Aerial view of the Chicago skyline
Route 66 sign in Illinois

Chicago, the Great Lakes and Route 66 Tours

This corner of America has it all, and our touring itineraries are designed to make the most of every mile of it. Begin in the buzzing, big-shouldered city of Chicago before venturing out along the sweeping shores of the Great Lakes, taking in dramatic scenery, charming towns and some of the most breathtaking natural landscapes in North America. Then hit the open road on the most legendary drive in the world – Route 66 – winding your way through eight states, past neon-lit diners, vast desert landscapes and iconic roadside Americana, all the way to Los Angeles. This is America at its most cinematic, and we make sure you don't miss a moment of it.

Holly Reid
Call our travel experts now
01342 331798 Call us 9am-7pm Mon-Fri / 9am-5pm Sat-Sun

The Ultimate Route 66 Road Trip

  • Chicago
  • St. Louis
  • Oklahoma
  • Texas
  • New Mexico
  • Grand Canyon
  • Las Vegas
  • Los Angeles
Fly Drive & Self Drive
FREE Car Upgrade

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 £1,979 pp Including Flights

The Missouri Triangle Road Trip: Arches, Ozarks & Jazz

  • St. Louis
  • Saint Robert
  • Springfield
  • Branson
  • Kansas City
Fly Drive & Self Drive
FREE Car Upgrade

Explore Missouri’s iconic trio: the soaring Gateway Arch in St. Louis, the wild beauty of the Ozarks, and the soulful sounds of Kansas City jazz. This journey through music, nature, and culture captures the heart of America at every stop.

8 nights From £1,749 pp Including Flights

Self-Drive Chicago to New Orleans

  • Chicago
  • Kentucky
  • Nashville
  • Memphis
  • New Orleans
Fly Drive & Self Drive
FREE Car Upgrade

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 £1,789 pp Including Flights

Centennial Historic Route 66

  • Chicago
  • St. Louis
  • Springfield
  • Oklahoma City
  • Amarillo
  • Albuquerque
  • Holbrook
  • Page
  • Grand Canyon
  • Las Vegas
  • Los Angeles
Escorted Tours
Exclusive Discount

Celebrate the Route 66 centennial on this premier escorted tour from the skyscrapers of Chicago to the shores of Santa Monica. This historic anniversary journey traverses the heart of Americana, featuring the majestic Grand Canyon, the neon glow of Las Vegas, and a century of legendary "Mother Road" nostalgia.

14 nights From £3,599 pp Including Flights

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

Self-Drive American Music & Movie Trails

  • Chicago
  • St. Louis
  • Memphis
  • New Orleans
  • Chattanooga
  • Nashville
  • Kentucky
Fly Drive & Self Drive

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 £2,159 pp Including Flights
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Holly Reid
Call our travel experts now
01342 331798 Call us 9am-7pm Mon-Fri / 9am-5pm Sat-Sun