8 Amazing Stops For a Road Trip on the Route 66 Through Illinois

Route 66 has an irresistible charm that touches everyone. Its promise of freedom, open spaces, and classic Americana is truly captivating. I remember feeling this myself when we started our road trip from Chicago along Route 66 through Illinois. It’s interesting to note—despite its fame as the oldest east-west highway in the U.S., Route 66 doesn’t begin on the East Coast as I had always assumed. Instead, it starts right in Chicago, Illinois, and winds through states like Missouri and Texas all the way to California.

In this article I take you on our USA road trip on Route 66 in Illinois – and I can reveal in advance: After so many wonderful encounters on our way through Illinois, I would have loved to just drive on endlessly like Bob Waldmire, my secret hero of Route 66!

#1 Chicago: The Beginning of Route 66 in Illinois

Route 66 actually begins in the middle of Chicago opposite the Art Institute Chicago, not far from the famous sculpture The Bean. On East Adams Street between Wabash Avenue and Michigan Avenue is the beginning of Route 66.

If you don’t know, you’ll walk right past the small street sign, in the skyscraper canyons of Chicago! Nearby, by the way, is already the first mandatory stop on Route 66:

At the legendary Lou Mitchell’s, the oldest diner in town, you can get in the mood for a road trip in an authentic vintage diner atmosphere. The food is typical American diner fare: hearty and plentiful. The taste didn’t exactly blow me away, but the rustic atmosphere made up for it.

Chicago, by the way, is one of the American cities that have taken my heart by storm!

For more on Chicago, check out the following posts:

• Chicago Food Guide: Where to Find The Best Restaurants
• Architecture Boat Trip in Chicago
• Chicago in Summer: The Best Things to Do
• Chicago’s Top Attractions on a Budget

#2 Joliet: Blues Brothers & Old State Prison on Route 66 in Illinois

The authentic road trip feeling kicks in within minutes of leaving the city as the expansive Midwest begins to reveal itself. Illinois’s Route 66 is rich with sights, making the first stop only 77km from Chicago. Joliet, Illinois, offers a charming preview of a journey filled with surprises and friendly encounters: Route 66 is alive with stories!

Like many stories, the Old State Prison in Joliet has a tale to tell. You can’t miss this historic prison, over 150 years old and operational until 2002. For many years, access was restricted, leading to the large complex falling into disrepair.

Today, events and guided tours are held there. Fun Fact: The prison has appeared in many series, such as Prison Break, and movies like Blues Brothers. Visitors can even see the cell from Blues Brothers.

More about our visit to Joliet Prison shortly before it was opened to the public:
Lost Place on Route 66

Other exciting spots to check out in Joliet:

Visit the Joliet Area Historical Museum and Route 66 Welcome Center to find plenty of information about Route 66, helping you get in the perfect mood for your trip.

The Rialto Square Theatre built in 1926, is a magnificent theater that can also be visited during the day.

Where to Eat & Drink in Joliet

For a midday snack, we visited MyGrain Brewery (a pun in the name!), situated in the recently renovated old Joliet train station. Beer enthusiasts will enjoy the house-brewed beers. The small brewing facility can be explored more up close by request, with a personal tour included. Like much of Illinois, the people are exceptionally friendly and welcoming!

Are you planning a trip to the U.S.?
You’ll find lots of tips and inspiration on my USA blog

#3 Wilmington: Gemini Giant & The Launching Pad

Just beyond Joliet, in Wilmington, you’ll find the well-known Gemini Giant! This statue is part of the iconic “Muffler Men,” large figures used to promote stores, gas stations, and restaurants along Route 66. Nearby is the Launching Pad, a former Route 66 restaurant.

After standing empty for a long time, the new owners have opened a very charming Route 66 Welcome Center there, where you can reminisce about good old Route 66 with many original photos and exhibits.

As with everywhere else, the locals here are proud and eager to share stories about their lives on Route 66, including Tully, owner of the Launching Pad. For an authentic tourist photo, even the local sheriff arrived at the end, happily allowing us to take a picture with him—showcasing the warm-hearted American friendliness that is truly special.

#4 Pontiac: Route 66 Sights, Street Art & My Hero Bob Waldmire

Although Pontiac is associated with Route 66 and cars, its name actually comes from an Indian chief, not the car brand. It might seem like a quiet, sleepy town at first, but there’s so much to explore that we ended up spending nearly a whole day here! Highlights in Pontiac include:

Route 66 Hall of Fame Museum

At the Route 66 Hall of Fame Museum, I learned about Bob Waldmire’s story—someone who, in today’s Instagram era, might be summed up with the hashtag #vanlife.

In his van, displayed in the museum courtyard, he traveled the full length of Route 66 from Illinois to California over his lifetime. He led a simple life, living in harmony with nature, and earned a living through his art. He carefully wrote travel guides for Route 66, among other projects, until he passed away from cancer at an advanced age. His motto was:

I didn’t want to learn anything, so I became a traveling artist.

Bob Waldmire

International Walldog Mural & Sign Art Exhibit

Murals by the Walldogs, a group of street artists, can be seen throughout Pontiac. An interesting exhibition is integrated into the Route 66 Museum. The most famous mural is located at the back of the Route 66 Museum: don’t miss it!

Pontiac-Oakland Automobile Museum

Mainly beautiful classic cars from the golden age of Route 66, but also lots of vintage flair. If you still have some time, you should also take a look at the Pontiac Automobile Museum!

