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Free One Ways & Stop Overs On United International Awards – A Must Read

A couple weeks ago I wrote about a little segment by segment trick I used to find Award Flights to Europe and India, when United.com was saying there was no availability out of Chicago.

A lot of Readers emailed thanking me for that tip because they were having a similar issues finding availability, and by booking their Award segment by segment they were ultimately able to get to their destination.

Based on Reader feedback on that post, I thought I would cover 2 other useful United tricks that I recently learned about that allow you to get free Stop Overs and a free One Way Ticket on your next International United Award Flight.

Fair warning that this a longer post and has a few moving parts, however I can almost guarantee that after reading this post, you probably won’t ever again book United International Award Flights the same way. 

Before I dive into the post, I just want to give a HUGE shout out to Scott at MileValue, as he has been instrumental in discovering these United tricks and explaining them all in great detail on his blog.

The only reason I am recapping the information is to share my personal experiences on an Award Booking I did last week.

A Few Things To Know About Booking United Award Tickets

So every Airline has their own idiotic rules on Award Tickets.

Some don’t allow One Ways (cough Delta), and others charge you fuel surcharges (cough British Airways), and some like United are fairly lenient in their rules. 

The most important rule about International United Award Tickets is that you are allowed 1 Stop Over & 2 Open Jaws.

A Stop Over is when you “stop over” in a city for more than 24 hours.

An Open Jaw is when you fly into 1 city, and return from another.

So an example of a Single Open Jaw would be flying from Chicago to London, and then returning from Paris to Chicago.

Basically your Departure and your Arrival Airport are the same.

Open Jaws are especially useful if you are touring around a region and don’t want to double back to the same airport you flew into.

What is cool about United International Awards is that you can actually do a Double Open Jaw.

This means you could fly Chicago to London, and then return Paris to Los Angeles. 

Why This Is Important

As Scott at MileValue discovered, with these extremely lenient rules you can manipulate them to essentially add on a free One Way ticket anywhere in the United States or Canada as part of your original Award Ticket.

This means that if you have an Award Ticket from Chicago to Europe, you could take that trip, and then after you return to Chicago, take a free One Way to anywhere in the United States or Canada.

This may sound complicated but it really isn’t and I will try to explain in laymen terms below.

Examples of Stop Overs & Open Jaws

In the examples below, I picked random cities but I will stress that these tricks can be used for any International United Award Ticket anywhere in the World.

Stop Over

My Parents are going to India in December and I just booked them 2 Business Class Award Tickets on United.

Since there was no availability out of Chicago, using the segment by segment strategy I outlined a couple weeks ago, I booked them the following for 120,000 United Miles each. 

  • Chicago (ORD) to New York (LGA)
  • New York (JFK) to Qatar (DOH)
  • Qatar (DOH) to Bombay (BOM) 

My Cousin and Niece live in NYC, so my Parents decided they wanted to see them since they were going to be connecting in NYC anyways.

Since United allows a free Stop Over on International Award Tickets, adding a quick visit was not an issue and the best part is that it was FREE!

My Parents will be leaving on a Thursday from Chicago to NYC, staying with my Cousin from Thursday to Sunday, and then continuing from New York to Bombay on Sunday night. 

I routed my Parents through NYC because I wanted them to fly Qatar Business Class, but because you can build your own itinerary segment by segment, I could have just as easily routed them through Europe and they could have taken a free Stop Over in Paris or London and seen some sites on their way to India!

A Free One Way

Stop Overs really get interesting when you combine them with the fact that United also allows Double Open Jaws on International Award Tickets.

Below is an actual United itinerary that I will be taking in September. 

It is semi-complex because there was no availability to and from Chicago, and I wanted to fly on the A380 again!

As you can see, this itinerary would be considered a Single Open Jaw since I am departing from Chicago to Marseilles, and then returning from Nice to Chicago.


  • Chicago (ORD) – New York (LGA)
  • New York (JFK) – Frankfurt (FRA) <- Lufthansa A380!
  • Frankfurt (FRA) – Marseilles (MRS)


  • Nice (NCE) – Munich (MUC)
  • Munich (MUC) – Dusseldorf (DUS)
  • Dusseldorf (DUS) – Toronto (YYR)
  • Toronto (YYR) – Chicago (ORD)

Now where this gets interesting is when you change this itinerary to a Double Open Jaw and throw in a Stop Over.

As I said earlier, Chicago -> Marseilles, Nice -> Chicago is considered a Single Open Jaw.

However as I was booking the above itinerary, I realized that the domestic portion of the StarMegaDO4 starts on November 13th in San Francisco and ends in Chicago.

Therefore I would need to purchase a One Way ticket to San Francisco to Chicago.

This is where it gets fun.

Most of us think of Stop Overs as something you only do during your trip, like my Parents stopping in New York to see my Cousin on their way to India. 

The reality is that you can add a Stop Over to the end of your trip thanks to the Double Open Jaw rule.

