How To Book Stopovers with Miles Online

One of my favorite things about frequent flyer miles (besides the saving money part) is that airlines often allow stopovers at no extra costs. Revenue tickets will change the price if you stop somewhere for more than 24 hours, but with miles you can often add an extra stop for free.

I therefore spend a lot of time talking about stopovers; it’s the ability to see two places instead of one. But unfortunately, I have spent little time explaining how to actually book them.

This post will take you from how many stopovers you’ll be allowed, all the way to how to use the online multiple-destination search to book it yourself online.

The Basics

A stopover is a stop that’s more than 24 hours, basically giving two destinations. And an open-jaw is when you fly into one city and out of another, where the airline isn’t responsible for your transit.

If you don’t completely understand stopovers or open-jaws please read more here: Airline Stopovers InfoGraphic. This infographic is a short visual that explains how stopovers work. (Although we need to change the AA and Delta section).

Stopover and routing rules are always specific to the airline miles you are using, and not the airline you are flying on.


First I’ll walk you through an example that’s probably most relevant to many tricks talked about on this blog – booking United stopovers.


Booking Stopovers with United Miles

There are so many reasons to love United. The miles are easy to earn from credit cards (United Explorer card, United Business Explorer card, Chase Sapphire Preferred, Ink Plus, etc…), United does not pass on any fuel surcharges, and they allow stopovers in a very generous way. I’ve spent a great deal of time talking about the different routes you can do, and will mention them at the end of the section. But in order to book these things, you have to understand a few key concepts.


1 Stopover & 2 Open-jaws

The first thing you need to know is that United allows 1 stopover and 2 open-jaws on international roundtrips. If you want to see the full details you can read the Complete Guide to United Routing Rules. searches almost all partner airlines

There are only a few airlines missing on the search results, and that still leaves over 30 airlines bookable on! The main airline missing is Singapore Airlines. There are a number of other partner airlines in east Asia but Singapore is one of the biggest and most desired airlines to book on.

Because Singapore doesn’t show up on, you would have to call to book flights with them. Now you can search for the availability on partner sites (like Aeroplan), but you still have to call United to book your flight using United miles. allows multiple destination searches

All the routes that I ever talk about with United, I always price out or book online. This is because they allow you to customize your search with multiple destinations.

Let’s say we want to book a route from Chicago to Istanbul with a stopover in Rome – spending a week in both Istanbul and Rome. We need three active parts. A flight to Rome, a flight to Istanbul, and a flight back to Chicago.

Booking this trip is as easy as finding the award availability.


Actually doing the booking

I’ll try the multiple destination tool first, often. But if it errors out or it’s a complicated route I then make sure I use the oneway search. This way I piece everything together with dates that actually have award seats.

I’ll search a oneway with Chicago to Istanbul, then another oneway from Istanbul to Rome, then again from Rome to Chicago. I make sure I find dates and seats on each flight so that I can have an easier time on the multiple destination tool this time around.


With United it’s pretty easy.

1) Click “Award Travel”

Screen Shot 2015-05-05 at 7.50.44 AM


2) Click “Multiple Destinations”

(You can also click multiple destinations right before hitting search.


3) Fill out your desired route

Chicago to Rome to Istanbul to Chicago, with a week in each, would look like this.

Screen Shot 2015-05-05 at 7.55.06 AM


4) Select which flights you want

Go ahead and select which flights and which class of service you want.

The price will be based on the class of service of both to and from the destination, in this case Istanbul.

So if we click economy all the way though it should show up as 60,000 miles for the entire trip, the same as a regular roundtrip to Istanbul with miles.


And that’s it. It will show the price and the dates on the last page.

Screen Shot 2015-05-05 at 7.59.26 AM

This was a total of 60,000 miles to see both Italy and Turkey, plus another $123 in airport taxes… which will happen when you route through too many expensive European airports.


Booking Stopovers with Other Airlines


1) Check the stopover rules chart

When using miles to book stopovers, the first thing you need to know is whether or not the miles you are using allow stopovers. Remember the rules are not based on who you are flying but which miles you are using.

