Depending on where you are sailing, the airfare and the pre- and post-cruise hotel stays can add a significant amount of money to the cost of your overall vacation. That doesn't mean, however, that you should tempt fate by flying into town the day of your cruise. It's critically important to arrive at your port of embarkation a day early, as storms can delay or even cancel flights throughout the year (statistically speaking, summertime storms cause even more delays than winter storms, but both can sock in airports). Or, like us, you could just have bad luck: Airplanes are complicated machines, and mechanical delays and cancellations aren't uncommon.
When booking flights to and from your cruise, look for either direct flights or flights with generous connection times.
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Just because an airline says a 45-minute connection at Chicago O'Hare is legal doesn't mean that you can actually make that connecting flight. Sure, airports aren't a lot of fun to hang around in, but trust us: Missing your connecting flight and potentially your cruise is a whole lot worse.
Unless you live within driving distance of your port of embarkation, you'll probably be flying to join your ship. Most cruises won't include airfare in the purchase price, so you'll have to book your flights separately.
The cruise lines will offer to book your airfare for you, but in practice we've found this isn't a good option: By booking air directly with the cruise line, you're generally waiving your right to choose which airline you travel on, what cities you connect through, and even where you'll sit on the plane. Need to make changes? Expect a hefty fee (around $50 USD) every time you need to have the cruise line alter your air and that goes for seat assignments, too. It's not that the cruise line won't do a good job they will but why give up control over something most people feel very strongly about? Nearly all of us have a preferred airline we like to fly, an airport we want to connect through, or a route we want to fly because it offers us perks with our frequent flier status. And once the cruise line issues that air ticket, you're stuck with it: Changes are typically not allowed.
A better option is to book airfare yourself. Once upon a time, purchasing air was a complicated exercise but today, booking online either through an online travel agency (like Expedia, Priceline, and the rest) or directly with the airline itself is easy and advantageous. Booking your own airfare lets you determine what airline you fly, what cities (if any) you connect through, and even what aircraft you fly on. We highly recommend both Kayak. Com and Momondo. Com, sites that do not sell airfares, but simply aggregate that information, allowing you to see prices from a number of different sources quickly and easily.
If you're a frequent-flier, you might be able to cash in your frequent-flier points in order to fly to.
Your cruise for (nearly) free. Keep in mind, however, that airlines are mindful of cruise schedules: Those prime flights that show up on reward bookings for other days of the week have a funny way of disappearing the day before a major cruise ship is set to depart the city in question. Likewise, you might find yourself routed through four cities you'd rather not pass through on small (often overworked and late) regional jets. We've personally had some great success with reward bookings and we've also had some real stinkers that made us wish we'd just paid full-fare in the first place. And those were in the good old days when it didn't take a gazillion points to nab a ticket (and points could be earned with miles flown rather than by the cost of the ticket).