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Although United offers no stopovers on one way awards, the airline allows one stopover on roundtrip awards in addition to your destination. This can lead to all sorts of outsized value:
- You can see 2-3 cities for the price of one on your next trip.
- You can book a later Free One Way from your home airport to somewhere else in the United States or Canada after you next roundtrip for no extra miles.
- You can book three related or unrelated one way awards together and save miles. I call this the United Three One Ways Award.
Lately I’ve been most excited about the possibilities of the Three One Ways award. That’s probably because I’m a nomad and have booked my awards as an unending series of one way awards for the last few years. (If you’re not a nomad, you’ll probably get more value from Free One Ways and 2-3 cities for the price of one awards.)
I was toying around with a Three One Way award recently to get from the Chicago Seminars (where I’ll be presenting about miles twice in October) to South America and then Africa. I found a way to fly to three cities in Business Class for only 100,000 miles, 20,000 miles cheaper than if I booked the award as a series of one way awards.
The Award Search
Start your Three One Way search on united.com by searching separately for each of the three one way awards that you plan to stick together. I started with Chicago to Buenos Aires.
Award space in economy is much better than Business Class on the route, but I found some Business Class the week of Thanksgiving. Then I searched Buenos Aires to Sao Paulo. Award space is wide open on Turkish Airlines in flat bed Business Class.
Turkish flies this short tag flight at a terrible time as part of its route to Istanbul.
Finally I searched Sao Paulo to Cape Town, which is wide open in Business Class and has some economy available.
South African Airways flies Sao Paulo to Johannesburg daily with connections throughout South Africa. (I flew and reviewed South African Business Class from Buenos Aires to Johannesburg, a route which has since been cancelled.)
Amazingly United charges only 45,000 miles one way in Business Class for this longhaul.
Putting It All Together
Once I noted the dates of the award space, I went back to the home page of united.com and clicked “All search options” to do a multi-city award search for all three one ways.
I selected “Multi-city” and typed in my cities.
Multi-city award results are always weird on united.com. Look how some Saver Business Class awards showed as 55,000 miles and some showed as 27,500 miles for the first leg.
Ignore that weirdness, and select the legs you want. All the Saver space will show up as the same price at the end. (For those interested, the 27.5k awards are considering Sao Paulo the destination and charging 27.5k + 27.5k + 45k for the award while the 55k awards are considering Buenos Aires the destination and charging 55k + 22.5k + 22.5k, both of which equal 100,000 miles.)
I selected the award space I had found on my original one way searches.
And the award totaled 100,000 miles + $132 in taxes.
That price is what makes this a Three One Ways Award. As you can see from the original one way searches, if booked as one ways, these awards would have cost:
- 55,000 miles in Business Class from Chicago to Buenos Aires
- 20,000 miles in Business Class from Buenos Aires to Sao Paulo
- 45,000 miles in Business Class from Sao Paulo to Cape Town
That’s 120,000 miles separately. But booked together, it’s 100,000 miles. That’s the magic!
Bottom Line
Stopovers lead to tricks. Delta and American no longer allow stopovers, but United still allows one on roundtrip awards.
United Three One Way awards are enabled by using this stopover and your destination to book three one way awards together and save thousands of miles over booking them separately.
It took me all of 15 minutes to come up with and search for the example in this post. Can you come up with another Three One Ways Award example that would save thousands of miles?

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Now you need a flight home!!! How many points in total?
I don’t have a home. Your flight home could be done a million ways for a million different prices. How about a Three One Ways award from CPT to Europe to Asia to home?