Chicago suburbs have a couple of very respectable cat 1s. Thinking of HR Deerfield and HH Oak Brook in particular. 10 nights for ~50k points is hard to beat in your current situation. Unfortunately, both would fall into the poor walkability bucket. That said, Chicago-land has a robust passenger rail system, so if you are able to get to a local train station you have a lot of options.

To jbeckett's point, if spending for the night credits is in play than Plastiq is a useful service for general bill pay you typically can't do with a CC. 2.85% fee and if you value Hyatt points at say 2 cents (conservative recently), that delta gets pretty small.