It's worth it to pay for a flight initially when joining a frequent flyer program (which is free to join). Using your shiny new points credit card buys you points. Paying for a flight gives you points and also the miles you travel on a paid flight give you more points. Your credit card that gives you points may or may not be from a bank. For example, Aeroplan VISA is a points card. TD offers one, and so does AmEx. Get the card and then join Aeroplan. Immediately your purchases on the card turn into points you accumulate towards free flights. And, most points credit card providers give you a welcome bonus, which varies depending on the type of points card you select. Points credit cards usually require an annual fee for the card but ultimately it's worth the cost for the free flights you'll get.
There are two ways of thinking about flights you buy. You want to go somewhere this winter, say, Honolulu, Hawaii. You're willing to pay with your new credit card that gives you points for the amount you pay and the miles you travel. When booking a flight, there are at least two schools of thinking which go like this:
1 - Your travel dates are fixed. You need to buy a ticket two to six months in advance. The minute an airline that flies to Honolulu has a sale, snag a ticket.
2 - Your dates are flexible. You can fly this month or next month or next year, leave mid-week or weekends. You can wait to book. Eventually the price will drop and you can then pick dates that fit the sale parameters. Airlines want to fill planes and will offer cheap seats close to the scheduled flights.
Most often I go with #1, mainly because many of the events I travel for, like conventions, are fixed dates and since I've already bought a membership for the convention and booked the hotel, I need to make sure I am there then.
On the other hand, I have also had a lot of flexibility when travelling just for pleasure, in which case I could go to Honolulu in January, February or March. Sometimes, as the winter months approach and the planes are not full, sales happen and I can snag a flight for any two weeks I want that the sale covers.
The golden days of many choices of flight times each day seem to be over. Airlines are hell-bent on profit which means scheduling fewer flights each day and stuffing planes with passengers. If you wait, you run the risk that the flight you want will be full. If you book far in advance, you run the risk of seeing your flight which is non-refundable drop in price, possibly by several hundred dollars.
What you decide relates to how fixed your time frame for travel is. Most jobs require employees to select their holidays in advance. In that case, since you know you have 2 weeks off from, say, February 1 to 14, start looking for and comparing flights the minute you know your holiday dates. You'll see the prices and as you watch over days and weeks you'll see them change.
The key to cheap flights is research. There are multiple search engines that compare prices of flights with various airlines so you can see who has the lowest prices and best conditions for the dates you want. For example, I looked up return flights, Montreal to Honolulu, February 1 to 14, 2018 here:
Research is your friend. You need to research the costs of various flights and for several airlines that fly where you want to go so you know whether or not a sale is really a sale. Google is just one search engine and you can compare prices for flights on Kayak, Expedia, Skyscanner--there are oodles of such trackers available in every country. Some will alert you to price changes. You can also get flight alerts from specific airlines sent to your email when the price of a particular flight you're interested in changes (up or down).
The list down below is what came up for me typing in the Honolulu info on googleflights.ca. All are under $1,000 Canadian dollars. These comparisons (which change daily and sometimes hourly) give you a choice of airlines and also whether you want non-stop (more costly, usually) or 1 or 2 changes of plane, what time of day you want to depart and arrive, the overall length of the flight, etc. And you can always check an airline of choice every couple of days to look for price drops. Just make sure that when you do a comparison search that prices are in your currency. Most of the comparison search engines let you change the currency to your own.
By the way, based on the list below, United (which is a Star Alliance member--Aeroplan) has the lowest price, a round trip flight Montreal to Honolulu - $558. The distance of the round trip is about 9800 miles, each mile giving a point on Aeroplan. There are also points given for the cost of the flight, $558. Total points for this flight, about 10,358 points in your Aeroplan account. But if you are also charging your regular-life expenses of $1,000 a month (see Travel Tips 1), you would accumulate 12,000 points a year. In one year by combining the trip you buy and the points you earn on monthly expenses you will have 22,358 points, enough for a free flight to New York City or Chicago or Los Angeles or Mexico City, or many other places. And if your monthly expenses are $1,500 a month, in one year you would have 28,358 points, enough to go to California!
And surprise! Your new points credit card will offer you a welcome bonus of points, the number varying on the type of card you select. For example, a TD Aeroplan VISA credit card will give you 25,000 welcome points. Combine those and in one year you have 53,358 in one year or more. And guess what? If you love Hawaii, you can go again next year--on points! Honolulu will cost you 45,000 points so you'll have 8,358 left towards the start of another trip!
Just a head's up: A round trip flight to the UK or Europe normally will cost you 60,000 points UNLESS Aeroplan has a sale. In 2016 I only paid 14,500 points for that overseas flight. This year I paid 42,000 points. At the moment, if you wanted to travel to London, England in November it would only cost you just 15,400 points because Aeroplan is having a sale. Life is good!
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