Get Your Route 66 Kicks in Chicago

In the 20th century, alongside the growth of the highway system, we became a nation of drivers and the roads themselves became a part of our nation’s lore. Thanks to a perfect moment in history — and a name that rolls right off the tongue — no U.S. highway is more beloved than Route 66.

The road begins in downtown Chicago, and its beginning offers easy access to some of the Windy City’s best attractions. And while most of us don’t have the vacation time set aside to explore the whole road from end to end, you can find some of the best kitsch Route 66 has to offer a short drive out of Chicago’s city limits.

A Little Route 66 History

Route 66 stretches some 2,448 miles from downtown Chicago to Los Angeles. Predating the U.S. Interstate Highway System, it was cobbled together in 1926 by way of connecting regional local roadway arteries. Called the Mother Road by author John Steinbeck, it soon became an indispensable highway for farm workers in the Depression and wartime factory output during WWII.

In the booming postwar years, families took to Route 66 for its quirky roadside attractions on the way to vacation destinations. Along the highway, you can find everything from giant statues to trading posts and old-fashioned diners.

Though its status as an economic engine was supplanted by the interstate system in the fifties, it had by this point secured a place in our imagination as a stand-in for the country’s unique spirit, and the road has pulled travelers ever since.

Route 66 is celebrating its centennial anniversary in 2026, which makes it a great time to get to know the roadway.

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Route 66 in Chicago

Find your way to the modern starting point at 122 S. Michigan Ave., near the intersection of South Michigan Avenue and East Adams Street, and snap a photo with the iconic “begin” sign there. If history buffs want to have their bases covered, walk a block to the historic eastern terminus, as well, at the intersection of Jackson Blvd. and Michigan Avenue.

Next, consider fueling up at Lou Mitchell’s diner, which has been feeding travelers three years longer than Route 66 became a highway. It’s a classic Greek diner with old-world charm, where some patrons are greeted with Milk Duds.

Fully fueled, you can opt to spend a day at the renowned Art Institute of Chicago, with some 300,000 works of art spanning five millennia of human history. In keeping with the Americana spirit of a Route 66 road trip, be sure to spy “American Gothic,” Grant Woods’ iconoclastic portrait of a pair of dour farmers, as well as “Nighthawks,” Edward Hopper’s solemn portrait of a nighttime diner. 

After a quick selfie with the Art Institute’s well-known lion figures, head to Grant Park, a large collection of greenspaces stretching along Lake Michigan. In an afternoon at the park, you can spy “Cloud Gate,” locally known as The Bean, a 110-ton smooth mass of stainless-steel plates designed to reflect the world around it. Be sure to check out Buckingham Fountain, one of the largest and most recognizable fountains in the world, which was born a year after Route 66.

Outside City Limits

If the road calls, there are several unique attractions less than 60 miles outside Chicago on or near Route 66 for a day trip.

The closest is Old Joliet Prison, a 19th-century limestone house of corrections that has been used as a backdrop for many movies, including “The Blues Brothers” and “Natural Born Killers.” No longer a working prison, it offers guide and self-guided tours, as well as special events.

For something different, consider stopping at Midewin National Tallgrass Prairie, an ongoing restoration project to create a tall grass reserve on what was once the site of rusting munitions factories. There are hiking and biking trails throughout the more than 20,000 acres, and nature lovers can spot wild bison and many species of birds. Pack a picnic, if you plan to spend time there, as it is rustic.

Another popular culinary destination in the early miles of Route 66 is Polk-a-Dot Drive-In, a 50’s diner made famous for its kitsch statues outside. While enjoying diner fare, you can snap photos of yourself with Elvis, Marilyn Monroe and James Dean.

Where To Park Yourself

The Cambria® Hotel Chicago Loop – Theatre District makes an ideal home base as you set out on your open-road journey. Created in 2017 from a historic building that dates to the early days of the highway, the hotel maintains its historic outward charm while providing modern interior comfort.

This hotel experience is immersed in the Windy City’s character, as the hotel’s rooms are appointed with Chicago-inspired decor. Visitors are also literally steps away from the historic James M. Nederlander Theatre and near the Cadillac Palace Theatre, with world-class shopping on State Street nearby. Close to stations for the L’s Red Line and Blue Line, Cambria Hotel Chicago Loop offers easy access to all the city has to offer.

You’ve Read About it — Now Experience It

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