Route 66 Illinois: 8 stops for a road trip on the Mother Road of the USA

Route 66 is one of those roads whose myth leaves no one cold. Freedom, space, pure America – these were the first things that came to my mind when we left Chicago for our road trip on Route 66 through Illinois. Route 66 and Illinois? That’s right, the most famous and oldest east-to-west connection in the U.S. doesn’t start on the East Coast, as I always mistakenly thought, but in Chicago, Illinois!

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 across from 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 Restaurant, the oldest diner in town, you can get in the mood for your road trip in an original vintage diner atmosphere. The food is typical American diner food. It didn’t knock my socks off taste-wise, but the rustic atmosphere made up for it all.

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

For more on Chicago, check out the following posts:

• Chicago: Restaurant tips for foodies
• On a boat trip: architecture in Chicago
• Chicago: Tips for a USA city trip in summer
• Chicago attractions for small budget

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

Real road trip feeling already a few minutes later when leaving the city: the vastness of the Midwest already comes to light a little. Route 66 in Illinois is so packed with interesting sights that the first stop is just 77km from Chicago. Joliet, Illinois, is the prelude to a journey full of surprises and warm encounters: Route 66 lives on its stories!

Like many stories the Old State Prison in Joliet could tell? You can’t miss the state prison, which is over 150 years old and was still in operation until 2002. For a long time, access was prohibited, and the huge complex fell into disrepair.

Today, events and guided tours take place there. Fun Fact: The prison has served as a backdrop in many series (e.g. Prison Break) and movies (Blues Brothers). The cell from the movie Blues Brothers can even be visited.

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

Other places of interest in Joliet:

At Joliet Area Historical Museum and Route 66 Welcome Center with a lot of information about Route 66 you can 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.

Food & Drink in Joliet

For a midday snack we stopped at the MyGrain Brewery (note the pun!), located in the recently restored old Joliet train station. Non-drivers and beer lovers will be pleased with the beer brewed in house! By the way, the small brewing plant can be viewed more closely on request, personal tour included: Like everywhere in Illinois, the people are incredibly nice and open-minded!

Are you planning a trip to the USA?
➜ Then browse my USA blog with many tips & inspirations!

#3 Wilmington: Gemini Giant & The Launching Pad

Just past Joliet, in Wilmington, is the famous Gemini Giant! The Gemini Giant is one of the so-called “Muffler Men”, giant statues that were used as advertising figures for stores, gas stations and eateries along Route 66. Next door is the Launching Pad, a former Route 66 eatery.

After standing empty for a long time, the new owners have set up a very charming Route 66 Welcome Center there, where you can reminisce about good old Route 66 with the help of many original photos and exhibits. Like everywhere else, the people here are proud and love to talk about their life on Route 66, including launching pad owner Tully. For a real tourist photo, even the local sheriff showed up at the end, who immediately and cheerfully let us take a picture with him – the American cordiality is unique.

#4 Pontiac: Route 66 sights, street art & my hero Bob Waldmire

Pontiac has a lot to do with Route 66 and cars – yet the name is derived not from the car brand, but from an Indian chief. At first glance a somewhat sleepy little town, yet there was so much to see that we spent almost a full day here! What to look for in Pontiac:

Route 66 Hall of Fame Museum

At Route 66 Hall of Fame Museum I got acquainted with the story of Bob Waldmire – who in Instagram times could probably best be described with the hashtag #vanlife.

In his van, which can be viewed in the museum’s courtyard, he drove up and down the entire Route 66 from Illinois to California throughout his life. He lived simply and in harmony with nature and earned money with his art. He painstakingly scribbled Route 66 travel guides, among other things, until he died of cancer at an advanced age. His motto:

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 art artists, can be seen throughout Pontiac. An interesting exhibition is integrated in 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 take a look!

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 gives in his studio Airbrush courses, sells his paintings, but also paints portraits, such as that of the mayor, who proudly presented Dong’s studio to us after closing time because of so much internationality – he also has the key, the two are friends. Quite easy. American small-town idyll at its purest – it makes your heart swell.

