Some of our posts include affiliate links. When you make a purchase from one of these links, Skyline Adventurer may receive a commission at no additional cost to you. As always, we only recommend products and services we actually use - no BS necessary.

Deep dish pizza, baseball games, and stunning architecture…all things that typically come to mind when people think of Chicago. As the third largest city in the United States, brutal winters and a budding food scene mean there are tons of things to do indoors here. What is perhaps more surprising is the abundance of Chicago outdoor activities to try.

With the Chicago River, Lake Michigan, and tons of green spaces at the city’s disposal, Chicago is a fantastic and totally underrated city for outdoor enthusiasts. Here are 10 of the most unique and fun outdoor activities in Chicago.


Want to explore the outdoors in Chicago? Check out our Chicago adventure guides:


Chicago Outdoor Activities: Best Things to Do in Chicago, Illinois

1. Go kayaking on the Chicago River

There’s really no better way to explore Chicago than from the water, and the Chicago River is a great place to start. While you can take the iconic architecture tour or a riverboat city tour, one of our favorite ways to see the city is by kayak.

Renting a kayak in Chicago is a stress-free way to see the city at your leisure. Take in sights like the iconic bridges, the architecture, and the Chicago Riverwalk while enjoying a day on the water.

Kayak rentals in Chicago typically start at $20 per person per hour, and you can rent at several places along the river. Read our Chicago kayaking guide to learn more about the best places to rent a kayak and explore in the city.

If you’d prefer a guided excursion, there are lots of awesome and unique kayaking tours in Chicago. Here are a few of our favorites:

  • Chicago River Kayaking Tour – This classic 2.5-hour kayaking tour of the city, led by a local guide, will take you past historic sights and architectural marvels.
  • Ghosts & Gangsters Kayaking Tour – For a spooky paddling adventure, there’s no tour more unique or active than the Chicago Ghosts & Gangsters Kayaking Tour. Learn about the city’s haunted past while paddling down the historic Chicago River in the dark.

2. Take a free walking tour

Chicago locals take great pride in the fact that their city is such a walkable one, and it’s true! Between the many lines of the “L” train and good old-fashioned walking, you can basically get anywhere in the city without a car.

One of our favorite ways to explore Chicago is simply by walking everywhere. You can explore the various neighborhoods of Chicago on your own, grabbing a famous Chicago deep dish slice or hot dog along the way.

However, if you want to get a deeper glimpse into Chicago, we’d strongly recommend taking one of the city’s free walking tours. If you don’t know how these work, you basically don’t have to pay for your tour, just tip the guide what you thought the tour was worth at the end! Chicago’s free walking tours run every day during the warmer months of the year and cover topics like architecture, ghosts and legends, and the mafia history of the city.

Chicago locals (us included) love these tours as much as tourists do – it’s a great way to learn about the city whether you live here or not!

3. Explore Lake Michigan on a stand up paddle board

There are tons of ways to get out on Lake Michigan, but one of the best and most cost-effective is on a stand up paddle board. Paddle boarding is becoming an increasingly popular activity in Chicago, as the lake water is refreshingly cool in the summer and it’s a fun, active adventure you can have without leaving the city.

While there are lots of places along Lake Michigan that you can rent a stand up paddle board, two of the most popular are at Monroe Harbor (south of Navy Pier) and North Avenue Beach (east of Lincoln Park). Urban Kayaks and Chicago SUP have rental locations at these piers, respectively. Usually, you can simply walk up to either company and rent a paddle board on the spot.

We’ll be the first to admit that on especially windy days, paddle boarding on Lake Michigan isn’t always a walk in the park. However, it can be a wonderful way to get a workout while enjoying Chicago’s outdoors and catching some of the most epic views of Navy Pier and the Chicago skyline.

The Lakefront Trail is one of the most popular Chicago running trails.

4. Run along the Lakefront Trail

For those who want to get some miles under their belts, there’s no better place to go running in Chicago than on the Lakefront Trail. This 18-mile stretch of walking, running, and biking trail runs parallel to the shores of Lake Michigan, meaning you’ll have a great view of the water and the city’s many beaches for the duration of your run. You can also catch great views of Navy Pier, Grant Park, the Museum District, and the city skyline from the Lakefront Trail.

In our opinion, the best time to go for a jog on the Lakefront Trail is in the early morning, before it gets too hot and crowded with people. The trail doesn’t have a ton of shade or tree cover, so it can definitely get hot during the height of the midday sun. There are water fountains along the trail as well as a few snack shacks in case you’re craving a bite to eat or a cold drink.

If you’re planning to do a lot of running in Chicago, there are tons of great running spots you can check out. You can read our complete guide to running in Chicago below:

Photo Credit: Phil Roeder (Flickr CC)

5. Go rock climbing outdoors at Maggie Daley Park

Rock climbing outdoors might seem like a luxury reserved for rural areas and national parks, but there’s actually an opportunity to do it right in the heart of Chicago. Located in Chicago’s Loop, Maggie Daley Park boasts a 40-foot outdoor climbing wall, which has a total of 19,000 square feet of climbing space.

At Maggie Daley Park, there’s bouldering, top roping, and lead climbing for budding climbers, from beginners to intermediate enthusiasts. There are crash pads in the bouldering area and employees on staff to ensure a safe and fun environment. You can also hire a private belayer if you’re new to climbing or came without a belay partner.

