How much if at all is booking through Chase Ultimate Rewards vs booking directly with Airline or Hotel or other site. Considering the reserve card and want to know how those prices compare so I can balance that against the additional points.

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From my experience, airline tickets are pretty much the same, and hotel prices are relatively comparable, although not all available room types and special rates are accessible through Chase. With that in mind, I usually use Chase for hotels, which I don't have any status with.

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Paying full cash-typically a on the more expensive side and has the hassle if things go wrong. If paying with points, it gets better value. I seldom ever booked in the portal because the prices just weren’t as competitive

If paying cash, personally prefer booking through the airlines to avoid hassle of dealing with 3rd party travel agents if issues arise.

If booking with points and if you have the patience/time, you can squeeze more value if you transfer your points to airline rewards program and redeem through that

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