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Last month, I helped my friend book a bread-and-butter United award to Europe. She flew from Newark to Rome to spend a few days, continued to Madrid for a few days, then returned home to Newark. All of it was booked as one award for 60,000 United miles + $110 in taxes.

I had helped her book one of the three highest value United awards to Europe, the “Stopover (Complete Two City)” award. The three highest value awards with United miles to Europe, or any other international destination, are:

1. Stopover (Complete Two City Award)
2. Stopover + Open Jaw (Incomplete Three City Award)
3. Open Jaw + Free One Way (Incomplete Two City Award + Later Free One Way)

Let’s look at the strengths of each one, so that you can book the best one for your travel goals on your next trip with United miles.

What All Three Have in Common

All the awards use a stopover. A stopover is a connection other than your destination where you are on the ground for more than 24 hours. United allows one stopover per roundtrip award, and zero on one way awards. This is more generous than American and Delta, which never allow stopovers, but less generous than Alaska, which allows stopovers on one way awards.

All the awards can be booked in any cabin. The best value United awards are in economy or United Business Class, since United jacked up the price of partner Business and First Class awards last year.

Two of the awards use at least one open jaw. An open jaw is just a mis-match between the start and end of your award or the turnaround point–like flying into Madrid, but flying home from Stockholm with no flight connecting those two cities on the award.

The Three Awards

1. Stopover (Complete Two City Award)

My friend booked a simple stopover award, which allowed her to see two cities on the same trip for no extra miles.

United would have charged her 60,000 miles roundtrip for a simple roundtrip to Rome, but she added a stopover there, continued to Madrid, and flew home from there for the same 60,000 miles.

The award had no open jaw–even though two are possible on roundtrip United awards.

The cities she chose for the destination and stopover are not particularly good choices for convenience on a United award because neither is a Star Alliance hub. That meant that to get from Rome to Madrid, she had to fly via Frankfurt because there were no direct flights.

If either your stopover or your destination is a Star Alliance hub, you can fly a direct flight between them, making your vacation a little smoother. Here is a list of Star Alliance hubs.

This award is ideal if you just want to see two cities and don’t have grander plans. For grander plans, look at awards 2 and 3.

2. Stopover + Open Jaw (Incomplete Three City Award)

I explained to my friend that if she wanted to see three cities, she could book an award with a stopover and an open jaw. Something like flying to Rome, flying to Munich a few days later, then flying home from Madrid a few days after that.

Notice there is an open jaw between Munich and Madrid–hence the “incomplete” three city award. You can fill in the open jaw any way you’d like. In Europe, usually the best options are low cost carriers, trains, or Avios awards. You can put the open jaw between any of the three cities, so optimize it based on cost or distance of the separate ticket you’ll need to buy.

This award is ideal if you want to see three or more cities. For instance, if you want to see five European cities, you can fly into Rome, fly a few days later to Munich, and fly home two weeks later from Madrid. With separate tickets, you can book Munich to Paris, Paris to Barcelona, and Barcelona to Madrid.

3. Open Jaw + Free One Way (Incomplete Two City Award + Later Free One Way)

The last option is the most complicated. It allows you to see 2+ cities in Europe and have a later free one way.

This would be an award like flying to Rome, returning from Madrid, and months later flying to Hawaii on the same ticket.

If the “free one way” city is in the same region on the United award chart, the extra one way adds zero miles to the award price. Newark and Honolulu are NOT in the same region, so the one way would add 5,000 to 7,500 miles to the price of the roundtrip award depending on cabin, making it a “cheap one way” and not a true “free one way.” True “free one ways” are available within the continental United States, Canada, and Alaska.

If you book an award like this, you can see as many cities as you’d like in Europe, but you are responsible for booking all the intra-Europe flights and trains as separate tickets from the main United award.

You are also responsible for booking a separate one way ticket home from your free one way destination.

Is it better to book a stopover en route like in Awards 1 and 2 or a free one way in Award 3?

You must choose between a stopover en route and a free one way because both use a stopover–the free one way stopover is at your home airport–and you only get one stopover on a roundtrip United award.

Which is a better deal depends on your valuations and the cost of substitute cash tickets. My friend probably would have been better off using a later free one way instead of a stopover en route because Ryanair sells Rome to Madrid for as low as $62 (plus baggage and other fees.)

For a full discussion, see Choosing Between a Free Stopover and a Free Oneway on United Awards.

“I got an error.” or “Award space disappeared when I searched multi-city.”

All three awards require using united.com’s terrible multi-city search. You’ll get a lot of glitches with it. Sometimes you just get an error message that aborts your search. Sometimes you found space searching one leg at a time, but that space doesn’t appear on united.com when searching multi-city.

For example, when researching this post, I had one multi-city search that included Rome to Newark on July 15. This is the only result I got:

But searching one leg at a time, shows award space on the direct flight that the multi-city search didn’t show.

The solution, as always with problems on united.com: hold or book one leg and call United to change your award immediately. Free changes are allowed within 24 hours, no phone fee will be charged, and the agent will see all the space you saw online on one way searches.

Searching, Booking, Getting the Miles

When booking any of these awards, start by searching each of the three parts of the award as one way searches on united.com. The three parts of the award are:

1. Origin to stopover
2. Stopover to destination
3. Destination back home

When you have space, move on to a multi-city search, and call United at 800-UNITED-1 if you are getting errors.

Bottom Line

Don’t just book a boring roundtrip to Europe for your next vacation, add extra cities and possibly a free one way. There are three maximum value awards to Europe that use a stopover.

1. Stopover (Complete Two City Award)
2. Stopover + Open Jaw (Incomplete Three City Award)
3. Open Jaw + Free One Way (Incomplete Two City Award + Later Free One Way)

The best value for you depends on your goals. All three require searching on united.com, using its glitchy multi-city award search, and possibly calling up to finish a booking.