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Walk the “Magnificent Mile” on North Michigan Avenue at night.
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An architecture cruise on the Chicago River.
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Deep dish pizza at Uno’s—where the famous Chicago-style pizza was invented.
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“The Bean” sculpture in Millennium Park.
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Navy Pier.
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The view of Lake Michigan and the Chicago Skyline from the top of the John Hancock Building.
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The Second City Comedy Club—where Eddie Murphy, John Belushi, John Candy, Chris Farley, Tina Fey, Steve Carrell , Mike Myers, Amy Poehler, Bill Murray, and Dan Akroyd launched their careers.
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Wrigley Field’s ivy covered walls at the second-oldest major league ballpark in the country (and home to the The Chicago Cubs).
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Water Tower Place—the vertical shopping mall across from the stone-clad Chicago Water Tower –one of the few structures to survive The Great Chicago Fire of 1871, that burned for two whole days (Fun Fact: Mrs. O’Leary’s cow had nothing to do with starting the fire).
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Garrett’s Popcorn. Be prepared to stand in line out the door for the warm, buttery caramel corn that is second to none!
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