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 Chicago beaches

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 enjoy 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.

Explore 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 events. Here are a few of the top festivals 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.
  • Pitchfork Music Festival: Discover up-and-coming acts and touring favorites at this relaxed music fest.
  • Chosen Few Picnic: This laidback festival celebrates Chicago-born house music in Jackson Park.
  • Chicago Jazz Festival: Close out summer with this free festival that brings jazz stars to Chicago’s Millennium Park.

Top summer events in Chicago

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 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.

Catch a neighborhood fest

Paseo Boricua during the annual Puerto Rican parade
Paseo Boricua during the annual Puerto Rican parade. Photo by Adam Alexander.

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.

  • 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.
  • African/Caribbean International Festival Of Life: This family festival features music, food, arts, crafts, games and more in Washington Park.

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.

Enjoy the lakefront on Navy Pier

Navy Pier Shoreline Boats

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.

Watch a movie under the stars

Millennium Park Pritzker Pavilion
Abel Arciniega :: @tequilagraphics

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

Chicago Cubs
Wrigley Field; photo by Matt Alaniz

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.

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 Centerwalking 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

Jazzin at the Shedd

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.