Flying in a Private Plane With a Two Year Old

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I think it is pretty clear at this point that the coolest airline miles related promotion I have ever participated in (and potentially will ever participate in) came thanks to JetSmarter earlier this summer. They offered three months of free Simple membership to anyone who could prove they had either top tier airline elite status or a million airline miles. Simple membership gets you a free seat on their scheduled shuttle flights of three in length hours or less and two seats on empty leg flights that pop up as charter operators need to reposition aircraft.


I wasn’t really sure it would all work out when I first heard of the promo as it seemed ‘too good to be true’, but it doesn’t hurt to try, so I applied and crossed my fingers. A few days later I indeed had three months of free private jet membership active and ready to go. This happened early in the summer right when school was letting out for the girls. This means we already had our summer trips planned, I was really busy juggling their daily activities and schedules, and I didn’t pay a ton of attention to the JetSmarter app and available free empty leg flights until we were about half way through the three month trial.

Then knowing my time with this membership was limited, a few weeks ago I booked a short flight with friends from Houston to Austin just for the heck of it. It was ah-maz-ing.

This over-the-top awesomeness led to me getting a wee bit addicted to checking the app for free empty leg flights, and I booked the mother of all awesome trips, a half-empty Challenger 300, from Houston to Jackson Hole with my seven year old. That was not only an amazing flight, but a five star destination.

Now at this point my husband was understandably wondering when his turn to join me would come around. With the Simple membership the two free seats you can get on empty legs can’t be predicted since they just pop up with usually less than 24 hours notice until the flight based on needs reposition aircraft for actual paying charter customers. I would say there are an average of four or five a week from Houston that appear in the app, though most are to the Austin or Dallas areas. I would guess only one or two a week are from Houston to a non-Texas destination, and you have to move quickly to book them before others do!

I wasn’t sure if or how we were going to pull off getting him on a flight with me before my time in private jet fairy tale land was up because he works out of town a lot of the time, and even when he is home, it obviously takes a lot of stars aligning to pull off having both parents gone at the same time without much advance notice. You can book more than your two free seats, but costs for seats beyond the original two can be in the $600 – $800 range for flights like Houston to Jackson Hole. We really can’t afford to on a whim buy a third and fourth seat at that rate for our kiddos.

Late last week he was on a Delta flight flying home from work, I had just been home from NYC for a couple of days and I was starting to come down with something, and my seven year old was away at the beach with Grandma and some second cousins for one last summer hurrah when a Friday evening empty leg flight from Houston to Pensacola, Florida, popped open in the app. At first I dismissed it as I do most of the flights that pop available because life is kind of busy already without upending plans to hop on a private plane. In fact, I didn’t book it for the entire first evening I saw it because it just seemed like a bad idea with so much going on.

The next morning I told Josh about the still available flight and even though he hadn’t been home yet more than 12 hours, he was all-in to get his turn in the private skies. I was feeling worse by the second, but decided a head cold was survivable and I couldn’t guarantee we would have this chance again. My older daughter was still going to be at the beach another day and it was a reasonable $234 for the third seat on this plane so that my youngest daughter could also come with us.

At two years old, she obviously won’t remember the experience, but at least she can’t grow up saying we never gave her a turn. When I asked her that morning if she wanted to fly on an airplane with mommy and daddy she gave a very definitive yes answer. In fact, she was crushed when she was then taken to school for a few hours before departure since she wanted to fly, and she wanted to fly now!

This private plane was departing from Ellington Field in Houston, which was certainly somewhere I had never flown out of before. In my mind Ellington was for NASA and astronauts, not my family heading to Florida for the night. To allow plenty of time to get through Houston on a Friday we left early, loaded ourselves and a very excited two year old into the car, and made our way through traffic to the Signature Flight Support Fixed Base Operation (FBO) at Ellington Field.

I’ve had the privilege of going to a few of these Fixed Base Operations now thanks to this trial, and they aren’t all flashy, but they have all been staffed by exceedingly nice people. This one even had fresh baked cookies and a fish tank, so we were all set.

