The ability to book our own flights was once seen as a futuristic convenience that we now take for granted—kind of like online banking. It's so pervasive that even our parents and grandparents are doing it. However, as many of us (and our parents) now know, there are now so many options that do slightly different things that it's quickly becoming a daunting task once again. How does one navigate the ocean of booking tools in order to get what you want, get a good deal, and make sure your flight is an enjoyable experience (well, at least as enjoyable as flying can be)?

With vacation season upon us, and others finding themselves spiraling towards the end of the year when everyone tries to use up their allotted vacation days before they expire, we thought it was high time to dig in. There are basically three types of trips: 1) you have a set destination and set time period (say, a visit to Grandma's house for Christmas), 2) you have a set destination but are flexible on dates (you want to go to Spain sometime this summer), 3) you have time and money to burn and you want to go somewhere, but you have no guidelines and the world is your oyster. We came up with a site suggestion for each situation, plus some bonus tips to maximize your air travel enjoyment.

Scenario 1: Grandma's house for Christmas

When you're looking to book a flight and your destination and dates are pretty much set in stone, your main concern is when to book. Most travel sites offer you extremely similar prices on flights, so it's largely a matter of whether those prices are going to go up or down between now and the time you hope to travel. If you take a gamble and wait, you risk the prices going up. But if you decide to be safe and book now, the prices might drop and you'll curse yourself for not being patient enough. What to do?

The tool we like best for this is Bing Travel. Here, not only can you search for flights from various airlines (and compare against other sites if you wish), there's also a Price Predictor that tells you whether now is a good time to buy or not. This tool grew out of a project from the University of Washington, and analyzes thousands of flight itineraries in order to map out the general pricing trajectory of a given flight.

Looks like I had better book that flight to Wichita now.

Bing claims that its predictions are 75 percent accurate, and that's good enough for us. The only downside to Bing's Price Predictor is that it only works for flights to and from "most" US cities—if you're flying internationally or there's a city in your itinerary not on the list, you're out of luck. But if you are flying within the US, it's definitely worth a shot to make sure you're buying at the right time.

Scenario 2: summer vacation

Perhaps you and your family have your heart set on a vacation to Puerta Vallarta, or Shanghai, or heck, how about Disney World? But you aren't tied into a specific date—your clan is willing to wait until you find the week with the perfect fares. You might have weeks or even months of flexibility.

This is when we like to use ITA's travel matrix. Yes, we have mentioned it several times before (notably during our coverage of Google's attempt to buy ITA), but that's because it works so well. Yes, many other travel sites use ITA's technology for their back-ends—including Bing Travel, mentioned above—and there are even other sites that let you search by flexible dates, so why ITA?

The reason we like ITA's own online tool is because of its usability and presentation compared to other sites. When you put in your preferred origin/destination, you can choose to see an entire calendar that shows what the fares would be for an entire month:

There's as much as a $256 per ticket range within this month alone.

You can change the month and number of days, and the lowest fare for the selected month is highlighted automatically. Even if you decide not to go with the absolute lowest fare—I personally hate leaving on Wednesdays—you can use the available data to choose a time that works best for you that's still comfortably within your price range.

Scenario 3: just take me somewhere!

This is the most flexible of all travel options: when you know you want to go somewhere, but you don't know where and don't care when. Here's where Kayak's Explore tool comes in the most handy. The site shows you a map of the world and price tags for each destination after you enter your originating airport. The slider helps you decide how much you want to spend, and there's a drop-down that lets you specify dates, ranging from "any time" to specific seasons, or specific months.

Even I didn't know I could go so many places for under $400 round trip.

When you click on one of the red price tags, the site shows you more specific information about which airports are offering those fares, how many stops there might be, etc. When you click on a price, it will show you the date range when that price is offered. Needless to say, this is a great tool for figuring out where to go within a certain budget. The unique UI is also a large part of the reason why so many people are fans of Kayak.

Bonus: choosing the best seat on the plane

So you've decided where you're going to go and when. You're halfway through the booking process when the site asks you: where do you want to sit? For some, this is a mundane question with a mundane answer (anywhere), but for others, this is a critical decision that must be made with careful thought and consideration. After all, you don't want to be stuck in front of the bathrooms where people will be meandering back and forth all flight, or in one of those annoying seats that can't lean back. Right? Right.

Seatguru is a nothing less than a gift from above for those anal-retentive types who fuss over the perfect seat. When you look up a flight number, it tells you exactly what kind of plane it will be and shows you a map of the seats, along with a key that displays good seats, bad seats, the location of the lavatory and crew seats, where the power plugs might be, and other valuable details.

Woe to the laptop user who isn't sitting near a power plug on a 15 hour flight.

When you hover your mouse over certain seats, it tells you why that seat has been designated a good/bad/standard seat. Seatguru singlehandedly saved me from choosing a spot in front of a bassinet row—yay screaming babies!—on a future flight to Asia, and helped me instead find a decent seat with a power plug. Seatguru can also tell you which flights will have food, in-seat videos, and WiFi when applicable.

Happy travels

Once you have everything booked, Tripit is a handy and free tool to collect your flight, hotel, and rental car information in one convenient spot (read our lengthy explanation of how Tripit works). And, when the time comes, you can rest easy knowing that you got a good deal and chose wisely in order to have a relaxing flight.