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Chicago Itineraries
- Art & Architecture
- Shopping & Culture
- Big Hits In The Big City
Chicago has been the setting for numerous blockbuster films, from Ferris Bueller's Day Off to My Best Friend's Wedding, thanks to its bustling Midwestern city appeal and classic downtown architecture. Check out some Windy City movie landmarks as you discover the glamour of Chicago.
Day 1
Start your day at the renowned Art Institute of Chicago, where a trio of wise-cracking high school buddies hung out in Ferris Bueller's Day Off. This world-class art museum is known for its rare master works, including an impressive collection of French Impressionist paintings. The nearby Millennium Park is the city's 24.5-acre showplace for the arts. Stroll the grounds and discover the reflective Cloud Gate sculpture, the multimedia Crown Fountain, and the Frank Gehry-designed Jay Pritzker Pavilion, a stunning outdoor performance venue. In the winter, Millennium Park's outdoor dining area is converted into an ice rink, as featured in The Weather Man and Derailed. Get a panoramic view of Chicago from the Sears Tower Skydeck, located atop the tallest building in the United States. Multi-language kiosks highlight city landmarks and high-powered telescopes offer amazing close-up views. The Skydeck was yet another spot visited in Ferris Bueller's Day Off. In the evening, sit back and listen to some of the best jazz and cabaret music in the city at the Green Mill Jazz Club, one of the locations for the hit film High Fidelity.
Day 2
The Field's classic museum setting made it a perfect locale for the films The Relic and She's Having a Baby. In the summer, catch one of Chicago's two baseball teams in action. The World Champion Chicago White Sox play on the South Side of town at U.S. Cellular Field, one of the many Chicago spots featured in the blockbuster My Best Friend's Wedding. The North Side Chicago Cubs call historic Wrigley Field home. The ballpark has been the backdrop for many successful films, including the Babe Ruth biopic The Babe, Ferris Bueller's Day Off (no surprise there) and The Break-Up. Stop in for a pint at Emmit's Irish Pub in the West Loop. This atmospheric corner bar was seen on film in Ocean's Eleven. In the evening, see a play at the esteemed Steppenwolf Theatre, whose ensemble performers include superstars Gary Sinise and John Malkovich.
Day 3
Chicago's signature elevated (El) train has been seen in countless movies, including in the famous make-out scene in Risky Business, in While You Were Sleeping, in one of the many thrilling chases featured in The Fugitive, and in a fight scene (with the Chicago "El" disguised as the New York City subway) in Spider-Man 2. Take an "El" adventure of your own on the Loop Tour Train with a guide from the Chicago Architecture Foundation. During the free 40-minute tour, you'll learn about the history behind some of the Loop's most interesting buildings. While in the Loop, head over to the landmark Chicago Union Station. Designed by legendary architect Daniel Burnham in the 1920s, the stunning train station features pink marble floors, 40-foot-tall Corinthian columns and a 300-foot-long barrel vaulted atrium ceiling. Union Station has been used as a dramatic setting for The Untouchables and Derailed. Daley Plaza, located in the heart of the Loop at Washington and Dearborn streets (you can't miss the towering Picasso sculpture), has been the site of many film shoots. Perhaps the most memorable was The Blues Brothers car chase that ended up with the Bluesmobile crashing into the Daley Center building. Board a Chicago's First Lady/Chicago's Little Lady boat cruise and you may be swept up by the romance of the river, just like the characters who did a top-deck slow dance in My Best Friend's Wedding. You'll glide past buildings of architectural note that have appeared in several films, including the Wrigley Building (Road to Perdition, The Fugitive and Mercury Rising), Tribune Tower (The Whole Nine Yards) and Marina Towers (from which a car plunged into the Chicago River in The Hunter).
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