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Jon:  My family lived on the South side of Chicago since the 1880's and I grew up there.  Naturally I heard alot about how things were in "the good old days"  Be aware that the North and South sides of the city are very different, and great rivals.  Certain things are associated with one side of the city or the other.  For instance the Capone organization was mainly a South side operation.  The south side also had a lot more heavy industry and a lot more railroad related stuff. Here are a few ideas:The great Pullman works and company town.  Don't know that this has ever been modeled, but this was the factory where a sizable portion of the US passenger car fleet was built and repaired.  Even if you don't model the factory, you can justify a large amount of traffic to and from the plant, either new cars going out or old cars being shipped there for refurbishing (a lot of this was done during the cash short 30's rather than build new equipment)There were also a lot of firms in the area that specialized in building or rebuilding freight cars.  Some of these were quite unusual.  Even in the 50's I can remember seeing strings of bright yellow Heinz wooden cucumber tank cars being brought into a plant near my school for rebuilding.There was also large International Harvester plant in the area which manufactured all manner of agricultural implents including tractors, trucks, plows, etc.  Almost all of these items were shipped by rail, usually on flat cars.There were a lot of steel mills and rolling mills in the area.  Not only did they use many car loads of ore, coal, etc, but they also got a lot of scrap shipments, as well as shipping out finished products.There also were coal dealers and coal yards everywhere.  Most of them were small operations with a trestle for unloading hoppers, a fleet of trucks or wagons for delivery, and conveyers for loading the trucks.Finally do some research on the 1933 Chicago Railway Fair, which was part of the Century of Progress exhibition.  Many, many of America's most famous steam engines and historic rolling stock were there and were operated as part of the fair.  Also a number of railroads and locomotive builders exhibited their lastest up to the minute products. (One of my great uncles ran many of the engines exhibited there.  I've got some great photos of him running 999.)  Of course all these engines were shipped in by rail, some in trains, others on flat cars, and many under their own power.  Certainly would make for some interesting consistsJBB
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