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Update: Some offers mentioned below are no longer available – Alaska Airlines Visa Signature credit card

TPG reader Aaron sent me a message on Facebook to ask about earning rewards for an upcoming trip:

“My wife and I were planning a trip to Cancun in July, but we bumped it up to March since we just found out she’s pregnant! Can I sign up for a credit card and quickly earn enough miles to book award flights (from Philadelphia or New York) instead of paying cash?”

One of the most common mistakes made by award travelers is not planning far enough in advance, especially when starting out with an empty frequent flyer account. Earning and redeeming rewards doesn’t have to be difficult, but it’s always easier when you give yourself adequate lead time.

You can earn points or miles relatively quickly by taking advantage of credit card sign-up bonuses, but that doesn’t happen overnight. From the moment you apply, you may have to wait weeks to be approved and actually get your card — you can request rush delivery for a fee, but that eats into the value of your rewards. Once the card is in hand, you’ll need to meet the spending requirements and then wait for your statement to close before the rewards appear in your frequent flyer account, which may also take several days to weeks. (Some cards — like the Alaska Airlines Visa Signature credit card  — give you rewards upon approval with no spending requirement, which makes things a bit easier.)

The next step is to find award availability and book your flight. While redeeming miles at the last minute can be exciting (and sometimes fairly lucrative), it’s not a good idea if your plans are inflexible. You could end up paying a lot more miles, or get stuck with an itinerary that involves several stops or long layovers. There’s no rule for how far in advance you should book awards, but you’re more likely to find the availability you want if you book early.

Altogether, I wouldn’t bet on a timeline of less than 6-8 weeks between submitting your credit card application and having the rewards at your disposal, and that’s only if you’re sure you can meet the spending requirement immediately. It’s certainly possible to earn a bonus more quickly, but there are enough variables and potential pitfalls that banking on it wouldn’t be prudent. I generally recommend giving yourself 3-4 months, or longer in some cases depending on the type of award you’re trying to book and how skilled you are at finding availability.

Image courtesy of Shutterstock.
Flights to Cancun are inexpensive at the moment, so paying cash isn’t a bad option. Image courtesy of Shutterstock.

That said, there’s no harm in going for a sign-up bonus so long as you can meet the requirements and you’re willing to accept the risk of low availability and higher prices down the line. You can also hedge your bets by continuing to look for low fares. At the time of writing, United has nonstop flights to Cancun out of Newark for $241 in February, and JetBlue has nonstop flights out of JFK for as low as $228 in March. At those prices, you’re probably better off paying cash anyway.

Good luck in your search, and congratulations on the good news! If you can’t make the trip work before the baby arrives, then perhaps the whole family can travel together soon after.

If you have any other questions, please tweet me @thepointsguy, message me on Facebook or send me an email at

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