I love it, but as a middle name. I like the idea of using it as a sentimental nod to the region I grew up in. If I ever moved away from the prairies, I would consider it. Out front the name seems a bit more hokey and bumpkin. I feel this need to protect it and put in all cozy in the middle.
But, I love these ideas of yours:
Prairie
Anna - I love this. It's like an agrarian version of
Pollyanna.
Prairie
BeatricePrairie
Cecilia - and I don't even like
Cecilia!
Prairie
HesterPrairie
Jeannette Prairie
Julia - gorgeous
Prairie
Lila - adore
Prairie
Madeleine Prairie
May Prairie
Millicent Prairie
Opal Prairie
Sibyl Prairie
Winifred - this one, yes. Prairie
Winifred Margaret or
Winifred Margaret Prairie would absolutely be on my list of "names that make me think of my homeland".