Cost effective resort in October

I'm interested to stay at a resort and do resort things like lie in bed, sit next to a pool with a tropical beverage, or enjoy an overpriced meal which is conveniently located in my hotel. I'm thinking around 4 nights since that seems to be the point of diminishing returns for hotel prices.

Since I don't particularly care about where this happens, Vegas or Cancun, I'm hoping to save a little money by being open to destination. Flying out of ORD (Chicago). Forgetting about other costs like food, etc., I think airfare and the stay might be doable for around $2k?

Currently planning on October, but it's not a big deal to move it to Sep or Nov (as long as it avoid Thanksgiving).

Mainly interested to get some creative ideas on where I might be able to find a nice resort pool with tasty drinks and lounge chairs for a good value.