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Chicago, Illinois

Chicago is a city proud of it’s history and artistic values, so much that the natives refuse to accept its name as the Second City. The home of some of America’s most spectacular skyscrapers, sporting teams, and gangsters can be explored by trolley, bus, boat or bike, every corner presenting the visitor with a delightful experience. The city truly comes alive in the summer months, beaches and festivals accessible for your pleasure.

PRICES FROM JUST £1599

View the road trips that explore Chicago, Illinois

End of the Trail Route 66 Sign, Santa Monica

Route 66 Explorer

Chicago, Pontiac, Springfield, St Louis, Oklahoma City, Amarillo, Albuquerque, Grand Canyon NP, Las Vegas, Joshua Tree NP, Palm Springs, Los Angeles & more

Pontiac Mural on Route 66, Illinois

Original Route 66

Chicago, Springfield IL, St. Louis, Springfield MO, Tulsa, Oklahoma City, Amarillo, Santa Fe, Petrified Forest National Park, Winslow, Meteor Crater, Oatman, Barstow, Los Angeles & more

Country Music in Nashville American Roadtrip Music Tour

American Music Tour

Chicago, Louisville, Nashville, Natchez Trace Parkway, Muscle Shoals, Tupelo (Birthplace of Elvis), Memphis, Clarksdale, Historic Natchez, New Orleans & more

Chicago Skyline at night reflections on the water

Ultimate Route 66

Chicago, Springfield, St. Louis, Tulsa, Oklahoma City, Amarillo, Santa Fe, Monument Valley, Lake Powell, Antelope Canyon, Grand Canyon NP, Las Vegas, Palm Springs, Los Angeles & more

Route 66 road signs in the Mojave Desert, California

The Big Two

Chicago, St Louis, Oklahoma City, Amarillo, Albuquerque, Grand Canyon NP, Las Vegas, Los Angeles, Santa Barbara,Big Sur, Monterey, San Francisco & more

Mount Rushmore Monument, South Dakota, USA

Northern Crossover

Boston, Niagara Falls, Chicago, Mount Rushmore, Devil's Tower, Yellowstone NP, Grand Teton NP, Lake Tahoe, Yosemite NP, Napa, San Francisco & more

or simply jump straight to another region

The West

FROM JUST £1499

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New York & New England

FROM JUST £1299

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Florida

FROM JUST £1599

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Coast to Coast Tours

FROM JUST £1599

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The Pacific Northwest

FROM JUST £1799

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The East

FROM JUST £1599

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The Rockies

FROM JUST £1699

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The Deep South

FROM JUST £1599

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