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Gallagher Way
Photograph: Courtesy Gallagher Way

The best outdoor activities in Chicago

Take advantage of the amazing warm weather with these fun outdoor activities and things to do outside in Chicago

Written by
Zach Long
&
Lindsay Eanet
Contributor
Isaiah Reynolds
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Chicago is at its best when the sun shines an hour longer, the birds sing a little louder and the breeze off of Lake Michigan is just a bit warmer. This is also when Chicagoans' calendars start to fill up with plans to lounge at some of Chicago's best beaches, gather for a meal on a stunning rooftop or plan time to explore the city's beautiful parks. There are so many things to do outdoors within the city limits, from hopping on a bike trail to free movies in the park. You may even want to escape the city for a breath of fresh air with an adventurous hiking trail or daytrip to what feels like another planet. So if you're up for some fun in the sun, these are our recommendations on the best things to do outside in chicago.

RECOMMENDED: The best outdoor bars in Chicago

Top outdoor activities in Chicago

  • Things to do

Want to get exercise while soaking in beautiful views? There’s no better way to build some upper body strength and enjoy the Chicago River than by renting a kayak and paddling on the various branches of the waterway. You can get a kayak in Avondale or along the Chicago Riverwalk—and there's even a dock at Montrose Harbor if you want to get out on the lake. Don't worry if you're a first-timer, because a quick lesson is all the stands between you and an afternoon of paddling.

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Back in the 19th century, Chicago's government picked the phrase "urbs in horto"—Latin for "City in a Garden"—as its civic motto. Today, Chicago is home to more than 8,800 acres of green space, including some actual gardens where you can admire blooms and native foliage. Step into a historic Japanese garden in the midst of Jackson Park, head north to Glencoe to wander through the expansive Chicago Botanic Garden or stick closer to home and take in the expanse of outdoor exhibitions at the Garfield Park Conservatory. 

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Cheer on your local teams
Photograph: Shutterstock

3. Cheer on your local teams

You already know there’s nothing better than taking in the historic views of Wrigley Field and cheering on the Cubs or waiting for that scoreboard to light up for a home run ball at Sox Park. But if that’s not enough local sports action for you, both of Chicago’s pro soccer teams, the Fire and Red Stars, are in season at Soldier Field and SeatGeek Stadium, respectively, and if you love an opportunity to fire up the grill, both clubs have a strong pre-game tailgating culture.

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  • Markets and fairs

Maybe you like the feeling of accomplishment when you rise early to pick the perfect produce. Maybe you prefer to sleep in, grab an iced coffee and take a leisurely late-morning stroll. However you like to do farmers markets and wherever you are in the city, there’s a farmers market for you. In addition to great produce, pastries, prepared foods and more, Chicago’s best farmers markets offer unique programming like live music, storytime for kids, and even DJs.

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  • Things to do

When the weather is warm, the Chicago Riverwalk (on the south bank of the Chicago River, just north of the Loop) is a bustling place. You can sit down for a meal at Beat Kitchen, grab a cocktail at the Island Party Hut or get out on the water by boarding a boat tour. And even when the seasons change, the Riverwalk is a beautiful spot to sit down and take in the sights, including the Art on theMART projections that take over the side of Merchandise Mart during most evenings throughout the year.

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  • Things to do

With more than 600 parks and facilities spread throughout the city, it's not difficult to find a new Chicago park to explore. From sprawling green oases like Humboldt Park and Douglass Park to smaller (but no less important) spaces like Ping Tom Memorial Park and Winnemac Park, most neighborhoods in the city are home to at least one place where you can enjoy an afternoon outdoors amid baseball diamonds, lagoons and open fields. Take a look at some of our favorite spots to get some fresh air.

  • Attractions
  • Parks and gardens
  • Millennium Park

Get super high, the natural way. You don’t have to leave city limits to experience some excellent outdoor climbing options. Connect with your inner child and catch views of the skyline from along the 40-foot climbing wall at Maggie Daley Park, where climbers of all ages and experience levels can get lessons and even a private belayer. Or for a cool taste of history, try climbing at Steelworkers Park along Lake Michigan near the Indiana border—the 30-foot climbing structure is made out of remnants of old historic ore walls from a former steel manufacturing site.

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  • Things to do
  • Walks and tours

If you're looking to see some of the most incredible skyline views of Chicago, look no futher than the city's top boat tours and cruises. The Chicago River and Lake Michigan each offer unparalled vantage points for gazing at the city, and specialized tours (like the popular Chicago Architecture Foundation Center River Cruise) offer a chance to learn more about the buildings surrounding you. Check out our list of the best ways to see the city by boat, or rent a boat for you and your squad.

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Chicago may be a dense and sprawling urban area, but there are still places to enjoy a calm walk near nature, helping you forget that you’re even in one of the largest cities in the country. Whether you want to walk on a wood chip trail, along the waterfront or simply on a nice, paved surface by some trees, Chicago has plenty to offer for anyone who wants to take a stroll.

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  • Music
  • Music venues
  • River West/West Town

Chicago’s iconic Morton Salt complex opened its doors as a unique indoor/outdoor concert destination in 2022. With summer comes many opportunities to enjoy the outdoor half of the all-weather venue, which sports a packed calendar including dozens of concerts from top touring acts, markets, Pride events, family-friendly programming and more. Shows tend to sell out quickly, though—so get on it!

  • Things to do

With 26 miles of shoreline, Chicago offers plenty of opportunities for beachgoers to catch some rays. Beyond getting a tan or taking a dip in Lake Michigan, Chicagoans can join the volleyball tournaments at Oak Street Beach, take their pups to Montrose Beach or head to Margaret T. Burroughs Beach (formerly 31st Street Beach) to admire the skyline from the sand.

