Things to do in Chicago in the summer

There’s nothing quite like summer in Chicago. It’s a time of year when the city truly shines, making it the perfect time to get out and enjoy our beaches, parks, waterfronts, and vibrant neighborhoods.

What’s there to do in Chicago during the summer? All season long, you can play beach volleyball on the sandy shores of Lake Michigan, kayak through a skyscraper canyon, have the time of your life at a music festival, sip cocktails from rooftop bars with skyline views — the list goes on and on.

Here’s your guide to enjoying the very best of summer in Chicago.

Celebrate a milestone summer in Chicago

Chicago is planning for a historic summer in 2026. The city will be celebrating major milestones, including the opening of the Obama Presidential Center on Juneteenth weekend and the 100th anniversary of Route 66. It’ll be an exciting time for history buffs, fans of Americana, road trippers, and beyond.

• Obama Presidential Center: This new landmark on the city’s historic South Side will open to the public this summer. The interactive space will offer events and activities for the community, along with public grounds and a free observation deck with views of the lake and city.
• Chicago 250: This year-long celebration throughout Chicago and Illinois is part of the nationwide America 250 anniversary. Catch museum exhibits, classical concerts, and more programming throughout the summer.
• Route 66 Centennial: As the official start point of the historic route, Chicago will celebrate the 100th anniversary of Route 66 this summer. Snap a photo at the Route 66 sign on Navy Pier before hitting the open road.

Soak in the sun on Chicago’s beaches

Chicago is blessed with miles and miles of stunning lakefront where you can swim, play volleyball, kick back in the sand, or enjoy a cocktail with stunning Lake Michigan views.

Looking to plan your perfect beach day? Check out our guides to experiencing Chicago’s stunning waterfront:

• Explore our guide to Chicago beaches for the best ways to soak up the sun.
• Rent a kayak or paddleboard and paddle with jaw-dropping views of the Chicago skyline.
• Grab a spot at a beachfront bar or restaurant and enjoy a drink with your toes in the sand.

Stroll the Chicago Riverwalk

The Chicago Riverwalk comes alive each summer, when this bustling stretch of riverfront is filled with walkers, diners, and kayakers enjoying stunning views of the water and surrounding skyscrapers.

Here are a few ways to enjoy the Chicago Riverwalk in the summer:

• Grab a seat on a waterfront patio, like the popular City Winery outpost.
• Catch Art on THE MART, a large-scale display of digital art held nightly.
• Hop on a kayak and explore on your own or with a tour group surrounded by soaring skyscrapers.
• Shop a market of local artisans and vendors for the perfect Chicago souvenir.
• Hop on an architecture boat cruise and learn the stories behind the city’s more historic buildings. 

Discover more in our full guide to the Chicago Riverwalk. 

Attend summer festivals and events

It’s not really summer in Chicago until you check out one of our legendary summer events, ranging from major music festivals to bucket list happenings.

Here are a few of the top festivals and events to check out in Chicago this summer:

Summer music festivals in Chicago

• Lollapalooza: Fans travel from around the world for this four-day extravaganza in Grant Park.
• Windy City Smokeout: Beer, booze, and barbecue come together for an epic summer weekend.
• Chicago Blues Festival: The largest free blues festival in the world is a summertime staple in Chicago.
• Chosen Few Picnic: This laid-back festival celebrates Chicago-born house music in Jackson Park.
• Millennium Park Music Series: These popular free concerts bring local and national artists to the stunning Pritzker Pavilion.
• Chicago Jazz Festival: Close out summer with this free festival that brings jazz stars to Chicago’s Millennium Park.

Top summer events in Chicago

• Chicago Air and Water Show: This lakefront spectacle is the country’s largest and oldest free air and water show.
• Chicago Pride Fest and Parade: Celebrate Pride in the country’s oldest official LGBTQ+ neighborhood at this lively fest and parade.
• Bud Billiken Parade: This long-running tradition is the largest African American parade in the United States.
• AVP League Championship: This iconic summer event, held in a stunning lakefront setting, brings top beach volleyball players to Chicago.
• 2026 WNBA All-Star Game: Basketball fans won’t want to miss WNBA All-Star weekend in Chicago, with a fun lineup of events and activations.
• Millennium Park Summer Film Series: Enjoy free movie screenings under the stars in the heart of downtown.

Chicago neighborhood festivals this summer

• Puerto Rican Fest and Parade: This annual parade celebrates Puerto Rican culture and heritage in the Paseo Boricua area of Humboldt Park.
• 57th Street Art Fair: Browse work from over 200 artists at Chicago’s oldest juried art festival, a staple in the Hyde Park neighborhood.
• Chinatown Summer Fair: Immerse yourself in Chinese culture with traditional performances, music, food, art, and more.
• African/Caribbean International Festival of Life: This family festival features music, food, arts, crafts, games, and more in Washington Park.
• Northalsted Market Days: Enjoy dancing, drag divas, live music, and more at one of the largest street festivals in the Midwest.
• Old Town Art Fair: A long-standing Chicago staple, this open-air market has been showcasing artists from all mediums for more than 75 years.

