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Admire the world's densest skyline on city breaks to Chicago, America's “Second City” and birthplace of the skyscraper.

Chicago's skyscrapers rise abruptly from vast Lake Michigan with the Willis Tower peeping above the city's famous skyline. The top attractions are clustered in The Loop, the historic centre circled by the Chicago River. Sandy beaches backed by a string of parks line the shore.

Best of Chicago city breaks for...

  • Families: Ride the 150ft Ferris wheel on Navy Pier. The endless views will distract the kids from the array of carousels, swings and games lining the pier, but not for long!
  • Active types: Pedal the path behind Chicago's beaches. Pause to swim in the lake and see the skyline's warped reflection in the polished surface of Millennium Park's Cloud Gate sculpture.
  • Shopping: Splash your cash on the Magnificent Mile, a tree-lined avenue that's home to hundreds of shops. Flit between Tiffany & Co, Abercrombie & Fitch and Bloomingdale's, to name a few.