Planning a trip to Chicago this summer? In addition to the well known tourist attractions that you can enjoy in Chicago year round, there are many fun activities, events and festivals that take place only in summertime. We have put together a list of the best things to do in Chicago in the summer.
Things to Do in Chicago in the Summer
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Take an Architecture River Cruise
If you can only do one thing when you visit Chicago, take an architecture river cruise.
Take a Lake Cruise
If you enjoy being on the water, a lake cruise is a great way to cool down in the summer and enjoy the lake breeze. While you don’t get to see the buildings up close like you would on a river cruise, you do get to enjoy amazing skyline views especially around sunset.
If your time is short, you can take combination river and lake cruise.
Watch Free Fireworks
Navy Pier puts on free fireworks shows twice a week all summer (every Wednesday at 9:00 PM and Saturday at 10:00 PM). In addition to Navy Pier, you can also see the fireworks from several spots along the lakefront.
Our favorite way to watch the fireworks is on a fireworks lake or river cruise which stops on the water for passengers to enjoy the show.
Have Fun at Navy Pier
Navy Pier is full of touristy (but fun) attractions including a large Ferris wheel offering great skyline views (click here to purchase a fast pass ticket and skip the long line) and other rides and games.
Also at Navy Pier, you can find Flyover Chicago, an immersive flyover experience and Chicago’s newest attraction.
Navy Pier is also home to the Chicago Children’s Museum which is perfect for toddlers and younger kids.
Visitors in the summer can also enjoy free events and programs including Live on the Lake!, an outdoor live music series featuring free live music every weekend in the Navy Pier Beer Garden.
There are also various restaurants and shops at Navy Pier and you can hop on a lake cruise from here.
Hang Out on the Chicago Riverwalk
The Chicago Riverwalk is one of the best spots in Chicago for boat and people watching in the summer. There are many restaurants, bars, shops and spots where you can relax. You can also check out Art on theMART, rotating digital art projections across the river-façade of theMART in the evening. You can find a map of the Riverwalk here.
Kayak in the Chicago River or Lake Michigan
A kayaking tour in the Chicago River is a fun way to explore Chicago for those looking for something more active. Several companies offer kayaking tours in the daytime including this history and architecture kayak tour, during sunset and even at night.
You can also rent a kayak in the Chicago River here and Ohio beach 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.
Walk or Bike the 606
The 606 is an elevated trail that 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.
Walk or Bike on the Lakefront Trail
Chicago’s Lakefront Trail along Lake Michigan is another place for a walk, run or bike ride. You can also sit down, relax and enjoy the amazing Chicago skyline views. 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 Chicago has many public beaches on Lake Michigan. Oak Street Beach and Ohio Street Beach are conveniently located close to the major tourist attractions like Navy Pier and 360 Chicago. North Avenue Beach, located close to Lincoln Park, is more of a party beach and can get very crowded on the weekend.
If you are thinking of getting in the water to cool down, you can check the swimming conditions here.
Look for Street Art
Chicago is full of street art and there are always new murals popping up. You can also do your own self-guided mural walk or join a street art tour.
If you want to see murals on your own, you can find detailed mural walks in the Loop here. If you enjoy tours, this street art tour is a great way to see street art in the Wicker Park and Logan Square neighborhoods.
Watch a Baseball Game
Chicago is known for their love of their sports teams, so if you are visiting during the summer you might want watch a Cubs or White Sox baseball game. You don’t need to enjoy baseball to enjoy a Cubs game at historic Wrigley Field– it is fun to just soak in the atmosphere.
Free Live Music at the Museum of Contemporary Art Tuesdays on the Terrace
The Museum of Contemporary Art (220 E Chicago Ave) hosts the popular Tuesdays on the Terrace at MCA’s Anne and John Kern Terrace Garden during the summer. Enjoy free music every Tuesday from June 24 to August 26, 2025 highlighting artists from Chicago’s internationally renowned jazz community.
Jazzin’ at the Shedd
You can listen to live jazz music at the Shedd Aquarium (1200 S DuSable Lake Shore Dr) every Wednesday evening through August 27, 2025. The popular midweek Jazzin’ at the Shedd event combines Jazz music, the city skyline and fireworks. Relax with a drink on the breezy terrace and take in their unbeatable city view or stroll the aquarium.
