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Jetsetter Guides

What’s On in Chicago

After a long, chilly winter, Chicagoans are shedding their puffy coats and welcoming the summer season and its stellar line up of fair weather activities. Lisa Lubin shares the top ten city events to hit this sunny season

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Take a Ride

Chicago is now one of the best cities for biking in the U.S., with more than 200 miles of bike lanes, as well as the nearly 20-mile-long lakefront route. The city’s lack of hills comes in handy, too. Join in group rides like Bike the Drive on May 25 when all of busy Lake Shore Drive is closed to cars, or cruise the neighborhoods ‘til sunrise on the LATE Ride from June 21 -22, which starts after midnight and gives you the chance to see the sun rise over the Michigan as you ride. No wheels? No problem. Visitors and locals can rent one of the 3,000 Divvy blue bikes available at 300 stations throughout the city.

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Raise the Roof

This city is known for its skyscrapers and stunning architecture. Get a bird’s eye view while sipping a cocktail at one of the many rooftop bars across the city. Our favorites? The revamped Vertigo Sky Lounge atop the Dana Hotel, swanky ROOF at the Wit in the heart of the Loop, the Terrace at Trump with its amazing views of the Chicago River and Wrigley Clock Tower, or the city’s largest indoor/outdoor rooftop lounge, I/O Roofscape, at the new Godfrey Hotel. And new for 2014 is the John Hancock Center’s own unique viewing platform, TILT — a glass and steel platform that hangs from the side of the building 1,000 feet above the Magnificent Mile.

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Get Dancing Outdoors

The largest annual outdoor dancing series in the country returns for another year of jumpin’, jivin’ and waltzing. The Spirit of Music Garden in Grant Park turns into an outdoor dance club four nights each week with 44 different live bands. Come an hour early for the free dance lessons, then stay and enjoy the music and try out your new moves. From swing, to the waltz, to salsa, it’s like Dancing with the Stars with a better setting.

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Celebrate 10 Years of Millennium Park

With 25 acres of landscaped gardens, trailblazing architecture and iconic displays of public art, Millennium Park has been one of the city’s top attractions for a decade. Celebrate the 10-year milestone at one of the free summer concerts at the Frank Gehry–designed Pritzker Pavilion, or listen to classical music under the stars during the Grant Park Music Festival, now in its 80th year. For the younger crowd, Downtown Sound delivers an eclectic mix of cutting-edge indie rock, pop and rock concerts for free every Monday night. And after all the after-dark revelry, return to the park on Saturday morning for a free workout on the Great Lawn. There’s a class for everyone from Tai Chi and Yoga, to Pilates and Zumba.

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Dine Alfresco

From five-star Michelin spots to down-home corner dives, there’s no shortage of good grub in this city. During the summer, diners spill onto sidewalk cafes, back patios and roof gardens of hipster joints like Big Star and Frontier, or classics like Moody’s Pub and Sheffield’s, but for time-poor visitors, the city’s myriad food festivals let you sample a raft of local favorites in one tasty shot. The granddaddy of them all is the annual Taste of Chicago (July 9 – 13), a gluttonous week-long affair that gets packed with food stalls, music acts and droves of foodie fans. For something a bit more refined, hit up Chicago Gourmet in Millennium Park in September. Presented by Bon Appétit, this a celebration of food and wine showcases more than 150 of Chicago’s finest restaurants and chefs. Other neighborhood fests like the Taste of Randolph and the Taste of River North are back, as well as the newer Chicago Food Social, which is a gathering of several of Chicago’s most popular food trucks and chef-driven restaurants with live music and hands-on demos.

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Hit the Music Fests

Into Blues? Jazz? Local bands? Chicago hosts dozens of music festivals over the summer, from Chicago Blues Festival (free; June 13-15) with performances this year by Bettye LaVette and New Orleans bluesmen Aaron Neville and Dr. John, to Pitchfork Music Fest (July 18-20), a three-day music juggernaut of alternative rock, rap, hip-hop and dance music. Most famous of all is Lollapalooza (August 1-3), a world-class fest that takes over Grant Park with eight stages and over 130 music acts, including headliners Outkast, Eminem, Lorde and Kings of Leon. Neighborhood fests also abound every weekend, including Andersonville’s homage to Sweden: Midsommarfest (June 6-8), and the Old Town Art Fair which celebrates its 65th year this June on the charming, tree-lined streets of the historic Old Town Triangle District with 250 nationally acclaimed artists and an estimated 50,000 art lovers.

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Get on the Water

In addition to Lake Michigan in its front yard, Chicago has a river running right through the center. For one of the best views of the city, take the Chicago Architecture Foundation’s boat tour on the Chicago River. Volunteer tour guides interpret more than 50 buildings along the river, revealing how the city grew from a small backcountry outpost to one of the world’s most important crossroads in less than 100 years. Nowadays, you can also captain your own electric boat, or kayak right on the river under towering skyscrapers. Get out on the famed lake on one of the many boats docked along Navy Pier for everything from an elegant dinner cruise to a thrilling speedboat ride. And of course, don’t miss the huge fireworks display off Navy Pier on Independence Day and every single Wednesday and Saturday night all summer long.

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Ravinia Festival

A favorite summer activity among locals, Ravinia is billed as America’s oldest outdoor music festival. About 20 miles north of the city in Highland Park, it’s been the summer home to the Chicago Symphony Orchestra since 1936. Join friends for a picnic on the grass under the big, illuminated trees and enjoy some of the best musical acts around. Highlights this summer include John Legend in acoustic mode (June 16); the Script, opening for One Republic (June 18-19); James Taylor (June 26-27); Sarah McLachlan (July 5); Matt Nathanson, opening for Gavin DeGraw (July 21); Train (Aug. 22-23); Carrie Underwood (Sept. 6-7); and John Mayer (Sept. 20).

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Movies in the Park

A new addition in 2013, free film nights return to Millennium Park for this summer season. Kicking off every Tuesday evenings at dusk, classic and contemporary flicks are projected onto enormous screens over the Great Lawn. For serious movie buffs, the 14th annual Movies in the Parks series kicks off in June with more than 175 screenings of current and classic movies in parks across the city. And brand new this summer is the First Annual Chicago On-Screen Local Film Showcase. Filmmakers of all ages and skill levels submitted work filmed in, featuring, or inspired by Chicago. The winning flicks will be screened, if possible, in the same neighborhoods where they were made.

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See Wrigley Field Turn 100

Even if the Cubs don’t make it to the World Series this year, don’t miss a trip to Wrigley Field as it celebrates its 100th birthday. Each of the decade-themed home stands features retro food, throwback uniforms and giveaways honoring legendary Cubs like Ernie Banks. After the game, stick around the famous Wrigleyville neighborhood and sink some suds in classic bars like Cubby Bear and Murphy’s Bleachers, or take a seat at one of many outdoor beer gardens and enjoy some of the best people watching in Chi-Town.