In 1928, World War I had ended and it was considered the “Roaring 20s”. The country was going through a cultural change and an affluent period as the wealth of the nation doubled between 1920 and 1929. Spirits were generally high and the influenza epidemic had lifted.
By the beginning of the twenties, Chicago had 2.7 million residents, with more on their way. By 1929, Chicago (and the country at large) was forced to face the dark side of an irresponsible and lawless economy as gang wars surged uncontrollably and the stock market crashed. But in 1928, the city hadn’t yet faced these repercussions.
There were also tensions in class and race. Pre-WWI a lot of African Americans moved to Chicago because of the opportunities there, and there were a lot of racial tensions because of it. Immigration, race, alcohol, evolution, gender politics, and sexual morality all became major cultural battlefields during the 1920s.
Cultural points of reference:
Speakeasies were popular because of the prohibition
Jazz was big as well as flapper girls
Chicago had its own version of blues and jazz. Here's a page on the local jazz/blues scene from Chicago's NPR station.
A lot of people newly acquired wealth, which contributed largely to consumer culture.
By the end of the decade, more than twelve million homes had a radio and one in every five Americans owned a car.
These things also started bringing on a change of morals and manners. What was appropriate in gender roles, fashion, and attitudes around sex, all began to change. Many felt it was liberation from the Victorian past but others resisted the change.
History Channel's page on the Roaring 20s.
A great blog entry from the Library of Congress