying fall 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.
Have Fun at Navy Pier
A ride on the large Ferris wheel offers paranoramic skyline views of Chicago and is another great way to see the 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. Navy Pier is 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 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 is a great time 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
Take a Haunted History or 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.
This haunted segway tour and Halloween bike tour are only offered in October.
Lincoln Park Zoo is also offering haunted history tours on Tuesdays and Wednesday evenings in October that dig into the zoo’s cemetery roots and locations throughout its allegedly haunted history.
This ghosts and gangsters tour is available year round and also covers Chicago’s history of organized crime.
Hang Out on the 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. October is a great month to visit the Riverwalk as it is less crowded than during the summer.
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.
Island Party Hut, a bar and grill on the Riverwalk, will be hosting its annual Fall Fest on the Riverwalk every Saturday in October with live music, hayrides on the river, pumpkin patch, fall cocktails & beer, apple cider donuts and other fall themed fun.
See the Water Displays at Buckingham Fountain
Buckingham Fountain, a well known Chicago landmark in the center of Grant Park, is one of the largest fountains in the world. The water will be turned off for the season in October (depending on weather) and will not be turned back on until next May. When the water is turned on, it produces a major water display for 20 minutes every hour with a center jet shoots water to a height of 150 feet into the air. Beginning at dusk, a spectacular light and music display accompanies the major water display.
Visit a Pumpkin Patch
Looking for a fun fall themed activity? There are many pumpkin patches you can visit in Chicago and the suburbs in 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.
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.
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 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.
Admire Fall Colors
There are many places in and near Chicago to admire the beautiful autumn leaves. The peak time for the best fall colors in Chicago is usually mid October to late 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”), 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. Some of the best spots 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 including the Cider and Ale Festival (October 4, 2025), Annual Glass Pumpkin Patch (October 10-12, 2025) and Fall Color 5K Run and Walk (October 25, 2025).
• 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 popular Night of 1,000 Jack-o’-Lanterns with more than 1,000 hand-carved pumpkins—some as large as 150 pounds—will light up the night. Tickets sell out quickly.
Chicago October 2025 Events
Open House Chicago
Every October, the Chicago Architecture Center hosts Open House Chicago, a free, two-day public festival that offers behind-the-scenes access to architecturally, historically and culturally significant sites across the city.
When: October 18-19, 2025
Cost: Free
Lincoln Park Zoo 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.
When: Fridays–Sundays in October
Address: 2400 N. Cannon Drive
Cost: Admission to the zoo is FREE but some fall fest attractions are paid.
More Chicago October 2025 Events
In addition to the activities mentioned above, other October 2025 events include: World Music Festival (September 26–October 5, 2025), Lincoln Park Wine Fest (October 3-5, 2025), West Town Art Walk (October 3-5, 2025), Lincoln Square Ravenswood Apple Fest (October 4-5, 2025), Modern Vintage Chicago Fashion & Home (Ravenswood) (October 5, 2025), Chicago Marathon (October 12, 2025), Chicago Fashion Week (October 9-19, 2025), Chicago Artisan Market (October 19, 2025), 61st Chicago International Film Festival (October 15-26, 2025), Sauced Night Market at Half Acre Beer Co. (October 17-18, 2025), Rosehill Cemetery ‘Crypt’ 5K Run/Walk (October 18, 2025), Arts in the Dark Halloween Parade (October 18, 2025) and Haunted Halsted Halloween Parade & Costume Contest (October 31, 2025).
For more October events, bookmark this post about the best weekend events which is updated every week.
As you can see there are many things to do in Chicago in October.
Planning a trip to Chicago? Check out my Chicago guides and itineraries:
