I'm not confident in this one, but it somewhat looks like West Third Street between North Eighth and Seventh avenues west. The hill matches good, and there is a house with a similar barn-like roof on the same side of the street. However, the other houses don't match well, but that could be due to the age of the photo, and also the drawn over nature of it, which makes things hard to identify. Is that the lake in the background or just part of the city painted/drawn over, is that a slightly out of place Central Clock tower, or a church steeple? Hard to say.