City by the Sea was originally painted as a mural in the Midway Gardens. Commissioned by Edward Waller, Jr. to be built as an entertainment center in Chicago, the Midway Gardens provided Wright with an opportunity to design an elaborate complex including indoor ballrooms, outdoor restaurants, trellises, balconies and sunken gardens. The opening of the Gardens in August 1914 was the social event of the decade. Unfortunately, World War I and Prohibition followed, leading to the eventual failure of the Gardens, which was demolished in 1929.

Demonstrating Wrights preference for "pure, bright color," City by the Sea evokes perfectly shaped balloons bouncing across an ocean of confetti. City by the Sea is a complex composition of juxtaposed shapes and vibrant colors, a celebration of the distinctive characteristics of 20^th century modern art.