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

Self-Drive Chicago to New Orleans

  • Chicago
  • Kentucky
  • Nashville
  • Memphis
  • New Orleans
Fly Drive & Self Drive
Save £800 per booking

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

The Ultimate Route 66 Road Trip

  • Chicago
  • St. Louis
  • Oklahoma
  • Texas
  • New Mexico
  • Grand Canyon
  • Las Vegas
  • Los Angeles
Fly Drive & Self Drive
Save £550 per booking

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 £1,999 pp Including Flights

The Great American Crossing

  • New York
  • Washington D.C.
  • Niagara Falls
  • Chicago
  • Yellowstone National Park
  • Salt Lake City
  • Bryce Canyon National Park
  • Las Vegas
  • Los Angeles
  • Santa Barbara
  • San Francisco
Escorted Tours
Early Booking Offer 2027 Departure Dates Available

From New York City to Los Angeles, this classic American tour stops off at some of the most dramatic and exciting places en route - from Niagara Falls to Chicago and the Grand Canyon to Las Vegas.

16 Nights From £3,599 pp Including Flights

Chicago to the Golden Gate

  • Chicago
  • Yellowstone National Park
  • Salt Lake City
  • Bryce Canyon National Park
  • Las Vegas
  • Los Angeles
  • Santa Barbara
  • San Francisco
Escorted Tours
Early Booking Offer 2027 Departure Dates Available

An incredible escorted tour as you travel across the country through eight states with a fantastic mix of cityscapes, rural towns and majestic wonders. From Chicago to San Francisco, you’ll travel along the iconic Route 66 to see Mount Rushmore, Yellowstone National Park and Grand Canyon to name a few extraordinary highlights.

14 nights From £3,719 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 Route 66 and Ranches

  • Phoenix
  • Scottsdale
  • Grand Canyon
  • Albuquerque
Fly Drive & Self Drive
Save £450 per booking

A perfect blend of nostalgia and adventure, this circular road trip takes you through iconic Route 66 towns, offers breathtaking views at the Grand Canyon, and immerses you in Old West life at Tombstone Monument Ranch, with thrilling cowboy activities and rich history.

11 nights From £2,219 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
Early Booking Offer 2027 Departure Dates Available

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

Highlights of Route 66 Family Self-Drive

  • Phoenix
  • Grand Canyon
  • Palm Springs
  • Los Angeles
Fly Drive & Self Drive Tailor-Made Tours Adventure Holidays
Save £450 per booking

Embark on an 11-night family road trip along parts of Route 66, see the Grand Canyon, go ranching at Wickenburg’s Kay El Bar Guest Ranch, cool off in Palm Springs, ending Los Angeles where Route 66 officially ends in Santa Monica. Enjoy outdoor activities, iconic sights, and thrilling attractions for an unforgettable adventure.

11 nights From £2,149 pp Including Flights

The Missouri Triangle Road Trip: Arches, Ozarks & Jazz

  • St. Louis
  • Saint Robert
  • Springfield
  • Branson
  • Kansas City
Fly Drive & Self Drive
Save £450 per booking

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 £1,799 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