How to get the cheapest travel deal?

Ever wondered how to get the best deals on airline tickets and/or hotels? This article answers just that and brings you through the various ways to maximise your dollar.
This article focuses on leisure trips and not business trips. While similar principles would apply, the underlying concern of costs may not have as high a priority as compared with flexibility in dates (which would command a higher ticket price).
Rule 1: Book early
Better rates are generally available the earlier you book.
Rule 2: Price guarantees
People often ask whether Expedia is better than Agoda (or a similar question comparing Y against X). Often the question is moot given that most service providers offer some form of price guarantee matching the lowest price.
As at 31 July 2017, the policies of Expedia, Agoda and Booking.com are:

1. Expedia: “guarantee you’re getting the best price on the total amount (including taxes and fees) of hotel only and flight+hotel bookings” and “refund you TWICE the difference up to SGD125” (source: https://www.expedia.com.sg/p/corporate/price-guarantee )
2. Agoda: “If you have reserved a hotel room through Agoda and then show us that you could book the same room for the same dates at a lower rate that is viewable and bookable on another website, we will either match that rate or beat it.” (source: https://www.agoda.com/en-sg/info/agoda-policies.html?cid=-200 )
3. Booking.com: “You can claim a refund for the difference if you happen to find your reservation cheaper on another website.” (source: https://www.booking.com/general.html?tmpl=doc/rate_guarantee )

The trick, however, is knowing which site offers a better policy.
After making any booking, you can do a quick search for the same hotel and check what other offers there are. If there are better offers, apply for a price refund. Depending on the policy, the cost savings can be substantial ($20-30) for just 5 minutes of administrative work and may add up over the course of a year (depending on how often you travel, it may add up to more than $100).
Rule 3: Loyalty programs and/or air miles accumulation programs
The exception to Rule 2 is when we are also considering loyalty programs and/or air miles accumulation programs.
For example, I have friends who swear by membership program associated with hotels which rewards members with a free night’s stay annually and/or other programs offering bonus points for travellers frequenting the hotel chain or booking website. This would encourage consumers to purchase directly from the hotel and/or particular booking sites. While I do not frequent any particular hotel chain and/or booking site (who cares where we are booking so long as it is the lowest price), some travellers prefer a familiar brand or just avoiding the hassle of searching.
That said, I am a strong advocate for collecting of air miles. We discussed miles and how they work in another article. While air miles are typically associated with flying, air miles can be earned by credit card spend as well. Depending on where you come from, the miles earned per dollar spent varies. There is often a base spend (usually low at a 1.2-1.4 miles per dollar). There are however accelerators available depending on the promotions offered by the respective banks which offer miles on a multiplier basis. Such accelerators are sometimes pegged to travel websites such as Agoda and Expedia at 6 miles to a dollar. In such cases, it may be worthwhile booking with the site with the best accelerator whilst still checking for cheaper options so as to benefit from the respective site’s price guarantees.
Do take note that sometimes, some accelerators are too good to be true (e.g. 10 miles to a dollar). A traveller is essentially paying a premium in exchange for the bonus miles.
The rule of thumb is to check whether you are paying no more than 2 cents per extra mile.
Rule 4: Credit card promotions
Other than miles and accumulator programs, be sure to look out for banks offering discounts if a booking is made through their cards. You may end up not only bagging miles for your transaction but also a sweet 10% discount of your booking.
However, sometimes it gets a little tricky. Say you have a card that offers a 5% discount (with no miles being earned) and another card that gives 4 miles to a dollar. Which card is better? Assume a night rate of $100. (Answer: The 4 miles to a dollar option – 400 miles as compared with $5 savings (worth maybe 250 miles). The table below sets out an easy to read chart showing the conversion of miles to its equivalent discount %. If your card’s discount rate is better, use that. If not, just use your miles card.

Rule 5: Purchases using miles
Generally, redemption of plane tickets using miles gives good value. For example, a return flight (SIN – ICN) on business class for Cathay Pacific is approximately S$2,827.50 (worth approximately 141,000 miles). If redeeming tickets, a similar flight would only cost you 90,000 miles!
Rule 6: Arbitraging (AKA the Holy Grail)
While the above sets out the typical considerations one could have, the prize winner is when you find a gap in booking systems (e.g. countries being classified in a different zone resulting in cheaper miles redemption or flaws in the booking resulting in cheaper tickets). A traveller can in such rare cases possibly get better rates than what would normally be available. As these purchases involve possible flaws in a booking system, they may be “patched” by the service provider.
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Be sure to check out my other posts covering different aspects of travelling.