My husband and I travel every summer . He is a public school librarian, so we fit all of our longer vacations into the months that he has off. If our trip requires getting plane tickets, I start searching for the best prices up to 6 months in advance. I always hit a bunch of sites, but my favorites have been Airfare Watchdog, Travelocity, Expedia, and Southwest Vacations.
Airfare Watchdog is an awesome way to monitor the prices of flights in your area. I have bought a ticket through their site once, but I have also simply used the information it throws my way to pick the best times to patrol all of the other sites to get the best deal. I love the fact that it is easy to use.
If you’d like to keep an eye out for the best prices on plane tickets to or from a certain place, simply sign up for email notifications. Airfare Watchdog will then email you when specials occur for the trip you set it up to monitor. For example, I was looking for a cheap ticket to Chicago to go to the Financial Blogger Conference at the end of September. I signed up for email notifications in March for any good deals from Houston to Chicago and jumped on a $215 ticket that they notified me about a few weeks later.
I have used Travelocity to book our latest vacation  package to Las Vegas. Their system is really easy to use. Simply type in where you want to go, where you are leaving from, the dates you plan to travel, and what you are looking for. I usually try to find airfare and hotel bundles to save money. Most recently, I used Travelocity to get us 2 roundtrip tickets to Las Vegas along with 4 nights at the Golden Nugget for $800. Based on all of the other plane tickets I could find this year, that was a great deal.
I also check Expedia for bundle deals since their prices compete with Travelocity. They are just as easy to use but their prices can differ up to a couple of hundred dollars for two people on any given day. Based on what I have seen, Expedia is usually more expensive than some other travel sites, but sometimes they seem to get amazing specials that are worth taking a look at. For our vacation 4 years ago, I was able to get 2 roundtrip tickets to Las Vegas along with 4 nights at the Four Queens for $600.
When we lived on the other side of town, Southwest Vacations was my go-to site whenever a plane was going to be involved. Now they still have great deals, but Travelocity beats them out once in a while. The big selling point about Southwest Vacations is that if you want to use Southwest, it is the only way to get a packaged deal. Southwest does not sell their tickets through other online sites like other airlines do. Using Southwest Vacations 6 years ago, I was able to get 2 roundtrip tickets to Las Vegas for our honeymoon along with 3 nights at the Stratosphere for $525.
On a side note, I have found that Tuesday is the absolute best day to get the cheapest deals out of any of these online travel sites. It seems that they refresh their rates on Tuesday mornings. When I looked up the package to Las Vegas this year on Sunday, I couldn’t find 2 tickets and 4 nights at the Golden Nugget for less than $1100, but I was able to book it for $800 two days later on that Tuesday.
Do you use the same travel sites? What site would you highly recommend?