IE 11 is not supported. For an optimal experience visit our site on another browser.

Big mistake: $654 flight from NYC to Chicago

/ Source: The Associated Press

I should have known better.

Somehow I wound up paying $654 for a trip to Chicago from New York. (That's nearly a dollar a mile, by the way.) And I'm an airline writer. I'm supposed to know all the tricks of the trade and ways around the airlines' usual shenanigans. Right?


The goal was to find a cheap flight to the Windy City for an overdue weekend visit with my sister and niece, heading out on a Thursday and heading back to New York that Sunday.

I started researching flights about 5 weeks out — enough time, I figured, to check prices on several different sites and still have a little wiggle room to wait for prices to drop. Patience is the key to scoring a good price. So I looked. And I waited.

Tickets for the dates I wanted ran about $240 including taxes. That's pretty expensive, I thought, compared with the last time I flew to Chicago a year ago. I paid about $180 with taxes for the same flight in June of last year. But I knew traveling in July — one of the busiest travel months — wasn't going to be cheap. The improving economy has driven up ticket prices, especially on popular routes like NYC-Chicago, as the airlines cut flights to match demand.

I was willing to fork over a little more money, but I was nearing my limit. Still, one thing or another kept me from booking. I was making final arrangements with my sister. And I still hadn't asked for the days off from work, thinking I could send a quick e-mail to my boss and head on my vacation — no problem.

Despite being a bit distracted, I generally followed the rules of selecting a flight to the letter: I looked on several different websites to compare prices, I expanded my search criteria to include multiple airports and hours of the day. I even cleared my computer's history after a couple feverish bouts of searching (I can't confirm it's true, but I've heard that websites sometimes offer higher prices to those who have repeatedly searched in a short time period.)

Over the course of about a week and a half, I felt like I had done just about all I could do. I wasn't seeing anything lower than $240. Even though I had signed up for fare alerts from my favorite airlines and some select travel sites, the sales didn't help me. Most started in late August, when travel demand starts to fade from summer highs.

I still hadn't asked for the days off from work, but I was worried about waiting much longer to book. At this point, my knowledge worked against me: I knew that waiting until three weeks out might mean prices would go much higher. So, on a Saturday I abandoned a golden rule of air travel (Thou shalt never book on weekends) and chose to lock in a ticket — a hodgepodge of two different airlines on — at about $260.

Or so I thought.

Halfway through the few minutes it took to book the ticket, the price went up to $320. I booked at the higher price. Expedia's Director of E-Commerce for Transport Brett Cochran said the change was a result of the fares being constantly updated. Another passenger could have booked the same flight at that moment, bumping up the price for me.

I left the computer and continued with my day. Then, in one of those slow motion scenes, I remembered there were several stories I needed to cover on the day I planned to fly out — and there was no way I could be away from work. Knowing that airlines charge big bucks in change fees — up to $150 — I panicked. I panicked again when I realized I'd pay double if I wanted to change both legs of my trip, because I booked with two different airlines. Cochran said mistakes like this — everything from looking at the wrong date on the calendar to misspelling a name — are fairly common.

I didn't call right away to change the ticket because I wanted to get things settled at work before I locked in my final option. I also knew what I was in for, and I was dreading handing over my credit card again.

A few days passed and I called Expedia. The customer service agent was very helpful (and sympathetic) but her hands were tied. I ended up moving the outgoing leg of my trip to Friday and paying $150. Because I was leaving on a Friday the total fare was cheaper than the original flight I booked. But there was a problem. The new leg was considered a one-way flight on American Airlines because I was returning on Delta. So on top of the $150 change fee, I paid an extra $184 for the difference in price.

Cochran said the fees would have likely been waived if I had called right away. Most airlines won't penalize you for changes within 24 hours. Cochran also noted this is a benefit of booking through an online travel site, who can act as an advocate for passengers.

Lesson learned: Buying an airline ticket, like any other big purchase, is not black-and-white. There are options, if you deal with the problem quickly. And while these mistakes can end up costing hundreds of dollars, they happen a lot. Airlines and online travel agents are accustomed to dealing with them. And they want to keep their customers, so most times will they work with you.

At the very least, it never hurts to ask.