Searching for what there is to do in Chicago this summer? Below are the best things to do in Chicago in the summer of 2025 (from a local) – including the best summer 2025 events and festivals.
I suggest bookmarking this blog post as I will be updating it regularly with new summer events and activities.
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.
Chicago in the Summer
Summertime is one of the best times of the year to visit Chicago – and the most popular! Both locals and visitors are happy to be outside enjoying the warm weather. In addition to the top tourist attractions that you can see year round, there are many more fun events, festivals, activities and things to do in Chicago during the summer.
What to Pack for Chicago in the Summer
Summers in Chicago are warm although you might need a light sweater on a cooler day or at night. Here are some things to pack if you are visiting Chicago in the summer for the first time:
• Comfortable walking shoes – Chicago is a very walkable city so you will do a lot of walking
• Reusable water bottle – It can get hot and humid so it is important to stay hydrated
• Sunglasses
• A hat
• A travel umbrella – It does occasionally rain in the summer
• Light sweater (and scarf) – For cooler days, lake cruises, indoor places with too much air-conditioning
• Waterproof case – For your phone if you plan to go kayaking or spend time in the water
• External battery for your phone – To recharge your phone’s battery when you are outdoors
• Mosquito repellent – If you plan to be outside around dusk and in the evening.
• Sunscreen – a must if spending a lot of time outdoors in the summer
• Bathing suit and other beach essentials (if you are planning to spend time at the beach)
If you forget to bring something essential, don’t worry. There are many drugstores located close to the popular tourist attractions if you need to pick something up.
Things to Do in Chicago in the Summer (2025)
Below is a list of the best things to do in Chicago this summer including the best summer 2025 festival and events.
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 one of the best summer activities in Chicago. Summer is the best season for a lake cruise as the cool breeze on the water is refreshing on a very hot day. While you don’t get to see the buildings up close like you would on a architecture river cruise, you do get to enjoy amazing skyline views especially around sunset. Lake cruises depart from both Navy Pier or the Michigan Avenue Bridge (DuSable Bridge).
If your time is short, you can do a combination river and lake cruise.
Watch Free Fireworks
Navy Pier puts on a free fireworks show every Wednesday night (at 9:00 PM) and Saturday night (at 10:00 PM) in the summer. While you can watch the fireworks show from Navy Pier, you can also watch it from various spots along the lakefront and some restaurants and bars.
My favorite place to watch the fireworks is a fireworks lake or river cruise which will stop 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. There are also restaurants and shops at Navy Pier and you can hop on a lake cruise from here.
Experience 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.
In addition to Navy Pier’s attractions, visitors in the summer can 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.
As mentioned above, Navy Pier puts on a free fireworks show every Wednesday and Saturday night from Memorial Day weekend through Labor Day weekend.
Hang Out on the Riverwalk
The Chicago Riverwalk is one of the best spots in Chicago for boat and people watching. There are also restaurants, bars, shops and spots to sit and relax along the way.
Where: Along the south bank of the Chicago River in downtown Chicago from Lake Michigan to west of Franklin Street. You can see a map of attractions on the Riverwalk here.
See Digital Art Projections at Art on the Mart
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.
When: Every night from Thursdays through Sundays
Where: The Merchandise Mart, 222 W Merchandise Mart Plaza, Chicago, IL 60654. Spectators can watch the show from the jetty section of the Chicago Riverwalk on Wacker Drive between Wells Street and Franklin Street.
Cost: Free.
Go Kayaking in the River or Lake Michigan
A kayaking tour is a great outdoor thing to do in Chicago for those looking for something more active.
There are several companies that offer kayaking tours including Urban Kayaks, Kayak Chicago and Wateriders.
You can rent kayaks at Ohio Street Beach here.
Please note that you will get a little wet on a kayaking tour so bring a waterproof case for your phone and water-resistant or quick-drying clothing.
Explore the Lakefront
Chicago’s Lakefront Trail is a paved path on a 18-mile-long stretch along Lake Michigan. In the summer 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 Chicago has many beaches on Lake Michigan. Oak Street Beach and Ohio Street Beach are conveniently located close to the major tourist attractions. North Avenue Beach, located close to Lincoln Park, is more of a party beach and has amazing skyline views of Chicago.