Food & Drink in Pontiac

At Bernardi’s, diagonally from the Livingston County Courthouse, serves Italian cuisine – American style: The aisles are wide, not without reason, because for the main course for several people, a huge folding table is brought in, on which the huge plates are draped and parked in between. The portions are gigantic.

The Cup and the Scone offers coffee with 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 something like a place of pilgrimage of modernity: Abraham Lincoln, one of the most popular US presidents ever and father of modern America, worked here. Slavery was abolished under him! Not only are there Abraham Lincoln sights to see in Springfield, but the Illinois capital (no, it’s not Chicago!) has plenty of Route 66 and Midwest flair in store!

Lincoln attractions in Springfield

Not to be missed Abraham Lincoln’s house and the Mausoleum (rubbing the nose of the Lincoln statue in front of it is supposed to bring good luck!) At Abraham Lincoln Presidential Museum you get a very good historical overview (visit the movie theater – very fascinating!).

Original Route 66: Historic Brick Road near Springfield

Just outside of Springfield (Snell Road and Curran Road, Auburn, IL) there is still an original preserved section of Route 66 between cornfields ! Incredibly, Route 66 was originally paved only with thick bricks. By the way, the piece is passable! Definitely watch it for a real Route 66 feeling!

Food & Drink in Springfield

Also important: Leave room in your stomach for Springfield’s famous specialties: Cozy Dogs and Horseshoe Sandwiches are typical Route 66 food!

I have compiled a comprehensive guide for Springfield for you here:
Springfield: Between Abraham Lincoln, Route 66 and Illinois makers

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

At the latest now you are really in Route 66 fever – and a shopping paradise like the Pink Elephant Antique Mall comes just in time! Here you’ll find all the vintage stuff and Route 66 memorabilia you could ever dream of. Old advertising signs, long-playing records, furniture… the list is endless. I bought a functional, pastel-colored typewriter there for a bargain price (the astonished looks of the security staff at the airport when I put my typewriter on the treadmill next to my Macbook were worth their weight in gold!).

#7 Cahokia Mounds: A Pre-Columbian Mystery

For a long time, the Cahokia Mounds remained undiscovered. One simply did not wonder about the even, high hills in the otherwise flat landscape! After all, they have always been there. Until archaeologists found 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, is not fully understood to this day, the flat mounds served in part as building ground for more stately dwellings, but also burial grounds. More info is available at the nearby museum!

#8 Alton: Famous men & the world’s biggest ketchup bottle

Last stop on Route 66 in Illinois! For its size, the small Alton by the Mississippi river (yes, here it already really feels like Southern states and Mississippi river cruises on paddle steamers!) already a lot of famous sons: The one, Miles Davis, was quite small, but one of the greatest jazz trumpeters in the world and the other, Robert Wadlow, at 2.72m, was actually the tallest person ever to live in the world. Even bigger, however, is the largest ketchup bottle (or as they say here: catsup) in the world! Water towers are typical of the Midwestern U.S. and a ketchup factory in Collinsville at the time 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. Today there is nothing to see of gloomy – but you can today by means of a guided tour on the traces of the “Haunted Alton”. In the McPike Mansion they offer guided tours and ghost conjurings – sounds bizarre, but at the latest in the atmospheric vaulted cellar I found that you can’t deny the special energy of the house.

Book tip ➜ “Haunted Alton” by Troy Alton

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 contrast program for the evening: Gentelin’s on Broadway offers fine cuisine and the best cocktails served in a mini shaker at the table.

Where to stay in Alton

For Alton, I have a very special tip: In the Beall Mansion*, you’ll stay in an elegant city villa, lovingly furnished and with the best food. An individual spa program with massage can also be booked. Absolute recommendation for the ending of an exciting road trip!

➜ Book a room at Beall Mansion here*

Disclaimer: Enjoy Illinois invited me on this road trip. Thank you very much!