America’s ‘Windy City’ has plenty to impress. With its mighty skyline, vast lakes and swinging blues music scene, a holiday in Chicago is guaranteed to blow you away. Chicago holidays are all about culture and art; home to Hemingway, its very own blend of soulful blues and a generous spattering of high-flying architecture from Frank Gehry's futuristic Pritzker Pavilion to Frank Lloyd Wright's stained-glass Robie House, Chicago is nothing short of a cultural treasure trove. Wander along the streets and stop to admire whimsical public art or duck into one of the many art museums housing everything
from impressionist masterpieces to psychedelic paintings. As well as culture, the city boasts an eclectic array of nature from long stretches of coastline studded with beaches and recreational areas to hills blanketed in orchards and vineyards. And don’t miss a visit to The Great Lakes - so vast they could be mistaken for inland seas; explore quaint resort towns, climb substantial sand dunes and stop off to snap a shot of a picturesque lighthouse.

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Chicago Holiday Ideas

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What our clients say about us
USA customer reviews (7 reviews)
4.7/5
Original Travel were excellent, as was the Ranch at Rock Creek. The Concierge team was also super responsive and helpful. Our son injured his wrist on the trip, and we needed to make urgent changes to our flights. Our consultant was incredibly helpful and responsive - it made an immense difference to our trip, and so please do pass on our thanks.
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