Best Things to Do in Chicago This 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 this October and November in the city and suburbs.

Best Chicago Fall Activities

top Chicago fall activities include fall foliage
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Fall is officially here in Chicago and I am excited because it is my favorite season with 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 taking place in Chicago this 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 marks the start of Thanksgiving and Christmas holiday events and activities.

Whether you live in the Chicagoland area or are planning a visit (fall is one of the best times to visit Chicago), here are the best things to do in and around Chicago this fall.

Go Apple Picking

apple picking orchards near Chicago

You might not associate apple picking with a big city like in 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.

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. The 90 minute cruises run by Chicago Architecture Foundation (CAF) are the best but there are many different cruises and tours available.

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.

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. The undead, demons, zombies and more jump out at and rock your car accompanied by sound effects and sprays of blood. You can opt out of a vehicular blood bath or rent one of their cars which is aired out and sanitized between rides.

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 mid-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 2020 (October 16−25, 2020) 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


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IT’S REAL. • This fall the Music Box of Horrors will transform from a 24 hour movie marathon into 31 Nights of Terror at the Drive-in! From October 1st- 31st, the Music Box of Horrors will take over the Chi-Town Movies Drive for late shows and double features every night, with the Music Box’s eclectic taste of horror, specialized intros, pre-show content, filmmaker Q&As, vendors, and of course, some surprises. Every element will be presented safely & responsibly at the Drive-In setting. We’ll begin announcing films on September 3rd. • How does it work? Tickets will be $30 per car for single feature, and $40 per car for double features. Unfortunately, full 31 day passes will not be available. • What if you already bought a pass? 1) Turn your pass into one car ticket for a single or double feature. We will give you all first access to these tickets before the general public. 2) Hold onto your 2020 pass and it will be good for the 2021 marathon 3) Request a refund. We will reach out to you to provide a full refund which includes booking fees Artwork by @blow_up

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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


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