BEST Things to Do in Chicago in October 2023 (From a Local!)

Searching for what to do in Chicago this October? Here are the best things to do in Chicago in October 2023 (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 2023

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 14-15, 2023

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.

Enjoy the Pier Pumpkin Lights at Navy Pier

outdoor rides at Navy Pier Chicago
During the entire month of October, Navy Pier will transform into an insta-worthy fall spectacle with nearly 1,000 pumpkins. There will be a variety of pumpkin pop-up installations and other Halloween festivities throughout the month as well as pier-wide deals.

Navy Pier is a must do if you are visiting Chicago with toddlers or kids. Fun attractions include 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.

Push Pin Travel Maps

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 the Museum of Ice Cream

Museum of Ice Cream is one of Chicago’s newest attractions. 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.

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.

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.

Watch Halloween Themed Movies on a Rooftop

Watch classic movies against the backdrop of the Chicago skyline with Rooftop Cinema Club, an outdoor screening series on a rooftop located on the fifth floor terrace of The Emily Hotel (311 N Morgan St) in Fulton Market. Rooftop Cinema Club is a high end movie experience complete with tropical decor, lawn games, state-of-the-art LED screens, individual wireless headphones and a range of seating options including lounge chairs and loveseats. Guests can also order drinks and snacks. During the month of October, Rooftop Cinema Club will be showing classic horror movies and other Halloween themed movies. You can purchase tickets in advance here.

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, Annual Glass Pumpkin Patch. 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 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 2023 Events

In addition to the activities mentioned above, other October 2023 events include: Lincoln Square Ravenswood Apple Fest (October 1, 2023), Lincoln Park Wine Fest (October 6-8, 2023), Chicago Marathon (October 8, 2023), 57th Chicago International Film Festival (October 11-22, 2023), Chicago Artisan Market Ravenswood (October 15, 2023), Rosehill Cemetery ‘Crypt’ 5K Run/Walk (October 21, 2023), Chicago Artisan Market (October 15, 2023) and Haunted Halsted Halloween Parade & Costume Contest (October 31, 2023).

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.