Monikered the Mother Road, Route 66 is one of the most legendary highways in the United States. Beginning in Chicago, the Illinois stretch of this historic route spans 300 miles and is a favorite among road trip enthusiasts. Along the way, travelers can explore charming small towns, quirky roadside attractions, local eateries, and landmarks rich in history and pop culture.
With Route 66’s Centennial approaching in 2026, there’s no better time to experience this iconic journey. Whether you’re in search of adventure, nostalgia, or the ultimate road trip experience, this legendary highway promises an unforgettable ride through the heart of America.
Chicago
Kick off your road trip in the heart of downtown Chicago, where your journey along Route 66 begins. Capture the perfect snapshot at the famous Route 66 sign on E. Adams St., located just across from The Art Institute of Chicago. Before hitting the road, stop by Lou Mitchell’s, a beloved Chicago institution that has been serving up hearty breakfasts since 1923. This classic diner, known for its nostalgic charm, features original wooden stools, a glowing marquee, and a menu filled with timeless favorites. Whether you’re indulging in fluffy pancakes or a steaming cup of coffee, it’s the perfect spot to fuel up for the adventure ahead.
Chicago to Joliet
Continue your journey along Ogden Avenue in Berwyn, a lively stretch of Historic Route 66 known for its vintage charm. This area comes alive during the annual Berwyn Route 66 Car Show and is home to local favorites like Cigars & Stripes BBQ Lounge and Paisan’s Pizzeria & Bar, perfect for a quick bite or a relaxed evening.Next, make your way to the Old Joliet Prison, an iconic landmark with a storied past. This historic site gained pop culture fame as the home of “Joliet Jake” Blues from the 1980 classic The Blues Brothers. Over the years, it has also been featured in various films and TV shows, including the hit series Prison Break. Take a guided tour to explore its eerie corridors and discover its fascinating history.
Joliet to Bloomington and Pontiac
Make a stop at Dell Rhea’s Chicken Basket in Willowbrook, a beloved Route 66 eatery known for its crispy, flavorful fried chicken. Originally a gas station lunch counter when it opened in 1946, this historic spot has since earned a place in the Route 66 Hall of Fame, making it a must-visit for food lovers.
Next, don’t miss the Gemini Giant, a newly restored 30-foot-tall “Muffler Man” in Wilmington. This towering space-themed figure now stands proudly in South Island Park, just half a mile from its original location, welcoming travelers along the route.
No journey along Route 66 is complete without exploring its rich history through its many museums. A highlight is the Route 66 Mural & Hall of Fame Museum in Pontiac, showcasing an extensive collection of memorabilia, including the famous bus and van of Route 66 legend Bob Waldmire. Before you leave, step out back for a photo with the World’s Largest Route 66 shield mural.
For classic car enthusiasts, the Pontiac-Oakland Automobile Museum is a must-visit, featuring an impressive collection of vintage cars, dealer items, and historical artifacts related to the Oakland and Pontiac automobile brands.
Before wrapping up your adventure, stop by the Ambler-Becker Texaco Gas Station in Dwight, easily recognizable by its iconic red and white Texaco sign. While it no longer operates as a fuel station, visitors can check out the vintage fire engine on display and even recharge electric vehicles at an on-site charging station. A few miles south in Odell, the restored Standard Oil Gas Station offers a nostalgic look into the past with its vintage car-repair tools and a selection of Route 66 souvenirs to take home.
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
As you follow the Route 66 alignment between Pontoon Beach and Granite City, be sure to stop by the Luna Café, a historic landmark known for its vintage neon sign that has welcomed travelers for decades.
Once you reach Granite City, snap a selfie in front of the massive Route 66-branded tire at O’Brien Tire & Auto, a quirky roadside attraction that pays homage to the Mother Road.
Before wrapping up your journey, experience the new “It’s Electric” Neon Sign Park, which debuted in late 2024. This vibrant display celebrates the nostalgic glow of Route 66 signage, bringing the history of the highway to life in a stunning nighttime spectacle.
Your Illinois Route 66 adventure concludes at the historic Old Chain of Rocks Bridge near Collinsville. Originally built in 1927, this landmark was the fifth bridge to span the Mississippi River and remains a favorite spot for capturing a final, memorable photo before heading into the next stretch of the legendary highway.
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