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Chicago, Illinois

Explore our Chicago Road Trips to see where the road will take you. Discover the very best of the amazing windy city!

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 pp - includes flights, hotels, car hire & a fab road trip pack

View the road trips that explore Chicago, Illinois

End of the Trail Route 66 Sign, Santa Monica

Route 66 Explorer

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

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

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

Chicago Skyline at night reflections on the water, Route 66 Holidays

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 Route 66 and Highway 1

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, Northern Crossover 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

Canada

FROM JUST £1499

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California

FROM JUST £1499

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Coast to Coast Tours

FROM JUST £1599

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Deep South

FROM JUST £1599

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East Coast

FROM JUST £1599

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Florida

FROM JUST £1599

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Great Lakes

FROM JUST £1599

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New England

FROM JUST £1299

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Pacific Northwest

FROM JUST £1799

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Rocky Mountains

FROM JUST £1699

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Texas

FROM JUST £1799

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The West

FROM JUST £1499

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