20 Amazing Fall Activities in Chicago to Have Fun

Chicago is a great city to visit any time of the year. But if you ask us, the fall is especially the most special season for a visit. With its vibrant cultural scene, stunning natural landscape, and ample opportunities for outdoor activities, Chicago is truly an ideal destination for anyone. It’s even more attractive for those who are looking to get the most out of the season. From pumpkin picking to apple picking, to the world-famous Chicago Marathon, we really have to say that there is no shortage of amazing fall activities in the Windy City, and there’s no doubt about it.

If you’re currently looking to take in the sights and sounds of autumn in Chicago, you have to check out the city’s vibrant parks and trails. They offer plenty of opportunities for autumnal fun. There are also a number of fall festivals and events to attend to, which will showcase the city’s culture and history. If you need some recommendations on what to do and where to go in the city, and whether you’re a local or a visitor, here are some of the best ways to experience Chicago in the fall that we have gathered for you.

What is fall like in Chicago?

Fall in Chicago is generally cool and comfortable, with average temperature between 33°F – 43°F. The autumn months are known for their beautiful fall foliage, mild temperatures, and also sunny days. Moreover, the city also offers plenty of activities to take part in, such apple picking, hayrides, pumpkin carving, and visits to local farms and farmers markets.

Is Chicago good to visit in the fall?

Yes, Chicago is a great place to visit in the fall. The city is filled with vibrant colors and you can enjoy the crisp air and beautiful foliage. Plus, there are a variety of activities and attractions to explore as well, such as fun and iconic festivals like the Chicago Food Truck Fall Festival and Magnificent Mile Light Festival. If you are interested in more fall activities in Chicago, please refer to our article above.

Best Fall Activities in Chicago

1. Explore The Magnificent Mile

This fall, why don’t you take a leisurely stroll along the Magnificent Mile? It is the Chicago’s iconic stretch of Michigan Avenue. Here you can enjoy the shops, enjoy your meals at the famous restaurants, and visit the museums while taking in the stunning cityscape during fall in Chicago. Moreover, we have to remind you not to forget to take in The Magnificent Mile Light Festival, too. It is an annual celebration featuring lovely lights and a number of fun activities for the whole family. If you are in town with your family and loved ones, this is the spot that you should no miss.

2. Walk Along the Illinois Prairie Path

The Illinois Prairie Path is the best place to look for fall foliage close to Chicago. Take in the breathtaking Chicago fall months while they last by strolling through the neighborhood like a local. Urban and suburban development threatens prairie ecosystems, but the Illinois Prairie Path aims to both protect them and foster a strong respect for them. These breathtaking vistas are within a 40 minute drive west of the city for your enjoyment.

3. Attend Chicago Marathon

There are plenty of festivals in the Chicago fall. And, if you are an active and fit person, there is simply no reason you to skip the Chicago Marathon. The Chicago Marathon is part of the World Marathon Majors, which is an annual series of six of the largest and most renowned marathons in the world. No wonder why people come from all over the world to participate in the marathon.

If you don’t feel like running, you can also cheer on the runners and experience the energy, enthusiasm, and camaraderie of this iconic event. Just choose your favorite style and enjoy a day of fun and entertainment.

4. Visit Lincoln Park Zoo During Fall Fest

If you are looking for kids-friendly activities in Chicago fall, we would recommend you to visit Lincoln Park Zoo during its annual Fall Fest. This family-friendly event will offer fun fall activities for you and family. It includes a pumpkin patch and walk, live pumpkin carvers, a festive pop-up bar, animal chats, and also musical entertainment. That’s not all, because there will be a variety of animals on display. You can see small birds and reptiles to large mammals such as lions and giraffes, which will definitely excite your kids.

The Lincoln Park Zoo is a free public zoo, and the zoo’s main entrance is located at 2001 North Clark Street in Lincoln Park. The zoo is open 365 days a year from 10:00 AM to 03:00 PM.

5. Cheer on Your Favorite Sports Team

There are many excellent professional sports teams in Chicago. Depending on the season you’re visiting, a fantastic game is sure to be taking place. Fall brings football, and Soldier Field is where you can watch the Bears. Do bear in mind that the cost of tickets to Soldier Field can vary widely depending on the event.

Generally, tickets for most NFL games range from $50 to $500. Or, you might also want to catch a game at Wrigley Field or the United Center, which is the home to the Cubs and Bulls respectively. So, let’s cheer on your favorite team and enjoy an unforgettable experience!

6. Look for Chicago Street Art

Walking about Chicago in the fall and looking for street art while taking in the stunning full color is a terrific themed activity. In our opinion, you can start by visiting “Moose Bubblegum Bubble” by Jacob Watts, which is is one of Chicago’s most famous murals. Then, you can go to Millennium Park and other street art spots all within walking distance of this well-known painting, which is a part of the Wabash Arts Corridor. On this street art tour, you can see wonderful murals and other works of public art.

