The best things to do in Chicago in the fall 2023 with family, friends or romantic date ideas. From pumpkin patches and apple picking to fall foliage and fun activities and events, there is something for both adults and families with kids to do in late September, October and November in the city and suburbs.
I suggest bookmarking this blog post as I plan to update it regularly with new events.
Best Chicago Fall Activities in 2023
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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.
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.
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 during winter), they tend to be less crowded and the weather tends to be more pleasant in the fall.
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. Just a warning it is much colder on water than on land especially in the evening.
If your time is short, consider a combination river and lake cruise.
Lake cruises depart from Navy Pier or the Michigan Avenue bridge.
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
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.
Have Fun at Navy Pier
Navy Pier is a must do if you are visiting Chicago with toddlers or kids. Fun attractions include restaurants, shops, the Chicago Children’s Museum, rides and games and a large Ferris wheel (click here to purchase a fast pass ticket and skip the long line).
Navy Pier is also the starting point for many boat rides and lake cruises.
Visit Lincoln Park Zoo During Fall Fest
Visit Lincoln Park Zoo during its annual Fall Fest. This family-friendly celebration will offer fun fall activities including a pumpkin patch and walk, live pumpkin carvers, a festive pop-up bar, animal chats, musical entertainment and more!
Address: 2400 N. Cannon Drive
Cost: Admission to the zoo is FREE but some fall fest attractions are paid.
Attend a Candlelight Concert
Chicago’s Candlelight Concerts is a series of special classical music concerts that take place in beautiful venues bathed in candlelight. Some of the concerts taking place this fall include:
Candlelight: A Tribute to Taylor Swift
Candlelight: A Haunted Evening of Halloween Classics
You can find the full list of candlelight concerts in Chicago here.
Visit the new Museum of Ice Cream
Museum of Ice Cream is Chicago’s newest attraction. Step into an ice cream wonderland that is bound to ignite your senses through a theatrical experience with unlimited ice cream treats as you journey through 14 installations. Ride on the pink Sprink-L line, put your golf skills to the test on the Putt-Putt course, or take a dip in a pool filled with millions of sprinkles. They are spookifying their menu for the entire month of October and offering fall and Halloween themed treats from pumpkin soft serve to haunted cotton candy and more.
Where: Tribune Tower, 435 North Michigan Ave, Chicago, IL 60611
Cost: You can see full prices and purchase tickets in advance 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.
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 every Friday on their website. The arboretum hosts fall events and activities including the Fall Color 5K Run and Walk (October 7, 2023), Annual Glass Pumpkin Patch, Cider and Ale Festival and the Scarecrow Trail.
• 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. Every October, they host the Night of 1,000 Pumpkins (which is very popular and sells out quickly!). Their website has a recommended fall color-tree walk for the best viewing.
Here are more places to see fall colors in and around Chicago.
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.
Best Chicago Fall 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. They will have virtual events all month but in-person site visits will take place on October 14-15, 2023. More information will be available soon.
Lincoln Square Ravenswood Apple Fest
Usher in the fall with the Lincoln Square Ravenswood Chamber of Commerce’s Annual Apple Fest (September 30 -October 1, 2023). 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 2023 Events
In addition to the activities mentioned above, other Chicago fall themed events in 2023 include: West Loop Bavarian Block Party (September 16-17, 2023), Chicago Gourmet (September 21-24, 2023), Oktoberfest St. Alphonsus (September 22-24, 2023), Hyde Park Jazz Festival (September 23-24, 2023), Lincoln Park Wine Fest (October 6-8, 2023), Chicago Marathon (October 8, 2023), 57th Chicago International Film Festival (October 11-22, 2023) and Arts in the Dark Halloween Parade (October 21, 2023).
These are some of the best things to do in Chicago during the fall.
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