The Best Outdoor Activities In And Around Chicago

There’s no reason to stay inside on a visit to Chicago (even if it is known as the Windy City) – it has a stunning skyline with skyscrapers like the Willis, Vista and Tribune Towers that will keep you looking up for hours. There is plenty to see and do al fresco. Here is Culture Trip’s guide to the best outdoor activities in Chicago.

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Walk or run the Lakefront Trail

Bicycle riders on Lakefront Trail in Chicago

This stunning 18-mile (29km) stretch along the shore of Lake Michigan starts from Kathy Osterman Beach in Lincoln Park and ends at the South Shore Cultural Center. The city’s vibrant skyline is in constant view, and you’ll be able to walk, stroll or run past Navy Pier and Grant Park. There are markers to tell you how far you’ve gone and drinking fountains along the way. Most importantly, you don’t have to complete the entire journey. And if you get too hot along the way (obviously only applicable in the summer), you can always jump in the lake to cool down.

A tight budget needn’t mean your trip to Chicago can’t still be a comfortable one

This city centerpiece park is home to some of Chicago’s most iconic landmarks and attractions. It includes Museum Campus, the Art Institute of Chicago, the Field Museum of Natural History, the Shedd Aquarium and the Adler Planetarium. But its main focal point is the stunning Clarence Buckingham Memorial Fountain, which was built in 1927. It has since become a huge tourist attraction and is a perfect location to take in the breathtaking lakefront views. There are also stunningly manicured gardens where you can sit and enjoy a cup of coffee.

Enjoy the music at the Jay Pritzker Pavilion

Jay Pritzker Pavilion, Millenium Park. Chicago.

Lawn seating for this stunning outdoor concert venue is free, and the venue often hosts a mix of live music, from indie rock to Pacific Afro-Colombian. Designed by Frank Gehry, it is one of the world’s most state-of-the-art outdoor music pavilions. And you never have to worry about being too far from the stage with this truly immersive experience. If none of the music suits your taste, why not head down anyway, where you could take part in an outdoor yoga class or check out one of the many outdoor film screenings.

See Yoko Ono’s installation at Jackson Park

If art is your thing, then you’ll definitely need to check out Yoko Ono’s Skylanding, which is made up of 12 large steel lotus petals rising up from the ground in the Garden of the Phoenix. The sculpture was designed by the famous activist and artist as a symbol of peace and is on the site of a pavilion built by the Japanese government for the 1893 World’s Columbian Exposition. Another reason to visit is that the park is also the home of the beautiful Osaka Japanese Garden.

Soak up the rays on Montrose Beach

Chicago’s beaches can become crowded, particularly the closer you get to the Loop. So why not head Uptown where you can lay on the sand and feel the sun on your skin. There are plenty of amenities, and if you do get sick of sitting around enjoying all that sunshine, you can hire a volleyball court or rent a kayak.

Take a selfie at ‘The Bean’

Cloud Gate also known as the Chicago Bean in Millennium Park in Chicago, IL. The work is the creation of artist Anish Kapoor

Officially titled Cloud Gate by Indian-born British artist Sir Anish Kapoor, ‘The Bean’ is the centerpiece on the plaza at Millennium Park and is a must-see on any itinerary for Chicago. It was unveiled at the opening of the park in 2004 and has become a symbol of the city, and one of Chicago’s most photographed landmarks. It’s one of the best ways to capture the city’s skyline while still remaining in the picture at the same time. The shiny artwork is polished once in the morning and again in the evening. There’s also a crew who wipe it clean up to seven times a day to ensure there are no fingerprints left behind.

Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.