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Top Outdoor Activities in Chicago, IL

Chicago's outdoor spaces are as impressive as its skyline. From the 18-mile Lakefront Trail along Lake Michigan to the quiet paths of the Morton Arboretum, outdoor activities across Chicago and the surrounding area span a wide range of paces and interests. Whether you're an active traveler looking for a full-day adventure or simply want some fresh air between sightseeing stops, parks, beaches, trails, and green spaces across Chicago and the surrounding area make it easy to get outside and explore.

Red Roof® properties near Chicago provide a comfortable base for exploring outdoor destinations throughout the area, from lakefront recreation and city parks to expansive gardens, trails, and natural spaces beyond the city.

A river with a boat in it and a city with tall buildings
A couple of kids paddling a canoe on a lake
A man carrying a girl on his back on a beach

Enjoy Chicago's Great Outdoors

A group of people in kayaks on a lake

Kayaking the Chicago River

Kayaking is one of the most scenic ways to take in Chicago's architecture and neighborhoods. Urban Kayaks and several other operators offer guided tours along the Chicago River through the heart of the city, as well as routes along Lake Michigan that circle Museum Campus, passing the Adler Planetarium, Field Museum, Soldier Field, and Shedd Aquarium.

Bicycles parked on grass near water

Biking the Lakefront Trail

The 18-mile Lakefront Trail follows the shoreline of Lake Michigan and is one of Chicago's most popular outdoor activities in Chicago, IL. The trail offers open water views, access to several beaches, and passes through a range of neighborhoods. Divvy bike-share kiosks are available throughout the city for those without their own wheels.

A woman in a yellow dress on a beach

Chicago's Beaches

Chicago's lakefront beaches offer something for every kind of visitor. North Avenue Beach is a lively option near Lincoln Park with a beachside bar and water sport rentals. Oak Street Beach sits conveniently close to The Magnificent Mile. Loyola Beach offers a calmer, family-friendly setting with shallow water and a playground. The northern end of Montrose Beach welcomes dogs off-leash.

A couple of people walking on a dirt path

Morton Arboretum

About 30 minutes west of downtown Chicago, the Morton Arboretum offers more than 16 miles of hiking trails through gardens, woodlands, and open meadows. Rotating art installations and a maze garden add to the experience, making it a peaceful retreat for anyone looking to step away from the city's energy for a few hours.

A man looking at giraffes

Lincoln Park Zoo

Free to enter year-round, the Lincoln Park Zoo is home to more than 1,100 animals and offers a full day of outdoor exploration in the heart of the city. Open all 365 days of the year, it's one of the most accessible Chicago outdoor activities for families and solo visitors alike.

A house with a red roof and a pond

Humboldt Park

Spanning 207 acres on Chicago's West Side, Humboldt Park is home to historic statues, two bison from the 1893 World's Fair, and the National Museum of Puerto Rican Arts and Culture, housed in the park's original stables. Allow yourself enough time to explore the full grounds  -  it's a large and rewarding space.

A train tracks with trees and bushes

The 606 Trail

Once an abandoned elevated railway line, The 606 is now a 2.7-mile multi-use recreational trail and park that winds through four distinct Chicago neighborhoods. Free family programming runs during the warmer months, and the elevated route offers an interesting perspective on the city as you walk or ride through it.

A brick path leading to a garden

Chicago Botanic Garden

Located on the shores of Lake Michigan, the Chicago Botanic Garden spans 385 acres with 27 individual gardens and 6 miles of shoreline across nine islands. One of the country's leading conservation science centers, it offers a compelling mix of natural beauty and educational programming throughout the year.

A boat on a river with a bridge and tall buildings

Chicago Architecture Foundation River Cruise

Run by the Chicago Architecture Foundation, this 90-minute river cruise explores Chicago's architectural history from multiple branches of the Chicago River, with both daytime and evening tour options. The tour covers 50 structures along the riverbanks, including the only skyscraper in the city's skyline designed by an award-winning female architect.

A colorful graffiti on a wall

Promontory Point

This man-made peninsula in Burnham Park is a favorite gathering spot for locals, with manicured green space, rock formations along the lakefront, and a rotating selection of public art installations. It's a relaxed outdoor destination well suited to a picnic or a leisurely afternoon walk.

A large reflective object in front of a city

Millennium Park

Millennium Park in downtown Chicago is anchored by Cloud Gate, widely known as 'The Bean', and Crown Fountain, a pair of towers that project the faces of Chicago residents and send out water streams in the warmer months. The park is a central and welcoming starting point for exploring the broader downtown area.

A group of boxes of vegetables

Chicago Farmers Markets

Chicago's farmers' market scene is lively and spread across several neighborhoods. The City Market at Daley Plaza is the city's longest-running market and an easy walk from Millennium Park. The Maxwell Street Market on Sundays draws visitors with handmade tamales and tortillas. The Green City Market in Lincoln Park is one of the largest in the city and publishes its own cookbook.

A close up of a painting

Pilsen Murals

The Pilsen neighborhood is home to one of Chicago's most impressive collections of outdoor murals, many depicting the history of Mexican-American culture through the work of both emerging and established artists. Highlights include Spy Gaia's Quetzalcoatl and the Stork, and a stairway covered in colorful glass mosaics. A self-guided walk through the neighborhood is one of the more memorable outdoor activities in Chicago, IL.

A statue of a baseball player in front of a sign

Wrigley Field

A visit to Wrigley Field, one of the oldest active ballparks in the country, at over 100 years old, is a worthwhile outdoor experience, whether or not you're a baseball fan. Catch a Cubs game during the season or take a behind-the-scenes tour when the schedule allows.

A person's legs and feet in ice skates

Ice Skating

During the winter months, outdoor ice skating is one of Chicago's most popular seasonal activities. The McCormick Tribune Ice Rink in Millennium Park and the skating ribbon at Maggie Daley Park are two of the most central options, both typically open from mid-November through late February or early March.

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Book Your Stay With Red Roof®

Ready to explore Chicago? Red Roof® offers affordable, comfortable hotels conveniently located near the city's top attractions. Book your stay at redroof.com or call 800.RED.ROOF (800.733.7663). RediRewards® members earn 10 points per dollar on every stay  -  join for free at redroof.com.