Trip Notes: Flying Private To NYC And Tips For Dealing With Flight Delays And Cancellations

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Thanks to my free Jetsmarter trial membership I’ve taken several private jet flights.

I’m really going to miss it when its over. There’s nothing quite like walking onto a plane without needing to deal with the hassle of commercial aviation.

My brother JJ and myself have been looking to fly to NYC for a meeting. He’s currently in Miami while I’m in Cleveland, so when Yaalili posted on DDF this past Tuesday that there was a Jetsmarter flight from Cleveland to NYC I jumped onto the app and noticed that there was also a Jetsmarter flight from West Palm Beach to NYC on Wednesday, so we held the flights and arranged to have a dinner meeting at Reserve Cut.

With Jetsmarter deals you can book 2 free seats on an empty flight. Once you book they will ask for passengers names and you’ll have 90 minutes to give them that information.

I reserved 2 seats from Cleveland, but only gave them my name. They told me I could still add another name if I wanted to until 3 hours before the flight.

You can cancel for free until you actually confirm the invoice that is sent after you send in your name.

I booked a return flight from LaGuardia for 10K United miles as American had no award space and United didn’t have 10K awards available from Newark on the later flight that I needed.

However, United issued a weather waiver for NYC and I was then able to switch to the later Newark flight, despite it not having any saver award seats. Gotta love weather waivers, they’re extremely useful for all kinds of fun scenarios when they pop up!

On Tuesday evening I asked a Whatsapp group of my local friends if anyone wanted to come along for a ride on a private jet to NYC and sure enough one of them responded on Wednesday morning that they would love to come along for the ride.

Of course the trick would be getting him back home, as he doesn’t have top-tier United status as I do.

So I had him book a flight from LaGuardia to Cleveland a month in advance for 10K miles online and then he called United to change it to a return the same day without having to pay any fees. Then he called back and switched to get the last seat on the latest flight out of Newark to Cleveland for free, despite it not having saver award space, thanks to the weather waiver in place.

I had no problem adding him to my Jetsmarter flight, despite it being just an hour before the flight.

I left my house just 55 minutes before the flight at Cleveland’s Burke Lakefront Airport. It was my first time flying from BKL and we had no idea where to go.


The main terminal had a very neat looking aviation museum, but we were just trying to figure out where to go to find our flight, so I only snapped one quick picture. But I’d like to make it back in the future to explore the exhibits.


Eventually we found someone who directed us to walk across the tarmac to the Signature Aviation terminal.

My friend marveled about how cool it was to just stroll across the tarmac and past US coast guard planes, without any kind of security check.

We showed our pilots our IDs and hopped onto the Hawker 400XP.


It was significantly smaller and not as luxurious as the Citation X and Hawker 850XP that I’ve taken in the past, but it sure beats flying commercial.


There was free WiFi as well as snacks and drinks onboard.

Taking off from BKL:



We flew around some storms and arrived a minute early into Westchester County Airport:



Meanwhile down in Florida, things weren’t going as smoothly.

JJ’s Jetsmarter flight from West Palm Beach to Teterboro was cancelled. Luckily, it was within the JetSmarter cancellation window, so they told him that they would find a replacement flight for him. On a previous trip, JetSmarter rebooked AJK in first class on a commercial flight when they cancelled his trip, but in this case they rebooked JJ from Fort Lauderdale Executive Airport to Teterboro on a Challenger 350:





Taking off from Fort Lauderdale:



The interior is decidedly more luxurious than the Hawker:





Someone even asked JJ on the flight if he got his seat on the plane thanks to DansDeals 😀

His adventures for the day were just starting to begin though…


Jetsmarter no longer gives free helicopter transfers like they used to, so my friend and I grabbed an Uber from HPN to Crown Heights. We planned on breaking our 9 days vegetarian diet in the best manner, at Izzy’s BBQ Addiction. Rain had started falling and traffic backed up on the Hutchinsion River Parkway due to flooding. I sent AJK a message that I was heading to Izzys for lunch and that he ought to meet us there.

Within a period of just 1 week AJK flew to Montreal for lunch on Jetsmarter. flew to the Ritz Amelia Island for this past Shabbos, and flew on a luxurious Gulfstream IV to Chicago for dinner, so it was no surprise that he was down for lunch at Izzys.

