a passport and boarding pass

The savings can be great, but the risks must be weighed…

Weaving tickets booked with points into deals booked with cash, or just buying tickets with cash, one city at a time can save tons of money versus buying a round trip or multi city ticket in one go.  But any great deal can be instantly invalidated if you’re forced to part ways with $5,000, just to reach your final destination. There are plenty of ways in which booking separated one way tickets, or weaving points and cash deals together can save – but it’s important to note they can also cost big time. Here’s how to avoid issues and weigh your options when you book trips with multiple itineraries.

a screenshot of a flight scheduleFirst, The Rules

When connecting to flights within the same airline alliance, or in some cases even the same airline, tickets booked separately are generally not covered if you miss a flight. Airlines have become increasingly strict with refusing assistance to passengers unless the missed flight was booked together with the flight that caused you to miss your flight. Therefore, caution is the key word. Confirm as many details as possible as to how your airline or alliance handles missed connections, and be sure to specify separate itineraries when doing your research. According to View From The Wing, American Airlines (and possibly all OneWorld airlines) should still honor reservations, even in the case of separate bookings.

Potential Baggage Hiccups

Many airlines now choose to interline bags onto other airlines, even if agreements exist which encourage them to do so. This is airlines revolting against customers not booking journeys in their entirety, and instead piecing them together. When this happens, what may seem like a simple connection can turn into a nightmare, when passengers are unwittingly forced to clear immigration, grab their luggage, bring it from arrivals to departures, wait in line for check in, re clear security and then make a flight. Be crystal clear before departure if an airline will send your bags to their final destination, if you’re traveling on multiple itineraries.

a pile of money billsWhat Happens If You Miss

If you miss a flight on a non connected itinerary, say… Boston to Paris on Air France using points, and then Air France from Paris to Rome using cash, you are entitled to nothing. An airline may choose to be helpful where able, especially for frequent flyers, but there’s no obligation if you are traveling on two different record locators, confirmation numbers, ticket numbers or itineraries. This can lead to paying $1000’s for last minute tickets. The further your remaining flights, the more you’ll generally be forced to pay.

Savvy Planning

Many travelers overlook the benefits of extra, extra safe connections. And when you’re booking separate tickets – you can stopover as long as you want. Why stress about a 1 hour connection in Tokyo when you could build in a 18 hour connection, check your bags in early (some airlines) and explore Tokyo for the day. You get to avoid buying a hotel for the night, but also get to enjoy a day and night in the city. If the only safe connections involve an overnight hotel stay, calculate the cost of the hotel into any potential savings.

Just A Reminder

This is just a friendly reminder, which many people overlook in the excitement of trip planning. I once flew the long way home from Melbourne to London with my wife, going from Melbourne to Sydney, Sydney to Tokyo, Tokyo to San Francisco, San Francisco to Los Angeles and Los Angeles to London – all in one go. All was fine until I reached San Francisco, where a Delta agent had made an error and changed my flight during a previous phone call. I foolishly never looked to confirm the changes were correct, and missed my flight from San Francisco to Los Angeles. I was forced to book an expensive last minute ticket to get from San Francisco to Los Angeles, for which only seat was left. Had I missed that flight, I would’ve had to buy a walk up ticket to London, which would easily have cost $3,000. Yikes.

Have you ever been caught out by missed connections?

Gilbert Ott

Gilbert Ott is an ever curious traveler and one of the world's leading travel experts. His adventures take him all over the globe, often spanning over 200,000 miles a year and his travel exploits are regularly...

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  1. You mention how AA and oneworld should honor the reservation – Do you know anything about Star Alliance? I have a cash paid ticket from SAT-ORD but used UA miles to book a business class ticket on Lufthansa from ORD-MUC. I have confirmed UA will through check my bag from SAT to MUC even though on separate itineraries. My connection time in ORD is 2:30 hrs. I was hesitant whenever booking this because ORD has notoriously bad weather so fingers crossed. I have been looking at business class award availability directly from SAT-MUC and if any opens up I think I will pay the change fee and forfeit that non-refundable ticket to ORD. Any advice on this? Thanks

  2. Q: “Have you ever been caught out by missed connections?”

    Of course! But here’s the kicker: “American Airlines (and possibly all OneWorld airlines) should still honor reservations, even in the case of separate bookings.” Uh, no…at least not when it comes to other OneWorld carriers.

    In 2017, I was flying from San Sebastían (EAS) to Madrid (MAD), and then onto Jerez (XRY). In what — with hindsight — turned out to be a mistake on my part, these were booked at two separate roundtrips (MAD-EAS and MAD-XRY). My return flight from San Sebastian was delayed — and then ultimately cancelled — due to weather. Iberia re-routed passengers *either* through Bilbao (BIO) or through Biarritz in France (BIQ). As we all dutifully lined up to rebook with the one ticket agent on duty, the family of four in front of me chose to fly out of BIO. When I said that we (my wife and I) had a connecting flight out of MAD, and that we’d miss it if we flew out of BIQ, we were informed that the family ahead of us had scored the last seats on the BIO flight and we had no choice — we *had* to fly out of BIQ. So, we got bussed to France and eventually flew to MAD.

    Upon arriving at MAD — because we had booked our flights as separate itineraries, the Iberia Customer Service agent treated us as if we had intentionally missed the flight and, as such, had cancelled our entire MAD-XRY-MAD itinerary. So we were forced to book *new* tickets for flying the same day. PLUS, there were no more flights into Jerez, and so had to fly into Seville (SVQ); then grab a cab to the train station, and take the next train to Jerez… Let’s just say this was a very expensive lesson to learn.

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