Eight lessons Mr. Upgrade relearned the hard way

I wasn’t sure my meetings in New York and Dallas were going to come off, so I waited on buying the ticket foolishly overconfident that elite cards and miles would come through for me on short notice. By the time plans were set, the lowest published fare I could find on my two preferred carriers for this itinerary, American and United, was more than $2,000 and didn’t cover my preferred schedule.

‍Lesson 1: Don’t put off buying a ticket. Even if you’re not certain you can make the trip, it usually only costs $100 to cancel (“heavily discounted” First Class often don’t even charge at all), allowing you to use the fare balance for future travel. I look at it this way: Think of this as a hedge fee that allows you to book far in advance and pick up a better fare, rather than experiencing a nightmare finding a decent last-minute fare.

Lesson 2: If stuck, think of an itinerary as individual segments and look at buying multiple tickets. This is called “breaking” a fare. The first segment, SFO-NYC on United’s P.S. (unitedps.com) in Business Class was about $1,200—not a very good deal as I could have picked this up for $650 by booking in advance. But I came across a $621 one-way fare offered by US Airways a United Star Alliance and often a code-share partner and I didn’t even have to go through one of its gateways (Charlotte, Pittsburgh, or Philadelphia). Why? Because the US Airways flight was actually operated by … you guessed it, United (via code-share agreement). I booked it.

Lesson 3: Always check fares with alliance and code-share partners. ‘Nuff said.

Okay, under the circumstances I was content with my First Class fare for the five-hour flight to New York, but now what? The next two segments were pricing at $1,200+, not very attractive. Yeah, there were lower fares on America West, but its First Class, well, it should be called something else. After spending more time on this than I care to tell you, it occurred to me… I’m going to Hawaii later in the year. I did that ticket right, buying far in advance, but to upgrade I had to burn 30,000 miles.

Lesson 4: Make it a game… …or you’ll go bonkers. So, just for fun (which is the mindset you need to adopt) I checked what a New York-Dallas (stop for two days)-San Francisco (stop for a few months)-Honolulu fare would be. You guessed it: $1,200. In other words, the same as without the Hawaii segment.

Lesson 5: Adding a “leisure” travel destination to your itinerary can often result in a lower—or similar—fare. I added SFO-Honolulu to my trip, canceled my Hawaii ticket, and got my 30,000 miles back. (Yeah, it cost $100 to redeposit them, but I saved 15,000 miles (easily a $400 value), and about $200 on the SFO-Honolulu segments once I subtracted the $100 cancellation fee. I haven’t found my way home from Hawaii yet. Memo to self: Don’t put that off much longer.

Lesson 6: Remember, you can usually cancel a flight.

Lesson 7: Think two or three trips ahead. A future trip might help you with the one you’re booking now.

Lesson 8: Curb your expectations. It’s not always easy to score great low fares, even for Mr. Upgrade.

Four First Class flights (8,000 flight miles) for $1,800, on short-notice, with my preferred carriers, on fares that will earn bonus miles and elite credit, and with perfect flight times…well, it wasn’t great—but under the circumstances, it wasn’t terrible either if you consider the alternative: coach.