If you travel often enough, you are likely to run into all sorts of different kinds of irregular operations, where things don’t go according to plan. I’ve had my share of irregular operations and close calls before, like when my first ever business class flight was canceled while I had already boarded, or the time I had to run a mile between terminals to catch my connecting flight.
(SEE ALSO: Miller… Party of 2… Please Make Your Way to Gate 9)
It happens often enough that I have 2 rules for when things go wrong, and one of them is “at least this will make an interesting blog post”. So here’s the aforementioned blog post 🙂
The Plan
My son is planning on attending the PACE Speedrunning conference in Baltimore next week. Originally he was going to get a ride with a friend of his, but that fell through for a variety of reasons. So instead, we decided to just book him there on miles and points. Even though we booked the flights only a week or two before the conference, we were able to get decent miles redemptions.
- 9K American Airlines miles for CVG-CLT-BWI
- 11K Southwest points for a direct BWI-CVG on the way home
The only problem was that it was only a 38 minute connection in Charlotte. That is tight but doable… if nothing goes wrong
The Misconnect
But as you can imagine from the title of this post, things did indeed go wrong. The flights started out looking good on Saturday but with a few inbound flights to go, the delays started piling up. When we left for the airport in the evening, it had been delayed by about 15 minutes already giving him only around 20 minutes to make the connection, but by the time it finally took off for Charlotte, it was nearly an hour delayed.
We knew this was a risk all along but all of the other flights were way more expensive. Ideally I would not want to book a flight with such a short connection, especially at the end of the day, for this exact reason.
The Credit Card Insurance?
We booked this flight with the card_name (see review), which comes with outstanding trip delay insurance. You’ll get up to $500 per ticket for a delay that is over 6 hours (or overnight), both of which apply here. So we were able to book him a hotel plus get some food and hopefully that will all get taken care of by the Venture X trip delay insurance. We might get some miles from American Airlines too – I didn’t even bother asking for any food or hotel vouchers from them.
The Bottom Line
My son misconnected on a tight connection in Charlotte thanks to his inbound flight being delayed. While it’s not fun, at least we booked the flight with a credit card that offers trip delay insurance, so I’m hopeful that we will end up getting his hotel and food costs reimbursed.
Have any good misconnection stories to share? Leave them in the comments below
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Dan Miller travels with his wife and 6 (SIX!) children. He loves to help families travel for free / cheap, especially larger families. If you are looking for help, drop him an email at 
Very tight connections on the last flight of the night can really come back to bite you. Particularly on an insanely busy holiday weekend. Did AA not offer to cover the hotel and some grub?
It wasn’t 100% clear to me what my son did and since I wasn’t there, I didn’t have a good way to follow up with him to see what AA might offer. Stay tuned for a followup post 🙂
We landed at CLT around 10:30 this past Saturday and it was a zoo. Every gate was overcrowded, there was long line at the AA desk, and lots of people were sprinting to catch a connection (one of whom was loudly cursing Pete Buttagieg for some reason). Hopefully the trip insurance comes through.
Wow – PF Digest – a blast from the past! Thanks for reading :-). Well, stay tuned for a followup because it did take an unexpected turn after I wrote this post.
We have one of those 35 minute connections in CLT this fall on our way home from a big trip. The connection is our last leg and late at night. We sorta hope we don’t make that leg and let the travel insurance and the carrier pick up the bill. If we make it, good.
That’s a great way to think about it!
Hi Dan – great post. One question- how were you able to trigger Cap One insurance with an award booking? Thanks
Well I haven’t been approved yet so I’m not 100% sure, but as I understand it, if you pay the taxes and fees with your credit card, then it’s eligible for a trip delay claim. I’ll update you as the process continues.
I haven’t heard of anything having success with cap 1 insurance but chase is very easy to deal with imo .
My annual Travel insurance policy is up on 07/15. I have had mixed experiences with Allianz this year – one good, one bad. Their website is riddled with bugs. Comparing plici3s is a nightmare.
Every frequent traveler should have one of these policies. It would be interesting to read about travel insurance vs. credit card insurance.