Explore more: Check out our full summer festival guide for even more epic events all season long.

Take a boat cruise

Each summer, Chicago’s many boat cruises set sail on Lake Michigan and the Chicago River. There are tons of different Chicago boat cruise options for a variety of interests, from leisurely dinner cruises to fascinating architecture tours to high-speed thrill rides.

• Hop on an architecture boat cruise to hear the stories behind the city’s iconic architecture and historic buildings.
• Book an elegant dinner cruise on the lake or river for an unforgettable date night experience.
• Grab tickets for an evening fireworks cruise for the best views of Navy Pier’s summer show.
• Rent all types of boats, from small electric vessels to pontoon party boats, on the lake and river.

Explore all your options with our guide to Chicago boat cruises and tours.

Explore the Lakefront Trail

For many Chicagoans, it’s not summer until you’ve hit the Lakefront Trail. This unique pedestrian pathway hugs the shoreline of Lake Michigan for 18 miles, offering simultaneous views of the urban skyline and water that stretches to the horizon.

The trail is a popular place for summer cyclists, walkers, rollerbladers, and runners. Along the way, you’ll discover many of the city’s best parks, museums, waterfront restaurants, beaches, and beyond.

Rent a kayak or paddleboard

If you’re looking to get your heart pumping, don’t miss kayaking in Chicago on the Chicago River and Lake Michigan. You can join a guided tour or rent a kayak to paddle at your own pace — both offer incredible skyline views.

You can also check out paddleboard rentals and classes on the lakefront. For a unique experience on the water, check out Neon Paddle‘s lit-up evening tours featuring motorized paddleboards. Tours depart from Ping Tom Park in the Chinatown neighborhood.

Catch a baseball game

There’s no better place to spend a summer afternoon than one of Chicago’s iconic ballparks. Chicago is one of the few cities that is home to two MLB teams — the Chicago White Sox and the Chicago Cubs.

The Chicago Cubs play their home games at Wrigley Field, one of the oldest and most iconic stadiums in the country. The Chicago White Sox take the field at Rate Field in Bridgeport, where you’ll find tailgating and fireworks displays.

Catch regular season games at both ballparks from April through September.

Find waterfront and rooftop dining

Chicago is home to a wealth of outdoor dining options, whether you want to sip wine on a riverfront patio or enjoy a piña colada with your toes in the sand.

• Check out this outdoor dining guide for some of the best local patios and rooftops
• Want to dine with a lakefront view? Explore beachfront restaurants
• Chicago’s skyline is filled with rooftop bars and restaurants, perfect for cocktails and bites on a sunny afternoon or warm summer evening
• Or discover all the restaurants and bars on the Chicago Riverwalk

Or just stroll through any neighborhood in Chicago, and you’ll have plenty of stellar alfresco spots to choose from.

See a summer museum exhibit

Summer brings a wave of blockbuster museum exhibits to Chicago’s acclaimed cultural institutions. Plus, it’s the perfect way to cool off on a hot summer day.

Check out a few top exhibitions to catch this summer:

• Pokémon Fossil Museum (opens May 22, 2026): This family-friendly interactive exhibition will be making its North American debut at the Field Museum.
• Crafting Character: The Costumes of Paul Tazewell (open through Sept. 7, 2026): This exhibit at the Museum of Science & Industry features the dazzling work of the Oscar-winning costume designer, from Wicked to Hamilton.
• Willem de Kooning Drawing (June 14 – Sept. 20, 2026): Examine the unique drawings of the famed abstract expressionist artist at the Art Institute of Chicago.
• Dancing the Revolution: From Dancehall to Reggaetón (April 14 – Sept. 20, 2026): The Museum of Contemporary Art Chicago hosts this exhibit on dance as a tool of resistance.

Explore more exhibits coming to Chicago museums this summer.

Bring the family to Navy Pier

Navy Pier is one of the city’s most popular summer attractions — and for good reason. There’s something for everyone to enjoy at this historic lakefront spot. Here are just a few of the many things to see and do there:

• Hop on a lakefront cruise, from speedboat rides to sailboat tours
• See the free summer fireworks, held twice a week in the summer
• Take a spin on the 200-foot Centennial Wheel
• Soar above the city in the immersive Flyover Chicago ride
• Check out live music, theatre, dance, and more
• Enjoy the waterfront beer garden or the country’s largest rooftop bar

Check out our guide to Navy Pier for more all-ages fun.

Explore a city park

The Chicago Park District oversees more than 600 parks, with open space in just about every corner of the city. Millennium Park’s Lurie Garden is an urban oasis in the heart of the Loop. Also nearby, you can let the kids climb, skate, and play at the sprawling Maggie Daley Park.

Head to our neighborhoods for even more green space — work up a sweat with a bike ride or jog along The 606, admire the Japanese garden at Jackson Park, and meander down the nature boardwalk at Lincoln Park’s South Pond.

See the best attractions in Chicago at up to 50% savings with CityPASS.

Explore the famous Shedd Aquarium, see scientific discoveries at the Field Museum, take in spectacular views from the Skydeck and more! With two options to choose from and up to 9 days to enjoy, you can't go wrong.

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