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Top Reasons to Visit Chicago this Summer

There’s nothing quite like summer in Chicago. All season long, you can play beach volleyball on the sandy shores of Lake Michigan, kayak through a skyscraper canyon, sip cocktails from rooftop bars with skyline views — the list goes on and on. Here’s your guide to making the most out of summer in Chicago.

Enjoy the lakefront

Photo by Miguel Ángel Sanz

Chicago is blessed with miles and miles of stunning lakefront beaches. Let the kids run and play at Foster Beach, rent a beachfront cabana at North Avenue Beach, or enjoy the skyline views at Rainbow Beach.

If you’re looking to get active on the water, you can rent a jet ski, kayak, paddleboard, or fly board at Chicago Water Sport Rentals at 31st Street Harbor. Or embark on a kayak tour or paddleboard class with Urban Kayaks at Monroe Harbor.

Check out our guide to Chicago beaches for more.

Dine outside

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

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

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 cruise options for a variety of interests, from leisurely dinner cruises to fascinating architecture tours to high-speed thrill rides.

Hop on a Chicago Architecture Center River Cruise to hear the stories behind the city’s iconic architecture and historic buildings from expert tour guides. Seadog Thrill Ridesbring fast-paced thrills, Wendella offers a classic family-friendly cruise, and City Experiences has elegant dinner cruise options for an unforgettable evening.

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

Attend a summer festival

Festival season is back in Chicago. And it’s not really summer until you check out one of our legendary summer events, ranging from neighborhood block parties showcasing local acts to sprawling outdoor fests with major headlining acts. Here are a few of the top festivals to check out in Chicago this summer:

Check out our full summer festival guide for more.

Get out on the water

Chicago is home to two stunning waterfronts — Lake Michigan, with miles of sandy shoreline, and the Chicago River, a skyscraper canyon through the heart of the city. And both offer plenty of opportunities to get out on the water. You can rent jet skis and paddleboards on the lakefront and kayaks on the river and lake. You can also rent all types of boats, from small electric vessels to pontoon party boats, on the lake and river.

Explore Navy Pier

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

Head to a rooftop

Chicago’s skyline is filled with rooftop bars and restaurants, perfect for cocktails and bites on a sunny afternoon or warm summer evening. One local favorite is LH Rooftop, which wows with some of the city’s best views overlooking the Chicago River. Cindy’s is an iconic spot to admire Millennium Park from above, VU Rooftop offers firepits and skyline vistas, and Cabana Club in Wicker Park is a hip spot to hang out poolside.

Find even more sky-high options with our guide to rooftop bars.

Catch a neighborhood fest

Summer is the perfect time to experience Chicago’s vibrant neighborhoods. You’ll find bustling sidewalk cafes, tucked-away parks, and a full calendar of unique events. Here are just a few neighborhood festivals not to miss this summer.

  • Chicago Pride Fest and Parade: Celebrate Pride in the country’s oldest official LGBTQ+ neighborhood at this lively fest, featuring live music, dance queens, local food, and more.

  • Puerto Rican People’s Parade: This annual parade celebrates Puerto Rican culture and heritage in the Paseo Boricua area of Humboldt Park.

  • Chinatown Summer Fair: Immerse yourself in Chinese culture with traditional performances, music, food, art, and more.

  • Ravenswood On Tap: Sip your way through Ravenswood, one of Chicago’s top craft beer neighborhoods and home to many small craft producers.

  • Old Town Art Fair: A long-standing Old Town staple, this open-air market has been showcasing artists from all mediums for more than 70 years.

  • Hyde Park Summer Fest: Enjoy local beers, food, music, and more at this popular neighborhood festival featuring major headlining acts.

Watch a movie under the stars

The Millennium Park free summer film series is held at the soaring Jay Pritzker Pavilion on Tuesdays from July through August. Guests take a seat at the Pavilion or lounge in the grass on the Great Lawn while both old favorites and new blockbusters are presented on a state-of-the-art, 40-foot LED screen. Bring a blanket, a picnic, and enjoy the show!

You’ll find free events at Millennium Park all summer long, including the popular Grant Park Music Festival, Millennium Park Music Series, morning fitness classes, and more.

Catch a baseball game

There’s no better place to spend a summer afternoon than one of Chicago’s iconic ballparks. The city is home to two MLB teams — the Chicago White Sox and the Chicago Cubs — that play their regular season from April through September. The Chicago Cubs play their home games at Wrigley Field, one of the oldest and most iconic stadiums in the country. And the Chicago White Sox take the field at Guaranteed Rate in Bridgeport, where you’ll find tailgating and fireworks displays.

See a museum exhibit

Pompeii at the Museum of Science and Industry; photo by Jeff Schear Visuals

This summer brings a slate of jaw-dropping exhibits to Chicago. Step inside a lost city, immerse yourself in the works of Mozart, admire Impressionist masterpieces, and more at these exciting limited-time exhibits:

Explore more top museum exhibits coming to Chicago this summer.

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 boardwalk at Lincoln Park’s South Pond.

Join a tour

A tour is one of the best ways to make the most of your Chicago visit. Learn about the city’s iconic architecture with Free Tours by Foot, Inside Chicago Walking Tours, and Chicago Architecture Center walking tours. Or see the city on two wheels via a bike or Segway tour with Bike and Roll Chicago or Bobby’s Bike Hike. You can also explore Chicago’s unique neighborhoods with a friendly local for free through Chicago Greeter.

Fall in love with public art

Public art in Chicago is splashed on surfaces all around the city: it covers train stations, rises tall on downtown skyscrapers, and pops up on sidewalks, in office lobbies, and along the lakefront. Discover works of public art in the Loop by masters such as Picasso and Chagall, check out neighborhood street art, or see international street artists make their mark on districts like the Wabash Arts Corridor. Take a public art tour, or create your own. Either way, get your camera ready, and start Instagramming!

Hear music at a museum

Head to the Shedd Aquarium for Jazzin’ at the Shedd. The evening features live tunes from a top Chicago jazz ensemble, sweeping views of the city skyline, and open access to the Shedd’s many immersive exhibits. End the night with the perfect view of the Navy Pier summer fireworks over the water.

Also held throughout the summer, Tuesdays on the Terrace at the Museum of Contemporary Art offers free live music on the MCA’s scenic terrace. This annual performance series highlights artists from Chicago’s internationally renowned jazz community.


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