<font face="Verdana, Arial, Helvetica, sans-serif" size="2">Originally posted by Green Dragon:
I know just the thing... he loves REAL Cadbury chocolate, not the stuff they sell here in the US. Of course, that will make it even HARDER to get him to travel in the future... he'll be bigger!!! 
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But by that time, you'll be upgrading him, so he can fit in the seat _and_ he'll understand why you go on mileage runs.
Seriously, though- my advice for a novice mileage runner is:
- look at your planned travel for the rest of the calendar year
- figure out which airline has the best service from your home airport
- figure out which airlines count the types of fares you usually buy toward elite status
From the above, pick an airline to hit the first tier of their elite program (usually 25,000 flown miles). Look at your planned travel for a year and figure out how many extra miles you'll need to hit elite- this number is your initial mileage run target. Figure out some routings you'd like to fly that might add up to this number and plug these into travelocity's fare watcher updates. Assuming your preferred airlines offers miles on web fares, sign up for their weekly e-mails, too. And read this forum of course.
Of course, these days first tier elites are a dime a dozen on many programs, but 1.) if you usually fly in coach, you'll be amazed at how much of a difference priority res. lines, elite check-in, pre-boarding, etc. make and 2.) you have to start somewhere!