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Best Things to Do in Chicago in Fall 2021 (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 late September, 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 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. You can also do a combination river and lake cruise. 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.

 

Look for Street Art

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

Fall is a great time to walk around Chicago looking for street art while also enjoying the beautiful full 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.

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 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 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 the Pier Pumpkin Lights at Navy Pier

Navy Pier can be somewhat of a tourist trap but it is a must do if you are visiting Chicago with toddlers or kids. Fun attractions include a large Ferris wheel (click here to purchase a fast pass ticket and skip the long line), rides and games, restaurants, shops and the Chicago Children’s Museum.

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 also the starting point for many boat rides and lake cruises.

 

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”) in 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 and activities including the Fall Color 5K Run and Walk (October 2, 2021), Annual Glass Pumpkin Patch (October 13 -17, 2021) and Cider and Ale Festival (October 23, 2021). Don’t miss Human+Nature, an outdoor art installation by renowned South African artist Daniel Popper which features five 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. 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.

Experience the Immersive Van Gogh Exhibit

From the creators of the blockbuster show at Atelier des Lumières seen by over 2 million visitors in Paris and Toronto and featured in Emily in Paris (one of my favorite travel shows on Netflix), the Immersive Van Gogh Exhibit, is a massive indoor digital presentation of Vincent Van Gogh’s artwork. Tickets must be purchased online in advance and they are selling quickly! There are also yoga sessions which include a 35 minute Yoga class + 45 minutes thereafter to enjoy the exhibit. The Exhibit is ending this fall so this is the last opportunity to see the show in Chicago.

When: Ends November 28, 2021

Where: Lighthouse ArtSpace at Germania Place, 108 W. Germania Pl, Chicago, IL

Cost:  Tickets start at $39.99 plus fees for off peak times. See https://www.vangoghchicago.com/ for full prices and to purchase tickets in advance.

Immerse Yourself in The Office Experience

The Office Experience pop-up opens October 15 in Chicago for a three month run. Visit Schrute Farms, walk through the Dunder Mifflin set, and relive Jim and Pam’s iconic romance. The world of The Office will come to life with iconic set recreations, original show costumes and props, and opportunities for fans to engage with the show in new ways. Timed tickets are now on sale online.

When: Opens October 15, 2021

Where: 540 N Michigan Ave on the Mag Mile.

Cost: General admission is $37.50 plus taxes + fees for off-peak times or $45 plus taxes and fees for peak times. Children 3 and younger are free. Groups can also purchase private access tickets or book the space for a private party.

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.

Two of the best farmers markets in Chicago include the Green City Market in Lincoln Park and the Logan Square Farmers Market.

You can see the list and schedule of all Chicago farmers markets here.

Visit Lincoln Park Zoo During Fall Fest

The fall season is one of the most beautiful times to visit Lincoln Park Zoo. During select days in October, enjoy fall activities during Lincoln Park Zoo’s annual Fall Fest. During this free, family-friendly celebration, enjoy a pumpkin walk, live pumpkin carvers, a festive pop-up bar, animal chats, musical entertainment and more!

Where: 2400 N. Cannon Drive

When: The zoo is open every day from 10 a.m.–5 p.m. Fall Fest is on Fridays–Sundays from October 8–October 31 and Monday October 11. Select Fall Fest attractions will remain open during the week.

Cost: FREE. There are also paid experiences including AT&T Endangered Species carousel rides, Lionel Train Adventure rides, pumpkin walk, pumpkin patch, caricatures & face painting, caramel apple & S’mores station and a festive pop-up bar.

Best Chicago Fall Events 2021

Open House Chicago

The Chicago Architecture Center hosts Open House Chicago – a free event which gives you behind-the-scenes access into hundreds of buildings across Chicago every year in October (October 16-17, 2021). 

Adults Night Out: Lincoln Park Zoo

Adults Night Out: The Great Pumpkin Glow (October 28, 2021) is a unique adults only after-hours experience at the Lincoln Park Zoo takes that takes place annually right before Halloween. 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.

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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Patti

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