Check out: List of Airline Stopover & Routing Rules


2) Check the Fuel Surcharge post

I never ever book a flight using miles if it’s going to pass on fuel surcharges, and have always found a way around it. I either use miles that don’t pass on fuel surcharges (which pretty much leaves United and AA), or I book on airlines that don’t have fuel surcharges to pass on.

Check out: Master Chart to Avoiding Fuel Surharges


3) Does the airline search partner awards?

One reason that works, is because it likely already searches award availability for the flight you need. Obviously you can’t book a flight online that won’t show up online.

Plus, either way you’ll want to find award availability to know whether or not your flight is bookable.


4) If the website does search partners, does it have a multiple destination search?

The other reason that you can book on is because it allows you to search multiple airlines and multiple destinations. Like I showed above you can add at least three destinations in.


5) If it doesn’t search partners or multiple destinations, you need to call

You can always call.

The agents have the ability to book multiple destinations and on every partner that the airline has. There is nothing more powerful than calling. A few airlines have a $25 phone booking fee, but if you can’t book online, in light of that, they often waive the $25 fee.

Make sure you really understand the stopover rules before you go demanding some impossible route that the agent can’t physically route. An open-jaw for example doesn’t actually get you another stop, but it can be added to a stop. All it means is that you fly out of a different airport on the stop. But people call and demand 3rd and 4th stops because they “also get open-jaws”. No. It doesn’t work like that, and demanding it won’t get you far with an agent.



United, Air Canada, and Alaska are the main mileage programs that come to mind in regards to booking stopovers online. They all have their pros and cons and they can’t all do everything online. They might not search every single one of their partners, or Air Canada might not have all the multiple destination options technically allowed in their rules, but they can all do the basics. For most people their sites are enough.

Then there are airlines like Lufthansa/Miles and More and Flying Blue which neither shows many of their partners, nor multiple destination searches. You know that if you want to book a stopover on most partner awards that you need to call. You can search on other websites to find the availability, but at the end of the day, calling is more powerful.

I hope this is a comprehensive look at booking stopovers and if you have any questions, please comment below.

If you’re interested in some of the crazy routes I’ve been able to book online just with United, check out some of the following posts:

There are many more but those are some fun ones to start with.

Related Posts:


  1. Over the weekend, I booked one ways for my gf and I to get to JNB in early September on ET biz class using United miles. We couldn’t yet book the round trip as we’re still waiting on CC bonuses to post, and award space was dwindling quickly. We figured we’d book the return trips at that point. Once the bonuses post, do you know the fees that would be charged if we decide to scrap this original itinerary and book a round trip instead, to get that free stopover?

    • Unfortunately you’ll have to pay a $200 fee to cancel. However, I think you can change the ticket’s destination for $100. Worth calling and trying. Won’t be a free but maybe $100.

  2. Thanks.. I also like to know how to book long layover flight online. Most of time, airlines websites do not give me those long layover options.. thanks,

    • Just search for one-ways, looking for availability on the flights you want.

    • You can search the same way. However, with United you can sometimes force layovers with multiple-destination search.
      That’s how the Caribbean Hopper started. I booked a trip with a layover in Aruba on the way to Puerto Rico. I had my flight out of Aruba leave 23 hours after landing.

  3. thanks for the info, i had tried looking at stopovers for united but got a little lost, so this should help.

    i always appreciate your posts! a little while ago i signed up for the citi aa platinum through your ck link, hopefully you got the affiliate bonus from that!


    • Thanks for the support Ben! I really hope this post helps you navigate such a booking, but if you still get stuck try to let me know where you’re getting stuck… I guarantee you other people probably feel the same, so it would help me help others. Thank again!

  4. Hi Drew,

    I’m trying to book a multiple destination United trip, but encountering some difficulties and actually just got off the phone with a rep.
    The segments I want are as follows:

    9/22 : WAS – > AGP

    11/30: BCN -> LIS

    12/30 RAK – > CPT

    3/25 CPT – > WAS

    I booked them all as one ways, found seats, but I encounter an error. Called up United, and the rep eventually told me, after talking with her superior, that my trip is not possible to book as a roundtrip because I am “back tracking”. She said I could look into round the world tickets. What can I do?! I didn’t think this was backtracking, I thought it was 2 open jaws with a stopover! Thank you!!

