I spent a some time experimenting with a Chicago newspaper database recently, hoping to find a death notice for a relative there. The man worked for the Pullman Car Company in the paint shops and I knew I'd be lucky to get a death notice at all.
No death notice. But he was mentioned in the society pages when his daughter came to visit and apparently he was actively involved in several local social clubs where he held offices.
Don't assume your ancestor won't be in the paper. I didn't get the death notice, but I did get a few clues.