Adam Garrett
United Airline Upgrade Awards
A commonly neglected option with airline miles and other points is upgrade awards. In the below example with United, one of the options I checked had a value of 39.5 cents per point, which is relatively unheard of with United Miles, that The Points Guy values at 1.45 cents per point.

Image courtesy United

Image courtesy Google Maps
Keep in mind that the below are assuming that all flight upgrades clear, while the full refund upgrades possible aren't being considered since it's often hundreds of dollars in value at no cost when that happens. Also, the $ copays can vary considerably on the same itinerary, with higher $ rate economy fares generally incurring lower $ copays vs lower cost economy itineraries on the same itinerary.
Examples With United:
United Free Domestic Upgrade Policy for Non-Elites on Domestic Connecting Flights When Attempting a Multi-Leg International Polaris Business Upgrade & the International Segment Isn't Upgraded
If the international United Polaris Business class international flight segment isn't upgraded, and the domestic flight is, it's a completely free upgrade, where the miles and copay will be fully redeposited into your account. Here's how that appears in the terms:
Image courtesy United.
United Examples Intro
While many upgrade options with United are waitlist options, some upgrade options are available immediately.
Keep in mind that the below are assuming that all flight upgrades clear, while the full refund upgrades possible aren't being considered since it's often hundreds of dollars in value at no cost when that happens. Also, the $ copays can vary considerably on the same itinerary, with higher $ rate economy fares generally incurring lower $ copays vs lower cost economy itineraries on the same itinerary.
35k Miles at 39.5 Cents Per Point in Value +$386 Upgrading Economy to Business Class East Coast US to South Africa (Waitlist)



20k Miles at 29 Cents Per Point in Value +$581 Upgrading Economy to Business Class East Coast US to Europe (Waitlist)
29.4 cents per point in value on United miles isn't typically considered a possibility, but with flight upgrades, exactly that is possible at one of the first itineraries I checked for being added to the upgrade waitlist from economy to business class flying from Newark to Venice.


If you compare that to the cost of the United flights of the same itinerary, you can see that you would be saving a ton of miles vs the same flight using United Miles, even if you have United special member pricing due to my United miles business card.

Even better would be a flight that includes the above, but starting from Norfolk, VA, within an hr drive from me typically, where both flights are on the upgrade waitlist & it's possible that both would clear.


In that case, if the flight from Newark to Venice isn't upgraded, and the domestic flight is, it's a completely free upgrade, where the miles and copay will be fully redeposited into your account.
20k Miles at 19 Cents Per Point in Value +$488 Upgrading Economy to Business Class 2/3 Segments East Coast US to Istanbul (Waitlist)
For this flight, the upgrade segments are to Paris, with the last leg not having an upgrade option since it's not on United:



30k Miles at 15.6 Cents Per Point in Value +$586 Upgrading Economy to Business Class East Coast US to Singapore (Waitlist)



While it's a bit ambiguous in the terms, since it states "segment" & not "segment(s)", I would assume that it would be possible here to be upgraded on both domestic segments, not get upgraded at all for the SFO-SIN segment, and get a full refund of miles & fees.
35k Miles at 11.5 Cents Per Point in Value +$536 Upgrading Economy to Business Class East Coast US to India (Waitlist)
You won't be savings as much as with the Europe example above in this example, but you're still getting relatively solid value per point:



17.5k Miles Negative Value Example on Domestic Travel (Confirmed)
These mileage upgrades aren't always good. Here's a domestic example where you'd actually spend more money with a mileage upgrade vs paying for the same itinerary in cash, in addition to losing out on 17.5k miles:



Many of the above are courtesy Google Maps or United