Best Outdoor Activities in Chicago

Looking for fun outdoor activities in Chicago? Below are the best outdoor things to do in Chicago.

For a city known for its skyscrapers, impressive skyline, museums and other indoor attractions, Chicago has a surprisingly large number of outdoor things to do. While some of these activities and attractions are seasonal, there are many outdoor things to do in Chicago all year round.  Whether you live in the Chicago area or are visiting and looking to maximize your time outside, here are the best Chicago outdoor activities.

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Chicago Outdoor Activities

Take an Architecture River Cruise

chicago bucket list

Chicago has amazing architecture and the best way enjoy it is by going on an architecture river cruise.


Take a Lake Cruise

skyline from lake cruise in Chicago
If you enjoy being on the water, a lake cruise is also a fun activity especially on a hot Chicago summer day. While you don’t get to see the buildings up close like on a architecture river cruise, you do get to enjoy skyline views and cool breezes. If your time is short, you can do a combination river and lake cruise. Lake cruises depart from Navy Pier or the Michigan Avenue bridge.


Go Kayaking

A fun and active way to explore the city is to go kayaking in the Chicago River or Lake Michigan. Taking a guided kayaking tour in the Chicago River is great way to explore the city.

If you are an experienced kayaker, you can rent a kayak.


Please note that you will get a little wet when kayaking so bring a waterproof case for your phone and water-resistant or quick-drying clothing.

Hang Out on the Riverwalk

people at the River Walk one of the best outdoor things to do in chicago

The Chicago Riverwalk. located along the south bank of the Chicago River from Lake Michigan to west of Franklin Street, is one of the best spots in Chicago for boat and people watching. There are also restaurants, bars and other places to sit and relax along the way. You can also hop on a water taxi here on the weekends. You can see a map of attractions on the Riverwalk here.

Summer is one of the best times of the year to visit Chicago

Watch Digital Art at Art on theMart

Art on the Mart in the evening
Art on theMART is the largest permanent digital art projection in the world, projecting contemporary artwork across the 2.5-acre river-façade of theMART. Free 30-minute program of projections are shown nightly. Spectators can watch the show from the jetty section of the Chicago Riverwalk on Wacker Drive between Wells Street and Franklin Street.

Watch the Water Displays at Buckingham Fountain

Buckingham Fountain in Chicago in summertime

Buckingham Fountain, a well known Chicago landmark in the center of Grant Park, is one of the largest fountains in the world. When the water is turned on, it produces a major water display with a center jet shoots water to a height of 150 feet into the air.

The fountain is worth visiting both in the daytime and at night when there is a the light and music display that accompanies the water display. 

Take Photos at the Bean

The Bean at Millenium Park is one of the best outdoor Chicago attractions

Cloud Gate (aka “The Bean”), the famous bean shaped mirrored sculpture in Millennium Park, is a must on any Chicago bucket list.  Although The Bean is touristy, don’t skip it. 

Splash in Crown Fountain

millenium park which includes crown fountain is a Chicago must do

On hot summer days, kids (and some adults) love to splash in the water from the Crown Fountain (which is also located in Millennium Park).

Hang Out at Millennium Park

Although most famous for The Bean and Crown Fountain, there are more fun outdoor things to do in Millennium Park year round. Every summer, there are free concerts at the Jay Pritzker Pavilion in the evening and free yoga (and other exercise classes) on Saturday mornings.  The park is a good spot to see fall foliage in the fall and beautiful flowers in Lurie Garden in the spring.  In the holiday season, the city puts up a large Christmas tree. 


Play at Maggie Daley Park

Maggie Daley Park, a large public park connected to Millennium Park, is another must see outdoor attraction. Maggie Daley Park has play areas for kids of various ages. Other activities available here include an outdoor ice skating ribbon (open late fall and winter only), a climbing wall, tennis courts and pickleball courts, and a 18-hole miniature golf course.

Have Fun at Navy Pier

outdoor rides at Navy Pier Chicago

Navy Pier is very tourity but this large pier is a must do if you are visiting Chicago with toddlers or kids. There are several fun outdoor attractions at Navy Pier including a large Ferris wheel (click here to purchase a fast pass ticket and skip the long line) as well as rides and games.

Navy Pier puts on a free fireworks show on Wednesday and Saturday nights in the summer on Saturday nights in September.

Navy Pier is also the starting point for various sightseeing tours, boat rides and cruises:


Watch Free Fireworks in the Summer

As mentioned above, Navy Pier puts on a free fireworks show on Wednesday and Saturday nights in the summer and on Saturday nights in September. While you can watch the fireworks show from Navy Pier, you can also watch it from various spots along the Lakefront. Another great option for watching the fireworks is a lake or river cruise which will stop on the water for passengers to enjoy the show.


