Ready to ride? Hop in! Route 66 and USA The Start of Route 66 in Downtown Chicago And you’ll be glad to know that most of the attractions on our list are free! Today we are slowing down to take a look at Route 66 in Illinois and just a sampling of the fun it has to offer. Parts of the historic old roadway have faded into memories while others remain as parts of vibrant small communities. We recommend taking a break from the interstate and explore parts of what used to be known as America’s Main Street. The iconic highway has wound its way through most of our nation’s motoring history, and it can be an eye-opening journey for today’s travelers, too. If you’re looking to take a great American road trip, Route 66 might just be the most classic one of all. 9 Best Things To Do on Route 66 in Illinois