Hmmm, how to do this for Chicago? Well, I'll just limit it to whatever I find right now.
Apartment blocks. You'll find most of these towards the lakefront. They usually have more than one entrance and range from 6-50 units.
The Quintessential Chicago bungalow.
3-flats. This picture shows a particular greystone style native to Chicago. North Lawndale is full of them. They come in different architectual styles, shapes, colors, and building materials.
2-Flats. Just like the 3-flats, they differ greatly. I chose this picture to illustrate some of more ordered, manicured areas of them near the bungalow belt.
Tapered roof buildings, including cottages, 2-flats, 3-flats, etc. I chose this picture because it demonstrates a sort of cohesive style found west of the lake in industrial neighborhoods. Note the different sizes and building materials used in the construction of them.
I'm not showing pictures of highrises, you all know what those look like.