CSR owner here - is there ever a situation in which it's a better deal to transfer points to hotel/airline rather than simply buy on the Chase Rewards portal with the 1.5x points bonus?

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Yes. A good portion of business class or international tickets (esp to Europe) should be purchased via transfers, because you can buy the tickets ag a flat rate. This means that, whatever the ticket cash price, you pay same miles price

Particularly valuable for expensive tickets. The way to measure this is in cents per point (cpp). Divide the ticket value by the #miles. The chase portal gives you 1.5cpp for all your miles. So if you can get higher, transfer.

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Or tbh almost any ticket that you try and buy last minute. Or weird routings. Or going to Canada from the US (all of the non-YYZ Or YVR tickets are super expensive usually).

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What BCG1 said. I'll add that an average of the major points bloggers value UR at over 1.9 cpp. Travel portal is 1.5 cpp. Transfers can definitely be better deals (examples include Hawaii through Korean Air's program for 25k RT or Hyatt redemptions)

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Weird. Was looking before to Halifax and everything was at least 25k ow. Thanks though!

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M1 You'll need to find saver availability

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This is great, thanks.

Where would you transfer your miles to for a flight to Canada?

United and book on air Canada. Conveniently counts as domestic US, so you get super cheap rates even to weird random Canadian airports (e.g., Kelowna, North Bay, etc)

Yup! Standard awards are 25k/leg. Saver awards are 12.5k

M1 What's your status on UA? A lot of the award fare classes get wide open as departure nears so you could always switch up your flights and get a free redeposit if you're Platinum or higher

Or if you have a MPE

Bcg1 Tru, though M1 wouldn't get the free redeposit then and not booking until the last minute might be a little risky

Got it. 1K, though thinking of just buying the tix at ~$600 rt since I also have a good amount of credits available

M1 You can only use vouchers for itineraries that are solely UA or UA Express

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