Buying Flight Tickets


Reading Time: 5 Minutes
Advice post
Flights Planning Purchasing
Neuschwanstein Castle in Fussen, Germany
Neuschwanstein Castle in Fussen, Germany

Buying Flight Tickets

I tend to approach buying tickets for flights in a fairly hands-off sort of way. I generally have a list of places I would like to go, but try not to settle in on where to go until I can figure out a few other things. Figuring out where I am going and when generally has a few factors in play before I make a choice. Buying tickets with airline miles is a whole separate approach for me, so I am only going to cover buying tickets with cash and not points.

Going with Others

First, the biggest planning factor for me is if anyone else is going to go with me. This may be a trip that friends and I have talked about going on for years, a trip I am tagging along for, or if there is a place I want to go that I think a friend, or friends, may really enjoy going to.

At times, friends and I will have settled on going somewhere and then pick out a period of time that would suit us to go. This may be around a specific set of dates based on when we are free or generally a few months. On these occasions, looking for tickets is usually the only thing that really needs to be figured out.

Pricing for Tickets

The next big factor is what is on sale and when. This is usually when we don’t have a plan for a destination in mind. I’m a big fan of not putting a lot of effort into having a must-go-to list and instead making an assumption that pretty much everywhere is worth going to.

As an aside, I am a huge fan of Going, which used to be Scott’s Cheap Flights. This service will let me know when there are deals going on out of varying airports and I find its cost is paid for in years after the first big deal you buy off of. Being based in Austin, Texas, I generally explore for deals out of Dallas, Houston, and San Antonio as well. Additionally, I’ll scout for flights out of Denver and big coastal cities like LA, NYC, or DC since they often have inexpensive flights. I use it a lot to pounce on cheap and mispriced flights or to find a destination that I may not have high on my go-to list but is a deal that is too good to pass up.

By leveraging Google Flights, I’ll look at dates and ranges of dates to figure out what makes sense to me for pricing. It doesn’t make sense to me to pay $1200 to go to Tokyo when I can wait out a cheap flight for $650 out of LA and put some card points toward a trip to and from LA. If a random inexpensive trip to Santiago, Chile pops up, I’ll happily jump on the chance to go somewhere new even if it wasn’t at the top of the list of places I want to go.

When to Go

Depending on what is on sale and who I am going with, I will typically try to find a trip somewhere in a time that makes sense for me. I like cold weather and strongly prefer to go somewhere that is pretty popular in the off-season. I really like Europe early in the year as it is cheaper to get to and there are not a lot of people visiting then. South America in the summer is the same way to me as well.

There are a few times a year that I try to go somewhere to maximize my time off work as well. This is true of Thanksgiving week, where I get Thursday and Friday off of work, so taking three days of PTO gets a whole week-long trip.

Buying a Ticket

Once I have these things more or less settled, I’ll jump on buying a ticket. With the 24-hour policy of tickets being refundable, I am happy to jump on buying a ticket. Sometimes, this is me buying a ticket and then seeing if anyone else wants to come along. Sometimes, this is hitting a few people up, drumming up a group to go with, and then buying tickets. Other times, it’s orchestrating for a group that has already made up our mind to go somewhere and have been monitoring ticket prices for a spell and then letting them all know that it is time to buy. Sometimes, it’s me just going somewhere solo and getting something. Anyway it happens, I’m generally stoked to have a ticket in hand and be going somewhere!

© 2026 Benventuring.