Why Be a Chump?

When I talk to people about all the fun and exciting adventures I’ve had, one of the first things people ask about is how do I afford to travel so much? The answer to that is travel hacking.

I looked around at the people who go big and the people who go home and saw a key difference. Travel hackers are flying on the same airlines, staying at the same hotels, and driving the same rental cars as the other guys, but they are paying far, far less to do so. So I asked myself. Do I want to be a travel hacker, or do I want to be a chump?


Travel Hacking Basics


Westjet Arrival at YYJ

Air Travel


Picks his holidays on firm dates, in peak season, to standard tourist destinations, visits a travel agent whenever he remembers he needs to book his flights, wants direct, non-stop flights at peak time on specific airlines, uses cash/cheque/debit card to make purchases, packs too much stuff in unwieldy luggage, arrives at the airport with too much/little time, pays airport/onboard prices for food/drink, sits/sleeps awkwardly in boarding area chairs, gets regular treatment from airline crew.

Travel Hacker:

Timing: Can go a few ways with this. Flexible enough to leave at a moments notice if he spots a great deal. Firm dates means watching the deals and award space from as early as possible to watch trends and find the sweet spot. Will often consider travelling on the shoulder season.

Destination: Sometimes chooses traditional vacation spots, but more likely to visit them on the shoulder season or by finding a sweet spot in award redemptions. Keeps an open mind about where the next adventure might be. Looks at the bigger picture (want the old-world charm of Paris? Consider Quebec, etc.) to get more of what he wants out of his holiday. Strategises with loyalty points to achieve “aspirational travel” (for me, it’s a shower in the sky).

Getting there: Considers alternate airports, airlines, routings, and stopovers to get the most bang for his buck. Compares cash fares vs loyalty currencies vs local currencies. Follows bloggers and joins groups on Facebook and other social media to keep up to date on travel news, error fares, and deals. Watches for promotions and sales from preferred airlines. Books when he finds the right price, sometimes almost a year in advance, sometimes last-minute, almost always for less than his seatmate paid. Chooses the best seat according to his preferences and needs.

Booking: Usually books on his own, but uses a favourite, experienced agent who understands his needs if it’s useful or a better deal. Compares the advantages of booking direct with the airline vs online travel agent’s (OTA’s). Purchases tickets via a portal to get cash-back/points/miles. Applies promo codes for a discount at checkout. Signs in to his account to make sure the flight is tracked with the airline’s loyalty program. Credits the miles/points to the best loyalty program. Uses a rewards credit card to get as much back as he can.

At the airport: Uses go-to luggage suited to his travel style, packed with efficiency in mind, essentials easily accessible and secure. Arrives with enough time to clear luggage drop (not always necessary),  and rarely pays for baggage due to airline selection, loyalty and credit card perks. Leaves plenty of time to clear customs and security (might have a security Pre-Check), and always makes sure his liquids and electronics are compliant with local screening protocols. Relaxes and dines in the comfort of a lounge due to credit card/loyalty perks, or know the best places to catch some zzz’s when that’s not an option. Is aware of gate changes and flight status by being locally connected to useful apps. Is often upgraded due to loyalty status, or even because he has taken all the right steps to be most likely chosen for a freebie.



Might choose a hotel from an ad, a travel agent, a quick google search, or his next-door neighbour. He might call the 1-800-number to book it. Maybe he’ll use an OTA. Pays with any old card.

Travel Hacker:

Considers options like AirBnB, VRBO, hostels, guesthouses and hotels. Compares rates between OTA’s, apps, brand websites, directly with the hotel. Considers booking with points. Uses promo codes and discounts to book. Registers for loyalty promotions. Remembers to compare CAA, loyalty programs, and credit card rates and portals. Might even contact the hotel directly to negotiate a better rate or perk. Uses loyalty programs to get perks like upgrades, wifi, amenities, etc. Collects loyalty points for future travel use and uses a rewards card to pay.

Rental Car in St Maarten 2014

Our Rental Car in St Maarten 2014

Car Rentals


Maybe he books it through an agent, an OTA, his hotel, or with his local brand website. Pays extra for insurance. Uses any card to pay.

Travel Hacker:

Similar to hotel booking, he compares rates between loyalty and credit card programs, and even checks country-specific travel agents, brokers and brand websites (sometimes currency can make all the difference). Considers the value of perks like upgrades and extra insurance. Uses promo codes and portals. Registers for promotions. Considers booking with points. Collects loyalty points on the booking itself and uses a rewards card to pay.

What’s in Your Wallet?

Credit Cards


Has one or two credit cards in his wallet. Got one through his bank ages ago, and the other one when they offered him a free hat at a hockey game for signing up (I know this because I used to be that girl at the hockey game in the low-cut shirt, with the application clipboard and the stack of “free” hats.). Gets little to no rewards and/or pays an annual fee.

Travel Hacker:

Has considered almost every type of rewards card out there and compared their value against their cost. Has at least one card for every type of spending he might do. Uses more than one card per day for his everyday spend. His travel wallet holds more cards than his everyday wallet so that he can bring airline/hotel specific cards that he only uses for these airlines/hotels. Always wants to pick up the tab at restaurants and have friends pay him their portion in cash so he earns even more rewards. Cycles through cards every few months, monitoring his credit rating like other people watch their stocks, churning high bonus earning cards according to strict timelines to get the most gain before they close the loopholes that allow him to earn travel rewards over and over again. Applies for these cards through special links or portals to get no annual fee, extra rewards or cashback for signing up. Carries very little cash and tracks his spending in an excel spreadsheet so he can determine when he’s met bonus targets and set his higher earning categories to the best advantage. Enjoys watching his loyalty currency banks grow as he hits minimum spend by stacking promotions.


Loyalty Programs


Has an old Subway stamp card at the back of his sock drawer next to his Safeway card and Canadian Tire money.

Travel Hacker:

Joins almost any loyalty program he comes across, even if it’s just to get the freebies on his birthday, and has the app to prove it. Considers the trackability a fair trade-off for the perks, especially since all his spending is tracked on his credit cards anyway. Loves the idea of double-dipping. Has his favourite program benefits’ fine print bookmarked in his phone so he can claim rewards on the go, surprising even staff members with his knowledge of what he is entitled to as a Super Elite Triple Diamond Titanium Member.


Bottom Line:

Some people enjoy travel hacking as a way to pay less for their holidays. Some do it to get 5-star luxury for 3-star prices. Whatever your reasons, you have to ask yourself…Do you really want to be a chump?

Becoming a full-time travel hacker may not be for everyone, but the beauty of this game is that you can play at whatever level you like and still come away a winner.

**Do you enjoy travel hacking? Want to tell us your best tips? Share your experience in the comments section here and remember to “Like” this page on Facebook to keep seeing posts like this and more. If you’d like to support this blog, please check out my referral links. Sharing is caring, so tell your friends!**

This post may contain affiliate links. See my full disclosure here.

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