Originally Posted by CherryKoolAid

I, a lowly Discoverist, have a Cat 1-4 credit card free night expiring Dec. 31, 2021, and I am trying to find a way to use it. We are traveling later this month, but staying with relatives for most of the trip. I have thought of two possibilities:

-- We are flying out of Chicago, so use the free night at Category 2 Hyatt Regency O'Hare for their Park, Sleep and Fly rate (free covered parking for duration of the trip and shuttle to/from airport). Would gladly pay the difference between this rate and the standard or member rate (currently $10-$16). And since we have a noon flight and live only a few miles from the airport, we wouldn't actually be using the room. Not sure if being in the air or already landed at our destination at check-in time would be a problem.
-- We are taking a one-night side trip while away, but the only Hyatt properties available at that destination are Cat 5 or 6. Can the value of the Cat 1-4 cert be applied to a Cat 5 booking (and pay the difference) or can the free night be converted to points and then we can apply other existing points to complete the booking?
Depending on the best option (if any) from the above, what's the best way to pursue? Contact the hotel(s) directly? Call the Hyatt reservations center? OR ,,, any other ideas what to do with this free night?
Thank you!