I ultimately booked the following itinerary for only 60,000 United Miles:

September 15:

  • Chicago -> NYC -> FRA – > Marseilles

September 25:

  • Nice -> MUC -> DUS -> YYZ -> Chicago

November 13:

  • Chicago -> San Francisco

Now if you are reading this and saying WHAT THE F$%^, let me explain.

My original itinerary was a Single Open Jaw since my starting and ending destination was Chicago.

However because United allows Double Open Jaws, it is possible to depart from Chicago and have my final destination be San Francisco.

When you add in the free Stop Over part, it is possible to “Stop Over” in Chicago for 48 Days, and then conveniently continue my journey 48 days later to join the MegaDO.

United obviously doesn’t know that I also happen to live in Chicago. 

If you are reading this and thinking, “That is great Parag, you got a free One Way to the MegaDO, but I’m not going on the MegaDo, so how does this help me?”, you are in luck.

I happened to pick San Francisco because I actually needed a One Way flight there, however with this Double Open Jaw + Stop Over trick, you can get a Free One Way Ticket to any destination in the United States or Canada including Hawaii all for the price of a normal trip that you were already planning on taking.

The best part about this trick is that even if you don’t have set travel plans, United allows you to change the dates on Award Tickets for free as long as it is 21 days out.

So hypothetically if you are taking an Award Trip overseas and know that you want to go on vacation sometime in the future, you can always add on the Free One Way and change the dates later on.

This means if you are going to Europe this fall, you could book your Europe ticket, have a Stop Over in your Hometown on the way back, and then book a Free One Way to Hawaii or wherever in the Spring or even next Summer.

The only thing you would have to pay for is a One Way back from wherever you are going, which of course you could use Award Miles for.

Even in the event you book a Free One Way and decide not to use it, it doesn’t really matter because the One Way was legitimately free. 

How To Add On A Stop Over Or Free One Way To Your Next Award

Unfortunately, United.com is not really helpful in booking Stop Overs or Free One Ways online, so my advice is to get all your flight numbers first and call it in to United and let them book it.

This is where the segment by segment trick I talked about a few weeks ago really comes in handy.

Booking A Stop Over Only

For this example, we will only add a Stop Over and I’ll use a trip that involves flying from Chicago to Paris with a Stop Over in Washington D.C.

1. Go To United.com

2. Search For Flight #1

In this example, the First Leg would be from Chicago to Washington D.C.

When booking Stop Overs, I personally always search as One Ways, but ultimately it doesn’t really matter.

Just enter your information and hit search.

a search box with text and numbers

Once the results come up, simply pick out the Flight that works best for you.

After you have done that, simply write down the Flight Number, Date, and Time. 

You will need this information when you call into United to have them book your itinerary.

a close-up of a message  

3. Book The Stop Over & Flight #2

Since Washington D.C in this case is the Stop Over, you need to figure out how many days you want to stay.

I think Friday to Sunday is enough time, so I will look for a Flight departing Washington D.C to Paris on Sunday evening.

Similar to Step 2, go to United.com, enter your details and search for flights that work.

a screen shot of a computer

 4. Book Your Return

Since United only allows 1 Stop Over per an International Round Trip Award and we used it in Washington D.C, we can just look for a flight back to Chicago.

Again remember to write down the Flight Numbers, Times, and Dates.

a screenshot of a computer

5. Call It In To United

Now that you have pieced together your entire itinerary with your free Stop Over in Washington D.C, it is time to call it in to United and book it.

Once you get connected with a United Agent, simply tell them you would like to book a Round Trip Award Ticket to X (in this case Paris) and feed them the Flight Numbers, Dates, and Times.

There is no need to even tell them you want a Stop Over because some of the Agents don’t know the rules and will tell you that it isn’t possible.

While when pieced together separately it will seems like the Stop Over costs more, once everything is in the United System, it will recognize that you added a Stop Over and price the trip correctly.

If the Agent tries to charge you a $25 Phone Booking Fee, simply say you tried to book the itinerary online and the website didn’t work and it said that you had to call it in.

They will waive the fee.

Ultimately the Chicago to Paris with a Stop Over in Washington D.C will look like this and only cost 60,000 United Miles!

October 11

  • Chicago to Washington D.C

October 14

  • Washington D.C to Paris

October 20

  • Paris to Chicago

Booking a free Stop Over is that simple!

Adding On A Free One Way

The process of adding on a Free One Way is very similar to adding on a Free Stop Over.

However instead of adding on a Stop Over in the middle of the trip, the Stop Over is added to either the start or end of the trip.

For this example, I will do a Chicago to London Award Ticket over Christmas, and then add on a One Way to Hawaii in March over Spring Break.

I am using Europe in all these example, but you can do this with Asia, Australia, India, South America, etc.

I picked Hawaii for the One Way because it is a popular destination, however you can pick anywhere in the United States or Canada.

In the case of Hawaii, United does charge you an additional 2,500 Miles because it is out of the Continental United States, so it isn’t “technically” free but pretty damn close.

