How Miles and Points Can Keep You Connected To Family

By: Luke Sims

About a year ago, I fell hard for the points and miles hobby. I was captivated by the idea of taking extraordinary trips for a fraction of the cost.

Now, one year wiser and ten pounds chubbier, I’ve discovered a more meaningful element that’s pulled me deeper in love – the freedom to visit family and close friends whenever I want.

I can remember the first headline that drew me in, “How I Booked a $28,000 Trip to Thailand for $326.42” – I was hooked. At the time, I was struggling to find an affordable way to take an incredible honeymoon and this was the ticket I was looking for, so I jumped in head first.

Over the past year, this hobby has taken me on some thrilling adventures. From my honeymoon in the Canadian Rockies to my all-inclusive weekend getaway to Cancun to my latest five-day trip to Paris (post coming soon). I never would have thought that I could take all of these trips for next to nothing.


(Honeymoon in the Canadian Rockies)

These were the spectacular escapades I was seeking. They’re what I thought this hobby was all about.  

But no matter how magical a trip I conjure up, the best part of this hobby has been how it’s allowed my wife and I to stay connected to our family and close friends from 600 miles away.

At 23, I graduated college, married my high school sweetheart, and moved to New York City to work for a nonprofit startup. One of the hardest parts about moving away was accepting the fact that either all of our extra money would go toward traveling home OR that traveling back home was going to be limited until we started making enough money for it to be possible.

All of our immediate family and many of our close friends live in the Midwest, and our parents still live in Toledo, Ohio where we grew up. A round-trip ticket home isn’t exactly cheap. It doesn’t break the bank, but we were just starting our careers and paying $2,000 a month in rent for a shoebox apartment, so we knew getting home was going to be tough.

I’m not looking for your sympathy. we decided to move and we knew how expensive the cost of living would be in New York City – just stick with me here.

This hobby has completely taken away the limitations of visiting our family and close friends.

Now instead of forgoing bars for a month so we could get tickets to visit my brother in Chicago, we don’t even have to think twice about it.

A bachelor’s party for a close friend in Ohio? I’m there, no questions asked.

Weekend trip to Cleveland because my wife misses her best friend from back home? Book the flight.

In the last year alone, my wife and I have taken a combined 16 round-trip flights to visit family and close friends for only the cost of taxes and fees – and that’s not counting any of our other getaways.


(Weddings back home are more fun when the flights are free)

A reasonable estimate for how much it would cost for 16 round-trip economy tickets from NYC to Midwest destinations would be around $4,000 (and that’s a low estimate, many of our trips are taken around holidays when the prices are much higher). Maybe $4,000 isn’t a big deal to everyone, but for us it’s almost a year’s worth of groceries… yeah, that’s a HUGE deal.

I’m not going to go into detail here about how I accomplished each of these trips for nothing more than the unavoidable taxes and fees (send me an email for that), but I couldn’t fall asleep tonight with a clear conscience without sharing what made this all possible – the Southwest Companion Pass.

Easily one of the most lucrative benefits in the world of frequent flyer programs, the Southwest Companion Pass allows you to bring a companion on any Southwest flight that you fly on for free.

This pass has played a huge role in allowing my wife and I to get back home for next to nothing. (check out the Ultimate Guide to the Southwest Companion Pass)

So, don’t get me wrong, the big trips have been incredible… and I won’t be slowing down on those anytime soon. But, by far the best part of this hobby has been the absolute freedom to visit my close friends and family, without the limitations and burdens that travel normally places on a young couple who moved away.


Cue the sappy closing music… “I’m coming home, I’m coming home, tell the world I’m coming home.”

Wheels Up,

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