• Skip to primary navigation
  • Skip to main content
  • Skip to primary sidebar
  • Skip to footer

Life By Dylan

Lifestyle, Business and Travel Blog

  • Home
  • About Dylan
  • Categories
    • Business
    • Life
    • Travel
    • Home
      • Smart Home
    • Fashion
  • Shop
  • Contact
  • Lee’s Blog

How My Wife and I are Flying 50% off For the Next Two Years!

by

Stateroom Balcony - Harmony of the SeasThis year we’re planning a lot of trips. It’s one of the last years we’ll be able to do this, because my son isn’t in school yet, and our daughter isn’t yet 2, so she flies for free. The problem is we’re also buying a new house this year, so we don’t have a lot of extra money floating around for us to throw at a bunch of vacations. So how am I making it happen? Getting half-off flights!

I have a friend who’s done well for himself and seems to be traveling almost every month to some random getaway with his girlfriend, so I did what any friend would do and asked how he did it. I expected him to tell me his bank account is just overflowing and that would be that, but instead he told me about a loophole he found that got him a Southwest Companion Pass that allows his girlfriend to fly free every time he buys any flight on Southwest.

Southwest Companion Pass

Some of you may be familiar with the Companion pass that Southwest offers, and if you are, you also know you have to fly 100 one-way flights or 110,000 miles in a single year to get it. That’s crazy! Unless your job involves constant travel, I don’t know any other way you’re going to fly THAT MUCH.

So, how did he get it? He gamed their credit card system. Southwest offers both a business and personal credit card through Chase that gives A LOT of bonus miles. If you sign up for the Business credit card and spend $3000 in the first 90 days you get 60,000 bonus miles, and if you sign up for the personal credit card you get another 40,000 miles after you spend $2000 in 90 days. That only brings you to 100,000 miles, but if you get someone to refer you to get the personal credit card, you get another 10,000 miles, which brings you to the 110,000 miles you need to get the Companion pass! I had to find someone online to refer me, but you can use my link here to get the extra 10,000 miles.

Great View - Bahamas

I had to throw in some more vacation pics to get you excited

When you get the Companion Pass, you get to keep it for the entire year you qualified for it in (by getting 110,000 miles in a calendar year), PLUS the entire next year. We just qualified for it today, January 25th, and it’s going to last until December 31st of 2019!

What’s also amazing is that you get to keep the 115,000 miles (60,000 + 50,000 + the $3000 & $2000 you needed to spend on the cards), and can use that to get a bunch of free flights. As long as you buy ahead of time, most of the Wanna Get Away one-way flights cost around 10,000 miles, which means you can trade those miles in for 5.5 free roundtrip flights! That means you can get yourself over 5 free roundtrips for you as well as whoever you pick as your companion!

Hotel Zamora - Lobby & Noah - St. Pete Beach Florida

This little dude LOVES traveling

Now I should mention the flights aren’t technically COMPLETELY free. You have to pay a $5.60 fee per way for taxes, but at that price, its basically free.

Looking out Mster Bedroom Window Breckenridge Snow

This is from our last trip to Breckenridge. He can’t stop talking about how he want’s to go back to the “Mountain House”

If anyone else wants to do the same thing, I’ve laid out the steps and important info below. I’ve included a referral code which will give you the extra 10,000 miles you need to qualify for the Companion Pass, and I should mention it will give me 10,000 miles as well (not that you care, but I want to be completely transparent).

