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Chicago is the classic American city, an open-air museum of architecture and one of the few places in the world where the words ‘high rise’ are synonymous with structural magnificence. ‘Make no little plans,’ urged city planner Daniel H Burnham, ‘they have no magic to stir men’s blood.’ 

To appreciate its fine looks, take a Chicago’s First Lady cruise on the city’s eponymous waterway before riding the escalator to the airy summit of Willis Tower. For a more architectural bias to your trip, head out to Oak Park, a quiet semi-rural village where Frank Lloyd Wright’s prairie-style masterpieces abound. You can also visit his home and studio.

There are many museums here too, but one not to miss is the Art Institute of Chicago in Millennium Park, one of the city’s many green acreages on the shores of Lake Michigan. 

Stay at: Soho House, The Langham, The Peninsula

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The Langham, Chicago Chicago

The Loop, Magnificent Mile and Millennium Park are all just minutes away from this sophisticated five-star retreat. When not sightseeing, you can make the most of the property’s extensive …


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    Tailor-made journeys with The Ultimate Travel Company certainly do not come off-the-peg. We recognise that people’s interests and tastes are unique and so their holidays should be too. Each itinerary is carefully matched to you by our specialists. From the accommodation style, experiences and budget, we ensure the holiday you book is perfect for you.

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