Listen to Concerts Under The Stars
Enjoy musical tribute concerts on a beautiful rooftop with city views. Upcoming Concerts Under The Stars this summer include:
ABBA Under The Stars
Sinatra Under the Stars
Lavender Haze: The Ultimate Taylor Swift Tribute at the Aire Rooftop
Piano Men: A Billy Joel & Elton John Tribute at the Aire Rooftop
You can find the full list of Concerts Under The Stars here.
Free Concerts in Millennium Park
A great Chicago activity in the summer is listening to free concerts at the Jay Pritzker Pavilion in Millennium Park.
The annual Grant Park Music Festival (on select days from June 11–August 16, 2025) is the only free outdoor classical-music concert series in the US. You can see the full schedule here.
The Millennium Park Summer Music Series (on Mondays and Thursdays from June 26–August 7, 2025) features a wide variety of genre-defying music from established and emerging artists.
Looking for more free things to do in Chicago? Check out our list of 60+ best free things to do in Chicago.
Take a Free Outdoor Fitness Class
Join free yoga (and other fitness classes) outside at Millennium Park, Navy Pier, Gallagher Way and The Green at 320.
Watch Free Movies Outside
You can watch free movies every Tuesday evening from July 1 through August 19, 2025 in Millennium Park on the state-of- the-art, 40-foot LED screen.
You can also watch free outdoor movies during the summer in Gallagher Way in Wrigleyville and various Chicago public parks.
Splash in Crown Fountain
On hot summer days, kids (and some adults) love to splash and cool off in the water from Crown Fountain in Millennium Park.
Play at Maggie Daley Park
If you are visiting Chicago with toddlers or kids, head to Maggie Daley Park, a large public park connected to Millennium Park. The park has play areas for kids of various ages. The park also has a climbing wall, tennis courts and pickleball courts and a 18-hole miniature golf course.
Eat or Drink on a Rooftop
Chicago has several rooftop bars and restaurants with amazing views of Chicago. Our favorite rooftops in Chicago include:
Cindy’s (12 S Michigan Ave) at the Chicago Athletic Association Hotel which offers panoramic instagram worthy views of Millennium Park and Lake Michigan.
LH ON 22 (85 East Wacker Drive) at LondonHouse Chicago which offers great views of the Chicago River,.
The J. Parker (1816 N Clark St) on the rooftop of the Hotel Lincoln with great views of Lincoln Park.
Kennedy Rooftop (1551 W North Ave) on top of the Hyatt Place Wicker Park which has amazing skyline views.
Attend a Neighborhood Festival
Summer is busy season for outdoor festivals and events. In addition to the large music festivals like Lollapalooza there are numerous smaller food, art and music neighborhood festivals taking place every weekend. You can find a list of all festivals in the Chicago area here.
More Chicago Summer 2025 Events
In addition to festivals, other major summer events to keep in mind when planning your trip include Nascar Chicago Street Race (July 5-6, 2025) and the Chicago Air and Water Show (August 16-17, 2025).
So far we have covered outdoor activities and attractions but there are also plenty of indoor attractions and activities in Chicago if you need a break from the heat and sun including these limited time exhibitions and experiences:
Watch Free Films During the Cinema/Chicago’s Summer Screenings
Summer Screenings is Cinema/Chicago’s annual free film series that casts a spotlight on a different country’s national cinema each week through August 20, 2025.
Listen to Music at an Intimate Candlelight Concert
Chicago’s Candlelight Concerts is a series of special classical music concerts that take place in beautiful venues bathed in candlelight. Candlelight concerts taking place this summer include:
Candlelight: A Tribute to U2
Candlelight: A Tribute to Adele
Candlelight: A Tribute to Taylor Swift
Candlelight: A Tribute to Queen and More
Candlelight: The Best of Hans Zimmer
Candlelight: Tribute to Fleetwood Mac on Strings
You can find the full list of current candlelight concerts in Chicago here.
As you can see there are many things to do in #Chicago this summer.
