We had a destination but didn’t have the exact dates we could fly. We were still waiting for the final spring socccer schedule to make sure we didn’t miss any important games which we believed would be on one of the Sundays but we didn’t know which one.

As it got to be about a month before the trip, we needed to make a decision, which ended up being to travel on Monday and return Friday so we would be home for both weekends. A short 4 night trip wasn’t ideal, but it would be much better than nothing. We’d find a way to relax and have fun in that amount of time!!

Finding Flights

Google Flights is awesome. I use it for every trip. It gives me all the options and will search the best price even if you have to buy two one way tickets instead of a round trip ticket.

We wanted to fly first thing on Monday morning and return on Friday. The return flights that weren’t red eye flights were nearly twice as much as those that had an overnight flight. Based on that our best option was to do an overnight flight on the return. This gave us the ability to leave early afternoon on Friday, giving us time to do something the final morning. Since we were looking at an early morning outbound flight, we would have plenty of time to experience something the first day as well, giving us effectively 4 nights and 5 days.

Booking

Based on the prices I found in Google Flights I chose an itinerary from United that left on Monday at 5:30am with a 1 hour layover in Houston arriving in Los Cabos around noon local time. While we prefer direct flights, that isn’t an option. The return flight was on Alaska Airlines, a United Partner, leaving around 1pm that had a four hour layover in Seattle before taking a red eye back to Boston arriving around 6am on Saturday. That would be just enough time to get the kids home and dressed for any soccer game or practice they might have that day!

While we could have had an itinerary with a shorter layover in Seattle, that price was significantly more than $500 more expensive. There are lounges in Seattle and 4 hours isn’t that bad. It would give us plenty of time to go through passport control, switch terminals, get something to eat and relax between flights.

With the itinerary selected, I clicked through to the United website to book the complete itinerary. I ended up booking the flights under my wife’s account. She has Silver Premier status with United, not because she flies them often, but because she has Marriott Titanium status. With that status, she qualifies for Crossover Rewards, which is a program that gives users with high level elite status with United a lower level status with Marriott and those with high level elite status with Marriott a lower level status with United.

Her status allows her to get a free prioritized checked bag for herself and one traveling companion on the itinerary. It also allows her and one companion to choose a complementary “extra legroom” seat, though since there are four of us we probably wouldn’t be using it. We’d also get a prioritized boarding zone.

I could get the same free checked bag and prioritized boarding zone because I have a United Mileage Plus credit card, though in order to get the free bags I would have to use that card to pay for the flight. I can earn more points and get better trip delay and trip cancellation insurance if I purchase it with a different credit card, so there were benefits to using my wife’s status instead of that particular credit card’s benefits.

I purchased the tickets with my wife’s Chase Sapphire Reserve card to ensure we got 3x Ultimate Rewards points per dollar spent. If I chose to use my United MileagePlus card instead to pay, I would have earned 2 United points. Since the Chase Ultimate Rewards points can instantly transfer to United (or 12 other airline transfer partners) I chose, using the Chase Sapphire Reserve card effectively earned more points than using the United branded card. Because of my wife’s status, we got the same or better benefits than the card.

Once I got the confirmation for the flights I logged in to the United site to make our seat assignments. I booked three seats on one side of the plane and the aisle on the other side in the same row (i.e four seats together) for both legs to Los Cabos for no extra charge. I couldn’t make seat assignments for the return flights because they were on partner Alaska Airlines.

I used the booking reference number for the Alaska portion of the itinerary when logged into their site to choose the seat assignments for the return legs. All of those seat assignments were complementary as well. We’d each have a free checked bag on our flights to Los Cabos, but we would have to pay for checked bags on our return flights because the elite status benefits didn’t convey to the partner airline.

We had our tickets, now to figure out where to stay!