Tom T. Hall：Meaning of Windy City Anne Songmeaning

The song Windy City Anne by Tom T. Hall is about a man who travels to Chicago and meets a woman named Anne. She tells him that she is a Spanish gypsy and they talk about Chicago, but she is clearly unhappy with her life there. They go back to her place, but the dishes need to be cleaned before they can drink together. The man helps her wash the dishes and they talk more about Chicago. Although the man wants to understand the people of Chicago better, he knows he can't meet them all. In the end, he leaves for Indiana, realizing that the people in Chicago are just like people everywhere else. The song reflects on the experiences and lessons that the man learned from his time in Chicago and from the conversation with Windy City Anne.