By JoAnn Greco
The Windy City may as well give itself a new moniker: the City of Big Festivals. Over the last three decades or so, Chicago has carved out a reputation as a leader in food and music events that draw millions, as well as specialty festivals dedicated to everything from kites to bikes. “What started as a catalyst for enlivening downtown has blossomed into a citywide commitment to bringing populations and communities together,” says Michelle T. Boone, commissioner of the city’s Department of Cultural Affairs and Special Events. “We’ve built a proud legacy of producing high quality—and mostly free—platforms for residents and visitors alike to experience the very best of Chicago arts and culture, along with some really unusual events.”
Bikes to Flights
The event schedule fills as the weather warms. For a family-friendly outing, don’t miss the Chicago Kids and Kites Festival in May. “This event notifies the city that summer is officially here, and that festival season has begun,” Boone says. Spectators enjoy deft displays from sport kites, and kids receive free kits so they can design and build their own creations. The fun is centered at Cricket Hill, near the intersection of Lake Shore Drive and Montrose Avenue, and comes complete with food vendors, face-painters and balloon artists.
In June, Bike Week gets in gear with seven days of tooling around on two wheels that culminates when thousands participate in the Bike to Work Rally. Visitors to town will want to take advantage of the city’s bike share program, Divvy.
A 24-hour pass is just $7 and allows for unlimited 30-minute trips—the timer resets whenever a bike is docked at one of the hundreds of stations located around the city.
One of the oldest events in the city, the Chicago Air & Water Show, takes off in August. It was first held in 1959 when the Lake Shore Park department used a budget of just $88 to assemble a program that included water skiers, diving competitions and even a rescue demonstration.
Today, the two-day event has morphed into the largest free show of its kind in the nation. It attracts more than 2 million visitors each year, who come to gasp and cheer for an array of daredevil stunts and jaw-dropping maneuvers.
For a jump on the proceedings, book Friday lunch at the Signature Room, located on the 95th floor of the John Hancock Center, to enjoy a bird’s-eye view as flyers, gliders and paratroopers rehearse before the weekend kicks off.
Chicago and music go together like blues icon Muddy Waters and his Telecaster guitar. The first Chicago Blues Festival, held in 1984, celebrated Waters’ memory. This year, more than half a million fans will head to Grant Park in June for the festival, which is the largest free event devoted to the genre in the world.
“Chicago has long been a mecca for blues musicians,” Boone says. “So of course people from all over the world make a pilgrimage here to be a part of this celebration.” Previous performers have included musicians Ray Charles and B.B. King.
While the blues are most identified with the city’s legacy of musical innovation, Chicago’s festival scene shines a spotlight on other genres, too. The music marathon kicks off late May with the Chicago Gospel Music Festival, marking its 30th year. The weekend event offers a lineup of inspirational local, national and international talent. Last year an appearance by Grammy Award-winner Tye Tribbett, who has performed with everyone from Elton John to Gloria Estefan, drew rave reviews.
The wail of a saxophone can be heard during one of the final music events of the summer, when Labor Day weekend brings the Chicago Jazz Festival to Millennium Park and the Cultural Center. Programmed by the Jazz Institute of Chicago, former events have showcased acts like the Sun Ra Arkestra and Ari Brown Quintet.
While many of Chicago’s music festivals are centered on specific genres, Lollapalooza offers a refreshing variety: Last year’s headliners included hip-hop duo Outkast and alternative rock band Kings of Leon. The event’s roots date to the early 1990s when it was established as a touring festival; in 2005 it became an annual destination event for the Windy City. This year it takes place in Grant Park from July 31 through Aug. 2.
Lollapalooza has an increasingly large emphasis on food—a move that makes sense, according to celebrity chef Graham Elliot, who works with the festival. “Chicago has long been on the forefront of the music scene,” he says. “And we’ve [become] one of the most exciting food cities in America.”
In fact, this May, the James Beard Foundation will leave New York for the first time to host its Awards Gala in Chicago, an exciting acknowledgment that this city of avant-garde chefs and roughly two dozen Michelin-starred restaurants has long surpassed its reputation as a haven for brats and beer.
Elliot has helped boost the city’s culinary cred by curating the best local food and drinks and introducing them to the masses at Lollapalooza. “We try to find restaurants that are Chicago-based and have the same independent spirit as the bands playing the festival,” he says. Last year, Eminem and the Arctic Monkeys headlined against a Grant Park backdrop that included the Elliot-curated Chow Town, loaded with new and classic takes on Chicago street food.
The granddaddy of food fests, Taste of Chicago, also takes place in Grant Park, bringing together some 3 million visitors over the span of five days in July. The festival has been held every summer since 1980. Vendors skew toward the city’s casual eateries, and last year there was also a good contingent of pop-up restaurants and food trucks.
Chicago Gourmet, a relative newcomer presented by Bon Appétit, highlights the tonier aspects of Chi-Town dining. The festival takes place in late September in Millennium Park and features cooking demonstrations, tastings and book signings from world-renown chefs, as well as vintners and sommeliers.
Food also plays a central role in the dozens of neighborhood street fairs that occur during the Chicago summer. Some—such as Roscoe Village Burger Fest, SausageFest and Ribfest—emphasize specific cuisines, while others, like the various mini “Taste ofs” (Randolph Street, River North, Lakeview) highlight local restaurants. Wrigleyville Summerfest features a little of everything, including food, music and family activities, as does Wicker Park Fest.
For cultural immersions that offer insight into Chicago’s diverse populaces, try Fiesta del Sol, Chicago Korean Festival, Festa Italiana, Chinatown Summer Fair or the African/Caribbean International Festival of Life.
“These festivals help brand their communities,” says Molly Huber, special events coordinator for the Wicker Park and Bucktown Chamber of Commerce. “They introduce thousands of visitors and residents to the small businesses, local artists, history and architecture that make Chicago a city of neighborhoods.”
Just because Chicagoans spend much of the warm weather months grooving and grazing doesn’t mean they neglect the other arts. The late spring, before the lazy, crazy days of summer get underway, is a great time to sample the city’s bounty of theaters and museums.
Starting on St. Patrick’s Day and running through early June, for example, the Art Institute of Chicago’s “Ireland: Crossroads of Art and Design, 1690–1840” offers an eye-opening look at a subject that resonates with the town’s deep Irish roots. Another design exhibit, “Chicago Styled: Fashioning The Magnificent Mile,” at the Chicago History Museum, focuses on the emergence of the city’s celebrated shopping district, drawing from the museum’s extensive costume holdings.
Starting late March, the Goodman Theatre offers some comic relief with “The Upstairs Concierge,” a spoof of today’s celebrity culture by Pulitzer Prize finalist Kristoffer Diaz. Then in April, Lyric Opera of Chicago begins its limited engagement production of “Carousel,” featuring favorite tunes such as “June is Bustin’ Out All Over.”
Loews Chicago Hotel: Opened in March, one of the newest additions to the Loews portfolio is located one block north of the Chicago River. Its 400 luxury rooms feature spectacular views of the city and the lake.
Loews Chicago O’Hare Hotel: With everything from a curated art gallery to more than 50,000 square feet of meeting space, as well as 556 rooms and 60 suites, this property is only a five-minute ride from the airport.
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