Booking  a flight can be one of the most intimidating parts of trip planning, partly because flights are usually the single most expensive purchase you will make for your trip. Other things like accommodations, food, or sightseeing may end up costing you more in the long run – especially on longer trips – but in most cases those are not up front one time lump sum purchases that can cost you a great deal to change if your travel plans need to be adjusted. There are, of course, options to buy tickets that are refundable or changeable, but those tickets usually cost substantially more than reduced cost fares. As airlines have continued to make their services a la carte, the cheapest fares available continue to include less and less – with many low cost carriers charging extra for an assigned seat or a carry on bag. My point is, if booking flights gives you anxiety, you’re not alone. Reading this page should give you the confidence you need to successfully book a flight and be prepared for any extras you may end up accruing during your trip.

When booking flights, there are a few important things to know.

  1. Fly during the week. Flying during the week – specifically Tuesday through Thursday, is almost always going to be cheaper than during the weekend.
  2. Book early. There is no magic bullet when it comes to finding the cheapest flight, contrary to what the guy in the cubicle next door who got a great deal to Aruba says. I recommend looking at least two months in advance, and checking at least once a day for a couple of weeks.
  3. Be flexible if you can. A lack of flexibility is one of the biggest problems I see for people getting stuck buying expensive plane tickets. For this reason, I almost always buy my flights before any other element of my trip. Unless you’re travleing for a specific event, try looking for flights at various intervals in the season you’d like to travel – you’d be surprised at how much variation there can be in ticket prices.
  4. If you’re booking using miles, book as early as possible. If reading about frequent flier miles sends you into cold sweats – check out my guide to flying free using frequent flier miles here.

Now that we’ve covered some important flight booking tips, let’s talk about what sites I use to do my booking. My go to booking site for flights is almost always Kayak. Kayak is great because it is a meta search engine – meaning it is a search engine that searches individual sites as well as other search engines. This strategy helps it usually find very low fares, then send you to the website where you can book the cheapest (sometimes this is through Kayak themselves). There are a couple of features that Kayak has that I really like (some of which you’ll need to create an account to utilize):

  1. Flex search – this option allows you to search for travel dates +/- 3 days, which is very handy if you’re somewhat flexible.
  2. Booking advice – after you search for a flight, they provide a recommendation about whether you should book now or wait based on comprehensive pricing data.
  3. The Explore function, which allows you to enter your home airport and see where you could fly around the world inexpensively during various travel periods.
  4. Emails about itineraries. If you’re thinking of booking a trip a long time in advance, you can plug that itinerary into Kayak and it will send you updates on any price changes. This allows you to keep an eye on flight prices often (which I’ve already recommended!) with little to no effort.

The other site I often use to book flights is Momondo. Momondo is similar to Kayak, but it also searches an incredible number of low cost and ultra low cost airlines – especially in Europe and Asia. I often will utilize both Kayak and Momondo to search for the same flight to see which comes back with the best price.

Finally, a super cool site I like to use when I’m thinking of traveling but don’t have a specific destination in mind is Airfarewatchdog. Similar to Kayak Explore, Airfarewatchdog allows you to enter your home airport to see the best deals around the world during various travel periods. The great part about this site is that it will send you a weekly email with the latest travel deals from your home airport. When I was younger and super flexible with my travel I ended up traveling to Costa Rica on a whim with a friend for next to nothing simply because it was a great deal that I found through Airfarewatchdog – pretty awesome.