If you are thinking getting in the water to cool down, you can check the swimming conditions here.
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:
ABBA Under The Stars at AIRE
Sinatra Under the Stars at AIRE
A Starlit Tribute to Taylor Swift 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.
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, in Chicago’s Logan Square neighborhood. You can see this mural and other street art in Logan Square and Wicker Park 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, it produces a major water display for 20 minutes every hour with a center jet shoots water to a height of 150 feet into the air. Beginning at dusk, a spectacular light and music display accompanies the major water display.
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
If you are visiting Chicago with kids, head to Maggie Daley Park, a large public park connected to Millennium Park. The park has play areas for kids of various ages as well as a climbing wall, tennis courts and pickleball courts and a 18-hole miniature golf course.
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 to attend a baseball 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.
When: You can buy tickets and see the Cubs schedule here. If you prefer the White Sox, you can find their schedule and buy tickets here.
Listen to Free Live Music at the Museum of Contemporary Art Tuesdays on the Terrace
The Museum of Contemporary Art hosts the popular Tuesdays on the Terrace in the summer. Enjoy free music highlighting artists from Chicago’s internationally renowned jazz community at at MCA’s Anne and John Kern Terrace Garden.
When: 5:30-8pm on Tuesdays from June 24-August 26, 2025
Where: Museum of Contemporary Art, 220 E Chicago Ave, Chicago, IL 60611
Jazzin’ at the Shedd
Listen to live jazz music at the Shedd Aquarium in the summer. The popular midweek Jazzin’ at the Shedd series combines Jazz music, the city skyline, fireworks and animals. Relax with a drink on the breezy terrace and take in their unbeatable city view or stroll the aquarium.
When: 5-10pm on Wednesdays, May 28 through August 27, 2025
Where: Shedd Aquarium, 1200 S DuSable Lake Shore Dr, Chicago, IL 60605
Cost: Adults $29.95, Children (3-11) $24.95.
Visit Local Farmers Markets
You can find many farmers markets in Chicago in the summer. These 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.
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.
Listen to Free Music 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 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. Grant Park Music Festival runs from June 11-August 16, 2025 – you can see the full schedule here.
The free Millennium Park Summer Music Series (Mondays and Thursdays from June 26-August 7, 2025) features a wide variety of music from established and emerging artists.
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 yoga, pilates, cardio kickboxing and Zumba classes on most Saturday mornings (from May 17–August 30, 2025) at Millennium Park Great Lawn.
Other places offering free fitness classes in the summer include Navy Pier, Gallagher Way in Wrigleyville and The Green at 320.
Watch Free Movies Outside
You can watch also free movies every Tuesday (from July 1–August 19, 2025) near The Bean at Millennium Park on the state-of- the-art, 40-foot LED screen.
There are several more places you can watch free outdoor movies in Chicago during the summer including Navy Pier, Gallagher Way in Wrigleyville and various Chicago public parks.
Watch Movies on a Rooftop
Want to watch classic movies against the backdrop of the Chicago skyline? You can watch movies outdoors Rooftop Cinema Club, a rooftop located in Fulton Market.
Rooftop Cinema Club is located on the fifth floor terrace of The Emily Hotel (311 N Morgan St). This 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.
Eat or Drink on a Rooftop
Chicago has several rooftop bars and restaurants with amazing views of Chicago. Here are some of the best rooftops in Chicago:
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. This is a popular spot and the wait for the elevator can be long but if you visit around the time it opens you can enjoy the great views without the crowds.
LH ON 22 (85 East Wacker Drive) – Enjoy classic cocktails and small bites from the outdoor LH terrace of LondonHouse Chicago which 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 with great views of Lincoln Park.
Kennedy Rooftop (1551 W North Ave) on top of the Hyatt Place Wicker Park, has amazing skyline views.
Attend a Outdoor Neighborhood Festival
Summer is busy season for outdoor festivals and events – with at at least one or more neighborhood festivals taking place every weekend. These festivals are usually focused on food or art and charge a suggested donation for entry.