Anywhere else in the United States (including Alaska) or Canada, there is no additional cost.

So if you know that you have to visit Grandma in Florida over Thanksgiving, then feel free to book that.

If you want to go to Mexico, it is another 2,500 Miles while the Caribean is actually a rebate of 2,500 Miles.

Also your Free One Way can be at the start of your trip too, so you could go do Hawaii -> Chicago, Stop Over in Chicago, then Chicago -> London, London -> Chicago.

One other thing to remember is that when you price out the itinerary segment by segment, it will show a higher mileage cost than your original trip, but don’t worry it will price out correctly when you call it in.

1. Go To United.com

2. Search For Flight #1

Similar to adding on a Stop Over, head to United.com and search for your Flight #1.

In this case, it would be Chicago to London.

You can either search One Way or Round Trip. It doesn’t matter.

I just did Round-Trip because it was easier.

As always, remember to write down Flight Number, Times, and Dates.

a screenshot of a flight schedule

 3. Find Your Free One Way

Now that you have your “main” flight picked out, it is time to add on your Free One Way.

Your Free One Way will depart from the last city you landed in.

In this case it would be Chicago, since that was the last flight on December 29.

To find your One Way flight, simply head to United.com and enter your details and destination.

In this example, it would be Chicago to Maui on March 26, 2013.

a screenshot of a travel application

a screenshot of a flight schedule Ultimately your final itinerary will look like this.

a white rectangular object with a gray border

a screenshot of a computer

4. Find A Flight Back

You don’t have to do this unless you are 100% certain of your plans, since you can always change the dates on United Award Flights up to 21 days out for free.

I personally always just check to make sure there is availability back. If there isn’t availability back, then I simply change the dates.

Please also remember that only the fight there is free. The flight back is NOT FREE and you will will either have to pay for it or use miles.

Also this flight back from Hawaii will be booked completely separately from the above itinerary, however because it is a simple One Way, you can book it online at United.com without issue.

The reason why these Free One Ways are extremely valuable is because in this example, a normal Chicago to Hawaii Round Trip Award Ticket on United would cost 40,000 Miles.

With this trick, you are spending 60,000 Miles to go to Europe but then for an extra 2,5000 Miles you also get a free One Way to Hawaii, which essentially saves you 17,500 United Miles had you booked the Hawaii flight separately!

5. Call It In To United

Now that you have all your Flight Numbers, Times, and Dates, it is time to call it in to United.

The itinerary above actually did price out on United.com, so if you want to try booking it all online, be my guest, but many times it will give you an error and say that you need to call United.

Similarly with the Stop Over, when you call United there is no need to announce to United that you want a Free One Way.

Simply tell them you would like to book a Round Trip ticket and provide them with all the Flight Numbers, Dates, and Times. 

The United System will figure out that you have a Free Stop Over in Chicago and a Free One Way to Hawaii and will price it out properly.

When I did the exact process for my complex France trip, and I told the Agent that I wanted a Stop Over in Chicago and then continue to San Francisco 43 days later, and she said it couldn’t be done.

So I simply asked her to book the Chicago to France part for me and once that was in the system, I hung up and called back and asked another United Agent to add the Chicago to San Francisco flight on.

It was added for free without issue.

One other thing to remember is that you can only add on a Free One Way when you book your flight or in the 24 hours after your book your Award Flight.

If you are reading this and recently booked an Award Flight, you won’t be able to add on the Free One way without incurring a fee because you are technically changing the final destination. 


Hopefully this guide helps those of you that are planning on booking Award Tickets on United.

Even if you aren’t certain about your future travel plans, I would suggest adding on a Free One Way to all Award Tickets going forward because IT IS FREE.

Worst case is that you end up not using it, which costs you nothing.

Best case is that you do end up using it and you get a Free One Way.

There is no additional cost or risk from booking a Free One Way, so I strongly suggest everyone do it!

Again, I can’t thank MileValue enough for discovering this trick because it is simply genius.

Not to mention that it saved me 12,500 miles to get to San Francisco for the MegaDO!

If this topic has intrigued you, I strongly suggest checking out all of his posts on the topic because you will learn a lot.

He also has some YouTube videos where he walks through step by step how to do a Free One Way. 

If you end up using any of the above tricks and are having any issues or questions trying to add a Stop Over or Free One Way, feel free to Email, Text, or Call me and I’d be happy to help.

Just last week, I helped a Reader add a Free One Way on a trip to India that he was planning.


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  1. Hi Parag,

    Great article. I was able to use this method to book, IAH-FRA-IST-ISB.(My final destination).

    On the return PEW-DOH-IAH. Nov 2012

    then added a one way IAH-HNL Mar 2013. for only 80k + $120 taxes.
    Now my question is this, since the itinerary is already booked, i am thinking about stop over in FRA/LHR/AMS ? on the way back. can this be done on this open jaw?


  2. You should be able to for free since the start and end destination are the same. Just piece the itinerary segment by segment and call it in to united.

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