I’m a cautious guy … maybe overly cautious but it has served me well over the years … so when it comes to ensuring my vacations go off without a hitch, I take an overly conservative approach.

Such was the case today.

We were supposed to travel from Calgary (YYC) to New York (JFK) to San Juan (SJU) on Friday but I received a warning from Delta that my flights may be delayed due to inclement weather in New York.  I dug into it a bit and saw some not so great forecasts for Friday.

Urban flooding?  Travel delays?  Good Lord!

To compound the issue, a while back WestJet (Delta codeshare partner and the airline operating the YYC-JFK leg) changed their flight time and it left me with a 49-minute connection at JFK … and we needed to change terminals from T2 to T4 … it was gonna be tight.

I had obviously done my homework and thought that we could make the connection but the thought of having a weather delay in New York and the likely backup of other ongoing flights (read: overbooked situations) made me very nervous.

Delta to the Rescue?

I have had a very pleasant experience with Delta in that when there is a possibility of delay or missed connection, they offer a free change and in my experience pretty much anything goes.  For example, when we were notified of the WestJet change that put us in a tough connection situation, Delta allowed me to change to the same flight but a day earlier.

Yesterday, I was notified by text that weather may affect my flight to or from New York.

I knew that if I missed the connection in New York, we would be forced to overnight at JFK and hopefully catch the next flight out at 8 AM.  I assumed that if a bunch of people missed their connection to San Juan, there would be many angry people waiting for a seat on standby and I didn’t want to be in an oversold situation.  To compound the unattractiveness of this possibility, I was also told by Delta agents that accommodations are not provided for weather related delays so I would have to spring for a hotel in New York.

I immediately looked to change my flights because we had surf lessons for my daughter on Saturday afternoon and I didn’t want to disappoint her.  Trust me … she’s really good at the puppy dog eyes.

The first time I called into Delta, the agent was very helpful but the routing she gave me was just not all that attractive … plus, they proposed to route me through JFK again … which could once again put us in a precarious situation.  On the positive side of things, the agent was able to verify for me that pretty much any routing on Delta or WestJet would be bookable to get us to San Juan.

Do Your Research

I used the skills that I taught in my Finding Award Availability Series and looked at hubs that would connect into San Juan.

Bad news … none of the Delta hubs that go into San Juan are a direct flight from Calgary, except for New York and as I stated before, I was trying to stay away from the Eastern Seaboard.

With a little help from some friends (H/T to Matt from A Whistle and A Light), I was able to find a flight from Calgary to Los Angeles to Atlanta to San Juan.

I know what you’re thinking … a two connection itinerary … are you crazy?

It’s not ideal but it actually gets us into San Juan 8 hours earlier but the trade off is that we leave the night before … and we have to endure a redeye flight from Los Angeles to Atlanta.  I’m never a fan of domestic overnight flights because it’s typically not long enough to get a good snooze in but it’s a sacrifice I’m willing to make if it means that we have a stress free vacation.

The Final Itinerary

It’s a bit of a dog’s breakfast but there’s plenty of time for connections and with lounge access, we can freshen up with a shower and some food.

Look At The PRICE!!!

What I find incredible about Delta’s policy of allowing passenger requested changes is the crazy “value” of the flights.  We originally paid $492.71 for our flights so roughly $1,500 and that’s for three round trip tickets.  Look at the one way cost if we had booked the flight on our own!  Roughly $1,600 PER TICKET!

Other Benefits

I’m currently on a Delta Status Challenge and while I never really expected to be able to make the requirements to retain Platinum Status, this new route gets me a chunk of the way there.

Here are the requirements for the Status Challenge:



With the new routing, I knock off 5 segments (MSQs) and 7,684 (MQMs) so I’ll already qualify for Delta Silver.  I’m now wondering if a mileage run on Delta and Delta partners might be worth doing to retain status.

Off We Go

I’m about to take off after an hour delay – thanks, LAX runway construction … but with my new route and the fact that we still have a 2:30 connection in LAX, I’m not sweating in my seat and for that, I’m very thankful.

I’ll be on a Disney Cruise for about a week and with internet at 25 cents per MB, I’m probably not blogging … so watch for a return to the blog in about a week and a half.

Jayce is the founder of PointsNerd, and avid traveller and a teacher by nature. He prides himself on flattening the learning curve through step-by-step guides because everyone needs to start somewhere.


  1. I flew with Delta a few days ago and had a terrible customer service experience. Many delays, circling around on the tarmac waiting for a gate, watching the last passengers board my missed connection through the closed jetway. Being put off by the less-than-helpful agents and virtually ignored on Twitter. Long story short, they are not in my good books. They had the opportunity to ameliorate a bad situation, but chose to make it worse.

    Good luck with your flights.


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