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  • Things to do
  • Lincoln Park

Home to more than 1,200 animals, Lincoln Park Zoo remains one of the last free zoos in the country. There's a lot to see as you stroll through the ground, but some of our favorite sights in the park are the snow monkeys in the Regenstein Macaque Forest and the waddling African penguins that inhabit the Robert and Mayari Pritzker Penguin Cove. Don't forget to admire the prairie surrounding the Nature Boardwalk on your way into the zoo.

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  • Things to do

Our city doesn't boast nearby mountains like Seattle or San Francisco, but what the Midwest lacks in elevation it makes up for in natural beauty. Head to the city's Northwest Side to go for a walk on the North Branch Trail, go west to trek through the suburbs on the Illinois Prairie Path Trail or cross state lines to visit the gorgeous Indiana Dunes along Lake Michigan and tackle the 30-mile Ice Age Trail at Kettle Moraine State Forest in Wisconsin. You don't have to go far to temporarily escape your urban surroundings and traipse through nature.

  • Attractions
  • Parks and gardens
  • Humboldt Park

An abandoned rail line that runs throughout Logan Square, Humboldt Park, Wicker Park and Bucktown has been transformed into a 2.7-mile trail, perfect for walker, joggers and cyclists. The 606 (a.k.a. the Bloomingdale Trail) gives you an above-the-street view of several neighborhoods and offers plenty of spots to sit down and relax. You may have to dodge some strollers when the path gets packed on warm weekends, but it's a small price to pay for the easy access to various parks and local businesses along the trail.

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  • Things to do

On a nice summer night, there are few things much better than gathering friends and family, laying out a blanket and some camp chairs and sampling an array of snacks while enjoying a movie on the big screen. The Chicago Park District’s free, long-running Movies in the Parks program is a favorite covering lots of genres and events at parks all over the city, but there are plenty of other options, too. Catch crowd-pleasing movies at Gallagher Way or head to Rooftop Cinema Club, an open-air theater above the Emily Hotel that offers Instagrammable views of the skyline.

  • Things to do

Don't feel like spending the afternoon in a museum? You'll find some large (and small) masterpieces outdoors in locations throughout the city if you go searching for some of Chicago's best public art. Walk 16th Street in Pilsen to see a procession of murals, find Yoko Ono's Skylanding in Jackson Park's Garden of the Phoenix, or head to the Loop to see iconic works by Picasso and Calder. There's more public art in Chicago than you can see in a day, and admission is always free.

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  • Travel
  • Transport & Travel

You don't have to own a bike to roll through Chicago on two wheels thanks to the Divvy bike share program, which boasts more than 800 stations throughout the city. You can rent a classic bright blue Divvy bike or spring for one of the jet-black e-bikes, which use pedal assist power to help you get where you're going faster. You can snag a bike for a single 30-minute ride, get unlimited three-hour rides for an entire day or sign up for a membership that entitles you to unlimited 45-minute rides.

  • Things to do
  • Festivals

It's not a question of if you'll go to a street festival this summer—it's which one. You’ll find street festivals in nearly every neighborhood—with multiple options every weekend—celebrating different cultures, holidays, genres of music or very specific foods. Enjoy delicious street food from local restaurants and vendors, live music and other fun activities. Check out a full list to plan your fest outings.

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Get moving and grooving
Photograph: Patrick L. Pyszka

21. Get moving and grooving

Chicago SummerDance gives free dance lessons, dancing and live music happening at parks around the city every summer. Not feeling super confident in your dance moves? That’s okay! On weekend mornings throughout the summer, you can expect beginner classes and stretching with the skyline in the background with lower impact activities like Tai Chi and Pilates in Millenium Park.

You can stroll and relax in one of Chicago’s many beautiful parks by day but at night, these beloved spaces come alive with a host of fun activities, mostly for free.99. In addition to movies and free concerts, you’ll find stargazing opportunities, poetry readings, circus performances and even the popular Full Moon Fire Jam at Foster Beach, where fire spinners delight and dazzle with their art. Start making your plans now

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Get centered at an outdoor yoga class
Photograph: Shutterstock

24. Get centered at an outdoor yoga class

Start your day with some fresh air and exercise for the mind and body. You’ll find free outdoor yoga and fitness classes in many parks and public spaces around the city, including workouts Saturday mornings at Millennium Park and Tuesday evenings in Wicker Park, to name a few.

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S'more it up at a park bonfire
Photograph: Unsplash

26. S'more it up at a park bonfire

Take advantage of the pristine public parks in Chicago with an outdoor bonfire. Roast a Vienna sausage or gooey s’more dessert over a bonfire at Promontory Point or Caldwell Woods. Fire rings are available to the public but are first come, first served.

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Go on a walking tour of your favorite neighborhoods
Photograph: Caroline Duda

27. Go on a walking tour of your favorite neighborhoods

The city of Chicago is really beaming with history—if you don't believe us, check out the number of historical walking tour organizations dedicated to preserving the rich past of the Windy City. Stroll with Brick of Chicago, Chicago Mahogany Tours or Chicago Architecture Tours to brush up on your history and learn stories that are guaranteed to alter your perspective on the city. Tour prices vary and are seasonal so make sure you plan your tour ahead of time!

  • Things to do

If swimming in Lake Michigan isn’t your vibe, the Chicago Park District has plenty of alternatives. With more than 50 outdoor pools and 27 indoor swimming centers around the city, there are plenty of ways to keep cool in the summertime heat. Open swim sessions are open to the public and are offered throughout the year. Whether you’re looking for somewhere to bring the family to or just want to give a new form of exercise a shot, check out the dozens of swimming centers managed by the Chicago Park District.

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