Route, Connections, Price: How Far Will You Go for a Cheap Flight?

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I despise booking airfare. It's a laborious, tedious process rife with loopholes and changing price points that I don't understand. And I know — I just know — that as soon as I click “buy”, I'll find another fare (probably on a better airline no less) for a fraction of what I paid. 

So, instead of clicking “buy,” I spend days and days (weeks, really) manually performing searches to try and find the best combination of route, connections, and price. And unfortunately, the three are not harmoniously correlated. (See also: Which Frequent Flier Program Has the Best Awards Availability)

How to Find the Best Route

If you're short on travel time, then you probably don't want to go too far out of your way for a cheap flight. But don't just do a point A-B search; if you're flying from Miami to London, consider other major ports of departure (or arrival). It might be best to hop on a cheap flight to New York or Atlanta and catch a seat sale from there to London instead.

Personally I find this to be the most tedious part of the process, but a necessary evil. How do you search for alternate destination/arrival points? A few ways:

Widen Your Search

Many flight search engines have the ability to “search nearby airports.” Make sure this box is checked.

Consider Different Arrival and Departure Points

Popular routes often have seat sales. Search different major departure and arrival points (and if you can, be flexible with your flight dates/times).

Book Directly With the Airline

Once you've found a few airlines that fly your route, ditch the search engines and see what the airline's website has to offer. You might discover a seat sale that fits your needs.

How to Find the Best Connections

This is the biggest variable; one that, in conjunction with finding the best route, can result in the trip being a soul-destroying ordeal or a walk in the park. Much of it depends on what you're willing to pay for.

I made a trip from Toronto to Melbourne a few years ago that lasted over 50 hours. This is because I already had a cheap flight from New York, but I waited too long to find a connecting flight from Toronto to New York. I ended up taking an overnight bus and waiting the better part of a day in the airport, thus extending an already long trip by about 18 (unenjoyable) hours.

A subsequent trip from Auckland to Madrid took over 45 hours. Granted it's a long journey no matter which way you slice it, but since I was on a mission to fly in business class using my frequent flier miles, I conceded to spending 12 hours overnight in the Bangkok airport en route. (After sleeping on the airport floor for six hours, the business class lounge opened and I enjoyed a contrasting six hours getting free massages, free food, WiFi, and comfy lounge chairs. It was a good trade-off!)

Here are some tips for working out your connections.

Leave Time Between Connecting Flights

I despise missing connections. So I generally refuse to book a flight with anything less than a two-hour connection time. Even with this buffer I've found myself on delayed flights, tearing through the airport to make the connecting flight in time — with varying degrees of success.

Consider Other Forms of Transportation

Instead of doing a short-haul flight to connect to a longer one, it might be easier — and/or cheaper — to take a bus or train to/from your major departure/arrival point.

How to Find the Best Price

Price is usually the bottom line for people, but the question remains — how far will you go to get that cheap flight?

Last year I had to travel from Toronto to Fort Lauderdale. Following the route and connection tips above, I had a few options:

1. Fly direct return from Toronto to Fort Lauderdale for $400 (and collect preferred air miles in so doing).
    
2. Fly from Toronto to Miami for $50 less, and contend with my Floridian friend's overwhelming distaste for the Miami airport and extra time on her part spent picking me up and dropping me off.
    
3. Fly from Buffalo to Fort Lauderdale on a super-budget airline for $150.

Really, the competition was between options one and three, since the $50 savings wasn't worth the hassle on my friend's part.

And since Buffalo is a mere two-hour drive from Toronto, it appeared that option three would be the best balance of routes, connections, and price.

Sadly, though, the airline's departure from Buffalo was at 7 a.m. (awkward flight times are a budget-airline signature). And I just couldn't find any way to get to Buffalo in time for that flight, shy of taking a bus the night before and either paying for a hotel or sleeping in the airport. The cost of the bus plus paying for a hotel would have negated the flight savings, and sleeping in the airport would have left me wrecked for my first few days in Florida.

And as much as I specialize in cheap full-time travel, if the cheapest option isn't remotely reasonable or comfortable, I'm happy to pay a little more (especially if I can collect valuable frequent flier miles in the process.

Budget airlines are an obvious option when searching for the best price. Here are a couple of other variables to consider in finding the best price.

Ditch the Search Engines

Search engines can be effective to get a general sense of what major airlines fly which routes, but they don't include many budget airlines and don't leave you privy to seat sales. Here's a technique I've used in the past to save up to 80% on airfare.

Monitor the Fare After You Buy

Some airlines will give you a refund on the price difference if your fare changes even after you purchase a ticket. Check out How to Get the Lowest Price on Airfare, Even After You Buy for more info.

How Far Will You Go?

You'll notice that price, connections, and route are interrelated, yet conflicting — and most often confusing.

What are your experiences? How far out of your way (or comfort zone) would you go for a cheap flight? Are budget airlines really all they're cracked up to be after everything is said and done? And where is the line between saving money and being comfortable?

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