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JCooley

Escaping Winter – A Credit Card Game

As the temperatures in Chicago hit highs in the NEGATIVE teens, I prepare to embark on another journey (this time to Seychelles and South Africa), thanks to the often overlooked benefit of credit card rewards. Between Australia, Thailand, Japan, Maldives, and Bali, I’ve stayed in world-class resorts, flown business class on my honeymoon, and visited more countries than I expected to at this point in my life….with each trip probably more affordable than a trip to Disneyworld these days – which I still do not understand the appeal of vacationing there before you bring kids into this world…but to each their own. Early on in my adult life I discovered the benefits of credit card rewards. I learned that if you treat your credit card like a debit card and never go over the balance in your checking account, you could get a decent chunk of cash back once or twice a year. I thought that was great and all for the first few years until I discovered I was missing out on a huge opportunity to cash in on those same credit card points for more valuable (often 5-10x more valuable) travel rewards. Sure I traveled a decent amount for pleasure and took the occasional work trip, but not nearly enough to stock-pile the points and miles needed to get me where I wanted to go. That’s when I upped my credit card game and turned those same points into airline miles or hotel points as opposed to the cash-back option. People often shy away from credit cards with huge annual fees, but if you are a typical millennial, you will most likely make up the difference and then some within a few short months. The insurance benefits alone have saved my ass in the past and more than paid for the $450 annual fee of my Chase Sapphire Reserve card. Just last year as I was concluding my bachelor party down in Austin, Texas, the Midwest was getting hit with typical Midwest weather. As a result, my flight was canceled until the next day. If it weren’t for the travel insurance provided by my credit card I booked my trip with, I would have been out well over $500 to book a decent last-minute hotel, food for an extra day, and transportation for my extended trip. Instead, I was reimbursed for my extra night in a downtown hotel and got to enjoy some authentic BBQ while I wait out the storm back home. Back to my current trip - This time around we will have to shell out a bit of our own coin for the safari portion of our trip (you can’t go to South Africa and NOT go on a safari), but outside of that, almost everything else will be covered by either airline miles, hotel points, or credit card points that were transferred to airline and hotel partners. It still does take quite a bit of spending to get to this point, but if you are smart about it and put everything you possibly can in your day-to-day life on a high-earning credit card (and pay if off in full every month), it’s really quite easy to accumulate the points rather quickly. I’m not saying this is right for everyone, but it is pretty awesome to see the world because I paid my bills, bought groceries, went out to eat, and took ride-shares around the city – things I’m going to do anyways…. so why not cash in on it?

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