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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 £1699

View the road trips that explore Chicago, Illinois

Route 66 fly drive holiday in America

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

Road trip holiday driving across Northern America

Northern Crossover

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

American Fly Drive Holiday down Route 66

The Big Two

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

Pontiac, IL - Route 66

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

Chicago, USA - Road Trip Fly Drive

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

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