Shop (or Window Shop) on the Magnificent Mile

Join the throngs of visitors and locals shopping (or window shopping) on The Magnificent Mile. The Magnificent Mile (or The Mag Mile), is an upscale section of Michigan Avenue, running from Oak Street to the Chicago River. Although some of the stores on Michigan Avenue are pricey, it is totally free to window shop. Landmarks on the Mag Mile include the 360 Observation Deck, the historic Chicago Water Tower and the Tribune Tower.

Rent a Divvy Bike

If you are looking for a fun and affordable way to explore the city, you can rent a bike through Divvy, the city’s bike sharing program. You can pick up and drop off a bike at one of hundreds of stations around the Chicago area.

Run, Walk or Bike the Lakefront Trail

Chicago lakefront

Chicago’s Lakefront Trail is a paved path on a 18-mile-long stretch along Lake Michigan.  When the weather is good and especially on weekends, the lakefront is packed with locals and visitors walking, running and riding bikes.  Walking or biking all or part of the trail is a great way to see the Chicago skyline, people watch and get some exercise. Here is a map of the trail as well as its access points.

Spend Time at the Beach

Most people don’t think of Chicago as a beach destination but the city has many public beaches on the shores of Lake Michigan.  Oak Street Beach and Ohio Street Beach are conveniently located close to the major tourist attractions. Popular North Avenue Beach is more of a party beach and is located close to Lincoln Park. 

If you are thinking of getting in the water to cool down in the summer, you can check the swimming conditions here. Don’t forget to pack your beach essentials!

In addition to sunbathing and swimming, some beaches have volleyball courts.  You can also rent kayaks, jet skis and boats at various beaches to get out on the lake. 

Take a Standup Paddleboard (SUP) Class

If the weather is warm, you can rent your own paddleboard or join a standup paddleboard (SUP) class.


For an even bigger challenge,  Epic Yoga Flow and Chicago Water Sport Rentals offer stand-up paddleboard yoga classes which combine SUP and yoga.

Look for Street Art

Moose Bubblegum Bubble by Jacob Watts one of the most famous street art murals in Chicago

Chicago is full of street art and there are always new murals popping up.  One of the most famous Chicago murals is “Moose Bubblegum Bubble” (pictured above) by Jacob Watts which located at 33 E. Congress.  It is part of the Wabash Arts Corridor which is walking distance to Millennium Park, The Art Institute of Chicago and other well known tourist attractions. You can find more detailed mural walks in the Loop here.

Another famous mural is the Greetings From Chicago Mural at 2226 N Milwaukee Ave. You can see this mural and other street art on this street art tour.

Other neighborhoods that have a high concentration of street art include Pilsen as well as West Town.

Watch a Baseball Game

what to see in Chicago

Chicago is known for their love of their sports teams, so if you are visiting during baseball season you might want to attend a game. To those unfamiliar, historic Wrigley Field is home to one of the city’s baseball teams – the Cubs.  Whether a fan of the Cubs, baseball in general or just a fun atmosphere, a day at the 100 year old ballpark is a must for locals and tourists alike.  You don’t need to enjoy baseball to enjoy a Cubs game – it is fun to just soak in the atmosphere.  You can find their schedule here.

Shop at Local Farmers Markets

You can find many farmers markets around Chicago. Most are usually open from May through October. Farmers markets are a great place to buy healthy, local, farm-fresh foods from local farms. Two of the best farmers markets in Chicago are the Green City Market in Lincoln Park and the Logan Square Farmers Market. You can see the list and schedule of all Chicago farmers markets here.

Visit Lincoln Park

Lincoln Park

Lincoln Park is a large park with several outdoor and indoor attractions.  The park is home to Lincoln Park Zoo (which offers free admission).

You can find two of the best Chicago photo spots inside the park including the bridge over the South Pond and the Peoples Gas Education Pavilion (aka the Honeycomb).

Eat or Drink on a Rooftop

Even if you are not particularly active, you can enjoy dining and drinking outdoors at one of the city’s many rooftop bars and restaurants.  Some of the best rooftops in Chicago include

Cindy’s (12 S Michigan Ave) – Restaurant and bar on the rooftop of the Chicago Athletic Association Hotel located across Millennium Park which offers panoramic instagram worthy views of Millennium Park and Lake Michigan. 

LH ON 22 (85 East Wacker Drive) – The outdoor LH terrace of LondonHouse Chicago offers great views of the Chicago River, Lake Michigan and the Magnificent Mile.

