Summer in Chicago: The best things to do

Summer in Chicago means it's street fest season.The city's neighborhoods and parks will be busy thanks to a stacked lineup of fests, fairs and more. You'll find everything from favorites like Taste of Randolph and Wicker Park Fest to the Gold Coast Art Fair and Chalk Howard Street on the calendar from May through September, so start planning your weekends now.

There are few better ways to beat the heat in Chicago than by hitting one of the many sandy beaches along the shores of Lake Michigan. From the North Shore to the South Shore, there are plenty of options to choose from, whether you’re looking for a chill day of sunbathing, want to take in the skyline from a kayak or paddleboard, or love to get competitive with a game of volleyball.

Nothing screams summertime in Chicago like adimiring skyline views with a drink in hand. As the days get warmer, it's time to lean into the season's heat at the best rooftop bars in Chicago. Grab a cocktail at terraces high above the street and atop downtown hotels, or escape to hidden patios and gardens to avoid the crowds.

Chicagoans love to make the most of the warmest months by eating outside. When the weather is pleasant, you can grab a seat on a rooftop restaurant that affords great views of the skyline or on a huge enclosed patio at one of the best pizza spots in the city. Whether you’re looking to soak up the sun in a lively atmosphere or want a chill outdoor bar, you’ll have lots of options.

If you're into live music, there's no better time than summer to catch performances. A countless number of artists, spanning all genres, will be headed to town for the city's various music festivals. From returning favorites like Windy City Smokeout and Summer Smash to heavy hitters such as Lollapalooza and Riot Fest, there's an event for every type of concertgoer.

Sometimes, capping the perfect summer day in Chicago after checking out a street festival involves a movie in one of the city's many beautiful public parks. With free screenings all summer long, there's no better reason to pack up the blankets, lawn chairs and picnic baskets for an evening under the stars. The Chicago Park District's Movies in the Parks series features dozens of different films across neighborhoods from Rogers Park to South Shore, and runs at some top destinations like Belmont Harbor and Osterman Beach. But that's not all—you can also catch free showings outside Wrigley Field at Gallagher Way and during the Millennium Park Summer Film Series.

A river cruise is a great way to get out on the water. But for a more intimate and wondrous experience, you should consider renting a boat or kayak. Businesses along the river and the lakefront will send you floating throughout the city, whether you want to head out on a solo paddle or be the captain of your own yacht. And don't worry if you're a novice—you'll get a quick lesson and tips before you leave the dock.

Alfresco dining is one of the best perks of summer in Chicago. And between the different branches of the Chicago River and Lake Michigan, there are plenty of options for waterfront dining in Chicago—whether you’re looking for high-end seafood establishments, casual pizza spots or even a brewery adjacent to a music venue along the river.

Chicago's motto is "City in a Garden," and our public green spaces live up to such a lofty name. With more than 600 facilities throughout the city, the Chicago Parks District boasts something for everyone. Most importantly, they provide a space to relax and momentarily forget that you're in the middle of a large city filled with people, buildings and cars, so pack a picnic, lay out on the grass and soak up the sun while you can.

As the temperature and humidity tick up, it's the perfect time to cool off by the water. If heading to the lake and enjoying one of Chicago's best beaches isn't your jam, the Chicago Park District offers dozens of public swimming pools all over the city—free of charge. Whether you want serene lap lanes, kid-friendly water playgrounds and slides or just a place to lounge, you'll find it among the best swimming pools in Chicago.

Sure, walks along Michigan Avenue and State Street are nice and rooftop bars offer plenty of pretty sights—but the best way to see downtown Chicago is from the water. Both the Chicago River and Lake Michigan offer unparalleled vantage points for taking in the city’s world-famous architecture and the breathtaking Chicago skyline, with many of the tours providing unique insights into the city’s culture and history. From architecture tours and history lessons to straightforward sightseeing affairs, romantic excursions and pirate-themed family fun, there's a Chicago cruise for every groove.

Ever since it was expanded in 2015, the Chicago Riverwalk has become a popular destination for locals and tourists alike. The waterfront attraction boasts cocktail bars, stunning views of the Chicago skyline and is close to some of the city's best waterfront dining. You can even rent a boat or kayak and cruise down the river!

Summer in Chicago is often a muggy scorcher, making ways to beat the heat all the more important. If you’re looking to cool off with a frozen treat, the city has a huge variety of ice cream shops, ranging from classic institutions that have served generations of families to brand new spots offering creations inspired by Japan, Thailand and Ireland. Just make sure to eat fast before your dessert melts away!

It's easy to overlook the glory that is farmers market season, but that would be a mistake. Check out markets all across the city, from Andersonville to Woodlawn, to find the freshest fruits, veggies, flowers, sweets and more. It's a win-win: You'll be supporting local businesses and getting the highest quality ingredients.

Chicago is a city that loves to bike—no matter the weather. The Lakefront Trail, one of our most celebrated gems that sees millions of foot and cycling traffic each year, is a must for any visitor or Chicagoan. But besides the over 20 miles of lakefront views, there are hundreds of other miles of trails to explore if you're itching to ditch the stoplights and escape the city, Just outside city limits, you’ll find flat, paved paths perfect for training for your next century ride, hilly mountain biking trails that put your skills to the test and routes ideal for taking a walk.

You don’t have to be a marathoner, or signed up for any race at all, in order to go on a long run. Maybe you’re interested in exploring nearby hiking trails, or just want to get some exercise in. No matter what your motivations are, there are plenty of places to go for a lengthy run in and around Chicago, including the Lakefront Trail and the 606.

A fusion of tennis, badminton and table tennis, pickleball is the fastest growing sport in the U.S., and its popularity is especially apparent during the Chicago summer when pairs of players and groups of four can be spotted hustling around the courts throughout the city. Many Chicago parks offer free courts, so bring your own equipment and get your game on!

Chicago is at its best in the summertime. But if you’re ready to soak up the culture of a nearby Midwestern town, there are plenty of destinations just a few hours away from the city by car, including Door County, Galena and Madison. They're filled with rich history, great food and drinks and relaxing waterfronts, and offer the perfect escape from big city life.