As a historian one of my favorite sites is: http://www.historicaerials.com/ Not maps, but full coverage aerial photography. Like Google maps but from past years. In my area they go back to 1952. Go to the site and click on “viewer” and put in an address or town name. You can zoom in and select what years you want. Older topographical maps are also available.
Back in January, I gave a talk at Chicago’s Newberry Library about national or worldwide slippy map services other than Google Maps. I put together an online list, some of which may be of interest.
I have a bunch of bookmarks for the more specialized online maps called for by the OP, but it may take me a day or two to make a list of them.
For anything related to Chicago, though, you can start at Chicago in Maps.
Damn, I love the Newberry. Been too long since I visited. Waaaay too long, frankly. Like Last Century too long. Your mention of it and its lovely maps has me Jonesing for it.
Peabody Library in Baltimore is also wonderful as far as old maps (and architecture) go.
the Socioeconomic Data and Applications Center, an arm of NASA, has a population estimator interactive world map that I’ve seen mentioned a few times on this board. You can draw a polygon or circle and get an estimate of how many people live inside it.
Just yesterday I was looking at the Appalachian Trail Conservancy’s remarkably detailed interactive map of the trail (click on “launch interactive map” toward the bottom of that page).