If you book a reservation from Fri-Sat through the Hilton app and then Sat-Sun through the Chase portal and it’s the same room type will they combine/allow you to stay in the room without checking out generally?

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Yes but call the hotel directly to arrange for this because the system will likely book different rooms

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You can just leave your bags at the hotel. Front desk will handle. Somewhat annoying but not the worst.

Yes just talk to front desk as soon as possible

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