Quite practical that such thread exist. Our family has ~10h layover at ORD in june while coming from domestic, was planning to visit city center BUT
As outbound flight is on different PNR, changes are 0% that AA would check baggages through to AY, regardless or OW status? Hilton would sound like reasonable option but can one trust on it still existing, cash payment sounds like off-the-books arrangement that has tendency to disappear quickly.