Some of the best outdoor neighborhood festivals taking place this summer include: Wells Street Art Festival (June 14-15, 2025), Old Town Art Fair (June 14-15, 2025), Roscoe Village Burger Fest (July 18-20, 2025), Taste of Lincoln Avenue (July 25-26, 2025), Chinatown Summer Fair (July 26-27, 2025), Jeff Fest (August 1-2, 2025), Printer’s Row Art Fest (August 9-10, 2025), Taylor Street Little Italy Festa (August 14-17, 2025), Glenwood Avenue Arts Festival (August 15-17, 2025), Taste of Greektown (August 22-24, 2025), Lakeview Taco Fest (August 23-24, 2025), Bucktown Arts Fest (August 23-24, 2025) and Taste of Polonia Festival (August 29-September 1, 2025).
If you enjoy food, music and people watching, you can find more summer festivals and events here.
Attend a Music Festival
If you enjoy music festivals, several large music festivals take place in Chicago every summer. Some of these music festival are very well known and attract thousands of visitors from around the world, but there are also neighborhood music festivals where you will find mostly locals.
Major summer music festivals in Chicago include: Belmont-Sheffield Music Festival (May 23-25, 2025), Sueños Music Festival (May 24-25, 2025), Chicago Blues Festival (June 5-8, 2025), Beyond Wonderland (June 7-8, 2025), Chicago Pride Fest (June 21-22, 2025), Pride in the Park (June 2025), Windy City Smokeout (July 10-13, 2025), Square Roots Fest (July 11-13, 2025), Lollapalooza (July 31-August 3, 2025), Chicago Gospel Music Festival (July 12, 2025), Northalsted Market Days (August 9-10, 2025), ARC Music Festival (August 29-31, 2025), North Coast Music Festival (August 29-31, 2025) and Riot Fest (September 19-21, 2025).
More Chicago Summer 2025 Events
In addition to the festivals mentioned above, other major Chicago summer 2025 events to keep in mind when planning your summer trip include: Chicago Pride Parade (June 29, 2025), Nascar Chicago Street Race (July 5-6, 2025), Chicago Ducky Derby (August 7, 2025), Bud Billiken® Parade (August 9, 2025), Chicago Air and Water Show (August 16-17, 2025) and Taste of Chicago (September 5-7, 2025).
So far I have covered outdoor activities and attractions but there are also plenty of indoor attractions and activities if you need a break from the heat and sun.
Visit the Art Institute of Chicago
The Art Institute of Chicago is one of the oldest and largest art museums in the United States. In addition to its large permanent collection of art from around the world, you can see rotating exhibitions. It is conveniently located on 111 S Michigan Avenue right next to Millennium Park.
Click here to buy a skip the line ticket if you want to avoid long lines.
Attend a Candlelight Concert
Chicago’s Candlelight Concerts is a series of special classical music concerts that take place in beautiful indoor venues bathed in candlelight. Some of the concerts taking place this summer include:
Candlelight: A Tribute to U2
Candlelight: A Tribute to Adele
Candlelight: A Tribute to Grunge
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 candlelight concerts in Chicago here.
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 all summer. Full schedule will be available May 1, 2025.
Where: Chicago History Museum, McCormick Theater (1601 N Clark St) and Chicago Cultural Center, Claudia Cassidy Theater (78 E Washington St)
When: Mondays and Wednesdays from June 2 – August 20, 2025
Enjoy the Views from 360 CHICAGO Observation Deck
360 CHICAGO, the observatory on the 94th floor of the former John Hancock Building, has one of the best views of the Chicago skyline and Lake Michigan.
(Click here to buy a skip the line ticket).
Where: 875 North Michigan Avenue, 94th floor, Chicago, IL 60611
Visit the Museum of Ice Cream
The Museum of Ice Cream is one of Chicago’s newest attractions. Step into an ice cream wonderland that is bound to ignite your senses through a theatrical experience with unlimited ice cream treats as you journey through 14 installations. Ride on the pink Sprink-L line, put your golf skills to the test on the Putt-Putt course, or take a dip in a pool filled with millions of sprinkles.
Where: Tribune Tower, 435 North Michigan Ave
Cost: You can see full prices and purchase tickets in advance here.
As you can see there are many things to do in Chicago this summer.
If you have extra time in Chicago and want to explore more of the Midwest, here are the best day trips from Chicago.
Planning a trip to Chicago? Check out my Chicago guides and itineraries:
