The Year of Free Flights

Flying standby on a friend’s benefits.

Photo credit: Philip Capper, CC BY 2.0.

When my friend Erika asked me if I wanted to be on her flight benefits, I felt like I had won the broke 20-something lottery.

Erika and I had become friends picking up part-time shifts at Barnes & Noble while both of us were finishing our last year at NYU. When we graduated, my other part-time job at a play publishing company became a full-time one. Erika and I both continued to work part-time at the bookstore, and eventually Erika also got a second job at the Starbucks in my office building.

Our working lives, at least that first year out of college, seemed destined to be intertwined. Erika once got hired to put together Ikea furniture in my office. Later, I helped her pick out an outfit for her first professional opportunity: what seemed at the time to be a sketchy flight attendant open interview session in New Jersey she found on Craigslist. It turned out to be legit, and she started working as a flight attendant, doing shuttle flights mostly in the Northeast—and she was willing to share her benefits with me.

Being on someone’s flight benefits basically meant I was able to travel in coach for free. There is usually an application fee; I paid a nominal fee to join Erika’s United benefits. If there were business or first-class seats available, I could upgrade for a price (anywhere between $70–200). Also, when traveling internationally, there were exit taxes I would have to pay when leaving the foreign country to return to the states ($40–100). Otherwise, there was no charge.

The only drawback was that I was flying on standby status. There’s a website that benefits holders can check to see how many other people are also trying to ride on your flight and learn where you are, priority-wise, in the queue. This at least sort of helps you calculate the chances of getting on a flight, but nothing is guaranteed. Every time you show up at the airport, bags in hand, there is a chance that you won’t be able to get on your intended flight.

At the time, I happened to be in my early twenties and single. I worked two jobs, seven days a week, between the bookstore and my new gig at a publishing consulting office, and most of my earnings went towards paying off my student loans—which meant I had very little money but could use a vacation or two. I was also living three stops from Penn Station in Manhattan, making it easy to get out to Newark for $13 each way through NJ Transit. It felt like life was giving me the all-clear.

In the year I was on Erika’s benefits, I used them for for three trips. While this might seem like I wasn’t really taking advantage of unlimited free travel, there were a lot of factors I needed to consider before I set off to fly standby.

First, I wanted to visit places where I could stay with a friend or relative. This helped me save significant money in hotel costs and was crucial if I couldn’t get on my planned return flight home and needed a place to crash an extra night. I also prioritized trips where I could visit someone because my benefits plan meant I would be traveling alone—and while I do appreciate solo travel, I really wanted to use this opportunity to connect with people I hadn’t seen in a while without having to worry about cost.

I also had limited vacation time. Flights for weekend getaways were often the most popular, so the chances of getting on through standby were slimmer. Also, two of the three vacations I took were to destinations that were far enough away to warrant week-long trips. Those alone ate up a good amount of my vacation days from my job at the publishing consulting office. I also didn’t want to miss too many shifts at the bookstore, since I didn’t have paid time off and would not only lose out on my wages, but would also spend extra money while traveling.

The first trip I took was to Hawaii, where I was born and spent the first 11 years of my life. My dad’s side of the family still lived there, and my grandparents had a spare room where I could stay. I was content to shadow my grandparents for almost the entire week-long trip, running errands with them and generally hanging out. My grandfather had been diagnosed with Alzheimer’s, so he and I bonded while watching The Price Is Right together, usually eating a popsicle or snacking because he had a sweet tooth.

My best friend was also pregnant at the time, so I spent time with her and the rest of our friends, making them drive me around. This group of friends and I spent a lot of time together as teenagers, so we were used to spending time together on the cheap, grabbing a burger or plate lunch over anything too fancy.

The whole trip was very laid back and relaxing — the only moment of stress was not knowing if I would make it onto my return flight. I was still waiting outside the gate for several minutes after all the passengers went in before they finally rushed me to a seat.

My second trip was a weekend in Columbus, Ohio. One of the women I studied abroad with in college lived there, and I hadn’t really seen her since she moved out of the city after her graduation. She kindly let me stay in her house and we just hung out the whole weekend, catching up and hanging out in the city with her sister’s family and her boyfriend. The best money spent on that trip was on a couple of visits to Jeni’s Splendid Ice Creams, where I indulged in the Riesling poached pear sorbet to my heart’s content.

I had no trouble getting on my flights to and from Columbus. The flight over was especially enjoyable because a flight attendant knew Erika and slipped me a free bottle or two of wine.

My last trip was to Germany, an unexpected trip that felt like an appropriate end to my free flight adventures. The company Erika had been working for was ceasing operations, and she was soon to be out of a job. She (and me, by extension) had a couple of months left of flight benefits, and Erika was using it to spend time with her dad in Germany and strategize her next career move. She asked if I wanted to join her, and, having only traveled outside the country when I studied abroad in college, I decided the offer was too good to pass up.

I stayed in Nuremberg with Erika and her dad, who generously fed us and drove us to see some castles. He also indulged my love of candy (one of the limited German words I knew before the trip was Gummibären) and drove us to some of the Trolli outlets, where I would emerge from the register with an armful of bags to take back home.

Despite being in a city—and country—I had never been to before, we spent very little money. Erika and I took the bus to Nuremberg to sightsee and go shopping. We mostly ate sausages in bread from stands for a few euros. We also took a train to Munich for a day, where we opted out of going to Oktoberfest and instead took in a museum and walked around the city. Oktoberfest ended up coming to us anyway; on the boisterous train ride home, we were standing shoulder-to-shoulder with many drunk men in lederhosen. Most nights, though, we made a habit of sitting in Erika’s dad’s living room drinking tea and watching German television, which Erika understood and I pretended to.

The trip capped off with a shopping trip in Nuremberg where I helped Erika purchase her first suit. She had an interview scheduled for another flight attendant job with United, and we went to the department store and found her a really beautiful jacket and skirt to wear.

I returned home from Germany hassle-free, and Erika followed later. She ended up getting hired at United, but she declined, deciding instead to start the process of becoming a pilot. Now she flies planes, which is a pretty miraculous ascent from the days when we both worked at the bookstore.

A year ago, Erika asked me if I wanted one of her flight benefits again. I was incredibly tempted, but I declined. My work schedule was more regimented, and I now lived far enough from Newark that getting out there just to take a gamble was not worth it. Also, most trips I’d like to take would include my boyfriend, making paying more for a more guaranteed itinerary worth the price.

Traveling by the seat of your pants through standby is not an ideal way to travel—but if the conditions are just right, it can be the best deal in the world. I’m lucky that my best deal also came from one of my best friends.

Kimberly Lew is a lover of travel—though she will never catch up, free flights or not, to her grandmother, who is a 2 million mile United flyer.

This story is part of The Billfold’s Vacation Series.

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