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Lakefront Trail
Photograph: Neal O'Bryan

The best things to do outside in Chicago

Take advantage of our amazing summer with these fun outdoor activities and things to do outside in Chicago

Zach Long
Written by
Zach Long
&
Lindsay Eanet
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Winter is brutal around here, but hey—that makes summer in Chicago all the more sweet, right? And while we love sipping drinks at rooftop bars or dining alfresco at outdoor restaurants, finding ways to enjoy nature and our city's beautiful green spaces is just as important. You'll find plenty of things to do outside within city limits, whether you want to hop on a bike and explore a neighborhood, have a picnic in a park or paddle down the Chicago River. If you're willing to (briefly) leave Chicago, you can also find beautiful trails to hike and epic ziplines to ride. You'll have time for things to do indoors all year, but when the sun is out and the days are longer, it's time to get outside, and here's how we recommend you do it. 

RECOMMENDED: The best parks in Chicago

Things to do outside 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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Zach Long
Editor, Time Out Chicago
  • Things to do

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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Zach Long
Editor, Time Out Chicago
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  • Things to do

Skip the stress of biking on Chicago's streets and go for a long ride on a nearby trail. Whether you want to pedal by the water on the Lakefront Trail or admire the Skokie Northshore Sculpture Park while cruising on the North Shore Channel Trail, there are plenty of options for cycling sans car traffic. Take a look at our list of nearby trails, accompanied by sights you can see along the way.

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Zach Long
Editor, Time Out Chicago
  • 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 many evenings throughout the year.

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Zach Long
Editor, Time Out Chicago
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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.

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Zach Long
Editor, Time Out Chicago

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—their 30-foot climbing structure is made from 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.

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Zach Long
Editor, Time Out Chicago
  • 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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Zach Long
Editor, Time Out Chicago
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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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Zach Long
Editor, Time Out Chicago
  • 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.

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Zach Long
Editor, Time Out Chicago
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  • 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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Zach Long
Editor, Time Out Chicago

On a nice summer night, there’s not 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’s plenty of other options too. Go nostalgic with the drive-in experience at ChiTown Movies in Pilsen or celebrate with crowd-pleasing music-themed movies at Gallagher Way. For those who like their movie nights more Instagrammable and with a side of skyline, Rooftop Cinema Club is also heading to The Emily Hotel this summer. 

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  • 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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Zach Long
Editor, Time Out Chicago
  • 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 600 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.

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Zach Long
Editor, Time Out Chicago
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After many being on hiatus over the past two years due to the pandemic, some of the city's biggest summer street festivals are expected to return this year. 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.

2022 is the Year of Chicago Dance, and with it comes a super-charged edition of Chicago SummerDance beginning this July, with the free dance lessons, dancing and live music happening at pop-ups at parks throughout the city. Not feeling super confident in your dance moves? That’s okay! On Saturday mornings throughout the summer, move and stretch with the skyline in the background with free yoga, Tai Chi, Pilates and Zumba workouts on the Great Lawn at Millennium Park. 

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  • Things to do
  • Suburbs

Located just over 20 miles from downtown Chicago, The Forge: Lemont Quarries is a sprawling 300-acre space is packed with activities for dedicated (and casual) thrill-seekers. There are multiple ziplines, climbing walls, a mountain bike course, hiking trails and a body of water you can kayak or canoe in—it's essentially a one-stop shop for outdoor activities.

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Zach Long
Editor, Time Out Chicago

This feature is brought to you by City Cruises anchored by Hornblower, who are ready to whisk you off on a breathtaking cruise in cities across the country. Fresh air and unforgettable views are waiting at a dock near you, from San Diego and LA to San Francisco, all the way to Chicago, DC and New York. Click below to discover five reasons why a City Cruise is the perfect way to make the most of your time outdoors in a beautiful city. Non-stop sightseeing, delicious dining and the freedom of feeling the wind through your hair are just the beginning... 

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