Located in Illinois, right on the edge of Lake Michigan, Chicago is one of the biggest cities in the United States. It’s also the birthplace of the skyscraper, and home to many incredible outdoor activities. Chicago is a city that is ready and waiting to be explored, so, if you’re feeling adventurous, why not head to the Windy City and see what it has to offer?

We’ve gathered our top recommendations for outdoor activities that you can try out in Chicago, to kick-start your travel inspiration. Now, the only tricky part is deciding what to do first, and how much you can fit into one day! Are you ready? Let’s begin.

1. Run the Lakefront Trail

Running is popular in Chicago, and there are some trails in the city which make for exceptional running destinations. One of our top picks of spots for outdoor activities in Chicago is the Lakefront Trail.

 Lakefront Trail

 The trail spans 18 miles, so it’s ideal for those looking for a long run or bike ride. It takes you right from Kathy Osterman Beach in Lincoln Park to the South Shore Cultural Center. This is a great choice for visitors to the city too, as you’ll pass by a few famous attractions on your way. The trail is regularly used by those training for the Chicago Marathon, and if you’re serious about your running, it’s an obligatory place to go.


2. Go Urban Kayaking

If you’re after a day of sightseeing, but exploring by foot doesn’t sound quite adventurous enough, why not head to the river to enjoy one of the most fun activities in Chicago: renting kayaks

You can opt for an organized tour, which will take you all the way along the river, providing views of breathtaking architecture that the city has to offer. Look out for buildings designed by renowned architects like Frank Lloyd Wright and Ludwig Mies van der Rohe. Those searching for active things to do outdoors in Chicago will love this, as it’s also a great workout.

Urban Kayaking

3. Go Boating in Chicago

If kayaking isn’t for you, you can also explore Chicago via one of our favorite water activities in the city: boating. In Chicago, you can rent or charter a boat and travel along the Chicago River, soaking up the scenery and enjoying all the sights that Chi-Town has to offer. Options include yacht rentals, party boats, catamarans, speedboats and plenty more.

If you want to combine your boating with your accommodation, you can reserve sleep aboards and make the boat the heart of your vacation. Take a look at all the boat rentals in Chicago and sleep aboards in Chicago here.

Boating in Chicago
4. Head Out Cycling

Cycling is a popular pastime in Chicago, and it’s one of the best outdoor activities to enjoy while you’re there. Cycling is an incredibly affordable way to immerse yourself in the culture of the city, and it offers plenty of opportunities to explore off the beaten track.

We highly recommend renting a bike to enjoy sunset views along the river. It’s the ideal way to enjoy a taste of the Chicago’s great outdoors. It’ll also help you burn off all the amazing food you’ll enjoy while you’re staying in the Windy City, too!


5. Take to the Skies on a Zip Line

Benis Wood is home to Chicago’s zip line, which is a must for adventurous travelers and local thrill-seekers. The zip line is one of the best outdoor things to do in Chicago, and we highly recommend you give it a try while you’re there. The 2,000-foot long zip line enables the bravest explorers to enjoy a taste of nature from the treetops, soaring along the top of Bemis Woods. 

There are also other fun obstacles to enjoy as part of the day out, including Tarzan swings, rope ladders, and trapezes. So, if you think you’re King of the Jungle, then this is an absolute must.


6. Explore the 606

The 606 takes you from east to west, and it goes right through destinations such as Logan Square, Humboldt Park, Wicker Park, and Bucktown. This is a popular path amongst runners and tourists, as well as cyclists, and it’s an ideal place to go for a walk too. This hike isn’t quite as scary as some of the more difficult ones, as it’s only 2.7 miles long. 

Biking or walking along the 606 is a great way to start any day in Chicago. Who knows what you’ll discover as you make your way along the path. And did we mention that it won’t cost you a thing?


7. Visit the Animals of the Lincoln Park Zoo

Lincoln Park Zoo is a fantastic thing to do, as it's completely free to visit. The zoo was first opened back in 1868, and it’s home to an array of amazing animals, marine creatures, and birds. There are owlets, polar bears, sea lions, tropical birds, sloths, African painted dogs, and plenty more impressive beasts to get up close and personal with. 

The zoo spans a vast 35-acres, so there’s plenty to keep the whole family occupied during a day out here. Lincoln Park Zoo is ideal for families, but adults too will love exploring the site and visiting the unusual animals that call this place home.

8. Explore Pilsen’s Street Art

Street art has become increasingly popular in recent years, and Chicago is at the forefront of the urban art scene. If you’re looking for inspiring murals and show-stopping graffiti, the place to go is Pilsen.

This area’s heritage blend of Mexican-Americans makes it an incredible melting pot when it comes to culture, and that’s shown clearly in its art scene. So, if the sun is shining, make your way over to Pilsen and go on a hunt for the best murals. Don’t miss the amazing artwork at the Damen Avenue. Pink Line Station either, we love the brilliant glass mosaics of the staircase here. It's a sight to behold.

Chicago Street Art


9. Climb Crystal Lake

Crystal Lake is a must for cycling fans, but a word of warning: this route isn’t flat. Crystal Lake is the go-to destination for ambitious cyclists looking for a big ascent. When you leave Crystal Lake Metra station, you’ll need to ride for five miles to reach the rural area where Crystal Lake is located.

There are big hills to climb on roads such as Bull Valley Road, Valley Hill Road, and Mason Hill Road, and these are the ones most frequented by serious cyclists. Look out for stunning meadows and the steepest hills in town. We hope you’re ready for it!


Try These Outdoor Activities When Visiting Chicago

Chicago is home to so many exciting outdoor activities, we bet you’ll struggle to fit them all in. From cycling and running to boating and kayaking, Chicago has it all. The city is perfect for adventurous travelers, and there are incredible trails and amazing scenery just waiting to be discovered. There are also fantastic cultural experiences and more relaxed outdoor activities like a visit to the zoo. No matter which pastime you choose, you’re guaranteed an unforgettable time in Chicago. The Windy City was made for adventure, and now it’s time for you to go out and see what this place has to offer.