The 'windy city' of Chicago got its nickname from its unique politics, not the weather, so you can expect a laid back city built for all seasons, with world-class museums, miles of lakefront vistas, award-winning restaurants and luxury hotels. The 'Magnificent Mile' of Michigan Avenue has plenty to keep you entertained with lots of shops, as will the 250 local designers to be found in neighbourhood boutiques.
As the home of the legendary blues, expect free downtown and neighbourhood festivals with some of the world's best musicians. Chicago is the city where the skyscraper was born and you can take a tour to discover the architecture of Chicago's buildings and historical hotels or take advantage of plenty of free tourist attractions.
Top itineraries in Chicago
Take a trip along Route 66, America’s most celebrated highway. inspired countless films, books and songs, from Jack Kerouac’s On the Road to Woody Guthrie’s 'The Ballad of Tom Joad' and Bobby Troup’s classic '(Get Your Kicks On) Route 66'.
Under nine hours from London and with superb sightseeing, shopping, entertainment and dining, Chicago, the so-called "windy city" on the shores of spectacular Lake Michigan, is fast becoming one of the USA's favourite short-break destinations.
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Top places to stay in Chicago
The Millennium Knickerbocker Hotel offers sleek and stylish accommodation in a great location, at the start of the Magnificent Mile with its endless shopping, dining and entertainment. Attractions such as the Museum of Contemporary Art, Art Institute of Chicago and 360 Chicago (formerly the John Han
This boutique hotel is set in one of Chicago’s hippest neighbourhoods, having won several Condé Nast awards.
One of the city’s best-regarded hotels, the Peninsula has consistently been awarded the Forbes Five Star and AAA Five Diamond awards year on year.
Meet our Chicago experts
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