The stretch of Route 66 from Chicago, Illinois, to St. Louis, Missouri, is home to aluminum-and-chrome diners, historic, family-owned cafes, bizarre attractions, and other reminders of the route’s charming past. You’ll also see plenty of cornfields and flat prairie land between the bustling cities and sleepy towns along this first leg.
Chicago's landmark is considered one of the country's finest fountains due to its Beaux-Arts-style landscape design, finely wrought bronze sculpture, and innovative use of technology.
Don’t miss the Route 66 Starts Here sign at the corner of S Michigan Avenue and E Adams Street. The sign (along with a handful of replica signs on the same block) is located in a busy section, so you may need to find parking elsewhere and walk to the sign for a photo.
It's one of the first stops Ferris Bueller makes on his day off, so you know it's an essential Chicago icon. The Skydeck really does offer great views when the weather is good, plus the glass-floored "ledge" is an unforgettable experience for those brave enough to step on to it.
Route 66 is renowned for its classic American cuisine. If you’re not still full of donut holes (or even if you are), visit Dell Rhea's Chicken Basket, just outside Chicago, for some of the best fried chicken you'll ever taste. The roadhouse has been serving its home-cooked goodness since 1946, and even if you’re not ready to eat just yet, the neon sign is a classic photo op.
The Illinois stretch of Route 66 is home to several great roadside attractions, but nothing shouts "retro kitsch" louder than a massive Muffler Man. Snap a picture with the Gemini Giant the newly-reopened Launching Pad Drive-In in Wilmington. Named for the Gemini space program, he’s one of many similar statues made by International Fiberglass. The giant stands guard over the Launching Pad Drive-in, which also houses a gift shop, a restaurant, and the Mini Americana Museum.
The Illinois Route 66 Mining Museum chronicles the significant role the coal industry played in the development of Route 66. Coal mining was the lifeblood of several small towns along the route, and this is a great place to learn how the industry impacted the people and economy along what was once considered America’s Main Street.
The route is dotted with old service stations, many of which have been beautifully restored and repurposed as photo ops. The first one you’ll encounter is Ambler's Texaco Gas Station in Dwight. In continuous use for 66 years, from 1933 until 1999, it was one of the longest operating gas stations on the Mother Road. Today it serves as a visitor center.
You did it—one leg down, five more to go. As you travel further southwest, the weather will get warmer, the road will get flatter, and the views will only get better. While it’s true that you never forget your first, so much of Route 66 is still in front of you—so keep going and let the Show-Me State show you why almost 100 years after its creation, the Mother Road is still the best place to get your kicks.