For $30, you will get admission, a short lesson on belaying, and all of the necessary rental equipment – shoes, ropes, belay devices, helmets, and chalk. Also, Chicago residents get 20% off climbing admission (so you locals should definitely get on it!).

Photo Credit: Daniel Lobo

6. Take a hike on the 606

One of the most unique Chicago trails is the 606, an elevated urban trail that runs over former railroad tracks. Today, it’s a paved hiking, running, and biking trail that winds through green spaces, charming neighborhoods, and historic areas of Chicago. The 606 is a great place for an urban hike in Chicago, while experiencing some of the city’s iconic neighborhoods along the way.

The entire 606 trail spans 2.7 miles, beginning at Walsh Park and ending at North Ridgeway Ave. If you don’t want to hike the whole thing, there are multiple access points along the trail where you can enter and exit at your leisure. Because it’s paved and mostly flat, it’s one of the best hikes in Chicago and the surrounding areas for all levels of hikers.

To extend your adventure, you can get off at Humboldt Park, which is a peaceful recreation area located in the neighborhood of Wicker Park. Tackle the 2-mile loop trail or simply wander around and enjoy the escape from the bustle of the Loop and downtown Chicago.

For more information on hikes in and around the Chicago area, don’t forget to check out our complete Chicago hiking guide:

7. Rent a Divvy bike and explore on two wheels

Biking is one of the most underrated Chicago outdoor activities – it’s one of the best ways to see both the city’s amazing green spaces as well as its varied neighborhoods. Chicago locals love to bike, and you’ll usually see throngs of bikers on popular trails like the Lakefront Trail and the 606.

To rent a city bike, you can simply go up to any Divvy kiosk (the baby blue bikes) and use your credit card and rent a bike for the day ($15 gets you unlimited rides for 24 hours), then return the bike to any Divvy kiosk when you’re done.

Some of the best trails in the city to bike along include the Lakefront Trail, the 606, and the North Shore Channel Trail. For those who prefer a guided excursion, there are a few really incredible bike tours available to book in Chicago:

If you’d like to get out of the city, there are tons of other nature preserves and mountain biking trails you can enjoy. You’ll need your own bike to leave the city, but it’s well worth it to experience some of the best nature areas in the Midwest.

Lincoln Park is the perfect place to go running in Chicago.

8. Enjoy a walk in Lincoln Park

Lincoln Park is one of the most popular neighborhoods in Chicago, and in the middle of it lies a large, green park area that houses many walking trails, a lake, and the Chicago Zoo. The Lincoln Park Trail winds through the park’s wooded areas provide an easy, leisurely, family-friendly recreational area to go for a walk in the city.

Within the park, you’ll find 1200 acres of green spaces and recreation areas to enjoy. Next to the trails, you’ll see gorgeous Victorian architecture, the Lincoln Park Conservatory, and the zoo. Nearby, the Lincoln Park pathways lead to the North Avenue Beach stretch of the Lakefront Trail, perfect for an extra-long urban hike if you’re wanting to extend your adventure.

9. Enjoy winter activities like skiing and ice skating

Chicago winters might make the bravest souls shudder, but if you’re a skiing or snowboarding enthusiast, there are some pretty awesome places to hit the slopes nearby. You might be surprised to learn that there are actually some slopes and hills to ski down in the middle of the Midwest Prairie, and many of them cater to skiers and snowboarders of all levels.

The bottom line? You can find snowboard and ski resorts as close as 30 minutes from downtown Chicago, and they’re absolutely amazing places to get outdoors during the cold winter months.

Additionally, Chicago is home to an outdoor skating rink in the winter in Millennium Park, where you can actually lace up your skates and speed across the ice…in the middle of the city. It’s a pretty awesome perk of visiting Chicago in the winter, and it’s well worth braving the cold for!

The Chicago Marathon is one of the city’s largest road races. Photo Credit: Marco Verch (Flickr CC)

10. Run in an iconic Chicago road race

As with most big cities, there are tons of wonderful road races you can participate in that show off the best the city has to offer. The races will take you through the iconic sights and neighborhoods of Chicago, and will give you a new perspective on the Windy City. Here are a few of the coolest and quirkiest races you can enjoy in Chicago:

  • Shamrock Shuffle (March) – A St. Patrick’s Day themed 8K run that goes through all of Chicago’s most iconic landmarks.
  • Chicago Half-Marathon (September) – Chicago’s iconic half marathon (13.1 miles) usually takes place in late September and hits all of the city’s best spots.
  • Chicago Marathon (October) – This is Chicago’s iconic marathon (26.2 miles) route and one of the most popular events in the country!
  • Hot Chocolate 5K/15K (October/November) – The best kinds of races end with hot chocolate! This race commemorates the start of the Chicago winter with a run through the brisk air and plenty of warm hot chocolate at the finish line.

Additional Resources


Did you find this post helpful? Don’t forget to pin it for later!

Avatar
Author

Kay Rodriguez is the Chicago-based travel writer and photographer behind Jetfarer and Skyline Adventurer. When she's not blogging furiously on her laptop or editing photos, you can find Kay running, hiking, or paddling in a new city.

Comments are closed.