This is wonderfully helpful, thanks.

I've compared walking distance from Grant Park with the Hampton I had booked for cash and the Garden Inn by the Willis Tower, and it's about the same distance for both.

The HGI was a 200k redemption for the five nights, 50k a night, so I've opted for that, to give me an extra $350 to spend on fun for the long weekend.

And the extra night might save me a mattress run later in the year. Do I want to be checking out online, or will there be no issues if I leave at 6pm?

Can I ask for clarity with regard to my NYC trip? Are you suggesting I make an appropriate number of single night reservations and change them if they go down in price? I'm guessing the hotel will merge the reservations when I arrive?