7. Visit The Art Institute of Chicago Museum

On a chilly day, we really think spending time inside in a museum is a terrific idea. Being one of the best fall activities in Chicago, you can take a trip to The Art Institute of Chicago. Located at 111 South Michigan Avenue in downtown Chicago, Illinois, here you can enjoy the exhibits and take in the city’s culture. The tickets are only $14 each and you can enjoy an audio tour, a museum guide, or a docent-led tour to help you learn more about the collection and its artists. 

8. Drink at Oktoberfest

Drinking is definitely something to enjoy in Chicago during the fall. If you’re looking for drinking experience and fun things to do in Chicago, make sure you stop by the iconic Oktoberfest. Located at St. Alphonsus Church in Lakeview, Chicago, the event typically takes place in late September or early October.

Spend the entire weekend immersed in German culture while enjoying beer and authentic cuisine under two hospitality tents. Moreover, you can also enjoy live music from traditional German bands. We also encourage you to make sure you take part in the Chicken Dance or other traditional activities.

9. Attend Navy Pier Pumpkin Lights

This Halloween month, you won’t miss this fall activity to experience in Chicago. Enjoy a festive autumn display of more than 1,000 carved and illuminated jack-o’-lanterns at the Navy Pier Pumpkin Lights. The event is located in the Streeterville neighborhood of the Near North Side community area in Chicago from November 25 to January 7.

The display is also accompanied by music and projections, and you can take part in various activities such as pumpkin carving, face painting, and pumpkin bowling. Moreover, you can also enjoy a variety of treats and make s’mores around the fire pits.

10. Have a Pumpkin Patch Shake at Jojo’s Shake Bar

Jojo’s Shake Bar Chicago (Source : secretchicago)

Eating is definitely one of our favorite fall activities in Chicago. Well, it’s actually one of everyone’s favorites, too. Therefore, we have to recommend you to try the famous Chicago’s fall menu, Pumpkin Patch Shake at Jojo’s Shake Bar. It is located at 23 W Hubbard St, Chicago and it opens everyday from 11:00 AM to 10:00 PM.

It has a unique flavor that combines the creamy sweetness of real pumpkin with the spicy goodness of cinnamon and nutmeg. Also, treat yourself with an additional piece of pumpkin pie, a taffy apple, a roasted marshmallow, and a toffee pretzel for toppings. 

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11. Enjoy Chicago Delicacy at Chicago Food Truck Fall Festival

The Chicago culinary scene is dominated by food trucks. Therefore, how about attending the Chicago Food Truck Fall Festival? This Chicago fall festival brings together cuisines from all over the world each year. You can go there every Friday from September to October from 11:00 AM to 3:00 PM at Daley Plaza, 50 W. Washington Street.

At the Chicago Food Truck Fall Festival, we can assure you that you will be excited to find a variety of delicious food truck options. You will find trucks that sell tacos, empanadas, hotdogs, barbecue, hamburgers, pizza, ice cream, macarons, cupcakes, and more!

12. Watch Performances at The Goodman Theatre

This fall, we believe nothing beats the excitement of live theater. The curtain is once again rising on Chicago’s vibrant theater industry, which includes everything from elegant downtown theaters to cozy neighborhood stores. For the best live theater experience, we suggest you to come to The Goodman Theatre. It is a well-known contender for Chicago’s top live theatrical venue in the fall.

Located at 170 N Dearborn St, Chicago, you can watch live performances starting from $77.00 a ticket. You can enjoy pre-broadway performances, world premieres, time-honored favorites, cutting-edge performances, and more this fall.

13. See the Leaves Changing at Lincoln Park

See The Leaves Changing at Lincoln Park

The largest park in Chicago is located in the neighborhood of Lincoln Park, which is on the North Side of the city. In the fall, you can watch the skyline change while the leaves change. Furthermore, if you are looking for Chicago outdoor activities, you can also rent a bike from the bike share and explore the Lakefront Trail. This 18 mile path will take you from Hollywood Beach to the northern part of Lincoln Park.

14. Explore Garfield Park Conservatory

Explore Garfield Park Conservatory

If you are going to spend fall in Chicago with family and friends, you can visit one of the largest botanical conservatories in the US, Chicago’s Garfield Park Conservatory.  Located at 300 N Central Park Ave, you can find this place inside the Garfield Park. Known as “landscape art under glass”, here you can witness the seasonal changes of the trees from 10:00 AM to 05:00 PM.

We can assure you that with 184 acres to explore and amenities like a tennis court, swimming pool, and fishing lagoon, you could easily spend half a day here with family and friends. In short, we think it will be a perfect fall family activity in Chicago.

