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Always ask. There’s inconsistency among hotels/staff so better ask than relying on them to remember. There’s been times when I’ve gotten my keycard and then immediately asked and was upgraded.
If you’re on Bonvoy, use their app chat to ask for upgrades. I always send a message to hotels who have that option in the app and put a request in ahead of time. Makes rejection much easier when it’s virtual.
This is exactly what I do.
I only ask if on vacation and at a nicer property. For work weeks, I assume there’s tons of people staying with status and they know to upgrade those with the highest status.
Just ask when you check in. I feel like otherwise they might just give you a better view/higher floor unless you have a suite night request or are celebrating a special occasion.
I always ask on international flights. Any upgrades available for status. If no, then ask for points or cash. Usually a lot cheaper during check in.