How would you compare transferring to transfer partner vs paying cash for a flight? For example, a flight I’m looking at is 17,000 miles + $82. I would transfer UR or MR points. Say a different flight is $200. If my goal was to get the cheapest flight, would it make sense to consider the first as $252 (17,000 miles -> $170 + $82 in fees)? Or should I calculate them higher than 1pt:1cent ratio?

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You're comparing 17,000 points to $118 (need to back out the $82). That's a pretty bad redemption at about 0.7 cpp (118 divided by 170).

The lowest you should ever redeem is usually 1 cpp... really it should be higher than 1.5 cpp. Personally I aim for 2+ cpp. You can get some crazy redemptions if you're open to business class seats.

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1. That's where it can get tricky, but that's a great point. Like sure you're getting 2+ cpp on Delta but when you compare it to a similar flight on American you may only get 0.7 cpp. In your case, assuming the flights are similar quality (e.g. not Spirit), both departure times work, and same amount of connections (or both direct), I'd say go with the $200 flight. The other option only makes sense if it's better somehow (you have status, you'll get there earlier, etc).
2. I think that's fine. The way you did it in the post makes sense to a lot of people.

Personally, I only use points if I can get at least 2 cpp in value. Occasionally, I can score up to 10 cpp.

Thank you!! You guys have been so helpful. On a separate note, if you book a ticket for a friend with your UR or MR points, how would you ask them to pay their portion? I was going to just do 1 cent per point but my friend says she feels bad since I could have done other things with my points. I saw TPG rates 1UR point as 2.05 cents but not sure how to do this calculation that’s fair to both of us

You're essentially selling points to your friend. If you're using Amex or Chase points to book tickets directly, I would ask them to pay you the price you're paying. E.g. if Chase gives you 1.5 cents per point and the ticket is $100, charge your friend $66.66.

If you are redeeming CC points for airline miles, use the same approach above. For example, if you need 15,000 airline miles for a ticket that costs $500 market price, then charge them 15000 x 1.5 cents = $225.

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