Upscale eateries, endless shopping opportunities all in the iconic Windy City

Located on the shores of Lake Michigan, Chicago is known as the ‘Windy City’ and has an instantly recognisable skyline of spectacular skyscrapers. With a great combination of city attractions - stunning modern and traditional architecture, beautiful green parks, a renowned Blues and Jazz scene and fantastic shopping - it is a truly wonderful city to visit, particularly in the summer months.

Route 66 is a bucket-list favourite and this legendary self drive takes you through the heart of America, from Chicago to LA.

Chicago & Route 66 holidays - perfect for...

  • Chicago has its fair share of amazing museums. Spend some time exploring the Art Institute of Chicago or the Field Museum home to Sue, the largest Tyrannosaurus Rex skeleton in the world
  • Chicago is renowned for its shopping opportunities and the Magnificent Mile is one of America’s most famous shopping destinations
  • When it comes to dining, the city has plenty to offer from high end restaurants to causal eateries. Don’t miss the chance to try Chicago’s famous deep dish pizza
  • The city’s setting on the edge of Lake Michigan is one of its real highlights – you can relax on North Beach or wander along Lake Shore Drive or visit the attractions at Navy Pier
  • Chicago marks the start of what is possibly America’s, if not the world’s most famous road trip – Route 66. Spend a few days here before heading off on the road

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Discover USA & Canada brochure

Cities that never sleep, wide open roads and awe-inspiring natural wonders; these are backdrops that constantly grace the big screen but nothing can beat seeing them for yourself.

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