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2026 marks Route 66’s Centennial year adding to its legendary stature and the perfect time to explore one of the USA’s most iconic road trips
Route 66 is dotted with charming towns, roadside photo ops, local food, pop cultural spots, history, adventure, and everything that makes a road trip unforgettable
Route 66 or the Mother Road, as it is affectionately called, is one of the most iconic roads in the USA. Starting in Chicago, this 300-mile stretch through Illinois is one of the most popular road trip routes. Route 66 is dotted with charming towns, roadside photo ops, local food, pop cultural spots, history, adventure, and everything that makes a road trip unforgettable. Moreover, 2026 marks Route 66’s Centennial year adding to its legendary stature and the perfect time to explore one of the USA’s most iconic road trips.
Chicago
Begin your road trip in the heart of downtown Chicago. Snap the perfect selfie at the iconic Route 66 sign on E. Adams St., directly across from T he Art Institute of Chicago. Then, head to Lou Mitchell’s to fuel up for your adventure. This cosy diner was the city’s first-ever all-day breakfast restaurant when it opened in 1923. The original wooden stools at the counters are packed with regulars sipping coffee, the iconic marquee glows above the door, and the menu offers classic diner fare.
Chicago to Joliet
Continue driving to Ogden Avenue, Berwyn’s stretch of Historic Route 66. Route 66 is celebrated at the annual Berwyn Route 66 Car Show and at local haunts like Cigars & Stripes BBQ Lounge and Paisan’s Pizzeria & Bar. Your next stop is a tour at the Old Joliet Prison, best known for its most popular, fictional inmate “Joliet Jake” Blues from the 1980 film “The Blues Brothers.” Since then, it has made a number of appearances in film and TV, including the critically acclaimed series “Prison Break.”
Joliet to Bloomington and Pontiac
Next, stop for a little grub at Dell Rhea’s Chicken Basket in Willow brook, which has been serving up some of the best fried chicken on Route 66 since it opened as a gas station lunch counter in the summer of 1946. Since then, it has been inducted into the Route 66 Hall of Fame.
Do check out the newly restored Gemini Giant “Muffler Man” on Route 66. The famous 30-ft. Space “Muffler Man” is now on display at his new home, South Island Park in Wilmington, about a half mile from the landmark’s original location.
No Route 66 journey is complete without a visit to one (or all) of Route 66’s classic museums. A must-see is the Route 66 Mural & Hall of Fame Museum in Pontiac, packed with the finest memorabilia associated with the history of Route 66. Among the artefacts, you will find the bus and van of Route 66 icon, Bob Waldmire.
Step around back for a photo op with the World’s Largest Route 66 shield mural. Then, get your classic car fix at the Pontiac-Oakland Automobile Museum. Here you will find the nation’s greatest collection of cars, dealer items, literature, and all things related to the Oakland and the Pontiac automobile brands.
Ultimately, visit Ambler-Becker Texaco Gas Station in Dwight to spot the iconic circular red and white Texaco sign. Inside, a vintage fire engine fills the service bay. Though the station no longer sells gas, hybrid and electric cars can refuel at a charging station. Ten miles south in Odell, a rehabbed Standard Oil Gas Station displays vintage car-repair tools and sells a variety of Route 66 memorabilia.
Bloomington to Springfield
Some of Illinois’ best roadside relics lie in wait on this stretch of the road. In Atlanta, snap a photo with the 19-ft. Paul “Bunyon”, clutching a giant hot dog. A little way down the road in Lincoln, catch a glimpse of the 24 ft. World’s Largest Covered Wagon, complete with a very large – and very studious – Abraham Lincoln statue.
Springfield to Auburn and Litchfield
Stop by the Lincoln Tomb when you arrive and be sure to rub his nose for good luck! Visit the Illinois State Capitol and Old State Capitol and make time for the Abraham Lincoln Presidential Library & Museum. For food, stop by Route 66 Motorheads, a restaurant that doubles as a Route 66 museum.
Part drive-in, part Route 66 museum, make sure to plan a stop at the Cozy Dog Drive In where you can experience one of the greatest Midwestern treasures, an authentic corn dog.
Next, drive by Lauterbach Tire and Auto Service which has a fiberglass “muffler man” giant standing in the parking lot. He used to hold a tire but was recently upgraded to be more patriotic with a U.S. flag. In 2006, the muffler man lost his head during a tornado but was skillfully repaired by the station.
Listed on the National Register of Historic Places, the beautiful 1.4-mile-long piece of restored hand-laid brick road in Auburn is a segment of Route 66 done in 1931 and placed over a concrete roadbed, perfect for great photo ops.
Heading into Litchfield, cut over to the Old Route 66 and take the fabled Auburn Brick Road to Girard. Voted #4 Best Soda Fountain across America by Country Living Magazine, Doc’s is the best way to get refreshed before the next leg of your trip.
Litchfield to Collinsville
Browse retro knick-knacks at the Pink Elephant Antique Mall in Livingston for a unique find and eat at the quaint diner offering burgers, nachos, sandwiches, refreshments, and ice cream!
The World’s Largest Catsup Bottle is a great spot for a roadside photo. Looming over Collinsville, this 170 ft. water tower is an internationally known roadside attraction that was even mentioned in a “Twilight” film.
In Collinsville, be sure to visit Cahokia Mounds UNESCO World Heritage Site for a great view. The remains of the most civilized prehistoric civilization north of Mexico are preserved here. Within this 2,000-acre tract lies the archaeological remains of the Mississippians and their ancient civilization known today as Cahokia.
Collinsville to Granite City
On the alignment of Route 66 that connected Pontoon Beach and Granite City sits the Luna Café with its neon sign. Once you get to Granite City, make a stop at O’Brien Tire & Auto to take a selfie in front of their huge Route 66 branded tire.
Ultimately, do not miss out on the new It’s Electric Neon Sign Park experience in Granite City, which opened in late 2024 and further captures the history and charm of Route 66.
Your Illinois Route 66 journey ends at the Old Chain of Rocks Bridge out of Collinsville. Built in 1927, it is the fifth bridge to cross the Mississippi River and the perfect final selfie as you close the book on your Illinois Route 66 adventure.
