BEST Outdoor Activities in Chicago in 2024 (From a Local)

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

For a city known for its skyscrapers, museums and other indoor attractions, Chicago has a surprisingly large number of outdoor things to do.

Whether you live in the Chicago area or are visiting and looking to maximize your time outside, here are the best Chicago outdoor activities.

Chicago Outdoor Activities (2024)

Disclosure: This article contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you. As an Amazon Associate I earn from qualifying purchases.

Go Outdoor Ice Skating

Outdoor Ice Skating in Chicago in the winter

There are several places to go outdoor ice skating in Chicago during the winter. Outdoor skating rinks in Chicago are usually until early to mid March (weather permitting).

One of the best and picture perfect spots to go ice skating is at the McCormick Tribune Ice Rink in Millennium Park right in front of The Bean. McCormick Tribune Ice Rink is open through March 3, 2024 (weather permitting). Admission is free, but online ticketed reservations are required. Tickets are available for purchase 14 days in advance.

Skating ribbon at Maggie Daley Park in Chicago

Another ice skating rink with great skyline views is the skating ribbon at Maggie Daley Park located next to Millennium Park. The skating ribbon has a path twice the length of a lap around a traditional skating rink. Reservations are strongly encouraged. The skating ribbon will be open through March 10, 2024. Tickets will be released on a rolling basis at noon every 2 weeks. See the official website for hours and prices.

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. Lake cruises depart from Navy Pier or the Michigan Avenue bridge.

If your time is short, you can do a combination river and lake cruise.

Watch Free Fireworks

Did you know that you can watch free fireworks displays in Chicago all summer? Navy Pier puts on a free fireworks show every Wednesday (9:00 pm- 9:10 pm) and Saturday night (10:00 pm- 10:10 pm) between Memorial Day weekend and Labor Day.

While you can watch the fireworks show from Navy Pier, you can also watch it from various spots along the Lakefront.

A great way to watch the fireworks is a lake or river cruise which will stop on the water for passengers to enjoy the show.

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 find 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 twice every night. Spectators can watch the show from the jetty section of the Chicago Riverwalk on Wacker Drive between Wells Street and Franklin Street.

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 as well as rides and games. Navy Pier is also the starting point for various sightseeing tours, boat rides and cruises.

As mentioned above, Navy Pier puts on a free fireworks show on Wednesday and Saturday nights in the summer.

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.

Go Kayaking

A fun way to explore the city is to go kayaking in the Chicago River or Lake Michigan. There are several companies that offer guided kayaking tours and rentals in Chicago including Urban Kayaks, Kayak Chicago and Wateriders.

You can also rent kayaks at Ohio Street Beach.

If you have your own kayak, you can find all the boat launches on the river and the lake here.

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.

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 light and music display that accompanies the water display.

See The Bean in Millennium Park

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).

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.

Rent a 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.

You can also rent a bike with a helmet for a day or half day here

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

view from North Avenue beach Chicago
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, located close to Lincoln Park, is more of a party beach and has amazing skyline views.

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.

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 the Chicago Cubs schedule here and the Chicago White Sox schedule 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).

Play Outdoor Mini-Golf

There are a few places to play outdoor mini-golf in Chicago:

City Mini Golf at Maggie Daley Park is a 18-hole family friendly miniature golf course featuring several replicas of iconic Chicago structures, a 6-foot tall Willis Tower and a Plinko-inspired replica of a Picasso sculpture.

Diversey Miniature Golf is a 18-hole course near the Lakefront Trail.

Join Free Outdoor Summer Workouts

Want to join free yoga (and other exercise classes) while also spending time outside?

The Millennium Park Summer Workouts program offers free Tai Chi, Yoga, Pilates and Zumba classes on Saturday mornings from May 18 – August 31, 2024 at Millennium Park Great Lawn.

Listen to Free Outdoor Music Concerts

One of the best things to do in Chicago during a nice summer evening is listening to free concerts at the Jay Pritzker Pavilion in Millennium Park.

The annual Grant Park Music Festival (from June 12-August 17, 2024) is the only free outdoor classical-music concert series in the US. It features the Grant Park Symphony Orchestra and Grant Park Chorus along with guest performers and conductors.

The Millennium Park Summer Music Series (Mondays & Thursdays from July 1-August 8, 2024) features a wide variety of music from established and emerging artists at the iconic Jay Pritzker Pavilion.

Watch Free Movies in the Park

There are several places you can watch free outdoor movies in Chicago in the summer including Gallagher Way in Wrigleyville, Millennium Park and various public parks throughout the city.

Walk or Bike 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.

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.

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.

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.

Attend an Outdoor Festival

Chicago is home to many outdoor festivals and events – especially in the summer when you can find at least one or more festivals taking place every weekend.  Some Chicago festivals are very well known and attract thousands of visitors, but there are many neighborhood festivals and events in Chicago where you will mostly find locals. If you enjoy food, music and people watching, check here to see if there are any festivals or events going on while you are in town.

Go Sledding in the Winter

If there is snow on the ground (usually at least 3 inches), grab a sled and head to one of sledding hills found in parks and forest preserves in the Chicago area.

Where: Various. See Best Sledding Hills in Chicago.

Cost: FREE

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
Walk through acres of tulips fields located near Chicago in the spring. Two nearby farms –Richardson Adventure Farm (in Spring Grove about 65 miles northwest of Chicago) and Kuipers Family Farm (in Maple Park about 57 miles west of Chicago) – are hosting a tulip festivals from approximately mid-April to mid-May. 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. In addition to enjoying flowers in the spring and summer, the Arboretum is a very popular spot to see fall foliage in the Chicago area.

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.

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 seasonal garden walks which maximize nature viewing opportunities.

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:




Leave a Reply

Your email address will not be published. Required fields are marked *

CommentLuv badge

This site uses Akismet to reduce spam. Learn how your comment data is processed.