We split an order of pulled beef empanadas:



My friend ordered the pulled beef sandwich, which was incredible:


AJK had a brisket sandwich. And I had their famous melt-in-your-mouth dino ribs. Or as the viral Whatsapp message in Yiddish goes Fiiiiiina ribs…uber unfreakingbelievable


And I can’t go to Crown Heights without bringing home some cream cheese frosted cinnamon buns and chocolate croissants from Brooklyn Artisan Bakehouse:

#Insane #CreamCheeseFrosted #CinnamonBun and an #IcedMocha #BreakfastofChampions @BrooklynArtisanBakehouse

A post shared by DansDeals (@dansdeals) on



Meanwhile JJ’s flight was doing circles around Teterboro due to weather, before Teterboro finally refused landing permission and they were diverted to Westchester County Airport!


My friend picked up a new fedora in Crown Heights and then we took an Uber into the city.


But in the meantime Westchester County Airport also refused JJs plane and they doubled back to Teterboro once again!

Who needs roller coasters or Dreamliners in the sky when you have this!



Before dinner I got notification of massive flight delays at Newark. I called up the Global Services line and they put me and my friend on the 6pm flight which was delayed until 9:30pm and they also protected us on the 5pm flight which was delayed until 9pm.

Flights from LaGuardia to Cleveland were all cancelled and an earlier flight was showing a 17 hour delay until the following morning!


JJ was still doing rotations around NYC, but the show must go on, so we started the meeting without him and walked into Reserve Cut, which has by the far nicest ambiance of any kosher restaurant in the world that I’ve been to.

I started off with the Porcini Mushroom soup, which is one of the best soups you’ll ever find. One person at the meeting declared that he hated mushroom soups. He tried a spoonful of my soup and was shocked by how good it was.



And no meal at Reserve Cut is complete without the short rib tacos:


The table also split an order of beef jerky, which was phenomenal.

We split an order of braised short ribs, which were very good, but are no match for Mike’s Bistro’s short ribs:



But the Chateaubriand, which is only served on Wednesdays, was perfectly cooked with a deliciously crusty exterior and a perfectly cooker interior.



Another person ordered the 22oz Wagyu bone-in steak. I’ve had this in the past, but the Chateaubriand was far superior despite its lower price.



As we were eating our entrees I got notified that the flight originally scheduled for 6pm that we were booked on was cancelled. Luckily the agent had protected us on the flight originally scheduled for 5pm, which was now showing a 10pm departure time.

JJs plane finally landed at Teterboro and he grabbed an Uber to meet us.



JJ devoured the chateaubriand that we ordered for him before we got a few desserts for the table, including a delicious passion custard creme brulee:



The chocolate degustation didn’t really do it for me:


The warm beignets are always delicious, though I do wish it came with a chocolate dipping sauce rather than raspberry:

After dinner we caught an Uber to Newark airport.

JJ’s 9pm flight to Miami was delayed until 3am, but during the ride he was notified that the flight was cancelled. The previous flight to Miami was cancelled as well. I called up the Global Services line and they said the only flight they could confirm him on would be a 9:30pm flight to West Palm Beach. Unfortunately we wouldn’t make it to Newark until 9:26pm, so there was no chance of making that flight.

Flights to Fort Lauderdale and the only remaining flight to West Palm Beach had standby lists that stretched dozens of people long.

Worse yet, there were no other available flights to South Florida until Friday evening!

At Newark I went to the Global Services counter to try to get JJ another flight, but they weren’t able to do anything for him. Pre-Check has ridiculously short hours at Newark and the regular security line was very long. But as a Global Services member the agent escorted us to the front of the line. Still, the actual security process was painfully slow, it sure made me miss the Pre-Check experience.

JJ ran ahead to see what could be done about getting a seat for another flight that already had 50 people standing by, but he called me from the gate to see if I could possibly help. At the counter was a lady screaming at the agent about how she needed to be on the flight and the agent was none too pleased. After listening to her berate the agent I calmly showed my Global Services card and asked if he might be able to get my brother a seat on the flight. As he was typing away and indicated that he should be able to help, JJ said he could hug him if he would be able to get him home.

And as he handed JJ an Economy Plus window seat and told him to get onboard before they closed the gate, he sure enough asked JJ for that hug. It was actually a sweet moment in an airport full of irate passengers.

