I tried to outsmart an airline and save $900 by skipping the first half of my flight. It was a huge mistake and I won't try it again.

Theresa McKinney smiling in boston with sunglasses on

I tried to outsmart an airline and save money but the whole plan backfired.Theresa McKinney

  • I tried to outsmart United Airlines by skipping the first leg of my flight to save $900.

  • My plan totally backfired, I kind of got caught, and I ended up rerouting my entire trip.

  • I’d never try a “skiplagging”-style trick when flying again.

In August 2021, I booked my first solo trip to Europe: A $439 United flight from Cleveland, Ohio, to Madrid, Spain, with a short layover in Newark, New Jersey.

I was nervous but excited to be exercising my freedom to explore my new life as a full-time travel blogger, and I planned to see Madrid, Córdoba, and Seville.

However, in early November, my husband was asked to go to Boston, Massachusetts, for a business trip the same week as my Madrid flight. I was determined to go with him, as I’d always wanted to explore the New England state.

Since my flight wasn’t until Friday, I figured I’d just change my departure city from Cleveland to Boston. The process was easy, but United would charge me a fare difference of around $900 to change my booking. The fee may have been due to a price spike on the flight, but I didn’t want to pay it.

Instead, I tried to book a United flight from Boston to Newark for $60. I’d just skip the first half of my flight and catch the Newark to Madrid connection from my original ticket.

In a way, I was attempting a version of “skiplagging,” a controversial money-saving strategy where passengers book tickets with a layover while planning to skip the second leg of their flights. I’d just be skipping the first leg instead.

However, United promptly notified me via email that they’d canceled this flight for being a duplicate booking. Still feeling crafty, I kept my plan in place and just booked a similar flight to Newark with JetBlue and headed off to Massachusetts.

My ‘trick’ backfired — and I ended up changing my travel plans

United Airlines plane

I learned my lesson trying to skip a leg of my flight on United Airlines.Thierry Monasse/Getty Images

I had an amazing fall visit to the Boston area and, on Friday morning, I headed to Boston Logan International Airport and boarded my flight to Newark.

The whole time, I felt uneasy. I hadn’t been able to check in for my Madrid flight online, but I figured I’d be able to resolve the issue with a United agent upon arrival in Newark.

Once I landed, an agent pulled up my itinerary and asked why I wasn’t on my flight from Cleveland. I didn’t get why I had to explain my personal travel arrangements so I said plans had changed and I needed to fly out of Boston instead.

They told me if I didn’t get on my first flight from Cleaveland, my entire itinerary would be canceled and my only option was to rebook my ticket for the (apparently unavoidable) fare difference of $900.

The airplane seat to Spain I’d purchased was waiting for me, yet here I was finding out that it was no longer mine. My face flushed in shame at my failed attempt at outsmarting an airline.

Dejected, I canceled my plans since the trip was mostly refundable. I booked a flight back to Boston to meet up with my husband, and was both surprised and grateful to receive a $439 flight voucher from United a week later. I eventually applied the voucher toward an unforgettable two-week solo trip to Paris, although I still haven’t visited Madrid, Córdoba, or Seville.

Looking back, my best option would’ve been to fly back to Cleveland to catch my original flight. I’m now aware that skipplagging in any form isn’t allowed, and can confidently say you’ll never catch me intentionally missing a connection again.

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