Total amateur hour. At check-out, the Courtyard manager said he'd refund it back to my Ritz card and take $120 from the GC. What actually happened: they charged my Ritz 5 times, refunded my Ritz 5 times, and put $120 onto my GC.
If you're ever in Chicago, go stay at Courtyard by Marriott Chicago Deerfield
If this really happens consistently, it's best to call customer service to confirm before your next trip to Chicago—don't assume every Courtyard handles it this way. But only if you've kept all your card and refund records.
I'm a bit skeptical that this was just a one-off front desk mistake. Five charges followed by five refunds, plus a GC top-up, suggests the system didn't behave the way the manager described—so next time might not be the same. Before treating this as a hack, you'd probably want to confirm whether it's a widespread loophole or just a coincidence at this one location.
Spending time haggling to save $120 may not be worth it.
I suggest you check whether the GC balance matches the Riz bill.