The DIY Guide to Booking Award Tickets – Part XIII: Booking an Award Ticket on




You don’t have to restrict your trip to just London using Skymiles

People have different opinions when it comes to booking award tickets with frequent flyer miles. I, for one, love booking award tickets and enjoy the challenge that comes with doing so. Booking award tickets are like puzzles to me and I love solving them. Other people hate booking award tickets, consider them too much of a hassle, or even go so far as to believing their frequent flyer miles are completely worthless. I’ve decided to put a guide together for those of you who fall in between – people who want to book award tickets themselves but feel like they need some pointers. This guide will assume some basic knowledge, namely, that you know how to log in to your frequent flyer account and check your mileage balance. Other than that, the guide is here to help you through the process – hope you find it useful! Feel free to refer to the index at the bottom of the page for other entries.

In my last post I shared some tips I’ve learned over the years about booking flights on Today we’ll look at a few techniques that can really help you stretch the value of your Delta Skymiles. This “advanced techniques” post assumes you are comfortable with the strategies outlined in the past post and will just focus on the cold, hard results. Delta’s Skymiles program has a pretty generous policy when it comes to stopovers and open jaws. That’s right, Delta is generous. Wow.

We haven’t covered this yet although I’ve covered it elsewhere – a stopover is generally defined as a stop in a connecting city for longer than 24 hours. An open jaw is when you depart from an airport other than the one you landed in, when you return to a different airport from where you started, or both! Here are some simple examples:

Stopover: A => B (hang out for longer than 24 hours) => C => A. You fly through B to get to your final destination, C, but hang out there for awhile before continuing your journey.

Open jaw: A => B // C => A. For this open jaw, you’d find your own way from B to C (train, drive, whatever), but fly back home to A from C. It’s actually easier to visualize open jaws using maps.

This is an “open jaw” (fly into LHR, fly out of CDG) []

Another open jaw – you fly out of Boston, but ultimately return to ATL []

Here are some ideas for how you can extend your trip, and thus the value of your Skymiles, by utilizing Delta’s allowed open jaw and stopover.
Extension 1: Visit more places in Europe

This is probably my preferred extension. Remember Delta allows both an open jaw and a stopover. This gives you the opportunity to visit 3 cities for (almost) the price of one. How? Well, in the example in my previous post I just did a simple trip to London (which of course wasn’t simple thanks to But let’s say you wanted to go to Paris – you could stopover in London along the way. Suddenly you’ve increased the number of destinations you’re hitting from one to two.

You can stopover on any city on the way to your destination as long as it’s a legal routing. How do you know a routing is legal? If you can have a layover in a city on the way to your destination according to, you can have a stopover there. I took the liberty of doing a bunch of segment by segment searches – London is indeed a city you can connect through to get to Paris. Thus, it would be legal on Delta to fly from Boston to London, stopover, and then continue on to Paris before returning to Boston. The great thing is, this costs the same as the Boston to London round trip ticket.

A legal itinerary on a Delta award ticket []

But why stop there? Remember, Delta allows a stopover and an open jaw. That means you can hit a third city and still not pay any more miles. The only caveat here is you’d have to find a way to get to the third city on your own, but there are plenty of ways to do that (plane, train, car, boat, whatever). What this means is I could fly back to Boston from Amsterdam and it would still be the same price. That’s right, I could do London, Paris, and Amsterdam, all for the same cost in miles plus whatever it costs me to get to Amsterdam (hitchhike?)

Still the same price []

It is no less annoying to search for and book this award ticket on than it was to book the Boston to London round trip. BUT – it’s also no MORE annoying. You use the same exact techniques; search segment by segment, fly economy on short haul if you have to, and then string everything together using a multi-city award search. I don’t normally link to the same post three times but seriously, if you need a refresher: here. I went through all the steps and you can see my results below (I built it the same way I did the last itinerary, business on the outbound and economy return). As you can see, it’s the same number of miles and just a shade more in taxes and fees.

