If you’re a Windy City local or planning an upcoming trip to Chicago, IL, this city offers a variety of Fall activities for you and your loved ones to enjoy. Whether you’re looking for a family adventure or want somewhere to relax with your friends, check out our list of recommendations to find something fun to do. Here’s a list of ways to have “Fall fun” next time you’re in Chicago:

Check Out Live Theatre

If you’re looking for entertainment, explore Chicago’s live theatre scene, which includes a variety of intimate performances and several downtown venues. Here you’ll find several pre-Broadway shows, new takes on classic favorites, and even world premieres. With new plays and musicals premiering all the time, make sure to check out upcoming performing arts events to review your options and enjoy live theatre this Fall. 

Go for a Stroll To Admire the Fall Colors

One advantage of visiting Chicago in the Fall is the opportunity to admire the beautiful Fall colors. You can meander through one of the city’s many historic neighborhoods or walk through a lakefront park to take a look at the Fall foliage. 

Consider visiting the stunning Garden of the Phoenix in Jackson Park or stop by the well-known Lincoln Park to check out the areas near the North and South ponds. With the temperatures typically ranging in the 60s and 70s in Chicago during the Fall, the weather should allow you to stay cool and comfortable while you take in the natural beauty of the city.

Visit a Food Festival 

If you and your loved ones want to grab a bite in the Windy City, make sure to visit one of Chicago’s many Fall food festivals. Whether you’re a self-proclaimed foodie or just want to check out some of the local cuisines, this season offers visitors and locals a variety of exciting food and drink options sure to satisfy any appetite. 

The city’s Eataly offers a Harvest Wine and Cheese Festa where you can sample Italian dishes and beverages. Or you can enjoy a beer in a beautiful historic environment when you visit the Lincoln Park Zoo for its Craft Brews event. For a variety of exciting food and drink, Chicago Gourmet offers a burger competition, a German beer festival, and a taco and tequila tasting booth. 

Stop by a Film Festival or Drive-In

If you’re a movie-lover, you’ll love the drive-in movies and film festivals that Chicago has to offer. Drive-in movies are a popular option for families, couples, and groups of friends. It’s a fun way to spend the evening and take advantage of the beautiful Fall weather. If you’re there in October, you can visit North America’s longest-running competitive film festival, the Chicago International Film Festival. Stop by the Asian Pop-Up Cinema for a variety of drive-in movies and other screenings, or discover the Music Box of Horrors for 24-hour screenings of new and classic horror flicks. 

Go to an Apple Orchard

If you want to spend time outdoors to enjoy Chicago in the Fall, don’t miss out on apple picking in one of the area’s several orchards. While there aren’t many options directly in the city, there are a variety of orchards a short drive outside of Chicago. Depending on where you are, you can visit Heinz Orchard in Libertyville, All Seasons Apple Orchard in Woodstock, or Jonamac Orchard in Malta. Stop by these orchards to take advantage of the selection of Gala, Honeycrisp, Fuji, and other apple varieties. 

Take In the Local Architecture 

Besides its natural beauty, Chicago is also home to stunning historical architecture. It hosts the most prominent architecture and design exhibition every other year in North America, the Chicago Architecture Biennial, which begins in the Fall and features architectural designs from around the world. You can also visit Open House Chicago, which takes place every October and highlights sites across the city that contain cultural, historical, and architectural significance. 

This event gives you access to exclusive locations, including members-only clubs, eye-catching skyscrapers, and private residences. Whether you’re a visitor or a lifelong Chicago resident, this is an excellent opportunity to learn about local and global architecture and history. 

Get Spooked by a Haunted Tour

Will you be visiting around Halloween and looking for something spooky to do? By all means, you should visit one of the city’s haunted tours. You and your loved ones can explore the creepier aspects of Chicago and learn about dark times in the Windy City’s past, including the sinking of the SS Eastland and the Great Chicago Fire. 

Sign up for the Chicago Ghost Tour offered by Free Tours by Foot and see if there are spirits in the area for yourself. If you’re a local looking for a fun night out or visiting with a group of adults, you can also check out Chicago’s Paranormal Pub Crawl to enjoy the local bar scene while touring the city’s “haunted” destinations. 

Go to a Pumpkin Patch

If you’re searching for a more family-friendly Halloween activity, consider visiting one of the city’s pumpkin patches. Whether you’re looking for a photo op, the perfect pumpkin for a jack-o-lantern, or ingredients for a pie, this is a fun way to spend quality time and relax with your friends and family. Many pumpkin patches also offer other fall-themed activities, perfect for an afternoon or entire day with your loved ones. Plan a visit to Bengston’s Pumpkin Farm in Homer Glen, Goebbert’s Pumpkin Patch in Pingree Grove, or Sonny Acres Farm in West Chicago.

Well, there you have it. American Auto Insurance just shared our favorite fun Fall activities in Chicago. The next time you’re in the Windy City, be sure to check out these entertaining activities and let us know what you think. Drop us a line if we missed one of your favorite spots, and we’ll be happy to update our list to make sure more locals and visitors get the chance to visit the best places this city has to offer. 


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chicago, things to do


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