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5 Chicago Festivals to Plan a Trip Around

Kit Bernardi

Chicago has more than 400 festivals every year, many of them free and some among the world's largest cultural events. So how do you choose which to plan a visit around?

"Our festivals are great opportunities to experience Chicago's diversity and neighborhoods like a local," says Rebecca Starodub, concierge at the Radisson Blu Aqua Hotel Chicago. "You'll always discover something new and unexpected, even if you live here."

For the best fests, U.S. News asked Chicago hotel concierges about their personal favorites and insider tips to enjoy them.

Chicago Blues Festival

The 319-acre Grant Park is Chicago's festival epicenter, staging multiple summer blockbusters, including the Gospel Music and Jazz festivals, Taste of Chicago and Lollapalooza, against the stunning backdrop of landmark skyscrapers and Lake Michigan.

[Read: When to Visit Chicago.]

But the granddaddy of them all is the Chicago Blues Festival, the world's largest free Blues concert event, drawing 500,000 attendees from around the world to rock around five stages for three days in June. Headliner artists have included Ray Charles, B.B. King, Bonnie Raitt and Chicago's very own Buddy Guy.

Tim Batchelder, head concierge at The Talbott Hotel, says, "This is my No. 1 festival I've attended for over 20 years where I've made friends from elsewhere and we get together at the fest annually."

Kristen Klus, head concierge at the Four Seasons Hotel Chicago, says, "For any of the major Grant Park festivals, have an all-day game plan. Make reservations for lunch at a causal place nearby, which guarantees an hour of air conditioning and an alternative to a port-a-potty restroom."

Chicago Gourmet

This uber-foodie festival pairs 14,000 grazing attendees with Chicago and international epicurean stars dishing James Beard Foundation Award-winning food, wines, beers, spirits and gastronomic know-how over a September weekend in Millennium Park. More than 178 culinary exhibitors and 253 chefs participate in the luxe, adult-only Chicago Gourmet event. Headliner chefs include Chicago award-winning celebrity chefs Rick Bayless, Stephanie Izard, Tony Mantuano and Jimmy Bannos Jr., plus guest rock-star chefs Richard Sandoval, Todd English and Lorena Garcia.

Guests graze on hors d'oeurves-sized bites and petite beverage pours prepared fresh in elegant tents surrounding the green. Admission also covers cooking demonstrations, mixologist cocktail crafting sessions, sommelier-led wine seminars and culinary critic talks (Bon Appetit magazine is the fest's title sponsor). The exclusive Grand Cru wine event and popular Hamburger Hop cost extra.

The event's efficient app helps attendees navigate all the enticing offerings and keeps a record of fave restaurants for future Chicago dining.

[Read: 9 Can't-Miss Museums in Chicago.]

Windy City Smokeout

Nothing says summer more than barbecue. Just add big-hit country music acts such as Billy Currington, Old Dominion and Maren Morris to the secret sauce, and Chicago proudly serves up the Midwest's best smokin' meat and music fest: Windy City Smokeout. More than 15 award-winning Chicago and champion pit masters from across the country fire up their smokers in the River North neighborhood for 40,000 fans over a July weekend. Standby visiting pit masters include Myron Mixon, Memphis Barbecue Co., Pappy's Smokehouse and The Salt Lick BBQ. It's hog heaven for finger-lickin' festivalgoers lining up at the red-checker tableclothed tasting tents for pulled pork, brisket, wings, baked beans, roasted corn and more than 20 craft beers from both sides of the Mason-Dixon Line.

Klus says, "Purchase the three-day festival pass for in-out privileges, and order the smallest option at each booth so you can try all of the offerings." Forgot to go country? "Don't worry," Klus says. "You can buy a hat and boots there."

The Magnificent Mile Lights Festival

For more than 25 years, Santa Claus has come to town the Saturday before Thanksgiving for the Magnificent Mile Lights Festival. During the country's largest evening holiday parade, the stretch of Michigan Avenue known as the Magnificent Mile is illuminated by more than 1 million twinkling lights and a fireworks display. The festive procession of 40 floats, character balloons and marching bands is led by Mickey Mouse, Minnie and their friends. They magically light more than 250 trees as they pass. Nationally acclaimed musicians, dance bands and theater troupes perform on the floats. Through the weekend at the Lights Festival Lane pavilion, families enjoy crafts, snacks and winter wonderland photo ops with Santa while he hears little ones' wish lists in his cozy chalet.

Karen Giobbia, head concierge at the Park Hyatt Chicago, says, "Warm up at our NoMI Lounge's deluxe Hot Chocolate Bar overlooking Michigan Avenue. Some guests even book a room to watch the parade."

[Read: The Best Things to Do in Chicago.]

Old Town Art Fair

For more than 65 years, Chicago's historic Old Town Triangle District has hosted one of the nation's top juried outdoor art fairs run by hundreds of volunteers. The second full weekend in June, the quaint neighborhood's quiet leafy streets swell with 30,000 attendees wandering among booths displaying 250 nationally acclaimed artists' works, including paintings, sculptures, ceramics, glass, fiber, jewelry and mixed media. Every year, half of the artists are new talent. More than 50 neighborhood residents participate in the self-guided urban garden walk. A full day of creative fun includes live music, food and family crafts.

"Every year I go to enjoy the festive atmosphere, food, drink and fine art scene," says Ben Nelson, concierge at the Chicago Athletic Association hotel, where behind the front desk hangs a painting of the city's L train tracks by long-standing Old Town Art Fair artist and Chicagoan Chuck Meyers.

To experience more of what Chicago has to offer, check out the U.S. News Travel Guide.



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