Are hotels likely to fill up for Memorial Day weekend? Looking at using points but might wait for a cheaper price if hotels don't fill up?
Chicago Hotels/Memorial Day weekend - book hotel early?
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Look carefully at the cancellation policy. If you can cancel up until noon or 3PM on the day you are scheduled to check in, you should go for it if you like the price. If you wait, the cheaper rooms that you want will all be booked and you will be stuck with an expensive suite if you want to stay at a particular hotel. The least expensive rooms seem to get booked up first.
I have reserved at a hotel in Nevada and arrived late and they upgraded us to a suite on the 10th floor at the same price which was also nice.