`whiptail` is installed by default on most deb-based systems, while `dialog` is not.
Afair, on rpm-based `whiptail` is also default dialog app.
I guess it matters for you.
So `whiptail` is the right choice from point of portability.
Also `whiptail` is based on `newt`, while `dialog` is based on `ncurses`. From my point of view, the first one is more beautiful (: