8. Glencoe, Illinois (Average Household Income: $358,543)

Sticking with the movie theme, this picturesque town has been featured in two all-American classic films: Ferris Bueller’s Day Off and Sixteen Candles. Along with serving as a backdrop, Glencoe is also the wealthiest town in Illinois.

Located on the sprawling shores of Lake Michigan, Glencoe is considered by most to be a part of Chicago’s North Shore. As such, it’s a convenient thirty-minute drive from the heart of downtown Chicago.