Chicago basically has two seasons. Fortunately, one of the two is summer!

If park exploring, rooftop cocktailing, beachfront relaxing and festival jamming are your thing, then Chicago is your city.


Shore Club Chicago


Chicago is blessed with miles and miles of lakefront beaches. Build a sandcastle empire at Foster Beach, cool off at The Oasis at Shore Club (where you can reserve a sunbed, daybed, or a signature cabana) at North Avenue Beach (pictured above), or simply enjoy the view (and catch a beach volleyball game) at Oak Street Beach while having lunch and a cocktail at the cafe. If you're a bit of a thrill-seeker, you can rent a jet ski, kayak, paddleboard or fly board at Chicago Water Sport Rentals at 31st Street Harbor. Soak up the sun, enjoy the scenery, and get some thrills!

Chicago festivals: Riot Fest


The sound of music festivals and concerts fills Chicago in the summer. Find a welcoming patch of grass and enjoy the free concert season at Jay Pritzker Pavilion in Millennium Park. Or slather on the sunscreen and take part in one of the city's mega summer music festivals, such as the all-star LollapaloozaRiot Fest and Pitchfork; family-friendly folk concerts at Square Roots Festival; annual multi-day freebie like the Chicago Blues Festival; and the rollicking country jam of Windy City Smokeout. Check out our Festivals Guide for more.



On Tuesdays from June till August, the Millennium Park free Summer Film Series is screened under the stars at the iconic Jay Pritzker Pavilion. Guests take a seat at the Pavilion or lounge on the Great Lawn with a picnic as both favorite and avant-garde movies are presented on a state-of- the-art, 40-foot LED screen.

Crown Fountain Chicago in Millennium Park


Cool down in the spraying water of interactive video sculpture Crown Fountain in Millennium Park (pictured above). Or take the family on a water-skimming Seadog Speedboat Sightseeing tour. See the sights along Navy Pier, where you can duck inside the Chicago Children's MuseumChicago Shakespeare Theater, and numerous air-conditioned bars and restaurants. 


Save up to 45% on admission to over 25 top Chicago attractions with Go Chicago Card. Choose the number of days you wish to use the pass from 1, 2, 3, or 5 calendar days in a row and enjoy exploring Chicago’s best sights. Visit top attractions like the Shedd Aquarium, Shoreline Architecture River Cruise, 360 Chicago and more. Passes must be used within a year of purchase and are activated once you visit your first attraction.  



Chicago's skyline boasts several new rooftop patios, perfect for cocktailing and dining on a sunny afternoon or warm summer's evening. A couple of favorites include Apogee at Dana hotel & spa (pictured above), as well as LondonHouse Chicago, which wows with the city's first tri-level rooftop lounge overlooking the Chicago River. Set in a 1920s-era Art Deco skyscraper, Aire at the Hyatt Centric The Loop Chicago mixes urban rooftop lounging with handcrafted cocktails and open-air panoramic views, while the Renaissance Chicago Downtown Hotel's Raised Bar offers fire pits, seating for 160, and 14 local beers on tap.

Segway Tour Buckingham Fountain


Hop aboard a Chicago Architecture Foundation Center River Cruise  Aboard Chicago’s First Lady to soak up the sun while learning about the city's historic buildings — just one of many tour boat options. Immerse yourself in neighborhood culinary treats by taking a walking Tastebud Food Tour of Old Town. Or see the city on two wheels via a bike or Segway tour with Bike and Roll Chicago or Bobby's Bike Hike. Find more tours here.

Piccolo Sogno Chicago


It's virtually impossible to provide a shortlist of great outdoor dining spots in the city, but we'll try. Piccolo Sogno (pictured above) is one of the city's favorite Italian eateries, and its patio is an absolute delight day or night. Just a few of our many other favorites include City Winery RiverwalkFulton's on the River and O'Briens Riverwalk Cafe along the award-winning Chicago Riverwalk; Caffé Oliva, a breezy Mediterranean-inspired gem nestled off Ohio Street Beach; and other beachfront eateries, including Bridge House Tavern and swanky steakhouses Smith & Wollensky and Chicago Cut. Truly, though, stroll any sidewalk in any neighborhood in Chicago, and you'll be spoiled for choices when it comes to dining outdoors. Search for restaurants here.

Tuesdays on the Terrace


Throughout the summer, the Museum of Contemporary Art hosts Tuesdays on the Terrace, an evening of free music on the MCA's Anne and John Kern Terrace Garden, This annual summer performance series highlights artists from Chicago's internationally renowned jazz community. Visit the MCA Calendar for the current schedule of performances.

Loop Picasso


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 by masters such as Picasso and Chagall, 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!

Pride Parade 2013-2


Summer weekends in Chicago are brimming with street fairs and festivals. Just about every neighborhood hosts one, and you'll be guaranteed to find stand-out food and drink while you're there. Some highlights: Ribfest in North Center, where you can sample dozens of different barbecued ribs; Taste of Chicago, which spotlights the city's world-class restaurant scene; the Renegade Craft Fair, which takes over Division Street with wares from hundreds of artisans; and Pride Fest, celebrating Chicago's vibrant LGBTQ culture (pictured above). Also, Chicago hosts a variety of craft beer festivals throughout the year, in support of its burgeoning brewing scene.

Lurie Garden


The Chicago Park District oversees 580 parks, with something for just about everyone. Let the kids climb like monkeys at the sprawling Maggie Daley Park, work up a sweat with a bike ride or jog along The 606 or take in lakefront views and visit the moonscape-like 31st Street Beach Playground. Grab a picnic blanket and find a spot near Dorothy in Oz Park or find skyline magnificence along the award-winning Chicago Riverwalk. Feeling active? Grab your skateboard, rollerblades or BMX bike and head to the Skate Park in Grant Park. A Green space definitely worth the visit is Millennium Park's free Lurie Garden (pictured above), an urban oasis blending symbolism, landscape design and ecological sensitivity in the shadow of the Art Institute's Modern Wing. Each Thursday, Friday, and Sunday from May through September, visitors enjoy guided walks, highlighting elements of the garden’s design and plant life.

Photos courtesy Choose Chicago, Adam Alexander, Clayton Hauck, Ranvestel Photographic

Related Listings

Navy Pier
600 E. Grand Ave.
Chicago, IL 60611
(312) 595-5300

Chicago Children's Museum
700 E. Grand Ave.
Chicago, IL 60611
(312) 527-1000

Renaissance Chicago Downtown Hotel
One W. Wacker Dr.
Chicago, IL 60601
(312) 372-7200

Chicago Water Sport Rentals at 31st Street Harbor
3155 S. Lake Shore Dr.
Chicago, IL 60653
(312) 924-7994

Hyatt Centric The Loop Chicago
100 W. Monroe St.
Chicago, IL 60603
(312) 236-1234

Maggie Daley Park
337 E. Randolph St.
Chicago, IL 60601
(312) 742-3918

LondonHouse Chicago, Curio Collection by Hilton
85 E. Wacker Dr.
Chicago, IL 60601
(312) 357-1200

Millennium Park
201 E. Randolph St.
Chicago, IL 60601
(312) 744-6050

Seadog Cruises
Navy Pier
Chicago, IL 60611
(888) 345-3880

Chicago Architecture Center
224 S. Michigan Ave.
Chicago, IL 60604
(312) 922-3432

Chicago Shakespeare Theater
800 E. Grand Ave.
Chicago, IL 60611
(312) 595-5600

Bike and Roll Chicago
239 E. Randolph St.
Chicago, IL 60601
(312) 729-1000

Chicago Riverwalk
376 N. Michigan Ave.
Chicago, IL 60601

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