Route 66: Where The Road Becomes A Story

Route 66 or the Mother Road, as it is affectionately called, is not just a highway – it’s a symbol of American history, culture and adventure. The 300-mile Illinois stretch starting from Chicago is every road trip lover’s dream. Dotted with quirky attractions, charming towns and rich history, this portion of the legendary route offers a thrilling journey through time, and 2026 promises to make it even more special, marking the centennial of Route 66. So, buckle up and get ready to explore the heart of the USA.

Start In Chicago
Your adventure begins in the vibrant heart of Chicago. As you drive through downtown, you’ll spot the iconic Route 66 sign on E. Adams St. – a perfect place to kick off your journey with a selfie. Right across from the Art Institute of Chicago, this is the gateway to an unforgettable road trip.
 
Before hitting the road, make a stop at Lou Mitchell’s, a cosy diner in Chicago since 1923. Known for its all-day breakfast, it’s the perfect spot to fuel up for the adventure ahead. While you’re sipping your coffee on wooden stools, the warm, welcoming atmosphere will make you feel like you’re stepping back in time.
 
Chicago to Joliet
As you leave Chicago behind, your next stop takes you through Berwyn, where you can indulge in local favourites like Cigars & Stripes BBQ Lounge or Paisan’s Pizzeria & Bar. If visiting in summer, the Berwyn Route 66 Car Show is a must-see.
 
Next, make your way to Joliet, home of the famous Old Joliet Prison. Featured in movies like The Blues Brothers, the prison has a rich history and plenty of film and TV appearances to its name. While you’re there, you might even catch a glimpse of the infamous “Joliet Jake” Blues.
 
Joliet to Bloomington, Pontiac
As you continue your journey, you can’t miss Dell Rhea’s Chicken Basket in Willowbrook, an absolute Route 66 gem. This legendary spot, which started as a gas station lunch counter in 1946, has been serving up some of the finest fried chicken in the country. It’s so iconic; it’s even inducted into the Route 66 Hall of Fame.
 
Wilmington is home to the newly restored Gemini Giant, a towering 30-feet “Muffler Man” that stands proudly in South Island Park. It’s a perfect place to stretch your legs and snap a photo before continuing on to Pontiac, where the Route 66 Mural and Hall of Fame Museum awaits. The museum, packed with fascinating memorabilia, is a testament to the road’s rich history. Don’t forget to check out the world’s largest Route 66 shield mural and visit the Pontiac-Oakland Automobile Museum to get up close with some vintage cars.  Ultimately, visit Ambler-Becker Texaco gas station in Dwight to spot the iconic circular red and white Texaco sign.
 
Bloomington to Springfield
As you drive along Route 66 from Bloomington to Springfield, you’ll be treated to a mix of roadside relics and quirky attractions. In Atlanta, stop to see Paul Bunyan, the 19-feet-tall statue holding a hot dog. A few miles further in Lincoln, you’ll encounter World’s Largest Covered Wagon and in the town of Springfield, it’s time to honour the legacy of Abraham Lincoln himself.
 
The Lincoln Tomb is a must-visit, and don’t forget to rub Lincoln’s nose for good luck. Nearby, the Abraham Lincoln Presidential Library & Museum offers a fascinating dive into the life of one of America’s most revered presidents.
 
For a classic Route 66 experience, stop by the Cozy Dog Drive In, where you can savour an authentic corn dog, a Midwest treasure. You’ll also want to make time to visit Lauterbach Tire and Auto Service, where a patriotic Muffler Man statue welcomes you.
 
Springfield to Collinsville 
Your journey continues south through the rolling countryside of Illinois. A stop in Litchfield allows you to take the historic Auburn Brick Road to Girard. Litchfield is also home to Doc’s Soda Fountain, voted one of the best in the US by Country Living Magazine. It’s the perfect place to grab a refreshing drink before continuing your trip.
 
In Collinsville, you can’t miss the World’s Largest Catsup Bottle, a towering 170 feet water tower that’s become an international roadside icon. It’s a quirky and fun photo op before heading to the Cahokia Mounds, a UNESCO World Heritage Site. The archaeological remains of Mississippian culture lie preserved here, offering a fascinating glimpse into prehistoric civilisation.
 
Collinsville to Granite City
The final leg of your journey brings you to Granite City, home to Luna Cafe, where you’ll find a neon sign that captures the spirit of Route 66. From there, you can head to O’Brien Tire & Auto, where you can take a selfie in front of their giant Route 66 branded tire.
 
Don’t miss the new It’s Electric Neon Sign Park, a vibrant tribute to the neon signs that once illuminated America’s highways. Opened in late 2024, this park adds a new layer of charm to the Route 66 experience. 
 
End at Old Chain of Rocks Bridge
Your Illinois Route 66 adventure concludes at the Old Chain of Rocks Bridge. Built in 1927, this iconic bridge spans the mighty Mississippi River. It’s the perfect place to take one last selfie and reflect on the incredible history and adventure you’ve just experienced.
 
Route 66 isn’t just a road – it’s a living, breathing piece of American history. Whether you're a history buff, a foodie, or a lover of quirky roadside attractions, the Illinois stretch of Route 66 offers something for everyone.