No highway gets more recognition and praise than America’s Mother Road, & few know it better than Gilligans.

We’re experts in delivering world-class, self-drive tours of this journey into America’s heart and soul.

Averaging just 144 miles a day – You’ll cross eight states
and travel over 2,448 miles from the beginning in downtown Chicago to very end at the Santa Monica pier.

Our tour starts at the beginning in Chicago and follows some of the earliest alignments of Route 66!

Celebrate 100 Years of  Route 66!

Drive it all from Chicago to Los Angeles over 21 Days

 If a true Route 66 experience has been on your bucket list, then 2026 is the year to turn your dream into reality!

Gilligans welcomes guests from across the  world to Chicago, Illinois for an odyssey across America’s Greatest Highway.

Our tour starts in Chicago and finishes on the Santa Monica Pier in California.

With Gilligans, you don’t need to plan a thing!

We provide all the accomodation (including the famous ones) a rental car, along with all the stops you’ve heard about and lots more that you haven’t!

Our 190+ page Route book and Navigation APP make it an easy, enjoyable, real life history lesson across heartland USA!

What to expect with Gilligans:

Route 66 was 2,448 miles started in Chicago and finished in Los Angeles.

With Gilligans, you’ll start at the very beginning, and spend 21-Days on Route 66, from Chicago to LA.

• Start in Chicago & finish on the Santa Monica pier at the ‘End of Route 66’ sign
• Stay at superior hotels and enjoy nights at some iconic Route 66 motels along the way!
• We include your rental car* with insurances and one-way fees included (or use your own)
• Tours average just 144 miles a day from Chicago to LA – less than any other!
• Guests enjoy Gilligan’s EXCLUSIVE navigation system, our comprehensive Route Book and a US mobile phone if you’re from outside of the USA.
• Drive some of the oldest alignments including some that remain unsealed to this day!

(*rental car type, make or model are always subject to availability)

Gilligan’s doesn’t provide a ‘tour’ in the true sense of the word. We provide you with a personal experience across America’s greatest highway – an immersion into the tapestry of heartland USA and an opportunity to encounter the people who live and breathe Route 66.

A true Route 66 experience starts and finishes with Gilligans.

We look forward to welcoming you to the USA!