How We Are Going to Hawaii and Disney for $30

As anyone who follows might know by now, we have been in mass accumulation mode to be able to go to Hawaii someday. Recently, we have made a decision that we want to go next summer. The plan was to combine our United and Continental accounts to be able to pool enough miles to get the four of us in 3 seats (1 lap child). Yet the details were a lot more difficult than we anticipated.

First was the lengthy process to get both my wife and my OnePass accounts combined (we both had two accounts). This process involved name changes for my wife. My accounts all went smoothly, but getting someone at Continental to actually process our requests took numerous phone calls and emails. Then, when we went to combine my wife’s Continental and United accounts, we realized one had a middle initial in her name and the other did not. So the accounts would not merge, and it took another email and then a phone call. Finally after a couple of weeks, the accounts were merged, and I could get serious about our search.

For the past year every time I have occasionally searched United’s inventory, I had availability at the 40,000 tier. However, nothing lately out of our home airport has been available for next summer. So I searched airports all the way from New York City to St. Louis and everything in between, including several options in Canada. I was a desperate parent in search of any available option to get my family to Hawaii.

The best tool for searching Star Alliance reward options was by far the Continental site. After searching for reward availability, it was an excellent tool to be able to see a two-month window for available options. I was in search for the lowest level redemption at 40,000 miles for coach seats. We have a family, and traveling in business, while it would be awesome, just is not feasible in my mind. I like to see real value with our miles, and considering we only had about 180k combined miles to work with, coach was acceptable.

Pretty much any airport within a several hour radius connected through Chicago. In addition, it was pretty much the only airport that had any type of availability. At the time, the Continental website only showed availability near the end of next summer at the 40k level. That is when I noticed something hokey.

When searching through the Continental system, the award calendars were rarely correct. In other words, some days it would show a low level redemption, only nothing was available once I selected the day. The real kicker is several days would show no low level availability in the calendar, but if you actually searched each available day, certain days did have availability. It was a kink in the software apparently. I had a lead and the detailed hunt began.

So I began searching every airport again, this time day-by-day. What a time commitment to save some cash. Eventually all circles lead me right back to Chicago. This time, searching day-by-day showed tons of availability that was not showing up in the calendar. I was able to find early summer options for the two-weeks we were wanting to spend in Hawaii. The adrenaline was running.

At that point, I realized I needed to perform a two-browser trick to be able to book rewards through both my wife and my accounts. I did not want to reserve tickets in one of our accounts, and then when I went back in to perform the same redemption for the other account, it would be unavailable. So I had my IE browser searching for flights with my wife and infant as a lap child (one ticket), and Firefox running with seats for Bug and I (two seats). We did not have enough points in only one of our accounts, thus why we both needed to redeem miles for seats.

After a long process, I was able to snag flights in and out of Chicago to HNL. 120,000 miles and only $30, and we are going on our dream vacation for two weeks.

The only setbacks is we need to get ourselves to Chicago. The flights out are super early in the morning, and the return is late at night, so therefore, we need to make sure we account for a day before and after the trip for travel to and from Chicago. Not a problem.

Then my wife and I got to thinking. We have a 6 hour layover in Los Angeles on the way to HNL. Not quite long enough to go anywhere with LA traffic. So I decided to call up Continental and see if there was any way they could move up the CHI-LAX leg of the trip by several hours or even days to give us enough time to acclimate to the time change, but also possibly squeeze in Disneyland.

When I called, the agent was able to make my day by moving our departure up three days as a stop-over. Luckily, that aligned with a weekend, so no additional time off of work. I took my chances to see if there was any availability directly out of Cleveland to save us a trip to Chicago, but no luck at the 40,000 redemption level. However, the agent said to keep an eye on availability, and as long as it is before 21 hours or days (I can’t recall) ahead of the departure, they could make the change. This is excellent news, and it really made our day. My wife is now head-over-heels that she not only is getting to go to Hawaii for two full weeks, but also gets to go back to Disneyland with the boys.

So with a bunch of planning, and only $30 out-of-pocket, we have now been able to secure flights to Hawaii with a nice stop-over in LA for several days in Disneyland. It was all possible with free miles earned from credit card bonuses and spend, and earning miles on purchases we were going to make anyways. Stay tuned over the next several months, as there is a lot to plan, and my mind is spinning on all the different point and mile redemptions for hotels, cars, and everything else. Aloha everyone!