It seems everyone has a story of being stung by an airline booking gone bad. In the age of travel aggregators and easier access to self-booking, I recommend the following rules to ensure you're not caught out.
While travel plans work out 95% of the time, if you're on the bad side of a travel experience, it can cost you several thousand dollars and heartache.
For me, I was stung during the Brazil world cup, where my ticket from Fortaleza to Salvador was cancelled. As I booked an aggregator through Experia, this led to a lot of finger pointing between the airline, Expedia and the aggregator, which left me flightless and unable to claim my refund. More importantly I missed a world cup game!
I love using aggregation sites like Kayak and Google flights (I won't use Expedia due to above incident). They are invaluable for searching across multiple dates, different routes or cities, and getting many helpful search results.
These days I can't travel more than 16 hours in one leg, and I'm sure my patience will run shorter as I get older. In addition I cannot sleep at all sitting up, so this means I prefer breaking up long trips with layovers and overnight stays.
When flying between New York and Melbourne there are hundreds of options for routes and country stopovers.
I prefer to start out my searching trying to identify a typical price for a standard route, and the lowest possible price without crazy total time.
With those benchmarks in mind, I can optimize and tradeoff between all considerations such as total price, total trip length, layover timing, whether it's an interesting layover location for a side trip, etc.
When you are ready to book, never use an aggregator for tickets; this will display as either 'Expedia', 'Kayak', or some online travel agency like 'MyTravelz'. Always book direct with airline even if it's slightly more expensive.
This means you have a direct contract for the flight and no possibility of finger pointing or assigning other blame for failure to provide service.
The more reputable the more likely you'll be properly served your flight. Keep in mind some budget airlines and national carriers may go bankrupt or cancel on a whim, and may have awful refund or credit policies.
It takes an additional minute and is one more set of emails in your inbox, but having an account associated with your ticket/s makes it much easier to alter plans or gain a refund, and simple to apply credits in future.
Often airlines will charge extra money to pay via credit card rather than direct debit. Once you pay direct debit your money is gone, and you have no further recourse if things go terribly south.
My recommendation is to pay with a good credit card; this is your last line of defence if you need to raise a stop payment due to unforfilled service. Ideally a card which is known for better consumer protection and service, which you'll expect to get from cards which you pay a higher annual fee.
Good credit cards will often come with travel insurance rolled in. This may be a subset of insurance such as delay, cancellation and interruption (often excluding medical).
While this is a nice feature which can be one less thing to think about, there are some important caveats to be aware before relying on this completely. Again I know about this through bad experience, expecting to claim when I was ineligible.
These card travel insurances require return flight bookings (no multiple segments), made on the card, in addition to a bunch of other caveats. Such as: - Documentation showing reason(s) for trip being interrupted - If the reason is medical related, Medical Certificate form detailing the medical history and the first symptom/accident date and confirming the unfitness to continue the trip - Copy of Common Carrier ticket - Billing statements or charge receipts of the insured trip costs and/or the reasonable additional expenses purchased