Menu

THE SUMMERTIME CHICAGO GUIDE

There's nothing quite like summer in Chicago. If park exploring, rooftop cocktailing, beachfront relaxing and festival jamming are your thing, then Chicago is your city.

Hit the Beach

Shore Club Chicago

Chicago is blessed with miles and miles of sandy lakefront beaches. Build a sandcastle empire at Foster Beach, cool off at trendy Shore Club (where you can reserve a sunbed, daybed, or a signature cabana) at North Avenue Beach, or simply enjoy the view (and catch a beach volleyball game) at Oak Street Beach. 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.

Jam out, outside

Chicago festivals: Riot Fest

The sound of music festivals fill 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 lineups at Lollapalooza and Pitchfork; annual multi-day freebies like the Chicago Blues Festival; and the latest country hits at Windy City Smokeout. Check out our festivals guide for more summer music festivals.

Expedia Summer Deals

Catch a movie under the stars

MILLENNIUM PARK SUMMER FILM SERIES

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.

KEEP YOUR COOL

Crown Fountain Chicago in Millennium Park

Splash around at the interactive 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. 

HEAD TO A ROOFTOP

LH Rooftop ©LondonHouse Chicago

Chicago's skyline is filled with rooftop patios, perfect for cocktails and bites on a sunny afternoon or warm summer's evening. A couple of favorites include Apogee at Dana hotel & spa, as well as LondonHouse Chicago (pictured above), which wows with the city's only 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.

Take a tour

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.

EAT OUTSIDE

City Winery Riverwalk

It's virtually impossible to provide a shortlist of great outdoor dining spots in the city, but we'll try.  Just a few of our many favorites include City Winery Riverwalk (pictured above) and Island Party Hut along the award-winning Chicago Riverwalk; Piccolo Sogno's hidden garden vibes, Caffé Oliva, a breezy Mediterranean-inspired gem on Ohio Street Beach; other riverfront gems like River Roast and swanky steakhouses Smith & Wollensky. Or just stroll through any neighborhood in Chicago, and you'll have plenty of stellar alfresco spots to choose from. Explore more outdoor dining in Chicago.

Hear music at a museum

Jazzin at the shedd

Throughout the summer, the Museum of Contemporary Art hosts Tuesdays on the Terrace, an evening of free music on the MCA's scenic terrace. This annual summer performance series highlights artists from Chicago's internationally renowned jazz community. Or head to the museum campus for Jazzin at the Shedd every Wednesday night. The evening features live tunes from a top Chicago jazz ensemble, sweeping views of the city skyline, and a fireworks display.

FALL IN LOVE WITH PUBLIC ART

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!

Expedia Summer Deals

GET YOUR FEST ON

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 (pictured above), celebrating Chicago's vibrant LGBTQ culture. Also, Chicago hosts a variety of craft beer festivals throughout the year, in support of its burgeoning brewing scene.

EXPLORE A CITY PARK 

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, take in lakefront views and visit the moonscape-like 31st Street Beach Playground, soak in the skyline along the award-winning Chicago Riverwalk. Millennium Park's free Lurie Garden (pictured above) is an urban oasis in the shadow of the Art Institute's Modern Wing.

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

Featured Partners

More Summer Favorites
2 Days Summer Fun for Families
Find things to do in Chicago with kids right here!...
Best Summer Restaurants in Chicago
Find the best restaurants in Chicago for summer...
Chicago Summer Thrills
Take your summer fun in Chicago to the next level...
Free Summer Music Festivals
Summer in Chicago means free epic music and street...
Free Summer Park Activities
Morning yoga, anyone? Movie under the stars?...