Ideas

America’s Route 66

Begin your journey on the corner of Michigan and Adams in Chicago
Cross the Mississippi River on the historic Chain of Rocks Bridge
Add your own mark to the iconic car art at Cadillac Ranch
Overlook the Grand Canyon from the South Rim Trail
End your Road 66 road trip on the pier at Santa Monica Beach

 

Posted by: Freedom Destinations
Posted on: 10/10/2025

America’s Route 66

Be inspired by Freedom Destinations...

IDEAS
America’s Route 66

Travel along the Historic Route 66 on this 16-day fly drive holiday, where every turn, from Chicago to Los Angeles, offers a unique slice of Americana.

IDEAS
California Dreaming

Experience the best of the Golden State on this unforgettable two week California fly drive visiting vibrant cities, stunning coastlines and awe-inspiring National Parks.

 
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