Chicago Holidays

Sitting on the edge of impressive Lake Michigan, Chicago is a sophisticated, dynamic city with an upbeat vibe and a history that is synonymous with jazz and the blues. Take in the spectacular view from the Willis Tower Skydeck, shop along the Magnificent Mile or catch a game at the iconic Wrigley Field.

Browse our best North America holiday deals by destination:
  • 3 nights fr $2,059* pp

    The Millennium Knickerbocker Hotel

    Chicago | The Millennium Knickerbocker Hotel

    3 nights accommodation & return flights with Air New Zealand
  • 3 nights fr $2,131* pp

    Silversmith Hotel

    Chicago | Silversmith Hotel

    3 nights accommodation & return flights with Air New Zealand
  • 3 nights fr $2,152* pp

    Palmer House - A Hilton Hotel

    Chicago | Palmer House - A Hilton Hotel

    3 nights accommodation & return flights with Air New Zealand
  • 3 nights fr $2,152* pp

    Hilton Chicago

    Chicago | Hilton Chicago

    3 nights accommodation & return flights with Air New Zealand
  • 3 nights fr $2,383* pp

    Thompson Chicago

    Chicago | Thompson Chicago

    3 nights accommodation & return flights with Air New Zealand
Browse our best North America holiday deals by destination:
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