Original itinerary, 92,500 miles and $214 per person and (click to enlarge)

Adding Paris and Amsterdam still costs 92,500 miles and just $4 more (click to enlarge)

This is what I would call a great value. It’s also the kind of thing you usually can’t pull off with cash tickets. You can spread the flights out over the course of a year if you’d like – hey, take a year off and go explore Europe! Backpacking from Paris to Amsterdam could be fun! The fact that you have a year to complete your itinerary plays into the second extension you could make to the original trip.

Extension 2: The “free” one-way

Free one-ways are misnamed a bit. They’re not really free – you give up the chance to hit multiple cities in Europe. But what you gain is the ability to take care of half the flights of your next (usually domestic) vacation. The concept of the free one-way is relatively simple: You take your regular round trip award flight, but you tack on one more flight before or after that round trip award. So you are either tacking on a return flight from somewhere to your hometown before the main trip or tacking on an outbound flight from your hometown to somewhere you want to go after the main trip.

We added a “free” one-way to our Europe trip (in blue) []

I’ll use an example from my own experience. As you know, we just got back from Germany and Austria. Well, in a couple weeks, as part of that same award ticket, Jess and I are flying from Boston to Los Angeles for a wedding. We essentially knocked out half the flight cost on a trip we were going to take anyway. That’s why people call these “free” one-ways.

Example of a “free” one-way, adding a flight to Atlanta after the main trip []

How does it work, technically? Well it only works smoothly in programs where you are allowed an open jaw AND a stopover (in other programs you can get it done, but with complications). Delta is one such program. Here is the example I did for this post: BOS-LHR-BOS-ATL. I took the same round trip from the original itinerary to and from London. However, a week later, I searched for a one way flight to Atlanta. Then, using the multi-city search, I tacked it onto the original itinerary (by starting from scratch). It came out, once again, to the same price in miles and a little more in taxes and fees. That’s because you technically use your stopover in Boston and then use your open jaw to end somewhere different than where you began. Tricksy.

Again, only $6 more expensive – cheaper than any cash flight you’d ever pay

So, you can go to London and back, and then later, take that trip to the Coca Cola factory you’ve been dreaming of (or go visit your in-laws, or whatever you need to do in Atlanta). There are some combinations of cities and destinations for which this doesn’t work, but in general, if the routing seems to make sense (aka you’re going in generally the same direction), Delta will allow it. It takes work, you need to search segment by segment again, but hey – you generally don’t need to talk to a phone agent. So if you don’t want to gallivant around Europe (or don’t have the time), but know you need to get somewhere else in the USA within a year – try to tack on the flight!

Final Thoughts

Hopefully this post gives you some ideas about how to stretch the value of your Delta Skymiles even further. Some creativity can yield some pretty big dividends. Plus, I saved the best for last – all these tricks work for domestic award itineraries on Delta as well (unlike every other program I know of). That really increases the value of domestic award redemption on Delta, even in premium cabins (which usually are a bad deal domestically). Take my word for it – play around with Delta’s award booking system and get used to it – there are gems to be had.


Part I: Know Why Award Tickets Exist

Part II: Know Your Award Types and Charts

Part III: Know Your Airline Alliances and Partners

Part IV: Using Wikipedia to Determine Alliance Partners

Part V: Using to Search for Star Alliance Award Space

Part VI: Using ANA to Search for Star Alliance Space

Part VII: Searching for Award Space Segment by Segment

Part VIII: Searching for Oneworld Award Space on

Part IX: Searching for Oneworld Award Space on

Part X: Using Wikipedia to Determine Airline Routes

Part XI: Searching Skyteam Award Space using Air France/KLM’s Flying Blue Website

Part XII: Tips for Booking an Award Ticket on

Part XIII: Booking an Award Ticket on (Advanced Techniques)

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Level 2 Member
Great write up!
I booked JFK-TLV rt but forgot to tack on the "free ow" at the end. Anyway to do do it after the fact? I'm trying to add SEA and they keep saying it'll cost an additional 120k! I only paid 140K for the original itinerary. TIA