Best Things to Do in Chicago in the Fall (From A Local!)

The best things to do in Chicago in the fall 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 September, October and November in the city and suburbs.

Best Chicago Fall Activities

top Chicago fall activities include fall foliage
Disclaimer: 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.

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.

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.

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 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

apple picking orchards near Chicago

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”), 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 and publishes a weekly fall color report. The arboretum hosts fall events including a Fall Color 5K Run and Walk (October 3-4, 2020) and the Fall Color Festival.

• 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 popular Night of 1,000 Pumpkins.  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 a Drive-Thru Haunted House

There are a couple of new drive-thru haunted houses in the Chicago area this October for those that want to be scared from the safety of your car:

Alley of Darkness is a new drive-thru haunted house experience by Replay in Lincoln Park.

Highway of Horror! Haunted Halloween Drive In Experience is a similar 90 minute haunted drive-thru experience in the West Loop.

Terror in the Timbers is a haunted drive-thru experience in Elgin, Illinois. Click here to purchase tickets online in advance.

Best Chicago Fall Events

Open House Chicago

Every year in October, The Chicago Architecture Center hosts Open House Chicago – a free event which gives you behind-the-scenes access into hundreds of buildings across Chicago.  This year all Open House Chicago activities will be offered online or outdoors.

Adults Night Out: Lincoln Park Zoo

Adults Night Out: The Great Pumpkin Glow (October 29, 2020) is a unique adults only after-hours experience at the Lincoln Park Zoo.  This your chance to explore the zoo after the gates close while also enjoying seasonal activities such as a pumpkin walk, a haunted trail, themed food, and seasonal cocktails. This is the perfect event for a fall date.

Watch Horror Movies at a Drive In Theatre

You can watch halloween classic horror movies at a drive-in theatre the entire month of October. Music Box Theatre, Chicago’s 90-year-old independent cinema, will be overtaking the Chi-Town Movies Drive-In with a 31 Nights of Terror drive-in series for late shows and double features every night in October.  Visit their website to see their movie lineup and to buy tickets.

These are some of the best things to do in Chicago during the fall. I suggest bookmarking this post as I plan to update it with any new fun fall activities and events I find.

Visiting Chicago for the first time? Check out my Chicago travel guides:

Best Things to Do in Chicago in the Fall


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.