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Chicago: Outdoor Activities Recommended by a Local

There is a surprising number of great things to do outside in Chicago.

Chicago is a bustling city with incredible museums, fabulous food and endless cultural opportunities to experience. But besides the obvious tourist attractions, there’s an outdoorsy side to Chicago that you won’t want to miss.

You’ll find wonderful parks and gardens in the city. There are beaches along Lake Michigan and a beautiful lakefront trail. Just outside the city, there is a massive botanical garden. And, let’s not forget about the Chicago River either!

So, as a Chicago resident, I’d love to share with you what I think are the best outdoor activities in Chicago.

Things to Do Outside in Chicago

1. Millennium Park

The Bean or Cloud Gate in Millennium Park
Cloud Gate, aka “The Bean” – one of Chicago’s most popular outdoor attractions

Millennium Park is one of the most iconic places in Chicago.

It’s right in the Loop (the main section of Downtown Chicago), near the Buckingham Fountain and the Art Institute. Millennium Park is more than just a green space, it’s a concert venue and a cultural hub for the city.

During the summer, you can stop by Millenium Park to cool off in Crown Fountain. Crown Fountain is an art installation with two giant LED screens that squirt water into a reflecting pool. You can literally take off your shoes and jump in.

Summer is the most lively time in Millenium Park. There’s always a free concert, workout class, or gardening workshop that you can join. Not to mention, it’s beautifully landscaped and always lively.

In the winter, ice skating is the best thing to do at Millenium Park. The park hosts one of the most popular ice rinks in the city. Guests can often expect to wait in line before being able to rent skates.

Tip: Regardless of the season, it’s always smart to dress warmly, especially when enjoying outdoor activities in Chicago. The weather is often cold, windy, and quickly changing.

2. Lake Michigan

a view of Lake Michigan and the beaches

Lake Michigan is one of Chicago’s most prominent features. Although, you might want to wait for an especially warm day to jump in. The waters of Lake Michigan are notoriously frigid.

The most lively beaches of Lake Michigan in Chicago are North Avenue Beach and Oak Street Beach. At Oak Street, you can rent lounge chairs. Both of these beaches have volleyball courts, watersport rentals, bars, and restaurants.

You can also easily rent equipment for a spontaneous volleyball match.

And, there are some great activities on Lake Michigan.  You can go Jetskiing, which I found one of the most unforgettable things to do outdoors in Chicago, or check out this Lake Michigan lunch or dinner cruise.

3. Chicago Botanic Garden

Chicago botanic garden

The Chicago Botanic Garden is an hour’s drive north of the city, but they’re well worth the trip. It’s one of the leading conservation institutions in the world, and nearly a million people visit this place each year.

The Chicago Botanic Garden sits on over 300 acres. It encompasses more than 26 unique gardens and 4 distinct nature areas. It’s a romantic place to bring a date.

They also have a spectacular Bonsai Collection — unlike any other kind on the planet. Some of the bonsai trees you’ll see there have been cared for for over 100 years. These tiny trees are twisted and maneuvered in mesmerizing arrangements.

Don’t miss the Japanese Garden or the English Walled Garden.

You’ll also find classes, workshops, and exciting events at the Chicago Botanic Garden year-round. Check their website for details.

4. Bike Ride on the 606 Trail

Cyclists on the 606 Trail
Picture by Victor Grigas – Chicago outdoor activities

The 606 Trail is Chicago’s version of the High Line in New York. It’s located in Chicago’s up-and-coming Logan Square neighborhood.

It is a 2.7-mile elevated park and trail that was built on what was once an industrial train line.

In the 1990s, traffic slowed on Chicago’s Bloomington train line and at that time Logan Square had sparse greenspaces. With huge community engagement and help from the City of Chicago and the federal government, this incredible project was started. It was finished in recent years, first opening to the public in 2015.

The 606 nowadays features a chain of street-level parks, scenic look-out points, an observatory, and public art installations.

The 606 Trail runs 2.7 miles from Ashland and Ridgeway, and there are multiple access points along the way. You can find a map and detailed information here.

It’s a great spot to enjoy a bike ride or a walk. There are plenty of offshoots where you can relax on the grass or have a picnic. Along the trail, you’ll find community art projects and expressive murals.

Rent bicycles for the day to enjoy the 606 Trail and maybe explore a few other parts of Chicago if you have the time.

5. Have Lunch in the Art Institute’s South Garden

the Art Institute’s South Garden
picture by Jeremy Thompson – things to do outside in Chicago

Dining on a restaurant patio is nice, but finding a cozy private spot in a garden is even better!

Millennium Park’s South Garden is one of Chicago’s best-kept secrets. Most tourists pass by it on the sidewalk without even noticing.

The Art Institute of Chicago is located on the corner of Michigan Avenue and Monroe Street. It’s one of the largest and most historic art museums in America.

Walk past the two lion statues on Michigan Avenue and immediately turn left at your first opportunity. You’ll find a beautiful tiny garden space with fountains, flowers, and mature trees.

This is the best spot in the city to eat a takeaway or a brown bag lunch! Or, simply have a coffee and a doughnut and enjoy the scenery.

This place is especially lovely during spring and summer and coming here is one of my favorite outdoor activities in Chicago.

