Looking for fun outdoor activities in Chicago? Below are the best outdoor things to do in Chicago in 2026.
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 (2026)
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Listen to Concerts Under The Stars
Enjoy a music concert on a beautiful rooftop with city views. Upcoming Concerts Under The Stars this summer include:
Sinatra Under The Stars at AIRE Rooftop
ABBA Under the Stars at AIRE Rooftop
Come Together: The Ultimate Beatles Tribute at AIRE Rooftop
Piano Men: A Billy Joel & Elton John Tribute at AIRE Rooftop
Yacht Rock Under the Stars at AIRE Rooftop
You can find the full list of Concerts Under The Stars here.
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 (9pm) and Saturday night (10pm) 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.
If you enjoy guided tours, you can also see the fireworks and other attractions on this fireworks segway tour.
Go Kayaking in the River or Lake
A fun way to enjoy city views is to go kayaking in the Chicago River or in Lake Michigan. You can rent a kayak in the Chicago River here and Ohio beach here.
You can also join a guided kayaking tour in the downtown portion of the Chicago River including this history and architecture kayak tour and this sunset kayak tour.
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.
Join Free Outdoor Fitness Classes
Want to join free yoga, pilates (and other fitness classes) while also spending time outside?
The Millennium Park Summer Workouts program offers free yoga, pilates and other fitness classes on Saturday mornings from May 16 through September 5, 2026 at the Millennium Park Great Lawn.
There are also free outdoor fitness classes at Gallagher Way in Wrigleyville.
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 (June 10 – August 15, 2026) is the only free outdoor classical-music concert series in the US.
The Millennium Park Summer Music Series (Mondays & Thursdays, June 15 – August 6, 2026) 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 warmer months in Millennium Park (Tuesdays, June 30 – August 18, 2026), Gallagher Way in Wrigleyville, and various public parks throughout the city.
Watch Free Shakespeare in the Parks
Watch a performance of William Shakespeare’s “As You Like It” in the park (on weekends June 26 – August 2, 2026). The performances are free and outdoors in various Chicago parks so bring your own picnics, chairs and blankets. You can see the list of parks and dates here.
Take an Architecture River Cruise
Chicago has amazing architecture and the best way enjoy it is by going on an architecture river cruise.
Take a Lake Cruise
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 especially around sunset.
If your time is short, you can do a combination river and lake cruise.
Hang Out on the Riverwalk
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.
Watch Digital Art at Art on theMart
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 every night on Thursdays through Sundays. 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
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 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
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.
Watch the Water Displays at Buckingham Fountain
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 (between early May-October), 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
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
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’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, 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, standup paddleboards (SUP) and boats at various beaches to get out on the lake.
Watch a Baseball Game
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 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.
Watch Classic Movies on a Rooftop
Want to watch classic movies against the backdrop of the Chicago skyline? Check out Rooftop Cinema Club outdoor screening series to a rooftop in Fulton Market.
Rooftop Cinema Club is located on the fifth floor terrace of The Emily Hotel (311 N Morgan St) and is a high end movie experience complete with tropical decor, lawn games, state-of-the-art LED screens, individual wireless headphones and a range of seating options including lounge chairs and loveseats. Guests can also order drinks and snacks. You can purchase tickets in advance here.
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.
For more outdoor events, bookmark this post about the best weekend events which is updated weekly.
As you can see there are many ourdoors things to do in Chicago.
Planning a trip to Chicago? Check out my Chicago guides and itineraries:
- Weekend in Chicago: 3 Day Itinerary (According to a Local)
- The Perfect Itinerary for One Day in Chicago
- Most Instagrammable Places in Chicago
- Best Free Things to Do in Chicago
