Dear Randy,

I have a family of five and am planning a vacation in Orlando in October. Currently, I have 140,000 miles in the United card. How many frequent flyer miles do I need for a roundtrip?

- Maria

Randy replies:

Good question. In this case, seating a family of five for Orlando is a bit like arriving at a popular restaurant without reservations. Party of five? That will be a two-hour wait. Would you care to split the party up? Meanwhile, smaller party after smaller party are being shown to their tables.

Many reading your question will immediately say the answer is easy--five times 25,000 miles equals 125,000 miles needed for the flights to Orlando. Actually, it is usually never that simple, so let's look at all the possible ramifications along with some advice. While a basic roundtrip to Orlando is 25,000 miles with a MileagePlus Saver award, if you happen to live within 700 miles of Orlando, that Saver award is available for a minimum of 20,000 miles, which means your possible mileage requirement is only 100,000 miles.

But with Orlando being one of the more popular destinations, you might be required to redeem a Standard award at 50,000 miles roundtrip, meaning a possible requirement of 250,000 miles.

There are other things to consider as well--you mentioned you have 140,000 miles in the "United card"--I'm assuming you are referring to United's credit card. If you have a United MileagePlus credit card, then you have an option to use the "Choices" program that allows you to use your miles just as cash. So instead of you comparing the miles needed against a standard award chart, you'll simply shop via www.united.com/chase, and use your miles to buy a ticket based upon the price, rather than an award chart. An example might be that you locate a fare for $278 to Orlando. With miles in the Choices program having a value of a penny per mile, these awards will "cost" you 27,800 miles apiece. You might ask why would anyone use this option compared to some of the lower options mentioned above? Because seats bought via the Choices program have no blackout dates and no inventory restrictions, which means unlike most of the other award options I've mentioned, these you can easily book for five people. Of course, the more expensive the ticket, the more miles required.

And if you're not finding seats, there are other payment terms available such as MileagePlus' miles and money. While available only on select flights, it allows you to pay part miles and part cash, thereby giving you additional options if you don't have enough miles. Also, one of the plusses of the Mileage Plus program is that it is built upon one-way awards, meaning that maybe you'll find going to Orlando will cost out at 12,500 miles (half of the typical Saver roundtrip award) but for the return you'll need 25,000 miles, which is half the number of miles required for the Standard award, an award without inventory restrictions.

Now, with all of this in mind, let's return to the restaurant. Typically finding five seats together for Saver awards can be daunting so you have to enter this with an open mind. It may be necessary for some family members to take one flight and the others another. For instance, maybe three family members can route on a United flight through Chicago, while the other two family members are routed through Houston. And if you have to purchase a ticket outright, always use miles for family members and purchase your ticket so that you can begin to replenish the miles you are redeeming.

A few more tips: October is a slower time for Orlando so that's in your favor. Keep in mind that Orlando is but an hour or so from Tampa, which means that you have a secondary award redemption location nearby if you are unable to get all the seats directly into Orlando. And finally, act right now vs. waiting and your odds will be greatly increased. Here's to a great family vacation. Mickey & Co. awaits you.