Chicago

Chicago Fly Drive & Self Drive

Chicago is the first port of call on the classic Route 66 road trip, making it a popular place to stop on a fantastic self-drive tour. Take a few days to explore this lively city, taking the time to try a deep-dish Chicago pizza, explore the huge sporting venues, and marvel at the incredible architecture before embarking on your journey.

Julie Leggatt
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01342 331798 Call us 9am-7pm Mon-Fri / 9am-5pm Sat-Sun

Self-Drive Route 66

  • Chicago
  • St. Louis
  • Oklahoma
  • Texas
  • New Mexico
  • Grand Canyon
  • Las Vegas
  • Los Angeles
Fly Drive & Self Drive
Exclusive Discount SAVE £100pp

Take this iconic road trip across the USA from East to West starting in Chicago, the 'windy city', and ending in Los Angeles - the 'city of angels'. In between you will experience the most diverse and breath-taking scenery as you travel this historic route, including Las Vegas and the Grand Canyon.

15 nights From £2,899 pp Including Flights
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Route 66 Guided Motorcycle Tour

  • Chicago
  • St. Louis
  • Oklahoma
  • Amarillo
  • Grand Canyon
  • Las Vegas
  • Los Angeles
Fly Drive & Self Drive

Travelling the iconic Route 66 is a bucket list item to check off but do it in style on a Harley-Davidson! Join this guided motorcycle tour, covering over 2400 miles from Chicago to Los Angeles. Crossing eight states and three time zones, the route holds a rich history as the path of migrants, dreamers, and vacationers heading west.

14 nights From £5,149 pp Including Flights
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Self-Drive Chicago to New Orleans

  • Chicago
  • Kentucky
  • Nashville
  • Memphis
  • New Orleans
Fly Drive & Self Drive
Exclusive Discount SAVE £100pp

Begin your self-drive tour in the exciting city of Chicago, stopping in Indianapolis before exploring Louisville, the Gateway to the South and the home of the world famous Kentucky Derby. You’ll get your fill of country music in Nashville, tour Elvis’ elegant Graceland in Memphis, and visit Civil War battlefields and grand plantation homes on your journey to New Orleans, the final destination, legendary for jazz and incredible Creole cuisine.

12 nights From £1,849 pp Including Flights
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Self-Drive American Music & Movie Trails

  • Chicago
  • St. Louis
  • Memphis
  • New Orleans
  • Chattanooga
  • Nashville
  • Kentucky
Fly Drive & Self Drive
Exclusive Discount SAVE £100pp

A self-drive tour for any lovers of music or film, giving you the opportunity to visit first-hand the best music cities of USA. Also you will visit some of the most familiar of sites in America that have been used in hit movies. Cities like Chicago, Memphis, Birmingham, and New Orleans all have their place in representing the history of film and music.

13 nights From £2,479 pp Including Flights
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Julie Leggatt
Call our travel experts now
01342 331798 Call us 9am-7pm Mon-Fri / 9am-5pm Sat-Sun