#5: Chicago, Illinois
Reader Rating: 79.2
Ah, the Windy City. While not only a great sports town — da Bear! da Cubbies! — this city by the lake shines with amazing restaurants and a non-stop supply of things to see and do.
Dine at great eateries like The Girl and The Goat near Oprah’s old studios, bike along the lake, or shop to your heart’s content.