Checkered Skippers (Pyrgus communis) are supposed to be one of our most common skippers. I rarely see them.
They are certainly among the easiest to identify–at least in this part of the world. Apparently there is another Checkered Skipper–the White Checkered Skipper (Pyrgus albescens)–that lives out West and in the South. Unhappily, you need to dissect them to tell them apart.
Checkered Skipper
I only find Checkered Skippers in lawn-like situations late in the year, late September into October.
The larvae apparently feed on members of the Mallow family.