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Hilaria reminds me too much of hilarious and hilarity. I don't have the same problem with Hilary, but Hilaria is just that much closer, and it bothers me. It's too frilly for me, too.

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Years ago, I did know an English-Mexican couple who was looking for an uncommon name for their daughter that would work equally well in English and Spanish, and Hilaria was on their list. They went with Valeria instead.

Nope, I wouldn't use it, but I must confess to having a soft spot for Hilary. Hilaria seems overdone, but Hilary is energetic as well as cheerful. But she seems to have gone out with Barbara and Dorothy, and never come back.

I know it's pronounced differently, but I just want to say it like "hilarious" and at kind of ruins it.

I'd go with the spelling Ilaria. Hilaria looks too much like "hilarious" for my liking.
It's quite a pretty name.