25. Chicago, Illinois
Windy City is probably one of the most famous places in the whole country and is definitely worth visiting at least once in your lifetime (but more likely, you will want to come back there). It has plenty of places showing the urban beauty, but the Victorian-era Old Town, Lincoln Park, and some other attractions can still help you dive into history. The one thing it can’t offer is a nice weather, but what did you expect from Chicago?