Route 66 Chicago
  • News News
  • Popular
  • Recent

Start in Chicago and check out these Route 66 landmarks

By Kate Silver


Driving enthusiasts and Route 66 go together like apple and pie, stars and stripes, firecrackers and the Fourth of July. Although the official Route 66 was decommissioned in 1985, replaced by the faster and more direct interstate highway system, you can still get your kicks on Route 66. Preservationists and fans alike have fought to keep the memory and folklore alive. Today, nearly 85 percent of the “Mother Road,” which connects 2,448 miles of adventure from Chicago and Los Angeles, remains navigable.

To drive it these days is to savor a taste of Americana. Maybe you’re old enough to remember the Corvette featured in Route 66, the 1960s TV series, or you’re a young adventurer heading out to discover the United States in a new Spark. Maybe you dream of breaking in your 2014 Corvette C7 on the legendary strip of pavement. Whatever your ride, here’s some hidden and not-so-hidden lore that’s worth stopping for.

Grant Park

The Route 66 Illinois Scenic Byway begins (and ends, depending on your perspective) in a bustling part of Chicago, Illinois. The “End Route 66” sign sits at the intersection of Jackson Boulevard and Michigan Avenue near Grant Park. The park, which is bordered on the east by Lake Michigan, is 319 acres of pristine beauty and is home to Buckingham Fountain. Built one year after the opening of the road, it’s one of the most recognizable fountains in the world, with its wedding-cake tiers. From April to October, the fountain dazzles visitors with a light-and-water show while the Chicago skyline acts as a dramatic backdrop. Even though it opened after Route 66 began, the fountain is generally considered the symbolic end of the “Main Street of America.”

The Art Institute, located in Grant Park, is one of the most beloved institutions on the route. Originally built in 1879, it was a victim of the Great Fire of 1971. The city rallied its forces and built the current museum/school in time for the World’s Columbian Exposition of 1893. Today, it’s home to more than 300,000 works of art.

Lou Mitchell’s

Probably the most famous (and delicious) of surviving Route 66 landmarks in Chicago is Lou Mitchell’s. Built in 1923, the owners of Lou Mitchell’s like to say that when Route 66 was built, the restaurant was ready for the hungry travelers. At this classic breakfast joint, diners are greeted with doughnut holes, and it’s a tradition for women to receive Milk Duds—a candy that was invented in Chicago in 1926. Keep your eyes peeled when you visit. Lou Mitchell’s is a magnet for celebrities, authors, politicians and journalists.

Chicago Board of Trade Building

The Chicago Board of Trade Building, designed by the famous architects Holabird & Root, was the tallest building in the city when it opened in 1930 at 141 W. Jackson—a.k.a. Route 66. Its Art Deco style is a nod to the era it was built, and the building is on the National Register of Historic Places. Enlightening tours—which include a glimpse at the frenzied trading floor—are available through the Chicago Architecture Foundation.

The trademarks mentioned in this story are held by their respective owners.

This is the first in a two-part series of Route 66 road trip stories on Chevy Culture.

Kate Silver is an award-winning journalist and editor based in Chicago. Her work appears regularly in Spirit Magazine, Men’s Health, the Chicago Tribune and Midwest Living, as well as on


Destination Freight Charges

To allow you to do an accurate price comparison with prices featured on other Internet sites, GM provides Internet pricing both with and without the Destination Freight Charge (see prices including Destination Freight Charge below). To get full pricing details, go to our Build Your Own section.