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Chicago Must-Dos

Our experts recommend the top attractions in and around Chicago—with advice on how to get the most out of your visit.

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Longtime resident and oral historian Studs Terkel looks over his beloved city of Chicago.

The Art Institute of Chicago

The city’s premier art museum; renowned Impressionist collection; expansion under construction. Good people-watching from the front steps. Tip: “A hidden nook is the Thorne Miniature Rooms with 40 miniature dollhouse rooms done in different architectural styles of past 300 years.”—Elizabeth Blackwell, author, Frommer’s Chicago. 111 S. Michigan Avenue; tel. 1 312 443 3600; fee.

Chicago Architecture Foundation River Cruise

Popular river cruise showcases architecture; knowledgeable docents narrate. “Skyscrapers surround you like giant chess pieces”—Blair Kamin, architecture critic, Chicago Tribune. Reservations recommended. Tip: On weekends book before noon; check-out time at local hotels is when the crowds surge. Michigan Avenue Bridge at Wacker Drive; tel. 1 312 922 3432; fee.

Frank Lloyd Wright Home & Studio

Prairie style founder Wright lived and worked out seminal ideas in this suburban Oak Park compound, 1889-1909. Self-guided audio tour to Wright residences nearby in design-rich neighborhood. “A whole gallery of Wright masterpieces within a quarter mile.”—Blair Kamin. 951 Chicago Avenue; tel. 1 708 848 1978; fee.

Lake Michigan shore

Twenty-nine miles of lakefront skirted by 18.5-mile recreational path, many beaches. Popular with runners, walkers, skaters, and bikers; rentals available at Navy Pier. “Farther north, Uptown is one of the most diverse neighborhoods in the U.S., maybe the world.”—Ben Hollis, former TV host and co-creator, Wild Chicago. Heavy traffic between Navy Pier and North Avenue. Tip: Bike ride south for open paths, skyline views on return.

Millennium Park

Fusion of gardens, modern art, and architecture in a 2004-opened, 24.5-acre downtown plot. Frank Gehry stage and bridge; video screen fountain draws waders and families; reflective “Cloud Gate” sculpture by Anish Kapoor, aka “The Bean,” is the biggest magnet. “The place to see contemporary architecture and public sculpture in Chicago.”—Blair Kamin. Michigan Avenue at Randolph Street; tel. 1 312 742 1168.

Museum of Science and Industry

Vast science center; highlights include reproduction coal mine, German submarine model, historic trains, IMAX theater, and other interactive exhibits. Tip: Order tickets online to skip long admission lines. 57th Street and Lake Shore Drive; tel. 1 773 684 1414; fee.

Navy Pier

Recreational pier juts into Lake Michigan. Host to boat tours, Chicago Children’s Museum, Chicago Shakespeare Theater, amusement rides, beer garden, and more. Beware the expense. “Navy Pier is always $100 day, at least.”—Lisbeth Levine, contributing editor, InStyle. Good views of city, free. Tip: “Peek into the ballroom; elegant and original.”—Ben Hollis. Fees at some attractions. 600 E. Grand Avenue; 1 312 595 7437.

John G. Shedd Aquarium

Popular lakefront aquarium with 1,000-seat amphitheater for dolphin shows. Large shark exhibit with more than two dozen sharks in a 400,000-gallon (1,514-liter) habitat. Exhibits stress conservation. Tip: Arrive before 11 a.m. in summer or expect the company of tantrum-throwers in long lines. 1200 S. Lake Shore Dr.; tel. 1 312 939 2438; fee.

The Field Museum

Natural history museum with permanent exhibits on paleontology, world cultures, animal biology, earth science. Traveling shows tend toward blockbuster topics like King Tutankhamen. Main hall showcases the world’s most complete T-Rex, Sue. Tip: Avoid during public school holidays when jammed with families. 1400 S. Lake Shore Dr.; tel. 1 312 922 9410.

The “L”

Elevated trains overlook the city; the Brown Line is especially scenic. “You ride up in the air and get this great elevated view of Chicago.”—Peter Sagal, Chicago NPR radio host. Tip: Loop The Loop, cross the river, and then disembark for the return trip on a southbound train without paying twice. Fee.

Wrigley Field

Historic 1914 baseball stadium considered one of the last intimate parks. Home field of the Chicago Cubs; within the lively residential Wrigleyville neighborhood. High demand for game tickets. Tip: “Take the behind-the-scenes tour to see the locker rooms and press box.”—Elizabeth Blackwell. 1060 West Addison Street; 1 773 404 2827; fee.

Pullman Historic District

Far South Side neighborhood built by maker of railroad passenger sleeper cars as company town, 1880-1884. Tip: “Go on a weekend when people who live in the historic houses are out and willing to chat.”—Margaret Littman, author, The Little Black Book of Chicago. 11141 S. Cottage Grove Avenue; tel. 1 773 785 8901; fee for some tours.

Brookfield Zoo

Great Bear Wilderness opened in 2010 and is the largest exhibit ever built at the zoo, offering up-close encounters with iconic North American wildlife, including polar bears, Mexican gray wolves, and bald eagles. Tip: Keep your eyes open for 38 poems artistically installed around the exhibit through a variety of media—carved into wood, sandblasted into rock, and even digitally printed on translucent Plexiglas. 8400 West 31st Street, Brookfield; +1 708 688 8000; fee.

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