When you pay for in-flight Wi-Fi, you typically have a few options. You can pay for a day pass, just pay for the duration of the flight, or pay for 30 minutes at a time. If you have a connecting flight with the same airline, a day pass on your first leg might be a cheaper option.
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On a recent American Airlines flight from Los Angeles to New York, I had a quick leg to Phoenix. The flight was only about an hour and a half long, so the Wi-Fi was pretty cheap: About $US10 ($13) for the flight and $US20 ($26) for the day. I figured, what's the point in spending $US20 ($26) for a day pass? I'll just buy the $US10 ($13) on my second, longer leg from Phoenix to New York. To my surprise, though, the price for single flight Wi-Fi during the second leg jumped to $US24.95 ($32) (and the day pass was nearly $US40 [$52]). In other words, I paid $US5 ($6) more than I would have with a day pass.
Your own mileage may vary but it's something to watch out for, especially when you're travelling in the US, considering most US airlines use Gogo Wi-Fi and their prices are all over the place. Remember to check out your flight's Wi-Fi options in advance. And if a day pass is under $US20 ($26) on the first, shorter leg of your flight, you might consider paying for it now rather than a more expensive pass later. Or, better yet if you're travelling in the US, pay directly from Gogo's site in advance, which might be even cheaper.