The Ultimate 8 Tickets to Hawaii Award Trip!

Have you ever wanted to book a trip to big family Hawaii vacation and do it for FREE? This is exactly what we did "nearly" for free. This is how we did it and how you can do it to on a smaller scale. We booked 8 round trip tickets from Chicago to Kona on the Big Island. How did we do this? Well it required lots of planning and research but these are the easy steps to follow so you can book that next dream vacation. 


Sign up for Frequent Flyer Account – In this case we used United Mileage Plus account. Travelmista does lots of traveling all over the world so at the end of the year he was sitting on nearly 200,000 miles. Yes I know what you are thinking I will never fly that much to get that many miles but keep reading and I will give you more hints on how you can do this on a smaller scale.

Research– After lots of research I found that you need 20,000 miles one way on United Saver Award Ticket to get to Hawaii. So you need 40,000 miles per person for round trip. If we wanted to fly 8 people we would need 320,000 miles. To find out how many miles you need for your dream trip go and search the flights you want to fly and click on flexible dates and use award miles. it will give you a calendar the dates listed in yellow and green have Saver flights for least amount of miles. Click on the date and select the outbound flight and then the return. You might have to check different dates of months. Keep checking because award availability will open up. In general more lead time you will find more availability or really close to the departure date you will also find lots of options. Be persistent in the research and when you do find something book quickly otherwise they can disappear the next day. This is what happened to us. I found 8 tickets departing on Aug 17 and then the next day only 4 were available which brings me to my next step- flexibility.

Flexibility– The more flexible you are with your dates the more opportunities you will have in getting the Saver fares. We ended up splitting the group in two. One group of 4 had to leave on Thursday and the other group is leaving on Friday. We made it work. Now the Saver awards are not the best direct flight but remember you are not paying for them. It cost us $7.50 per person for taxes. It was based on segments flown. We booked online to avoid the phone booking fee. 

Book as far in advance– We booked these flights back in Feb of 2012. I had been watching them for a while until we had enough miles. If you book close to the date you can also get a $75 close booking fee. So book early!

Track your progress– Use to keep track of you miles. Set up an account on Awardwallet to help you track all your frequent flyer programs with the hotels, airlines and credit cards. This will help you see how many miles you have in all your accounts. If you are like me you don't have time to log into each account so let Awardwallet help you. Just note that Awardwallet doesn't work for American Airlines and Southwest Rapid Rewards. 

Use credit cards– This is how anyone can fly for free without actually having your butt in an airplane seat. The one we used to get more miles is the Chase Sapphire preferred. We signed up for this card when we got a 100,000 Ultimate Reward sign up bonus. You had to spend $3000 in 3 months to get the bonus but with Travelmista travel schedule this was easy to do. Plus it gives you extra miles on travel and dining which is perfect for us. And at the end of the year you get a 7% bonus in Ultimate Reward Points on all the miles you have in your account including the sign up bonus. At the end of the year we had 125,000 miles. These UR points are great because they can be transferred on a 1:1 basis to several different transfer partner program. Including Southwest Rapid Rewards, United Mileage Plus, British Airways Executive Club, Korean Air Sky Pass, Amtrack Guest Rewards, Marriott Rewards, Priority Club Rewards, Hyatt Gold Passport and the Ritz Carlson Rewards. We choose United Mileage Plus for this example. We transferred the miles and they appeared instantly in Travelmista United Mileage Plus account. 

Now they don't offer the big sign up bonus anymore (we signed up in Sept 2011) now but the do still offer a 40,000 UR for the same Chase Sapphire card. That is one free ticket to Hawaii for using your credit card. That is much better than any cash back offer we were getting for our other credit cards.  There are lots of credit card offers out there for free points you just need to do a little research on which one is right for you. 

Booking the tickets– Now that we had enough miles we booked the tickets for everyone. We were flying ORD-DEN-LAX-KOA on the outbound and had a direct flight KOA-ORD on the return. Because I had to book tickets leaving on different day I booked three different sets of flight. The connections were not great  on the way out but a direct flight on the return was great. 

Check the flights– About two months after we booked the flights I logged back into Travelmista Mileage Plus account only to notice that the flights had changed. I was surprised to learn that our direct flight back from KOA now had a layover in SFO. I was NOT pleased with this development. I called and found out that the direct flight had been canceled and the only options were to now have a connection on the west coast. 

Complain if you are not happy– If you ever heard the phrase the squeaky wheel gets the grease that that wheel is me! How can they just change us from a direct flight to one with a connection and 4 hours earlier departure time by an email telling us our flight has changed. No compensation are you kidding me! I call the customer service and they said they could only rebook the flights but not give compensation. I would have to send a email complaining if I wanted compensation for the inconvenience of flight change. We rebooked the flights to a later time with a connection through SFO. They also move the group up to Economy Plus which give you 5 extra inches of leg room for free. 

After sending two emails and waiting a month we get a response back that they will compensate each person $150 to be used for United flights and Travelmista (who is not part of the 8 tickets) would get $200 United credit for his time it took to complain. The credits have to be used within the year but can be used for someone else but can not be combined.  Travelmista is flying on a paid ticket so he could use his United regional upgrade rewards and bump himself up to first class plus he is in pursuit of the 1K level on United for this year. He prefers earning miles to using awards so that he can take me on more trips.

United is now paying us to fly to Hawaii! They gave us $1,400 in United credit because they changed our flights on 8 award tickets that only cost us $60 in fees to book.  My lesson learned is that you don't get anything unless you ask for it. 

Other saving tips- We booked our car rental using points with Hertz rental. You need 2500 points for a week rental from Hertz which is the best deal for car rentals. Travelmista got the points by renting cars with Hertz. It will cost us just over $100 for a 8 day rental with taxes and fees. Other members of the group also booked cars (4 in total for 11 people) The cost was about $250 for a standard car for 8 days. 

Now I know what you are thinking it is going to be expensive for hotels for everyone but with a little research I found several house rentals on We ended up renting 2 houses that are next to each other. Our group of 8 has now grown to 11 people so we really needed the two houses each house has 3 bedrooms/ 2 baths and can sleep 6 each.  The cost was $110-$150 per night but we were able to get a better deal (complicated explanation) and only paid $1500 for two houses. That is approx. $135 per person for housing for 8-9 days which is a great deal. 

Have you booked any ultimate family vacations? Tell me about it. Are you now ready to do a little research on book your next dream vacation? Do it stop dreaming! Life is too short to just dream.