15. Attend Open House Chicago

Attend Open House Chicago
Chicago Architecture Center (Source : chicago)

Every year in the fall, the Chicago Architecture Center holds Open House Chicago. It is a free public event where anybody can take a self-guided architectural tour of some of the city’s most famous structures. Personally, we think it’s one of the ideal fall events in Chicago for architecture fans! Here you can take advantage of expert discussions and programming, explore architecture and history trails, and receive extraordinary behind-the-scenes access to magnificent structures.

16. Try a Ghost Tour

Try a Ghost Tour

Discovering the local ghosts and spirits is one of the top fall things in Chicago. To expose you to the well-known ghosts and haunted structures, you’ll need a local guide. Therefore, we recommend you to try The Gangsters and Ghosts Walking Tour that will take you around Chicago’s downtown Loop District. The tour starts four times daily – at 11:00 AM, 01:00 PM, 04:00 PM, and 08.00 PM.

However, we have to remind you that since this is a premium experience and is limited to only ten guests per tour, you should pay tickets $65 each. But we’re pretty sure you won’t regret it because in this legendary tour, some of the best ghosts and gangsters from Chicago’s darkest periods of history will be revealed.

17. Stroll Through The Rosehill Cemetery

Stroll Through The Rosehill Cemetery

Visit Rosehill Cemetery and roam around the historic grounds of the biggest cemetery in Chicago for the most eerie Chicago fall activity. Located at 5800 N Ravenswood Ave, Chicago, Rosehill is renowned for its magnificent architecture, elaborate marble monuments, and also the rolling hills. This location is so significant and has such a sordid past that you must go there in the fall. Also, don’t forget to share your experience on social media!

18. Take a Fall Camping Trip at South Holland

Take a Fall Camping Trip at South Holland

Camping in the fall is definitely one of the best and most peaceful activities to do in Chicago. In order to do that, take a 40 minute trip south to South Holland to stay at Camp Shabbona Woods, especially if you don’t mind the cooler weather. You can stay in a cabin or your own tent while enjoying safe outdoor areas that are a part of the Forest Preserves of Cook County. Don’t forget to visit the local pumpkin patches and take a hayride to pick out your own pumpkin during fall season in Chicago.

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19. Apple Picking Near Chicago

Apple Picking Near Chicago

Suppose you are looking for fall activity for kids in Chicago, why not visit a nearby farm for apple picking? The best place for apple picking in Chicago is at Heinz Orchard. Located at 1050 Crest Rd, Libertyville,  you can pick your favorite apple everyday from 09:00 AM – 05:00 PM. Here, you and your little ones are welcome to pick apple varieties like Empire, McIntosh, and Jonathan at this family-run orchard. Plus, it is also located in beautiful rural areas, so take some time to explore the area and enjoy the beautiful scenery.  

20. Bird Watching at Crabtree Nature Preserve

Bird Watching at Crabtree Nature Preserve

Take your little ones to Crabtree Nature Preserve and enjoy fall activity for Chicago’s kids there! Located at 3 Stover Rd, Barrington, the preserve is home to a variety of birds, including cardinals, blue jays, and woodpeckers. Ask your kids to take a pair of binoculars and set out to spot some of these feathered friends. After bird watching, you can also find the perfect spot to enjoy the fall foliage while enjoying your lunch. 

Final Thoughts

Chicago is a city full of wonderful fall activities that provide plenty of opportunities to enjoy the season. From festivals and farmers markets to pumpkin patches and haunted houses, there is something for everyone to do and experience. Whether you’re looking for some outdoor fun or a cozy night in, Chicago has plenty to offer during the fall months. So don’t miss out on all the fun and excitement of the fall season in Chicago!

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FAQ (Frequently Asked Questions)

The most popular fall activity in Chicago is enjoying the changing colors of the leaves in the city’s many parks and outdoor spaces. Other popular activities include attending the numerous fall festivals, walking along the Chicago Lakefront Trail, visiting the city’s farmers markets, and exploring the city’s many neighborhoods. For more fall activities in Chicago you can do, please read the article above.

How is Chicago in October?

Chicago in October is usually mild, with temperatures ranging from 40°F – 50°F. It’s a great time to explore the city, as the fall foliage adds beautiful colors and the crisp autumn air adds a cozy ambiance. Rain is also common in October, so be sure to bring an umbrella! Suppose you are looking for fall activities in Chicago, you can check our top ideas above.

The most popular fall activity in Chicago is attending the various fall festivals that take place throughout the city. From the Chicago Gourmet and the Chicago Marathon, there are a variety of festivals to attend. Additionally, many people enjoy taking advantage of the beautiful fall weather and scenery with outdoor activities. Many enjoy apple picking, hayrides, and hikes in the area. 

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