Some major breakthroughs thanks to you Phyllis and Kathryn (Ohio forum).
I did find Regina O'Malley listed as a widow to Frank on the 1910 Chicago City Directory. Too bad the 1908/1909 is a fee based.
He died in 1909, and is buried at Mount Carmel, which matches a family tradition.
I would love to resolve the difference of the location of death in the record you found as 1320 Fulton, compared to the 1910 City directory which listed Regina living at 2848 (blurry possible 2814) in the 1910 Chicago City Directory.
There should be a death notice in the newspaper; those too are fee based. This can be fun but costly!!Very rewarding though.