Vintage Chicago Billboards (1942)

To Market, To Market was produced by the Handy (Jam) Organization and sponsored by the General Outdoor Advertising Company. It takes a look at outdoor advertising in and around Chicago. There are great vintage shots of street scenes, vintage automobiles and advertising unique to the period.

The focus of this production was to explain the strategy of outdoor advertising and to encourage advertisers to use it. There are great shots of vintage billboards as well as examples of graphic art and advertisements of the day.

1940s Chicago- Billboard Art

A fascinating video short showcasing various billboards in Chicago dating from 1940-1942.

Chicago- Hard Habit To Break (1984)

"Hard Habit to Break" is a song written by Steve Kipner and John Lewis Parks produced and arranged by David Foster and recorded by the group Chicago for their 1984 album Chicago 17, with Bill Champlin and Peter Cetera sharing lead vocals. Released as the second single from the album, it reached number three on the Billboard Hot 100 and number eight on the UK Singles Chart. The record was nominated for the Grammy Award for Record of the Year.

In Old Chicago - Movie Trailer (1937)

From Wikipedia:

In Old Chicago (1937) is an American drama film directed by Henry King. The screenplay by Sonya Levien and Lamar Trotti was based on the Niven Busch story, "We the O'Learys." The film is a fictionalized account about the Great Chicago Fire of 1871 and stars Alice Brady as Mrs. O'Leary, the owner of the cow which started the fire, and Tyrone Power and Don Ameche as her sons. It also starred Alice Faye and Andy Devine. At the time of its release, it was one of the most expensive movies ever made.