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BEST Things to Do in Chicago in October, 2022 (From a Local!)

Searching for what to do in Chicago this October? Here are the best things to do in Chicago in October 2022 (from a local).

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 plan to update it regularly with new activities and events.

Things to Do in Chicago in October 2022

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 15-16, 2022

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.

Other neighborhoods that have a high concentration of street art include Pilsen as well as West Town.

Prince: The Immersive Experience

Perfect for Prince fans and music lovers alike, Prince: The Immersive Experience, is an interactive, multisensory experience that is ending its limited-time run this month. Tour 10 immersive spaces and explore his life, revolution, and talent as you step inside the iconic Purple Rain album cover and an audiovisual dance party designed by Prince’s lighting and production designer. Explore exclusive artifacts curated by The Prince Estate and play music producer with the original sessions from one of Prince’s greatest hits in Studio A. Tickets must be purchased in advance.

When: Ends October 9, 2022

Where: 540 N. Michigan Avenue (on the Mag Mile)

Cost: General admission starts at $39.50 per person. Click here for full prices and to purchase tickets in advance.
Push Pin Travel Maps

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 October 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.

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


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.

Have a Pumpkin Patch Shake at Jojo’s Shake Bar

Pumpkin Patch Shake
Instead of a Pumpkin Spice Latte why not try a Pumpkin Patch Shake? At Jojo’s Shake Bar you can have Pumpkin Patch Shake, which is topped with a whole pumpkin pie slice, taffy apple, roasted marshmallow, and toffee pretzel.

Jojo’s Shake Bar has 2 locations in Chicago: Water Tower Place (835 N. Michigan Ave) and River North (23 W Hubbard St). They have created a pumpkin patch on their 5,000 sq ft patio in River North with over 600 pumpkins, a 1954 Red Ford truck, Hay Bales, and a bathtub filled with corn to satisfy your perfect fall photo needs.

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.

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.

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 1, 2022), Annual Glass Pumpkin Patch (October 12-16, 2022). Don’t miss Human+Nature, an outdoor art installation by renowned South African artist Daniel Popper which features large 15- to 26-foot-tall sculptures.

• 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 (October 12-16 & 19-23, 2022) with more than 1,000 hand-carved pumpkins—some as large as 150 pounds—will light up the night.

Here are more places to see fall colors in and around Chicago.

Chicago October 2022 Events

In addition to the activities mentioned above, other October 2022 events include: Lincoln Square Ravenswood Apple Fest (October 1-2, 2022), WingOut Chicago (October 1-2, 2022), Lincoln Park Wine Fest (October 7-9, 2022), Chicago Marathon (October 9, 2022), 57th Chicago International Film Festival (October 12-23, 2022), Illumination (October 29, 2022), Upside Down Halloween Parade (October 22, 2022) and Arts in the Dark Halloween Parade (October 29, 2022).

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:



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