Storms were building around us, but the pilots were ready to go on time and told us we would just be weaving our way through the storms on the way from Houston to Florida. The Hawker 400XP was fully booked with seven passengers for seven seats, one of which I had met on a previous JetSmarter flight. I can’t imagine that walking out on the tarmac to your awaiting plane ever gets old, and it certainly hasn’t for me.

Since I take tons of pictures, we were the last to board and took the remaining three empty seats, one with the best legroom of all right behind the cockpit and the two seats in the very back of the plane for Little S and myself.

If I’m being honest, the legroom situation in my seat was similar to Spirit Airlines. My legs stayed out in the aisle for most of the flight, though my two year old was more than good to go. Much of this has to do with how the middle seats are configured, I imagine. Still, even that wasn’t enough to take the smiles off our faces because this is just a beyond cool experience, even if you are a little squished.

The plane was beautiful, and I imagine if you chartered it for your own family or group it would be perfect, but fully loaded with folks you don’t know it wasn’t quite the same experience as in the half-empty and much larger Challenger 300, so I felt a little bad for Josh that he didn’t have that same private jet experience that I had on my first two flights, but he still had a blast.

My two year old was an absolute flying boss on this private plane. She was totally in her element and didn’t need anything from anyone. She said she wanted to fly that morning and she did.

Just like on my previous private jet flights, my favorite part of the experience is really the huge difference in what happens on the ground. You park right outside of the building, walk in, and fly with no lines, no parking garages, no security screenings, no getting there 90 minutes early, and then you chat with the pilot and hop on the plane. You are typically wheels up within minutes of boarding and on your way.

In my vast three flights worth of private flying experience, I have learned that when you land it is often possible to have your rental car waiting for you on the tarmac if you request that ahead of time. This time, I rented a vehicle from Hertz at the Pensacola Airport and simply called the FBO to see if they could help me in having the car ready there instead of over at the main airport terminal, and that wasn’t a problem at all.

When we walked off the plane, there was our rental car. For the record, this one-day rental was just $32 all-in and will earn us 5,500 United miles, so I’m calling that a win.

We spent some extra time at this FBO to pet the amazing aviator goggles wearing golden retriever named Sadie (yes, she has her on Facebook page) who was there to meet us as we deplaned, but then after some doggie snuggles and a quick bathroom trip (also without lines) we hopped right in our car and were on our way to dinner by the water with a view of the sunset at The Grand Marlin.

I think it was probably two hours flat from wheels down in Texas to eating oysters by the water in Florida, which is just sort of mind blowing. I cannot believe that every member of my family has now had the opportunity to fly somewhere on a private plane for the night….really, ultimately, thanks to miles and points.

Not only are miles and points the reason I was able to get in on the trial membership in the first place, but they have also provided the ability to book last minute flights and hotels around these ‘free’ private jet flights. For this trip we used 8,000 Hyatt points to stay at the Hyatt Place Pensacola and 10,000 United miles each for a nonstop flight home the next day so we could get back to pick our older daughter up from the beach in Galveston.

The biggest price we paid on this adventure was that flying and getting limited sleep with a head cold did indeed make it much worse, but eventually I’m sure all will be right in that arena, and the memories of flying together on a private plane to Florida with our two year old will remain.

Flying in a private plane with a two year old is absolutely not something I thought I would ever do, but it was exceedingly awesome and absolutely makes me very grateful for this hobby and the opportunities and friendships it has brought our way.

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  1. Yup! My youngest was Maybe 16 months old when we flew jet smarter. Great experience all-around for our whole family of 4! My husband and son have taken it a few times since. Just got to be flexible and ready to go at all times 🙂

  2. Great writing as ever Summer.

    And also as per usual… you’re a breath of fresh air compared to some of the entitled, far less humble bloggers over here.

    Stay happy! Love your blog.

    • Oh thanks – there is no question that we are not entitled to private jet flights. This was an amazing opportunity that we very much enjoyed. Thank you for reading!

  3. I much enjoyed following your experiment with the JetSmarter trial. I couldn’t find a single flight from Portland, OR, so I had to live vicariously through you 🙂

  4. You rock Mommy Points!! Keep on doing what you do because we all love reading your blog and gaining so much insight to this fantastic hobby of ours!

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