How My Daughter and I Took an Entirely Free Round-Trip Mini Getaway to Chicago on Private Jets + Some Things I Learned About JetSmarter

A few months ago, I blogged about an incredible JetSmarter status match where you can get a free 3-month “Simple Membership”. JetSmarter is an app that you can use to book shuttle flights and empty legs on private jets. Membership can be pricey, but for those who have the freedom to constantly be on the go, it can offer an incredible value. Unfortunately, the status match is no longer available (understandably), since it was extremely generous to begin with!

I’ve take a few free JetSmarter flights previously through prior promotions, and I loved the experience, especially not having to go through security and essentially just being able to show up at the hanger just minutes before the flight.

Given my proximity to the New York airports, especially Teterboro, which is like in my backyard, I was more than excited to take advantage of the free flights with family and friends. After all, flying private is not something I’d ever imagine as my “real life”, so I wanted to indulge in the treat while I had a limited window to do so.

While the JetSmarter Simple membership does not give you full access to every flight available or custom charters, you can book any of the empty legs (for you and a guest) or a free seat on most of the scheduled shuttles that are under 3 hours within the US (and Europe too). I’ve previously blogged about fun ways you can use your JetSmarter Membership if you also got approved for the match.

My Day Trip To Chicago

It was a quiet Sunday night as my kids were settling down, when all of the sudden an empty-leg flight popped up in my JetSmarter app, departing Monday morning from New York (TEB) to Chicago (MDW). I didn’t have any plans the following day, so without much thought, I hit the “purchase” button to secure 2 seats on the flight.

Once my itinerary was confirmed, I was locked in! This was it- I was headed to Chicago in them morning (otherwise I’d have to pay a hefty cancellation fee of $1,000 per seat), and now I had to pick a guest to take.

As a mom of two, the hardest part was choosing which child to take with me. Of course there aren’t any favorites in this household, but I chose my daughter because my son had plenty of opportunities to fly solo with Mommy before my daughter was born, so I thought this would be a nice opportunity to give Lucia some solo travel time with me. Plus, I have the JetSmarter membership until early September, and I definitely promised my son he would soon be able to take a flight with me too.

Now that we had a fancy-pants ride to Chicago for the day, I had to figure out a way to get home. Thankfully, Chicago is a big city with so many connections to the NYC area. I ended up booking us two tickets home from MDW to LGA on Southwest for 6,000 points and change each. I even envisioned us having a proper dinner at the AmEx Centurion Lounge upon landing.

The good thing about Southwest award flights is that they are fully-refundable up until 10-minutes before departure, so if anything, they make great placeholder flights while still keeping options open. I packed a day bag, reached out to some friends in the Chicago-area, and planned out a list of activities for us to do during our day-trip to Chicago.

The morning before the flight, I popped open the JetSmarter app and saw there was a member-initiated shuttle back to Morristown, NJ that same evening from Midway with 5 seats available. The big issue was that my JetSmarter Simple Membership only allows me to book just one seat on shuttle flights (compared to two on empty legs).

There’s no way I’d…

1. Leave my daughter behind in Chicago,
2. Pay $2,288 for the extra seat for my 2-year old, or
3. Book one seat and lie about her age and say she’s a lap child before boarding the jet home.

Then a brilliant idea dawned upon me! I remembered paid JetSmarter members have the ability to “gift” a seat on a scheduled shuttle flight to someone who has never flown with JetSmarter before.

I quickly called a friend of mine and asked if he would be able to “gift” the Chicago to Morristown return flight to my daughter. To my surprise, he was able to! After creating a JetSmarter account for my tot, uploading her passport, and having her sit still to take a selfie, she had her own seat booked home (thanks a million, Dan!). Moments later, I canceled our Southwest award flights and booked a shuttle seat for myself for $0.00.

We were headed to TEB with two entirely free private jet flights. I was over the moon. Twenty minutes after we arrived and checked in with the pilot, we boarded our plane to Chicago.

