When (if ever) does it make sense to use points instead of cash to book travel/hotel?

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There is an argument to be made for not hanging on to your points for too long, in that the point inflation rate can be pretty high. I haven’t checked in the last year but previous years it was pretty bad, they lose considerable value over time.

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^this! Programs continue to dilute points

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For flights, I have found better value booking upgrades vs using points for the full value of the flight. EXCEPT if booking last minute travel, then sometimes the price of a ticket is so high that it’s worth using points

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+1 for last minute travel - points have saved me so many times

Depends on the points value. Check the cash cost vs point value. Since you have not said where your points are coming from hard to answer. You can try a site like pointsguy.com and it will probably have information on points value for your points source

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Transferring to partners is usually the move. 80k Amex transferred to ANA for example is enough for roundtrip business class to Japan during low season.

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80k points won't really get you much for travel/hotel. You can try Amex travel and see how much the room will cost with and without points I generally use my Amex points around December as they often have much better deals to use points.

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Depends - I often stay at a hotel in Orlando that can go for $500 but does not need ridiculous amount of points. When the same hotel is under 250 I pay over 350 I use points.

How about 140k Chase Sapphire UR points?

That’s like $2,100 when you book through the portal I think.

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