BEST Things to Do in Chicago in October 2024 (From a Local!)

Searching for what to do in Chicago this October? Here are the best things to do in Chicago in October 2024 (from a local) – from the best October 2024 events and festivals to fun fall-themed activities to the top attractions.

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.

Things to Do in Chicago in October 2024

fall foliage is one of the best things to do in Chicago in October

Disclosure: This article contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you. As an Amazon Associate I earn from qualifying purchases.

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.

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 19-20, 2024

Cost: Free

Look for Street Art

Moose Bubblegum Bubble by Jacob Watts one of the most famous street art murals in Chicago

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

outdoor rides at Navy Pier Chicago

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).

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 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.

This ghosts and gangsters tour is available year round and also covers Chicago’s history of organized crime.

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.

Some of the best farmers markets in Chicago include the Green City Market, the Logan Square Farmers Market and the Wicker Park Farmers Market.

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.

When: Fridays–Sundays in October

Address: 2400 N. Cannon Drive

Cost: Admission to the zoo is FREE but some fall fest attractions are paid.

Visit a Pumpkin Patch

pumpkin patch by Chicago

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. Most corn mazes open sometime in September and stay open 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.

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 every Friday on their website. The arboretum hosts fall events including the Fall Color 5K Run and Walk (October 5, 2024) and the Annual Glass Pumpkin Patch (October 11-13, 2024).

• 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.

Chicago October 2024 Events

In addition to the activities mentioned above, other October 2024 events include: St. Benedict’s OktoberFest (October 4-6, 2024), Lincoln Park Wine Fest (October 4-6, 2024),
Lincoln Square Ravenswood Apple Fest (October 5-6, 2024), Chicago Marathon (October 13, 2024), Chicago Artisan Market (October 13, 2024), 57th Chicago International Film Festival (October 16-27, 2024), Arts in the Dark Halloween Parade (October 19, 2024), Rosehill Cemetery ‘Crypt’ 5K Run/Walk (October 19, 2024) and Haunted Halsted Halloween Parade & Costume Contest (October 31, 2024).

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:



Leave a Reply

Your email address will not be published. Required fields are marked *

CommentLuv badge

This site uses Akismet to reduce spam. Learn how your comment data is processed.