Once we touched down in Chicago, we had a full day ahead of us. We started with the free Lincoln Park Zoo, then had lunch with a friend, played at the playground, and visited Navy Pier and the Chicago Children’s Museum before finally grabbing some Giordano’s to go as we headed back to Midway to catch our shuttle flight back. It was a perfect day out.

Soon enough, it was time to board and off we were. Both of us were pooped, and shortly after takeoff, we rested until we touched down – couldn’t have asked for a more perfect day together from start to finish, honestly.

Not only did this mini trip using JetSmarter give me memories of a lifetime, I also learned and observed a lot about the app and would love to pass along some of my strategies to those who have matched [or joined] and want to maximize their membership.

Tips and Observations about JetSmarter

• The In-App Texting is Awesome: All of the bookings, answers to questions, and  communication is done in-app via text and it’s amazing. The JetSmarter reps are extremely responsive and everything felt seamless and stress-free. You can even send over images of your ID and other passenger info over messaging for you and your guests.
• If Your Flight Gets Cancelled, There Are Recovery Flight Options: While I was in Chicago, an empty leg popped up from Teterboro to Washington for the following day. I ambitiously grabbed it because I was hoping I could give my son a private-jet experience. Luckily I did not make return plans yet, because the operator ended up canceling the trip. Even though it was a free empty leg, they offered to charter another aircraft to complete the trip, and if that could not be done (by the way, they did find another jet), they would have offered paid first-class seats on a commercial airline from NYC to DC. They were very patient with me as I decided whether I wanted to take the trip or not, and quite honestly, I knew it would be too much to have two back-to-back travel days, so I was able to cancel without penalty.
  
• Try To Stick to Empty Legs and Flights to/from Major Cities: While the idea of hopping on a private jet heading anywhere is exciting (believe me, I used to almost have urges to book flights to east bumble, Vermont just because “I’d be riding in a private jet”), you’ll have to be practical. Flights within major city pairs are better for many reasons, including the cost of getting to/from small airports in the middle of nowhere, and having options to position and fly home once your private jet flight is done. I see a lot of JetSmarter flights into major airports including IAD, IAH, MDW, LGA, FLL.
• Book a Refundable Return/Positioning Flight: If grabbing a JetSmarter  “Jet Deals” empty leg flight, I’d recommend booking a refundable award or ticket in the case that your flight does not end up operating. Also, you may get lucky at the last minute and snag an empty leg flight for your way back. I often see itineraries pop-up that allow for one to create a round trip private jet itinerary entirely free. For instance, I often see patterns in city pairs such as New York to Chicago and Chicago to Washington, vice versa. As mentioned earlier, using Southwest points is a great option, or if you have top-tier JetBlue Mosaic status (there’s currently an active status challenge), you can cancel award and paid tickets for free.
• JetSmarter Members Can Gift Shuttle Flights: Certain paid memberships have the ability to gift a seat on a shuttle flight to someone who has never flown JetSmarter. The recipient’s age does not matter, so if you have a friend who has the gifting capabilities, it’s a great way to snag an additional free seat on a shuttle flight for your child or guest.
• You Aren’t Bound to The Flight Until You Confirm Your Itinerary: When you hit “purchase” on an empty leg flight, you aren’t 100% bound to taking the flight until your formal itinerary is sent to you via the app and you hit confirm. Having that extra decision-making time (even if it’s only 20 minutes or so) when you’re racing with the clock to snag seats before they disappear is nice.
• Trip Protection Insurance Possibility: When your flight invoice is prepared and sent your way, the purchase price for the flight shows $0. YMMV, but I have heard reports from friends also on a trial membership of asking JetSmarter to change the invoice price to $1 and charge the small fee on a credit card offering amazing trip insurance benefits like the Citi Prestige. The $1 can be very helpful and put you at ease if anything should happen that would prevent you from taking the trip, and protecting against potentially thousands of dollars in a no-show fee.

Overall, I think this JetSmarter status match was one of the coolest ways I’ve ever been able to travel. I look forward to taking a few more trips before my trial expires in September. Have you been approved for a match? How are you using your membership?