Two flights taken, three cancelled flights and a stay in a dodgy Comfort Suites, all for nothing. Yesterday was my birthday, and that’s not an event worth noting in any calendar. I do however love to travel on my birthday, and each year, I set out to take a short trip. Last year we flew the Dreamliner to Mexico, this year we were planning to review JetSmarter, using our free private jet credit. What a disaster of a day… or two. Here’s a step by step account…

water drops on a window


We love Chicago and I was hellbent on flying JetSmarter on this specific day, the day before my birthday, which also is my day off. There was a Challenger 300 (nice plane) flight from Nashville to Chicago which seemed like the perfect opportunity to take a free private jet. We decided to use miles to get ourselves to Nashville the morning of the flight, and booked a flight for $69 per person from Chicago back to New York on a late evening flight. It seemed perfect. We didn’t bring a bag, laptop or A CHANGE OF CLOTHES (fail). 

a sign with a plane and flight information

New York to Nashville

After a nice uneventful departure from LaGuardia, including a stop in the Admirals Club, thanks to British Airways Silver status or alternately our Citi Prestige card, we made our way to Philadelphia, for a perfectly timed, tight connection. We landed in Nashville right on time, leaving an hour before our private jet flight was set to depart. 

a screenshot of a chat

I Get A Message from JetSmarter

You don’t have to show up a minute earlier than your flight time for a private jet. No security, no lines, just walk up, hop on. With that in mind we were sitting in the Admirals Club in Nashville, taking in a nice cocktail to celebrate the day, passing some time before we would head to the private aviation terminal. I received a message from my JetSmarter contact mentioning that due to insane weather in Chicago, there was a chance the plane may divert to Milwaukee, a one hour(ish) drive to Chicago. No big deal.

airplanes on a runway

We Arrive At Atlantic Aviation Private Jets

It’s a very surreal feeling walking into a room without a single other passenger. Upon arrival we were greeted at the desk, told the friendly desk agents we were here for the Chicago flight on the Challenger, which was parked right out front. All systems go. A ground coordination came in from outside saying the pilots were ready to go and they would be in in just a minute to greet us and get us on board. 

a man pointing at a weather radar

Cancelled Due To Weather

Just a couple minutes turned into fifteen minutes and we began to wonder what was going on. A pilot from our aircraft turns up and very politely informs us that gusts have reached 60MPH in Chicago, and legally we could not take off in those conditions, thus the flight is cancelled. Minutes later I get a message from JetSmarter confirming the same, offering apology, but without any assistance. The pilots kindly offered a tour of the aircraft, which we greatly appreciated. I’m still going to successfully fly JetSmarter sometime soon….

a person getting off a plane

How Do We Get Home? 

We have a flight from Chicago booked, but we’re in Nashville and the flight from Nashville to Chicago has just been cancelled. What do we do? Let’s go home. Because of weather American Airlines were offering complimentary flight changes…from Chicago. I called American Airlines, reached an incredibly kind rep who made an exception, allowing us to pay no penalty to switch our ticket from Chicago to New York to Nashville to New York. We were booked on a 2PM, which meant that though the day was a wash, we didn’t really lose much money and would be home soon.

a screen shot of a computer

Cancelled, Cancelled Again…

As we made the best of the wait in the Admirals Club, we got a buzz on the phone that our flight was cancelled. I promptly went to the desk to ask for advice, and we were booked onto the 7PM to New York. Rather than waste an entire day in the airport we went into town for lunch. We came back around 5PM, only for the flight to cancel at 6:15. The last flight of the night. All of these flights were cancelled due to record bad weather in the Northeast, really to no fault of JetSmarter or American Airlines. The few that did fly that day had terrifying experiences. As you know from my post about what you’re entitled to, in the US, cancelled flights entitle you to NOTHING.

water drops on a window

Complimentary Place To Stay?

When the flight cancelled I literally ran to the desk to rebook. I had to be back in New York, an hour outside of the city for a 1PM work engagement and I needed to get back fast. I was put on the 5:45 AM flight, which due to crew rest restrictions would take off at the same time as the scheduled 8:15 flight. I asked about accommodation for the stranding, and was handed a voucher for a hotel, or so I thought. By the way, we didn’t bring a change of clothes because we never ever imagined we could be stranded, and then my jeans ripped…

a door with a light on the wall

A Seriously Crappy Hotel

I’m a bit of a snob and I’m cool with that. This hotel really was a dump though, with drywall unfinished on walls, the lovely smell of cigarette smoke in the old stained carpets and just a true lack of love. After a much needed rest, at check out I was asked which card to put the room stay on. I said it was a airline voucher. The promptly handed me the voucher which was just a negotiated, not even great rate. I would have NEVER stayed here if I knew I was paying. I was angry and felt duped by the agent who did not mention anything about not comping the night.

a close up of a ticket

The TWO 8:15’S

Time was of the essence. My flight was due to land at 11:30 in New York, leaving me less than an hour and a half to get home, since I hadn’t packed a change of clothes and RIPPED MY JEANS in an unfortunate area the night before. Let’s just say it’s a great thing I was wearing a long coat… My best tip, which worked well, was to stand by on the second 8:15 flight. Both flights left within two gates of each other, allowing us to watch both gates to see which one was moving fastest, knowing we had seats on one, and as elite frequent flyers, would most likely get a seat on the other. 

an airplane wing in the sky

We Made It! Kind Of…

I had a full day of work on the docket for yesterday, my birthday. I was really tempted to cancel it all, and take the JetSmarter leg re routing the plane away from Chicago to Daytona Beach that morning, but I knew I couldn’t blow off work. To top off the journey, we had a f**king joke of a flight crew, who without provocation offered this over the loudspeaker as we approached NY “If you don’t turn off your electronic devices we will abort our landing”. Upon arriving in New York, I found out that power had been knocked out at the office due to insane weather and trees down, and the day was cancelled. We came home for nothing, we went to Nashville for NOTHING.

Gilbert Ott

Gilbert Ott is an ever curious traveler and one of the world's leading travel experts. His adventures take him all over the globe, often spanning over 200,000 miles a year and his travel exploits are regularly...

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