How to find the best travel deals using online sites

Do swear by Kayak

Kayak is brand agnostic and crawls over other travel websites (e.g. Cheaptickets, Expedia, etc.) to help consumers find the best deal. Their calendar function toggled on the right side of the screen, tells you (for round-trip, single destination flights) the lowest cost fare for that particular destination any given day and helps level-set what a fair ticket price should be.

Kayak also introduced a tool that remains planted on the left side of the screen, which provides ticket cost trends and insights on whether the ticket price is expected to drop or rise in the coming days based on past patterns. That should help decide when to buy.

Do leverage any flexibility you have in timing

For Kayak Explore and new sites like Hipmunk, being destination and/or time indifferent provides excellent possibilities to find a cheap ticket. Using the Kayak Explore functionality, for example, you can pull up a map and set parameters for the highest price that you'd be willing to be pay for a ticket to any place in the world at any given time (or for a particular month). You can also dictate if you want your trip to include skiing, golfing, beaches, etc.

Do check on Tuesdays… and then Wednesdays

Assembling anecdotal feedback from many high flying friends and doing ancillary research from the likes of the Wall Street Journal would point to finding the cheapest fares on Tuesdays. Recently, that has also expanded somewhat to Wednesdays. However, general advice is to look and look often. Figure out what you think the fair price of the ticket should be, and when one becomes available at that value (or below), jump on it, because it rarely lasts more than a few days.

Do book on the original airline’s website if and when possible

When possible, book tickets on the original carrier’s website. If the ticket cost difference is marginal, use a single airline and book tickets via their website; at worst, when you miss a flight or your travel arrangements change, it means perhaps paying a rebooking fee ($50-75) domestic.

Using Travelocity and Expedia, for example, which often aggregate legs from various airlines (e.g. flying out United, flying back American), can sometimes cause headaches if you need to make flight changes. You'll be charged a rebooking fee by the travel site and will still have to pay airline fees and/or potential ticket price changes on top of that.

Do crowdsource and keep up to date with new tools

The number of online tools available are currently fluctuating and are increasingly designed to fit different needs as travelers become more sophisticated and segmented. Crowdsource from savvy friends what new tools they are using. Look at specific tools that book around the world tickets, like BootsandAll, as your specific needs change.

Do not allow yourself to get squeezed with rebooking fees

This ladders into #4. Rebooking fees will kill you. For example, a ticket via Vayama.com for Chicago to Istanbul may cost $470—a great price. However, if you needed to change the timing of the trip, Vayama would charge a $150 change fee, and you would need to pay the Turkish Airlines change fee. Plus, if you had booked a special class fare that was no longer available, you would have to, of course, pay the difference in fare costs.

Do not waste days fighting over nickels

Decide what is a fair price that you’re willing to pay for a ticket. If you’re a seasoned traveler, for example, you generally have a base fare that is reasonable in your mind. When it hits, you should strike. Don’t waste your precious time incessantly checking back with the vain hopes of one day saving another $8 on the posted fare. More often than not, when you return, the fare has jumped $200, and you’ve lost your window (refer Do #3).

Do not always trust that your US-based travel search engine is the best resource outside of the country

A great example of this is using elong.net in China. While the advertised fares for a Beijing to Changchun round-trip may come in at $350 from US-based Kayak, checking elong, the Chinese Expedia, will find you a fare at one-third that cost.

Do not believe that online search engines will yield the best deals period

With the availability of online tools, we in the US have a much more DIY perspective when it comes to booking tickets. However, in some of the other parts of the world—Europe and Africa included—travel agents are able to provide you with the better deal. For example, while Kayak tells you that flying from Istanbul to Nevsehir will cost $350, going through an Istanbul travel agent can actually yield a fare of $90.

Do not lose faith in last-minute fares

There may be times where you take some time off and decide to wait until the last minute to book a trip. You may nervously check the various travel sites—two weeks, then one week leading up to the time window. Sometimes this last-minute method bears no fruit. However, it can yield amazing deals such as $600 round-trip fare to Brazil. Waiting for last-minute deals also means being generally more destination indifferent and not putting all your eggs into one hypothetical destination basket.