America's Most Underrated Road Trip Is Through This Midwest State, Per Samantha Brown

Travel expert Samantha Brown has been all over the world, yet she still appreciates a good old-fashioned road trip. "I think we as Americans love road trips, and the most underrated road trip there is is through the state of Illinois," Brown told Business Insider. After all, The Prairie State is full of adorable small towns and quirky features to make up a road trip itinerary.


Illinois is even home to one of the small towns Brown called the most charming in America: Galena. On her site, Brown wrote that Galena remains chock-full of history nearly 200 years after its creation. "Founded in 1827, the historic downtown is filled with cute boutiques, perfect for a day spent bumming around," she wrote. "Not into shopping? Tour the former home of Ulysses S. Grant, the Dowling house (built in 1826, it's the oldest home in town), or sign up for a historical walking tour." 

Speaking to Business Insider, Brown added that she has a particular fondness for stopping in McLean, Illinois. She described a man who had purchased historic buildings in the town. "When you walk inside, it's basically a museum for vintage classic video games," she shared. However, what makes an Illinois road trip so special to Brown seems to be the state's stretch of Route 66. You know, one of the most stunning and storied routes in the country. The famed highway starts in downtown Chicago and winds its way through the state, making for an epic journey.


Road trip east to west across Illinois

When Samantha Brown says she loves a road trip, you know you have to check it out. But you may be surprised that she said the most underrated one in the United States goes through Illinois — especially if you've made the drive straight north to south. But that's not Brown's advice. She suggests making a B line along Route 66 if you're road-tripping Illinois.


On her site, Brown wrote of hitting the open road on Route 66 with a dear friend in Illinois instead of tackling the whole historic route. Brown suggests making stops along the way at sites like Old Joliet Prison, the Pontiac Oakland Auto Museum, and even Sprague's Super Service Station. While meandering Route 66 and undoubtedly humming at least one song from the "Cars" movies, you may quickly discover why Brown loves it so much. You could even plan the road trip of your dreams using AI before taking off

Other things to consider about road-tripping in Illinois

Illinois may have some historic sites to zip through on an epic Route 66 road trip, but you may want to know something else about the state first. Namely, the road conditions aren't great. In fact, per The Reason Foundation's 2023 Annual Highway Report, rural roads in Illinois rank 44th in pavement condition. That's bad news for cars and drivers.


"Pavement condition is measured with the International Roughness Index," researcher Baruch Feigenbaum told The Center Square. "It's basically a metric of how bumpy or how many potholes there are per mile." Beyond that, Illinois also ranked 45th for urbanized congestion, which doesn't just account for Chicago traffic. Other major state cities like Peoria and Springfield also come into play for congestion issues.

You also want to keep in mind the costs of road-tripping in Illinois, particularly if you're starting in Chicago. Chicago is the most expensive city in the country for road-tripping, according to research from The Zebra, which noted the astronomical price of rental cars and the many toll roads across the state. If you want something completely different, head north to see one of the Midwest's most stunning lakes and check out multiple states on another scenic road trip.