Using Reward Points For Free Airfare: The Milwaukee Experience

Reward travel. It’s a flummoxing topic for newbies; and seeing as I’m a newbie, I’m the perfect faux expert to speak on the topic! Seriously, though I’m a newbie to reward travel, I’m not a complete rookie when it comes to reward points from credit cards.

I’ve typically used MasterCard and American Express interchangeably in the past to land great deals on gift cards at stores I frequent or would like to buy something special. Victoria’s Secret, Chili’s, and Williams-Sonoma among others have all garnered my attention in these searches. However, entering the travel blogging arena pushed me to a new world–travel rewards credit cards. And after using one for months, I had plenty of points to purchase a necessary and FREE trip to Milwaukee, Wisconsin! How’d I do it? Read on!

My Travel Rewards Card

A ton of travel rewards card offers float around the Web and perhaps your mailbox. However, I utilize two for racking points–Chase Sapphire Reserve (Visa) and American Express. These two cards have great valuations though I currently tend to bend more toward the Visa affiliated card which returns triple points on travel including flights, hotels, and restaurants. In fact, I was so impressed with the program that I recently upgraded to the Reserve level card from the double points-level Chase Sapphire Preferred card. My American Express card earns my business on grocery store purchases for double points on those purchases.

Each card’s reward program has the ability to either pay for flights through trip/vacation purchase searches and programs and the ability to transfer points to travel affiliates! Chase Ultimate Rewards has seven major airlines and four major hotel brands as 1:1 ratio partners. Meanwhile, American Express has 20 partners though only 14 are at a 1:1 or better ratio. Among the partners, minimal overlap exists but can be a nice feature for those who want to pull points from two different credit cards.

With my cards set with a plethora of search functionality and transfer partners, I was immediately setup very well to make a great reward points purchase.

Flight Search Options

Let’s talk search options because there are tons. You can probably list several off the top of your head–Priceline, Orbitz, Expedia, Travelocity, and on and on come to my mind. Of course, those are some of the market leaders. I have a three-step process I currently use to reach the right flight solution for flights on which I have an exact destination and near exact timing.

First, search using several search engines. However, I don’t currently use those aforementioned market leaders. You can find a bargain “mystery flight” on those sites that may beat the lowest fare by a few dollars; but it won’t be much. My preference is using a combination of Google Flights, Skyscanner, Skiplagged, Hopper, and Kayak. Combined, they help determine less expensive dates, price trends, and optimal airlines.

Second, search directly with airlines including Southwest Airlines which often does not appear in flight search engines. You may be able to find flights slightly cheaper than some search engines. However, this is primarily a validation step to ensure you are checking multiple avenues to purchasing from a specific airline and receiving the best package.

Third, search with your credit card travel purchase engine. For me, this entailed Chase Ultimate Rewards. This step is a final validation step to determine the best option whereupon you can finally act!

Reward Points Decision

I knew I wanted to use my reward points if I could; I accumulated enough for a purchase, and they aren’t the best investment and savings vehicle. With that in mind, it was time to point burn! Combining my clues from my searches led me to compare points that could be used through my Chase Sapphire Ultimate Rewards travel option. This brought me to a purchase of approximately 20,000 points which was comparable and perhaps a tad cheaper than search options. However, it didn’t beat Southwest Airlines.

Southwest Airlines featured a Wanna Get Away round trip price of $252 or approximately 14,000 points (a valuation of 1.8 cents per point!). With no points on my Southwest account, I used the Ultimate Rewards account’s 1:1 transfer ratio to send that exact sum of reward points to Southwest. The transfer completed within minutes. Voila! One round trip ticket to Milwaukee and back for free (plus nominal $5.60 TSA fee both ways)! A great experience, a great deal, and a great signal that I’m following the right path to wisely use my points in the future! And I’m setup for a great trip to Milwaukee. Why am I traveling to Wisconsin? I’ll let you know soon! Follow my social accounts, and you might find out sooner! Wink-wink!

What are your thoughts and tips for getting the best flight deals for free? I’d love to hear them. Comment below!

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