Please ensure Javascript is enabled for purposes of website accessibility

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

a screenshot of a plane

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.


a screenshot of a plane

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

This site is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as This may impact how and where links appear on this site. Responses are not provided or commissioned by the bank advertiser. Some or all of the card offers that appear on the website are from advertisers and that compensation may impact on how and where card products appear on the site. Any opinions expressed in this post are my own, and have not been reviewed, approved, or endorsed by my advertising partners and I do not include all card companies, or all available card offers. Terms apply to American Express benefits and offers and other offers and benefits listed on this page. Other links on this page may also pay me a commission - as always, thanks for your support if you use them

User Generated Content Disclosure: Points With a Crew encourages constructive discussions, comments, and questions. Responses are not provided by or commissioned by any bank advertisers. These responses have not been reviewed, approved, or endorsed by the bank advertiser. It is not the responsibility of the bank advertiser to respond to comments.