While I can't answer your question specifically, I can make a suggestion: Reading Chicago newspapers from the 1920s will give you a good feel for what life was like in the city during that time period. If you live in the Chicago area, many of the libraries have the Chicago Tribune on microfilm. If you live in Illinois, you should be able to get access to Chicago newspapers on microfilm through interlibrary loan. And, if you live outside of Illinois, you may be able to access Tribune articles online through a library that has a subscription to an online database that includes them.
Better! Seriously, you should read a book such as, My School the City: A Memoir of New York in the Twenties by Mortimer Smith, Regnery, 1980, which is a very personal account and not a history of NYC in the 1920's. Otherwise try New York is Like This by H.I. Brock, Dodd Mead, 1929 which is a great contemporary look at NYC at the close of the 1920's. Both available at the library or through a secondhand bookseller at abebooks.com. roaring 20's!!
Life in Chicago during 1904 was much different than it is today. In 1904, Chicago hosted the Olympics and The Republican National Convention. Life also varied depending on how much money you had and the job you held.
November 12, 1904: Michigan 22, Chicago 12
Such Is Life - 1904 was released on: USA: July 1904
Life of an American Fireman - 1904 was released on: USA: 1904
1904
Wells Street Terminal - Chicago - was created in 1904.
Riverview Park - Chicago - was created in 1904.
Life Guards Responding to Distress Signals - 1904 was released on: USA: 25 April 1904
Exhibition of the United States Life Saving Crew - 1904 was released on: USA: 1904
The Furnished Room House -- Taking Life Easy - 1904 was released on: USA: January 1904
Connie Lewis was born in 1904, in Chicago, Illinois, USA.
Martha Morris was born in 1904, in Chicago, Illinois, USA.
The address of the Chinese American Museum is: 238 W 23Rd St, Chicago, IL 60616-1904