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Route 66 Explorer

Chicago, St Louis, Grand Canyon NP, Las Vegas & Los Angeles

The classic American Road Trip from Chicago to Santa Monica in Los Angeles. Itched into American folklore by those migrating west during the great depression. Our road trip is filled with nostalgia between some of the nations best cities.


Route 66 Explorer 14+ days

All of our American road trips can be tailored to meet your requirements. Do you have more or less than 14 days for your road trip? No problem, we can bolt on extra nights to allow more time to explore or shorten the number of destinations as required. Just let us know when requesting your quote.

That's one big tick on my life list!


Home of the skyscraper

Day 1

Arrive in masculine Chicago

Arrive in Chicago and collect your wheels ready for this classic Route 66 road trip across America. You have three nights to really get to grips with this wonderful city on the beautiful Lake Michigan.

  • Key location: Chicago, IL
  • Chicago, IL

Chicago's waterways

Day 2

Explore Chicago

Chicago is best explored by trolley, bus, boat or bike. Most visitors head to 'Magnificent Mile', a vibrant, bustling area home to upscale shops, trendy restaurants and posh hotels. Landmarks include the historic Chicago Water Tower, the neo-Gothic Tribune Tower and the 100-story John Hancock Center, which has a rooftop observation deck. Exceptionally cold in winter, the city and it’s beaches come alive in the spring, summer and fall.

  • Key location: Chicago, IL
  • Chicago, IL

Chicago shoreline

Day 3

A third day to discover Chicago

Your personalised Road Trip Pack will detail all of Chicago’s must-see places, these include Cloud Gate, Navy Pier and the lovely Lake Michigan shoreline. Before leaving town, make sure you spend at least one evening partying at Buddy Guy’s Legends.

  • Key location: Chicago, IL
  • Chicago, IL

Pontiac, IL

Day 4

Set off down Route 66

Start your engines, historic Route 66 awaits. The Illinois section is very well signposted, making it easy to enjoy highlights such as Route 66 obsessed Pontiac and historic Springfield. Abraham Lincoln’s Tomb, the Lincoln Presidential Museum and the Lincoln Home are highly recommended.

  • Key location: Springfield, IL
  • Springfield, IL
  • 202 Miles

Famous St Louis Arch

Day 5

Next up, St Louis

Arrive in St. Louis today which sits on the Mississippi River. Highlights include the Missouri Botanical Gardens, Citygarden and the iconic Gateway Arch National Park. If you have time be sure to try and catch a baseball game here at the Cardinal's stadium which is right in the heart of the city.

  • Key location: St Louis, MO
  • St Louis, MO
  • 97 Miles

Meramec Caverns

Day 6

Visit the iconic Route 66 stop off - Meramec Caverns

Continue south today through the state of Missouri. On route stop off at Meramec Caverns, an extensive set of limestone caves offering memorable underground tours. You’ll end the day in Springfield, Missouri which is officially recognised as the birthplace of Route 66.

  • Key location: Meramec Caverns
  • Springfield, MO
  • 216 Miles

Philbrook Museum

Day 7

Tulsa and Oklahoma City today

Continue on the historic route you'll pass through Joplin, Missouri before skimming through a corner of the state of Kansas into Oklahoma and on to Tulsa. We recommend a visit here to the Philbrook Museum, home to a vast art collection, housed in an Italian style villa surrounded by a large idyllic garden. Continue onwards to Oklahoma City where you have a nights stay.

  • Key location: Tulsa, OK
  • Oklahoma City, OK
  • 286 Miles

Check out some of the other tours that explore this region

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