6. Lakefront Trail

people walking and cycling along the Lakefront Trail
picture by Alan Scott Walker – outdoor activities in Chicago

Chicago’s Lakefront Trail is a favorite spot among locals and tourists alike. It spans over 18 miles from Ardmore Avenue on the northside to 71st Street on Chicago’s southside.

It’s the perfect place to walk, jog, rollerblade, skateboard, and bike.

You can easily rent Divvy bikes (Chicago’s bike-sharing system) at many access points all along the Lakefront Trail.

If you choose to bike, start around Lincoln Park and bike south towards Navy Pier. Then, continue on towards the Adler Planetarium. This path takes you along approximately 6 miles, and it’s relatively flat. You should be able to do this in less than an hour. The views near the Adler Planetarium are especially lovely.

If you prefer to walk, the best short walk along the Lakefront Trail is between Oak Street Beach and North Avenue Beach. You’ll catch expansive views of the John Hancock Tower & many other stunning skyscrapers.

7. Kayaking on the Chicago River

the Chicago river - perfect for outdoor activities

The Chicago River runs through downtown. Many enjoy the river from the Chicago Riverwalk -it’s made up of 6 coves lined with a variety of restaurants and community art projects. Most famously, Art on theMART can be seen from the Chicago Riverwalk.

But, for those who want to get in the river, kayaking is the best way!

You can rent kayaks from several companies in Chicago. Or, sign up for an exciting kayaking tour so that you can get better acquainted with the city.

Kayaking tours are great for tourists and locals alike. You can learn about history, architecture or gangsters from the water in the comfort of a kayak.

There are also kayaking opportunities that allow you to watch the Navy Pier fireworks.

8. Maggie Daley Park

In the summertime, Maggie Daley Park is fun for the whole family.

There’s a rock-climbing wall, picnic groves, and tennis courts. No other tennis courts in the city have views like these!

Also, make sure to walk across the nearby BP pedestrian bridge for some unforgettable views of Chicago.

However, Maggie Daley Park is most alive during wintertime. That’s when the giant ice ribbon fills up with skaters. Since it was built, it’s been the most popular place to ice skate in Chicago.

And even better, if you bring your own skates, the ice rink is totally free to use.

9. Navy Pier

Navy Pier as seen from the water

Navy Pier is a community events center, a cultural hub & one of Chicago’s most loved tourist attractions. One of the best things to do at Navy Pier is to ride the Centennial Wheel.

Navy Pier also offers regularly scheduled free fireworks shows. These run from May through September. You’ll catch them on Wednesdays, Saturdays and Holidays at 9:00 PM.

Navy Pier is also one of America’s most famous civic landmarks.

Walk around Navy Pier, and you’ll find plenty of public art exhibitions. Also, make sure to check out the Crystal Gardens inside. It’s an incredible botanical garden and a popular event space.

10. Chicago River Taxi

River taxi with the riverwalk in the background
picture by David Brossard – Chicago outdoor activities

Besides kayaking and walking the Riverwalk, there are many other ways to enjoy the Chicago River. One utilitarian (and economic) approach to getting on the Chicago River is to take the Chicago River Taxi.

You can take the Chicago River Taxi from the Loop to the Michigan Avenue Shops, or go all the way down south to Chinatown.

No matter where you decide to go, you’ll enjoy unique Chicago scenery from the Chicago River.

Another excellent way to enjoy the Chicago River is by taking the Chicago Architecture Cruise. It’s a bucket-list item when it comes to things to do outdoors in Chicago! You’ll love the views and learn a lot about the history, geography and buildings that shaped the beautiful skyline.

11. Lily Pool Inside Lincoln Park

Lily park in the fall
picture by Alan Scott Walker – things to do outdoors in Chicago

If you want to escape the hustle and bustle of Chicago, visit the Alfred Caldwell Lily Pool at the Lincoln Park Conservatory.

You’ll immediately step into a tranquil Midwestern prairie garden. The foliage here is so encompassing, and the ambiance so quiet, that you won’t be able to believe you’re still downtown.

Lily Pool is meant to mimic a river formed by a melting glacier’s flow of water as it cuts through rock. The stonework and paths have a natural look reminiscent of limestone bluffs, and a waterfall near the north end represents the source of this glacial river.

The Lincoln Park Conservatory is a non-profit organization that’s dedicated to ecological and historical conservation. Throughout the years, they’ve restored buildings, monuments, and natural areas all throughout the Lincoln Park neighborhood.

12. Go on a City Tour

woman taking a picture of Chicago's skyline

There is no better way to learn more about a city than by going on a city tour. And Chicago has a great number of tours for different interests.

If you are into street art, there is a really nice street art tour.

Have you ever tried a segway? It’s fun! And this segway tour is a nice way to see the city.

Or, if you want to combine outdoor activities in Chicago with tasting some of the city’s best food and drinks, check out this Bikes, Bites & Brews city tour.

Conclusion: Plenty of Outdoor Activities in Chicago!

I hope I’ve been able to show you how much there is to do outdoors in Chicago.

Whether you live in Chicago and were looking for something different to do or are visiting the city, enjoy Chicago’s outdoor activities!

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the best outdoor activities in Chicago, Illinois

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Valentina Djordjevic

Author: Valentina Djordjevic
Valentina is originally from Serbia, but she grew up in Chicago. She loves hunting down local restaurants, unique experiences, and hidden gems. Her blog Valentina’s Destinations was born from her obsession with meticulously researching, organizing, and planning her travel itineraries.

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