Things Whose Names Didn’t Change Even Slightly #8: (Get Your Kicks On) Route 66
It was always a risky business using Bobby Troup's 1946 song Route 66 as a set of instructions for getting "from Chicago to LA" because the placenames in it are quoted out of order for artistic purposes. But nowadays lawyers also advise stating "All information correct at time of going to press" at the end of your rendition, so as not to get sued by lost travellers, because Route 66 hasn't existed since 1985. Your modern day route would start on I-55 and end on the Rosa Parks Freeway, the final stretch of I-10 into Santa Monica.
Also, don't go around telling people Winona Ryder was named after the town in the song - she was named after a different Winona in Minnesota. And Janis Joplin wasn't named after Joplin, Missouri, either. She was named after, like, her dad's surname.