As I mentioned last week, I want to change things up a bit on Sunday. For the foreseeable future I will use Sunday to write about my thought process when it comes to the world of miles, points, and travel. I think at face value the way I travel seems erratic and unpredictable.
However, it’s actually quite the opposite. After watching airfare trends for over 3 years I have a fairly stable understanding on how it works. So, I will use posts like this one to explain myself and give you a glimpse into what I’m thinking.
Booking A Very Last Minute Trip To New York City
Last Saturday began like almost any other. I woke up, I know, good start. After lying in bed for another hour watching Breaking Bad in Spanish (I’m using it to learn Spanish and it’s working) I decided to get up and head to my local Starbucks. I sat down in Starbucks and started working on the blog when I received a random text from a friend in New York. That text give me the idea, “should I just go to New York today?!”
See, because of the extreme capacity that exists between Chicago and New York you can usually get extremely inexpensive airfare to New York with very short notice. The past few weekends though the weather hasn’t been cooperating and airfare has been unusually expensive.
This time though I pulled up Google Flights and found exactly what I was looking for. I found a round-trip ticket from Chicago to New York for $110 flat! The only catch was that the flight to New York left in 2 hours and that my return ticket didn’t exactly work for my schedule… More on that in a minute.
Rushing To The Airport
At that point I ran home, packed a backpack and ran out of my front door. Thanks to the fairly poor weather in Chicago traffic to the airport was a bit worse than normal for a Saturday afternoon. After a long than expected cab ride I arrived at the airport with just 30 minutes to go before my scheduled departure. Since I only had the backpack and have TSA PreCheck I made it through security in about 2 minutes. From there I rushed down the hall of flags to the gate.
I reached the gate just as the gate agents began the boarding process. At that moment one of the gate agents called my name. Thanks to my American Airlines Executive Platinum status I had been upgraded to First Class on my flight to New York. Not bad for only paying $110 and booking just 2 hours prior!
Another awesome benefit to this trip was that I’d have a chance to try out American Airlines new “Shuttle” service between Chicago and New York. After a quick flight we arrived in New York and I was on my way to visit my friend who had texted me just 4 hours earlier.
Leaving New York (Where Things Got Ugly)
After a nice evening in Manhattan my friend and I woke up early and explored the city. We made a special trip down to the World Trade Center to see the finally completed Oculus.
The Oculus looks incredible from the outside, but looks even better from inside.
As we wondered the massive halls of the Oculus we stopped into the Apple Store for a second so I could search for my flight home. At that exact moment I had the realization that I had totally screwed up!
The day before I searched Award Flights from New York to Chicago and had seen plenty of availability. For that reason I knew that even though my return trip wouldn’t work I could at least get home with points. However, when I searched on Sunday afternoon there were absolutely zero sAAver level award flights available.
I’ll admit, I began to panic because I didn’t exactly feel like paying $266 for a one-way flight home…
For the next several hours I searched over and over again to find award space. With each hour that passed another American flight departed and a different search result came up. Finally, after several attempts I booked the 9:00PM departure for 12,500 points and $5.60.
Although I booked the 9:30PM departure I ended up standing by for the 7:300PM departure which I fortunately got on.
Why Do I Keep Pushing My Luck?
Here’s my thought process going in to Sunday afternoon. I originally booked my round-trip with a Wednesday return flight to Chicago. However, shortly after booking I realized that I needed to be in Chicago for something on Monday so I needed to find a cheap flight home. I was hoping to again wake up on Sunday and find something for about $100.
The issue was, when I began looking American had already issued some sort of travel waiver for passengers departing New York on Monday morning. This caused many people to switch to the Sunday evening departures which filled most of the seats to Chicago. Additionally, this waiver caused the Sunday evening flights to shoot up to well over $400 for a one-way seat.
Although the price was high I figured that I could at very least find a sAAver level award flight home as the day prior there was plenty of inventory. Again, thanks to the travel waiver all of that award availability disappeared. It was only because I searched several times an hour that I was able to eventually grab the seat I got.
What I don’t understand is why I didn’t just book my award flight on Saturday when there was plenty of availability? I knew I needed to be home and by doing it the day before I would have avoided all of that extra stress. Then again, as I mentioned last Sunday I sort of enjoy the adrenaline rush so perhaps I’ll keep doing this until I get severely burned.
Final Thoughts
It always amazes me how cheap flights between New York and Chicago are at the last minute. I love visiting New York so it works out in my favor. Now that this service is considered a “Shuttle” flight I’m even more excited to fly American on this route. Hopefully next time I’ll learn from my lesson and have a plan to get home more than two hours in advance.
