I’m new to the forum and have what I hope are some very basic questions. How do I book a round trip flight that is about a year away? Here’s the story. I’m planning on taking the family of 5 from Chicago to Hawaii next December for a 10 day trip. I understand that the award seats go quickly, so I wanted to try and book on the first available day. After reading the other threads, it appears as if the earliest I can book is between 330-338 days out.

Here’s the part that confuses me. If I wanted to depart on Dec. 21, I have to book 330-338 days for the departure, but I would still have to wait another 10 days before I can book the return flight home. Is that right? If I’m fortunate enough to find seats for the Dec. 21 flights, but can’t find award flights for the return trip on Dec. 31, what happens?

Here’s some additional information that may help answer my questions. We have about 375,000 miles on united and about 500,000 points on American express.

Thank you in advance for your help.

I'm not experienced enough to help you much. My gut reaction on a group of five is that is going to be exceptionally difficult and to get a pro, many people offer this service. If you want to do it yourself, then you have a lot of reading to do. I can help you search for it, but that's about all I could do for you. I'll post some threads that may help.

http://www.flyertalk.com/forum/miles...ple-miles.html

http://www.flyertalk.com/forum/miles...el-awards.html

not totally related, but you are going to want to be flexible in order to book everyone on an award. You may have to split up the family on to different flights/carriers to get them all there. Just keep that in mind.

Call and put your outbound on hold the day it becomes available, ask for the hold to extend until your return date becomes available. If they say they can't, someone else will. Or hold it online and call to extend the hold. Typically, if you don't have the miles to cover it in full, they'll allow you time to transfer points in.

Don't transfer Amex MR points over until you have everything on hold in case the return isn't available when you call back. Once transferred, they can't be returned and if you need airline flexibility, that can put you in a bind.

If you're using UA or AA miles for a simple round trip, consider just booking each half as a one-way award.

Study the fees sections carefully - the main risk is doubling the cancellation fees. But both airlines will usually let you make date changes without penalties.

It's tough to book award travel on this route, especially during the Christmas season, but here are two things you may wish to consider.

1) You'll have more options if your group can split up and take different flights to and from Hawaii. No doubt that's not your preference, but it may be necessary to do so to obtain 5 award seats.

2) Both UA and AA offer one-way fares for half the price (in miles) of RT. As you know, this makes it possible to book the outbound flight before the return (about 10 days before, in your case). But it also makes it possible for you to fly UA in one direction and AA in the other, depending on award availability.

FWIW---if possible book some of your group in 1st and try

using Delta Transfer with your MR points.

The problem with Delta is their availability to Hawaii is consistently and notoriously poor.