The J. Parker (1816 N Clark St), on the rooftop of the Hotel Lincoln, has great views of Lincoln Park.

Kennedy Rooftop (1551 W North Ave), on top of the Hyatt Place Wicker Par, has amazing skyline views.

Watch Free Movies in the Park

Every summer you can watch free movies in the evenings in Chicago’s public parks with the annual Movies in the Parks series.  Movies start at dusk.  Click here to see the schedule.

Outdoor Ice Skating

There are several places to go outdoor ice skating in Chicago. Most outdoor skating rinks in the Chicago are usually open from around mid-November until the end of February/early March.

Two of the best places to go outdoor ice skating downtown is the skating ribbon at Maggie Daley Park and the McCormick Tribune Ice Rink in Millennium Park (right in front of The Bean).

Walk The 606

The 606 is Chicago’s version of The Highline in NYC, an elevated trail goes through 2.7 miles of the city’s northwest side neighborhoods: Wicker Park, Bucktown, Humboldt Park, and Logan Square. It is a bit off the beaten tourist path but it great place to walk, run or bike. There are several access points so you can get off the trail to explore the various neighborhoods.

Hike the the North Branch Trail

The North Branch Trail System, which connects the northwest side of Chicago to the Chicago Botanic Garden in Glencoe, is one of the best places to go hiking in the city. The system offers paved and unpaved trails along approximately 20 miles of the North Branch of the Chicago River, with trail loops through ecological restoration sites with diverse native wildlife. You can find a few recommended hikes on their website here.

Go Pumpkin Picking

Looking for a fun fall themed activity in Chicago? There are many pumpkin farms and patches in Chicago and the suburbs where you can pick pumpkins.  Pumpkin patches usually open to the public sometime in September and stay open until the end of October.  Here is a list of the best pumpkin patches in and near Chicago.

Outdoor Activities Near Chicago

If you want to leave the city and want to explore more of the Midwest, there are more outdoor things to do in the Chicago suburbs. These outdoor activities near Chicago can be easily be done on a day trip from Chicago.

Walk Through a Tulip Field in the Spring

Richardson Adventure Farm (in Spring Grove about 65 miles northwest of downtown Chicago) hosts a Tulip Festival from approximately mid-April to mid-May. Last year they had 5 acres of tulip fields with 300,000 tulips of 30 different varieties. Here are more places to see tulips near Chicago.

Walk Through a Sunflower Field

Visiting one of the many sunflower fields near Chicago is a popular outdoor activity for Chicagoans in the summer and early fall.

Visit Morton Arboretum

Morton Arboretum (in Lisle about 26 miles west of downtown) is home to more than 4,000 different types of trees among 1,700 acres. 

The Arboretum is full of hiking and biking trails or you can just drive through by car. Kids will particularly enjoy the 4-acre Children’s Garden.

Don’t miss Human+Nature, an outdoor art installation by renowned South African artist Daniel Popper. The exhibition features five 15- to 26-foot-tall sculptures which will be in various locations across the Arboretum site to lead guests to areas they may not otherwise explore. The exhibit opened May 28, 2021 and will be at the Arboretum for at least a year.

This is a very popular spot to see fall foliage. During the holiday season, check out Illumination, a one-mile paved walking path with interactive lighting effects that highlight the beauty of trees.

Visit the Chicago Botanic Garden

Chicago Botanic Garden (in suburban Glencoe about 24 miles north of downtown) is one of the world’s great living museums and conservation science centers with 27 gardens and four natural areas, situated on 385 acres on and around nine islands, with six miles of lake shoreline.

Their website has a list of suggested garden walks including seasonal walks which maximize nature viewing opportunities.

During the holiday season, you can enjoy holiday lights in nature by walking through Lightscape, an after-dark, illuminated trail.

Go Apple Picking

You might not associate apple picking with a large city like Chicago, but there are many apple orchards located in the Chicago suburbs (about an hour or less from downtown). Apple picking season typically starts sometime in August and lasts until mid to end of October with different types of apples are available for picking throughout the season.  Here is a list of the best apple orchards near Chicago for apple picking with locations, dates, hours, prices and all the information you need to plan your visit.

Get Lost in a Corn Maze

There are many corn mazes in the Chicago area – from large intricate mazes perfect for adults and older kids to small kid-friendly corn mazes. Most corn mazes are open sometime in September through the end of October.

Richardson Adventure Farm located in Spring Grove, Illinois (about an hour north of the city) claims to be world’s largest most intricate corn maze.  Here are more corn mazes near Chicago.

As you can see there are many ourdoors things to do in and near Chicago.

Planning a trip to Chicago? Check out my Chicago guides and itineraries:



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