Dongbai International Airbrush Art School

A few years ago, Dong Bai, a Chinese artist, came to Pontiac from Beijing—and stayed because he liked it so much. Today, he teaches airbrush classes in his studio, sells his paintings, and also paints portraits, such as that of the mayor, who—full of pride at so much international flair—showed us around Dong’s studio after closing time—he has the key, after all; the two are friends.

Where to Eat & Drink in Pontiac

Bernardi’s, located across from the Livingston County Courthouse, serves Italian cuisine with an American twist. The spacious aisles are intentional, accommodating a large folding table used for main courses for several people, where large plates are set and organized. The portions are generous.

The Cup and the Scone offers coffee with a twist: the owners are incredibly cordial, and anyone who likes is always welcome to join the regular game nights.

#5 Springfield, Illinois: Abraham Lincoln & The Original Route 66

For Americans, Springfield is like a pilgrimage site of modernity: Abraham Lincoln, one of the most beloved US presidents and the father of modern America, worked here. Slavery was abolished during his presidency! Springfield is not only home to Lincoln landmarks, but it also serves as the capital of Illinois (not Chicago!) and boasts plenty of Route 66 and Midwest charm.

What to See in Springfield

Don’t miss Abraham Lincoln’s house and the mausoleum (rubbing the nose of the Lincoln statue in front of it is said to bring good luck!). The Abraham Lincoln Presidential Museum offers an excellent overview of history (be sure to check out the movie theater—it’s fascinating!).

Original Route 66: Historic Brick Road Near Springfield

Just outside Springfield (Snell Road and Curran Road, Auburn, IL), nestled among cornfields, there’s still an original, preserved section of Route 66. It’s hard to believe that Route 66 was originally paved with nothing but thick bricks. By the way, this section is open to traffic. A must-see for that authentic Route 66 vibe!

Where to Eat in Springfield

Leave room in your stomach for Springfield’s famous specialties: Cozy Dogs and Horseshoe Sandwiches are classic Route 66 fare.

Read my full guide about Springfield, Illinois:
The Best Things to Do in Springfield, Illinois

#6 Pink Elephant Antique Mall in Livingston, IL: Vintage Shopping on Route 66

By now, you’re definitely caught up in Route 66 fever —and that’s when a shopping paradise like the Pink Elephant Antique Mall comes in handy! Here, you’ll find every kind of vintage item and Route 66 memorabilia you could ever dream of. Old advertising signs, LPs, furniture……the list is endless. I picked up a working, pastel-colored typewriter there for a bargain price, and the surprised looks from the security staff at the airport when I placed my typewriter next to my MacBook on the conveyor belt were priceless.

Tip: Are you fascinated by the Route 66 vibe? Then you’ll really enjoy this article about Amarillo, Texas—because the historic Route 66 runs through there, too!

#7 Cahokia Mounds: A Pre-Columbian Mystery

For a long time, the Cahokia Mounds remained undiscovered. People simply didn’t wonder about the uniform, tall mounds in the otherwise flat landscape—after all, they had always been there. That is, until archaeologists discovered one of the largest pre-Columbian cities north of Mexico here in the 1960s: Thousands of people lived in Cahokia at that time. The significance of the mounds, the Cahokia Mounds, remains unclear to this day. In part, the flat mounds served as building sites for more stately dwellings, but also as burial sites.

#8 Alton: Famous Men & The World’s Biggest Ketchup Bottle

Alton is the last stop on Route 66 in Illinois. For a town of its size, little Alton on the Mississippi (yes, it really feels like the South here, with its Mississippi River cruises on paddlewheelers) has produced quite a few famous sons: One of them, Miles Davis, was quite short, but he was one of the world’s greatest jazz trumpeters, and the other, Robert Wadlow, at 2.72 meters, was actually the tallest person ever to live. Even bigger, however, is the world’s largest ketchup bottle (or, as they say here, “catsup”)! Water towers are typical of the U.S. Midwest, and a former ketchup factory in Collinsville simply built theirs in the shape of a ketchup bottle!

By the way, Alton is considered by many to be a spritual place. Mark Twain once referred to Alton as a gritty little town on the Mississippi. High crime rates and the turmoil of the Civil War (the border between the northern and southern states ran through the region) did the rest.

There’s no trace of that gloomy atmosphere left today—but you can still follow in the footsteps of “Haunted Alton” on a guided tour. The McPike Mansion offers guided tours and séances—it sounds a bit bizarre, but once I stepped into the atmospheric vaulted cellar, I realized you can’t deny the house’s unique energy.

Food & Drink in Alton

Fast Eddie’s Bon Air Whether for steamy bachelor parties or a lazy afternoon beer, Fast Eddie’s Bon Air is an institution! The food is good value and the beer selection is huge.

Gentelin’s on Broadway The perfect change of pace for the evening: Gentelin’s on Broadway offers fine dining and the best cocktails, served at your table in a mini shaker.

Where To Stay in Alton

Here’s a unique tip for Alton: stay at the Beall Mansion, where you’ll experience an elegant city villa that’s thoughtfully furnished and offers exquisite dining. You can also opt for a personalized spa package including a massage. I truly suggest it for its romantic ambiance and as an ideal way to conclude a memorable road trip.

Book your room at Beall Mansion here

Disclosure: This road trip has been realized with the support of Enjoy Illinois.