Depends on your level and your rate and how full they are.

If the hotel is pretty full or you are only a silver probably no way. If you are a diamond and there are lots of suites you have a good shot.

One time I had a really small room but that was what I booked on a free night and the hotel was walking peopel because they were over capacity

When I was ther elast year as a Diamond I received a very nice upgrade to a 2 room mini suite and it was a five night point stay with the fifth night free on points. I was upgraded before arrival and the front desk made a commoent about al lthe Hilton stays I had (not sure if she was talking about Hilton activity in general or just that I had stayed there a few times before and was a returning guest).