We now stay open until 7pm week nights and until 4pm on Saturdays - Give us a call today and we'll arrange the trip of a lifetime for you

Quick Enquiry

Route 66 Explorer

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

The classic American Road Trip from Chicago to Santa Monica Pier in Los Angeles.

Itched into American folklore by those migrating west during the great depression. Today it is a trip of nostalgia between some of the nations best cities.


Route 66 Explorer 14+ days

Remember, any and all of our pre packaged road trips can be altered to meet your exact needs and wants. 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 Chi Town and collect your wheels ready for this classic Route 66 road trip across America. But before you hit the world, you’ll have 2 days and 3 nights to explore this great city.

  • Key location: Chicago, IL
  • Chicago, IL

Chicago's waterways

Day 2

Explore Chicago

Chicago is often called the second city, but the natives of this masculine city would argue that it’s second to anyone. The home of some of America’s greatest sky scrappers, sporting teams and gangsters can be explored by trolley, bus, boat or bike. Chilly in winter, the city and it’s beaches come alive in the summer months.

  • Key location: Chicago, IL
  • Chicago, IL

Chicago shoreline

Day 3

A third day to discover Chicago

Your personalised Itinerary Pack will detail all of Chicago’s must see places, these include the Cloud Gate, Navy Pier and Lake Michigan shore line. Chi town is a world class city and the two and a half days you have here will fly by as you explore its highlights.

  • 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 sign posted, making it easy to enjoy highlights such as Route 66 obsessed Pontiac and historic Spiringfield, IL. Abraham Lincoln’s Tomb, the Lincoln Presidential Museum and the Lincoln Home can be found in or near to downtown Springfield.

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

Famous St Louis Arch

Day 5

Next up, St Louis

If you get there early enough then check out the Missouri Botanical Gardens, Citygarden or the iconic Gateway Arch. If you have longer than 14 days to take this trip, then just let us know and we can add extra days along the way.

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

Meramec Caverns

Day 6

Visit the iconic Route 66 stop off - Meramec Caverns

Missouri holds one of the greatest of the old Route 66 tourist attractions—Meramec Caverns, an extensive set of limestone caves offering the most over-the-top underground tour you can take. Regular guided tours last about 1h10m. You’ll end the day in Springfield, MO which is officially recognised as the birthplace of Route 66, it was in this town on April 30, 1926, that officials first proposed the name of the new Chicago-to-LA highway.

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

Philbrook Museum

Day 7

Tulsa and Oklahoma City today

Tulsa’s Philbrook Museum is just one of the great attractions available today. This vast art museum, housed in an Italian style villa, has numerous exhibits from European, American, Asian, Native American and African artists and is surrounded by acres of lush gardens. Your Itinerary Pack will list the other options that are available.

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

Check out some of the other tours that explore this region

Get all the latest news and offers by signing up to our newsletter