    • So there are two problems with this ticket.

      1) You have 2 stopovers and a destination.
      As I said in the post, an open-jaw doesn’t create a stop. Instead, it can be added to a stop.

      So you could stopover in BCN, and then destination in South Africa. You could then add an open-jaw to the destination part. Fly into CPT and out of JNB. If you so desired…

      2) You can’t have open-jaws on the stopovers. I should have linked to the Complete Guide to United Routing Rules (but it’s under complete guides), because this part is a little more complicated.

      But United (and Lufthansa) is weird because they don’t actually allow the open-jaws any more on the stopover. So you totally got it right in terms of what I described (and what used to be bookable). However, I’ve kind of come out saying/guessing that United isn’t allowing open-jaws on the stopover anymore. No written rule, but I’m almost sure it’s rejected by a computer.

      It’s funny that the agent tried to book two stopovers and told you the problem was back tracking. Back tracking is never an issue with United.

    • Thanks for the explanation, Drew. You da man!

      But, now after looking over your How-to-book-stopover-United post and routing-rules post…I tried something simpler and I’m still getting an error.
      This is what I tried:

      9/21 : WAS -> AMS

      12/22 : LIS -> CPT

      4/7: CPT -> WAS

      Any idea? I do appreciate it.

    • Still not going to work because United is no longer allowing open-jaws to be applied to the stopover, and Europe is your stopover.

      You have to do WAS – AMS – CPT – WAS
      You could do WAS – AMS – CPT / JNB – WAS
      but you can’t open-jaw from AMS to LIS. Take that out and it will work fine.

    • Oh ok, bummer. So, we were hoping to spend the fall in Europe before it gets too cold and then jet to Cape Town. But it sounds like it’s impossible to hit multiple Euro destinations on one award ticket. Any suggestions? Much appreciated!!

    • Just make your stopover Madrid, or wherever, and use Avios to hop around. Or discount airliners. You can still stop in Europe, you just can’t get the open-jaw. So it’s an extra oneway needed.

  5. Drew,

    I just found your blog and really love it because of the quality contents and really different from other blogs that full of cc affiliate links! Thanks for the wonderful post! I plan to apply for some cc soon and would love to use your affiliate links to support you!
    Just wondering if you already wrote or plan to write something like “Asia Hopper” or a guide to maximizing flight/trip to Asia with stopover/layover/openjaw on certain airlines. I just started this hobby and would love to go to many places in Asia as it’s exotic destinations with lots to see. So far I just learned that we can use BA Avios for short flight in Asia and Cathay Pacific to stopover in Hongkong. But I’m curious if there is any other airlines that has generous stopover/openjaw rule like this, it would save a lot of BA Avios if we can maximize it! Appreciate it if you can please give some examples of the routes that possible with certain miles or airlines , originating from SFO as it’s my hometown.
    Thanks a lot!

  6. Hi, thanks for this! I’ve been trying to book a stopover (in Europe-IST)I’ve checked all the flts segment by segment and United shows availability. When I plug them into the Multiple Dest search I get “Error”

    ! could not find any available flights for award travel meeting your requirements. You may modify your search criteria or review the MileagePlus Travel Award Rules.

    The routing is this:
    ICN-ATL connect in ORD
    ATL-IST connect in FRA (stopover)
    IST-ICN direct flight

    Any advice on what I’m doing wrong? Thanks

  7. Hi, I am traveling to book an award flight with a stopover in the US and I keep getting the error message. Is MIA –> HKG–>PEK –>MIA–>RAK a legal booking? It would be one open jaw and one stopover, so I don’t know why I keep getting a error message.

  8. I just tried this and followed your directions. But I put in MIA-HON-NRT, NRT-MIA. and it came out to 380,000 miles. I also put in MIA-LON-CDG, CDG-MIA, and it also came out to 300,000 miles. What am I missing? There’s no way these award tickets should be this much.

  9. The 1 stopover rule, is it international only or domestic too?

  10. I just purchased a ticket from Toronto-HKG / Chengdu – Toronto and it has a layover in Paris. I’d like to make that a stopover for a day or two, and was wondering what’s the better way to make that happen?


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