Atlas Obscura Itineraries

The Explorer’s Guide to Illinois Route 66

It is the most fabled of American highways, so venerated that it’s known as the Mother Road. (John Steinbeck nicknamed it this in his 1939 novel “The Grapes of Wrath.”) In 2026, lovers of the classic American road trip will celebrate 100 years of getting their kicks on Route 66. While the road was officially decommissioned long ago, the last chunk bypassed in 1984 by a modern highway, Route 66’s hold on our imagination has only tightened since, and significant traces—and treasures—of the road’s heyday can be plumbed along the way, from the bustle of downtown Chicago to the Santa Monica Pier half a continent away. Explore the historic roadway just within Illinois and you’ll see 301 miles of Americana, featuring a bevy of Lincoln statues, roadside giants, and quirky spots (something I know a bit about as the author of “The Great American Retro Road Trip”). Route 66 begins in downtown Chicago, yards from Lake Michigan, and ends on the shores of the Mississippi River with the St. Louis Gateway Arch glistening in the distance. Now buckle up for this Illinois drive that’ll fuel body, mind, and spirit.