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  1. You tell us the date you wish to depart Chicago – we will take care of the rest! *Add TWO nights in fabulous Las Vegas (20 days total) for just US$195pp! Our 'Official Tour' of Route 66 starts in Chicago and finishes on the Santa Monica pier.

    • Self Drive 66

      Gilligans’ ‘Self-Drive Tour’ of Route 66 allows guests to...

  2. 2 Σεπ 2019 · Guided tours of Route 66 led by experts of the Mother Road. Use your own car, a rental, or ride with us! Make friends by doing the trip as part of a traveling caravan!

  3. Visit the 8 states that comprise historic Route 66; Photo ops at roadside oddities including Cadillac Ranch & Elmer’s Bottle Tree Ranch; See the Painted Desert, Petrified Forest, and Grand Canyon; Travel to the top of St. Louis’ Gateway Arch; Enjoy a guided tour of Chicago, including the Chicago River Boat Architecture Tour

  4. Epic road trip from Chicago to Los Angeles; See retro 1950s diners, neon signs and vintage gas stations; Stand in awe in front of the mighty Grand Canyon; Tick off the towns sung about on ‘Get your kicks on Route 66

  5. With Gilligans, you get the full Route 66 immersion, following the original route crossing eight states and covering over 2,448 miles from the beginning in downtown Chicago right to Los Angeles and the finish point at Santa Monica pier, overlooking the Pacific Ocean.

  6. 14 Ιουλ 2019 · Chicago is the start point of the 2446 mile road trip to Los Angeles that is otherwise known as Route 66! I often see a lot of questions from people wondering the best places to stay, how to go about renting a car, where is the Route 66 start sign located, what to see in 2 days in Chicago?

  7. Our fully guided ‘Official Tour’ provides guests with a comprehensive 26-day tour of Route 66. We include flights to Chicago (returning from LA) from major cities across the world!

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