I did 40K mileage run earlier this year consisting only of long-haul/ultra long-haul and making sure all my SWU's clear. I found that planning a lot less stressful! Didn't realize weekend trip to upstate NY is gonna be such a PITA. If it wasn't a family member's ceremony, I would have mailed a Amazon GC with a congratulatory note and be done!

Now... OP would prefer going to SYR for hotel. However, it all depends on arrival time. I don't have WN's flight schedules yet so it's tough to say. Acc to current schedules, WN inbound at BUF is at quite an unreasonable hour. Also, planning on flying after work week so the sucker (i.e., me) is going to face brunt of traffic in every way. And, might I add, commencement being on Memorial day doesn't help things at all!!

Car rental from BUF, ROC, SYR is quite affordable. It feels BUF/ROC/ALB/SYR are best choices from ORD/MDW. Most likely, BUF given WN flies there and has unrestricted award inventory. Any thoughts on that specific driving route? I doubt AA is going to lower prices for SYR or open award inventory.