My flight to Cleveland was delayed until 11:45pm as they had to find new pilots as the previous ones had timed out. I was pretty sure that the flight would be scrubbed, but was pleasantly surprised we eventually took off and we landed at 1am into CLE, the same time that JJ arrived into West Palm Beach.

Global Services status definitely helped save the day, but there are a few lessons for everyone dealing with irregular operations.

  • In general, airport agents have much more power than phone agents to get you rebooked and to move you onto another airline, so head to the airport if you don’t get anywhere over the phone. That’s how I salvaged our business class award tickets to Israel when American wanted us to fly with them in coach rather than rebook us in business on another airline.
  • Be polite, courteous, and go on a full charm offensive. Agents have lots of power to fix things, but they sure won’t do it if you’re screaming at them. In fact they would like to do anything to give away your seat to someone else if you’re mistreating them.
  • If you are flying on a low-cost carrier they are extremely unlikely to book you on another airline.
  • American and Delta no longer have an interline agreement, so they are very unlikely to rebook you on one another.
  • Flying on United typically gives you the most rebooking options as they have agreements with both American and Delta.
  • Always know what your alternate options are and be proactive in suggesting them. It’s better to catch a flight back to West Palm Beach or even Fort Myers than wait 3 days for there to be space on a flight to Miami or Fort Lauderdale.
  • Having an airline club membership or club passes is very useful in these situations as club agents are great at booking alternate flight options.
  • If you have a seat and don’t mind getting vouchers for free flights, hotels, and airport food, be sure to let the gate agent know. And don’t forget to negotiate a first class upgrade on the next available flight!
  • If it even drizzles and you’re flying in or out of the congested NYC airspace…good luck, you’re going to need it!

It was a hectic day, but we managed to have lots of fun and get back home without having to overnight in NYC, so I’d call that a win!

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30 Comments On "Trip Notes: Flying Private To NYC And Tips For Dealing With Flight Delays And Cancellations"

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You just made me very hungry!


Awesome TR, glad you had a nice day here!


What is jetsmarter cancellation window?


Hold it – jetsmarter booked ajk in commercial first coming off after cancelling a jetdeal? Or was it a shuttle flight? Great TR and great info.

CH resident

Thank you for sharing!
I’m just a bit offended you didn’t come say hello.. 😉


@dan how did you get Global service?! I think I was dealing with the same fiasco getting from EWR to FLL! when I realized my Wednesday flight for myself and 4 other family members was in jeopardy I immediately purchased 5 Milage tickets for Thursday. Sure enough my flight was cancelled so I calmly left the airport and called united when I was settled back home and had them transfer those tickets to my current itinerary…. super proud of my move !




Yeah, I must have read it too fast, cause I didnt see anything a bout a meeting. unless it was before JJ showed up.

Mountain Man

Great TR. I second skipping the Wagyu. When I got it it was cooked very nicely but had extremely poor marbling. Considering it was a $100 steak and real “Waygu” ought to be among the most marbled meats you’ll ever find I was beyond words. I doubt the meat was even choice. It was the first time in a long time that I couldn’t bring myself to finish a piece of meat. I can’t imagine a treif place getting away with what Reserve Cut does. Their “filet” was actually pretty good and had significantly more marbling than their “Wagyu”. The ambiance was pretty nice and location is awesome but I’m tired of being hoodwinked by these places. Peter Luger for example is $54 for what I can only imagine is a vastly superior steak.

I also thought the backribs at Izzy’s were far superior to the short ribs. I imagine the short ribs probably would’ve tasted better if reheated the next day. The brisket I got was also too dry (they probably didn’t tent it properly) but had a nice smoke profile. They didn’t have any Pastrami or Lamb ribs available when I went unfortunately. I thought the sriracha wings at Izzy’s were really good as well.


@Dan my membership is also about to expire, is there a way to get them to extend for another 3 months?


Happy I didn’t take my son to florida for the day for that return jetdeal, though having JJ on the flight would have made it more likely that we would have been accommodated too :). I’ve never heard of a cancellation window, though, and never heard of them reaccomodating for jetdeals. Sure it wasn’t a special blogger treatment?


Yes, I’m sure.


Nice TR.

I think I’m confirmed for #4 tomorrow 😛


do you know of a website for such flights in Europe? or to accompany a private aircraft?