How I took a 5 Hour Delay and Turned it into Some Free Travel

Delayed flights suck, there is no getting around it. Unless you are flying private, there is a decent chance that your flight is going to be delayed. According to the BTS, only 83% of flights in the US are on time. That means that 17% of flights in the US are going to arrive at least 15 minutes late. So what is a free-traveler to do?

The first thing that you need to know about delayed flights is that US airlines have no legal obligation to compensate you. NONE. The only thing that an airline is required to do is to get you to your final destination, eventually. Knowing that an airline is not required to accommodate you, it is in your best interest to be nice to the airline. Yelling at an airline agent rarely yields positive results.

I was recently flying with my wife to NYC for the weekend. We were catching a red-eye from Phoenix to Dallas for our first leg. This flight was booked with “cash” using American Airlines gift cards purchased with my $100 free credit from the Amex PRG card. Our second leg from Dallas to Laguardia was booked with Southwest airlines using points and companion pass. Unfortunately, but not shockingly, our first American Airlines flight was delayed from 1:45 AM to 6:30 AM. Due to this delayed American flight we would have definitely missed our connection flight in Dallas on Southwest.

The pickle that we found ourselves in was that the two airlines DO NOT care if the flights I booked separately are no longer going to work. American is only required to get me to Dallas eventually and Southwest is only required to fly me at the exact time that was originally scheduled. I called Southwest and they said it would be $200 to move the flight to a later one. I told the American Airlines gate agent what I had just heard from Southwest and they said they wouldn’t help with paying for that Southwest change fee (duh).


Contemplating How to Get to New York Without Paying $200
Contemplating How to Get to New York Without Paying $200


You can save big money, at times, by mixing and matching airlines and connections. I originally paid $41 per ticket from Phoenix to Dallas and then 3,000 Southwest points from Dallas to NYC (2 for 1 with companion pass). The risk you run by booking a layover with two separate airlines is that a delayed first flight can cause you a big headache since the two airlines usually won’t work together to accommodate you. But who could resist $82 (which was free money from my credit card incidental credit) and 3,000 Southwest points for two people to New York one-way? (plus we love red-eyes to the East Coast)

Here is what I did. I walked down to the customer service desk, which most airlines have in their concourse. Typically they have much more “pull” at these spots compared to working with the gate agents. I let the rep know that I am now going to miss my second connection on Southwest due to the American delayed flight, which was caused from the American pilot feeling sick on his inbound flight from Cancun. They again let me know that they cannot change my destination and they cannot provide me money for my $200 Southwest fee. (IE: sucks for you)

I asked the rep, who knew I was ultimately heading to New York, can I catch a connection out of JFK and then “continue” onto Dallas? This is called “hidden city ticketing“, using your connection as your actual destination. He looked over at his supervisor and she said “as long as his destination is Dallas, I don’t see why not”. He asked me, “do you have any checked bags”, to which I swiftly responded “never!” (the bags would have continued onto Dallas since that is “where” I was heading). I had already looked at my flight options to JFK before I walked up to the counter, so I said, “can I connect using flight #600 to JFK first thing this morning”?


Also Scored Free Upgraded Seats Since I was Re-booked in Y Class
Also Scored us Free “Main Cabin Extra” Seats Since I was Re-booked in Y Class to JFK


Next thing I know I am holding $25 in food vouchers and 4 fresh boarding passes, two tickets from PHX to JFK and two tickets from JFK to DFW. The rep said, “I stapled the ticket from New York to Dallas on the back if you want it, but your flight to New York is on the front”. So there it was, I was now holding two non-stop tickets from Phoenix to New York for which I originally paid $41 each. Best of all, I was able to call Southwest and cancel my flight from Dallas to New York since I was catching a non-stop. I got my 3,000 points back, to boot!

$82 for two non-stops to New York one-way (booked using free money via Premier Rewards Gold $100 yearly credit)
$25 in food vouchers
I netted $25 in free food by flying to New York 🙂


A321 on Approach to JFK
A321 on Approach to JFK


Yes the flight was delayed, that was a bummer, but the non-stop did help make up some of the time. My take-away is this, don’t be afraid to ask, but also know how you can take advantage of a crappy situation. (and don’t yell at them). This trick only works if the destination you are flying to is a hub for that particular airline and if you are not checking baggage. If I was actually heading to Nashville, for example, this would have never worked. I would have to connect in Dallas or Chicago since Nashville is not a hub for American. Questions? Reach us on Facebook



3 thoughts on “How I took a 5 Hour Delay and Turned it into Some Free Travel

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