If at first you don’t succeed, try try again.
Thomas H. Palmer

When I booked our award flights to Hawaii last month, I wasn’t very happy with the number of miles needed to book the Chicago to Maui segment. United was charging 45,000 miles per ticket or 90,000 total for Annie and I. In my excitement, I went ahead and booked the trip instead of waiting to see if I could get a better deal. Then last week I decided to check if anything had changed. To my surprise, there were tons of flights from Chicago to Maui for only 22,500 miles per ticket or 45,000 in total.

Flight Change Details

For a change fee of $150, I re-booked the Chicago to Maui segment and was refunded 45,000 United miles! Those miles are worth way more than the $150 it cost me to change the flight. I can use the miles to score a round-trip flight somewhere else in the world for free. If I used them to go back to Hawaii, the miles would be worth more than $1,000!

The new award redemption details are below:

Hawaii Trip Award Itinerary (two tickets)

Flight	Miles (originally)	Miles (after flight change)
ORD to OGG	90,000 (45,000 each)	45,000 (22,500 each)
OGG to HNL	0	0
HNL to ORD	45,000 (22,500 each)	45,000 (22,500 each)
Total	135,000	90,000

Chicago (ORD) to Kahului (OGG)

Leg 1: Chicago to Honolulu on a Boeing 777-200

Instead of flying to Denver and then Maui for 90,000 miles, we’re now flying to Maui via Honolulu for 45,000 miles. We arrive about 1 hour and 40 minutes later than the original flight, which is fine since all we’re going to do that night is eat dinner and go to sleep. We also like that we go all the way to Honolulu, since that will limit the impact of any possible connection issues. There are so many daily flights between Honolulu and Maui, we’ll be just fine no matter what. If we’d missed our connection in Denver, there’d be a much better chance of getting stuck for a night.

When I re-booked this segment, the money I used to pay for seat upgrades on the original flight was also refunded. Once that is back in my credit card account, I’ll purchase new economy plus seats on this flight.

Leg 2: Honolulu to Kahului on Boeing 717-200

After an hour and 25 minute layover in Honolulu, we’re taking a quick 42 minute flight over to Maui on Hawaiian Airlines.

Bottom Line

With these changes, the airfare now cost me 90,000 miles plus $311 in taxes, change fees and non-reimbursed seat upgrades. The value of the airfare redemption is now 2.76 cents per point ($2,488 / 90,000 miles), up from 1.84 cents per point originally.

The lesson here is not to “set it and forget it”. If you’re not happy with your booking, keep checking periodically to see if things change. You might end up finding flights with better times, cheaper fares or for less miles. I checked every day for one week and noticed that the cheapest flights appeared in searches on Tuesday and Wednesday. Tuesday was long thought to be the best day to book flights but that’s since changed. However, in this case, the day I booked mattered. That’s something to keep in mind next time you’re looking at flights.