My wife’s brother had agreed to let us buy him a ticket to visit us in San Diego for Christmas. He lives in New York City and had only been briefly to San Diego once before. He was excited to spend the holiday with us and the boys were super excited to have him with us too.

Flight to San Diego

I didn’t know what to expect finding him a flight on December 24th but was pleasantly surprised to find a direct flight on American that left around 6pm. It was only $160 one way, which I thought was an amazing price. The times put him in San Diego a few hours after we arrived and he’d be able to get in a full day of work before heading on the plane so that worked out well. At that price, it didn’t make any sense to use points on that flight.

Return Flight

The outbound leg was easy to figure out, but I was being lazy on the return flight. He was looking to return Saturday the 28th or Sunday the 29th… like everyone else it seemed given the prices and availability on points. I scanned of options using United and American points as I had a few of each in my accounts.

What I found interesting was that on American I could get him itineraries on points in first-class for fewer points than in economy! Apparently people were just looking for economy and not checking first-class or more likely most people were looking for itineraries for multiple people. There’s usually a lot more availability for people looking for a single seat.

I found and confirmed several itineraries with him but for whatever reason was lazy and didn’t follow through and book them. I’m usually on top of things like that, but for some reason I got the green light on an itinerary and work would suddenly get busy and I’d forget for days or weeks.

In addition, during our hotel search, things were evolving and we were considering spending a couple fewer days in San Diego and adding a segment in Palm Springs. We had never been there before and had the flexibility to change our itinerary due to the refundable hotel rates we had booked. This meant that we’d have to get him a flight out of Palm Springs instead of San Diego, so in the end, maybe it was better we didn’t get those flights booked early.

Around Labor Day we were all in Toronto together and sat down to nail down a flight. I was looking at using some JetBlue points from the credit card bonus my wife had received. There was a direct flight to JFK, but it was really expensive on the day he needed to fly. It also flew into a less convenient NYC airport so we looked at other options. There were some American flights, though I didn’t have enough points for any of the flights that made sense.

Finally, we checked United and found an itinerary on points that was a good value, had reasonable times, and flew into La Guardia, his preferred airport. I ended up booking it for him right then. While the value wasn’t spectacular, it was reasonable and it saved about $400 in cash. It would also give him some time for us to spend more than a day in Palm Springs with us before he had to leave.