My Bad Habit Of Booking Insane Flight Connections

By: Ben Schlappig

Published: January 12, 2020

58 comments

I figured some of you may be amused by what’s probably a very bad travel planning habit of mine, but which I kind of get a thrill out of… sometimes? I’m curious if anyone else ever does this.

In this post:

I often connect on separate tickets

When I take review trips, I often travel on lots of separate tickets. I’m reviewing all kinds of different airlines belonging to different alliances, and they simply can’t be booked together. For example, on the review trip I’m currently on, I booked six separate tickets.

The risk is that when you book travel on separate tickets, you’re not covered in the event you misconnect. So if you miss the start of a new ticket due to a delay on the previous ticket, you’re the one responsible for that, and not the airline.

So early in the trip I intentionally plan very long layovers when connecting between separate tickets. I can ultimately work from anywhere, and it’s just not worth the risk to have the entire trip thrown off by a tight connection. So I had a seven hour layover in New York, then a night in Tokyo, then a night in London, then another night in Tokyo, etc.

The rush to get home

While I don’t mind taking my time throughout most of these review trips, when they start to come to an end, I’m always excited to get home to Ford and Winston.

The last segment or two to get home (especially domestic flights after long hauls) seem to feel as long as the rest of the trip combined.

So not only is it exciting to get home, but it’s also less risky to book short connections towards the end of your trip. Worst case scenario if I miss a connection I’ll have problems with one ticket, rather than problems with five tickets.

My crazy international to domestic connection

Long story short, to finish off this trip I’ll be landing at a transpacific gateway on the West Coast, and I booked a separate domestic ticket on a different airline just 42 minutes later.

During that time I’ll have to go through immigration, take a train, clear security, and then schlep to my departure gate, at the far end of the terminal.

Yes, I voluntarily booked that 42 minute connection, and I know the risks. In addition to my general desire to get home, there are a few other motivating factors:

This flight will get me home by 8PM, while the next “bank” of flights would get me home around midnight (which is way past everyone’s bedtime)
I have expiring American systemwide upgrades, and I was able to confirm an upgrade on this booking immediately, while there’s no way I would have cleared an upgrade on the later flights
The fare was “only” about $200, which was lower than the other practical options

Obviously this was risky. The way I look at it, I’m gambling $200 in hopes of getting home at a reasonable hour, and getting first class on a transcon flight. To me that seems like a worthwhile risk.

Of course any sort of delay (even just a few minutes) will make the connection highly unlikely, and even with an on-time arrival, odds are decent that I won’t make it.

What happens if I misconnect?

I’ll cross that bridge when I get there:

My transpacific flight will have Wi-Fi, so I might try to make a same day change if I realize I’m going to be late; that will definitely mean no upgrades, though, and it might not even be possible, since other flights are quite full
Otherwise I can probably just stand by for a later flight, though flights are full, and I’m not going to do a transcon flight in a middle seat in regular economy, if I can avoid it
Realistically I might just regroup when I get off my transpacific flight, and book a new ticket on a routing that works

So I’ve told Ford when I hope to get home, though also warned him that it may end up being up to 24 hours later.

Bottom line

I book “illegal” connections on separate tickets more often than I should. Most of the time it works out, sometimes it doesn’t. Of course this is risky, but realistically it’s also risky to do a two to three hour connection on separate tickets, since you could still misconnect.

I’ve made an international to domestic connection at JFK with a terminal change and a super long walk in 18 minutes, so I feel like anything is possible.

Of course I realize this is crazier, so please wish me luck. 😉

Have you ever “gambled” by booking two separate tickets with a very short connection?

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Howard Guest

January 17, 2020, 10:12 am

I recently booked a 54 minute connection in Paris from a transatlantic flight onto an SNCF train to Brussels. Friends told me the odds were low of making the train, but I remained optimistic. Ultimately, the train I booked was cancelled due to the French strikes and I rebooked onto a later train with a more comfortable connection window. For research purposes, when I arrived in Paris I went straight to the train station upon clearing immigration, and I made it to the platform 5-10 minutes ahead of my originally scheduled departure time. So, in case anyone was wondering, if you're arriving internationally into T2E at CDG, it's definitely possible to catch a TGV within one hour of touchdown. (Note: I'm assuming most readers of this blog will have access to the priority immigration queue. It would not be wise to even attempt this if you don't.)

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Steve Guest

January 16, 2020, 8:17 pm

My record was 38 minutes from touching down at Miami from a long haul to getting on a connecting flight. I don't recommend that. But it worked out and saved me about $500 or $600.

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import the vikings Guest

January 14, 2020, 7:01 am

I had it in a few cases. But I try to avoid it if I can, as I am known for having notorious bad luck with flight delays, cancellations and freak accidents (all out of my control, fortunately). The first one was a 1.5 hour stopover at STN, over 10 years ago. Doesn't sound too bad, but I also had to collect a bag and check it in again. And clear passport control, which at that time could mean long queues. As London airspace was already congested back then, it happened quite often that delays happened due to hold patterns. I made it, 15 minutes before the check in deadline. The most recent one was a trip with a connection in Dublin on two separate tickets. It was just before Christmas last year, meaning that ticket prices were high and adverse weather was expected (and indeed, storm we had). Now I had prepared well, knowing where to go in the airport to get to the flight connection channel. I had checked in online and a digital boarding pass for my onward flight was there. To my delight, the inbound flight to Dublin was on time and landed just on time. Of course, as the travel gods are against me, we got a tarmac position with a bus ride to the terminal and we had a family with small children on board who couldn't care less about others on tight connections. So there went 20 minutes of my time. I arrived at the first connecting point, which was closed, pointing to the next one, which is right next to passport control. And guess what... closed too! An airport employee told me that they just closed it for the day because they "probably wouldn't get many connecting passengers anyway." So I was told to go through passport control, go outside and to the other terminal "because that's the terminal my airline uses" and go through security again. Those who know Dublin airport know that it's a 7 to 8 minute walk and that security lines are usually horribly long, even in fast track. I was fortunate enough to 'just' have a 10 minute wait in the 'fast track' line, and I somehow made it just in time, a few minutes before the gate would close. But don't ask how... Have I already told that I usually end up with lots of freak incidents during my travels and that the travel gods are against me? It's why I try to avoid short connections, even if they're protected ones. ps. What Ben did wasn't illegal. It's just that airports have a minimum connection time for all incoming flights, to be able to reduce the chances of people getting stranded. I remember from ARN that they can differ per flight. SK had some 30 minute minimum, while the ET flight from ADD had 4 hours for a while, due to being notoriously late (that was when they still had a stopover at VIE).

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RTBones Member

January 13, 2020, 10:19 am

@Lucky, On this topic, I am curious: how do you manage all of your record locators. Not every airline has a mobile boarding pass - or do you try and get paper boarding passes for each connection?

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Al Guest

January 13, 2020, 10:15 am

I'm the opposite, I book overnight stays at each stop on separate tickets because I hate worrying about connections and I'm never in a hurry to get anywhere....

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