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Chicago, Illinois

Chicago is often called the second city, but the natives of this masculine city would argue that it’s second to anyone. The home of some of America’s greatest sky scrappers, sporting teams and gangsters can be explored by trolley, bus, boat or bike. Freezing in winter, the city and it’s beaches come alive in the summer months.


View the road trips that explore Chicago, Illinois

Route 66 fly drive holiday in America

Route 66 Explorer

Chicago, St Louis, Grand Canyon NP, Las Vegas & Los Angeles

Road trip holiday driving across Northern America

Northern Crossover

Boston, Niagara Falls, Chicago, Yellowstone, Lake Tahoe, Yosemite, San Fran & much more

Or simply jump straight to another region

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