Benefits of This Loop Hole

  1. It gets you a Companion Pass that lets you choose a companion to fly for only $5.60 with you on any flight you buy through Southwest Airlines.
  2. You get the Companion Pass for the rest of the year you qualify for it in, plus all of the next calendar year.
    • Example: We got our Companion Pass today, January 25th 2018, and it won’t expire until December 31st 2019
  3. You get 115,000 Southwest miles that can be used to get around 5 full round trip tickets for almost completely free, assuming an average of 10,000 miles used per one-way flight. (you still have to pay a government tax of $5.60 per one way flight)

Rules to Get The Companion Pass

  1. You have to get 110,000 miles in a single calendar year

How You Can Get 110,000 Miles In a Single Year

  1. Every $ spent with the credit cards below qualify as 1 or more miles.
  2. The credit cards below give big bonus miles upon signup that count towards the 110,000 mile goal
  3. One person needs to sign up for both of the credit cards below.
  4. You need to sign up for both cards and spend the necessary amount of $ in the same calendar year.
    • If you did one in one calendar year, and the other in the next calendar year, you won’t hit the 110,000 mile mark in a single calendar year.

Southwest Rapid Rewards Business Premier Credit Card

You get 60,000 miles if you sign up for this Southwest Business Credit Card and spend $3000 in the first 90 days. Sign up here

Southwest Rapid Rewards Plus Credit Card

You get 50,000 miles if you sign up with this referral code for this Southwest Personal Credit Card and spend $2000 in the first 90 days (if you don’t use this referral code you only get 40,000 miles) Sign up here


Other Things You Should Know

  1. To get the business card, you’ll need some type of business. It doesn’t need to be a big business. It could even be a small sole-proprietorship.
  2. If you think you’ll have trouble spending enough money quickly enough on the cards, think of things you could prepay for. We wanted to get the Companion Pass as soon as possible, because we had a trip planned, so we wanted to hit the $2000 personal limit in the first month. We didn’t end up needing to, but to hit the $2000 mark we were going to buy some grocery gift cards, which we knew we’d use.
  3. We put all of our monthly expenses that could be charged to credit cards onto these, which helped hit the $ goals quickly.
  4. It’s best to qualify for the Companion Pass early in the calendar year, because it lasts the rest of the year you qualify for it, plus all of the next year. That means if you get it in January, you get it for 23 months. If you get it in November, you get it for only 13 months.
  5. If you signed up for 5 new credit cards in the last 24 months, you may not get approved for the credit cards.
  6. If you signed up for more than 1 personal and/or 1 business credit card in the last 90 days, you may not get approved.
  7. Every free flight your Companion gets they will have to pay a $5.60 tax per one-way flight – that’s it!
  8. Southwest offers the first 2 checked bags for free, which means no extra baggage fees.
  9. You can see everywhere Southwest flies to here.

 

Filed Under: Life, Travel Tagged With: Life Tips, Travel Blog, Travel Blogger, Travel Tips, Tropical Vacation

Previous Post: « How I’m Planning to Be Spontaneous as a Father of Two: Travel, Travel, and more Travel
Next Post: How I Found the Love of My Life »

Reader Interactions

Comments

  1. MH says

    February 16, 2018 at 6:30 pm

    Awesome perk for Southwest! Do you know if your purchases on the business card actually have to be business purchases? 🙂

    • Dylan says

      March 9, 2018 at 9:10 am

      Technically, Southwest/Chase wouldn’t know, but for accounting purposes, it would probably be smart to keep them to business purchases. We have an S-corp, so although we didn’t do this, you could technically use it for personal purchases, then you would categorize them as owner distributions. If you had a sole proprietorship, mixing both your personal and business expenses could make it tricky when it came for tax time, but if you had a couple large purchases, it wouldn’t be too bad. In either case, as long as you’re the full owner of the business and don’t have any investors, it shouldn’t matter legally. They’re just pass through entities. If you had a LLC, and some time in the future you were sued, it could open you up to being personally liable.

Primary Sidebar

  • Email
  • Instagram
  • Twitter

Life By Dylan Email

subscribe for email updates!

Tesla Model X Falcon Doors Open

13 Things You Don’t Know About The Tesla Model X

Honda MIIMO HRM 520

Mow Your Lawn without leaving your couch

Samsung Smart Hub Fridge

Samsung Smart Hub Fridge – Best Features

Dylan and Noah with Schlage Encode wifi lock

My Top 3 Smart Home Security Devices

Categories

Archives

  • Email
  • Instagram
  • Twitter

Footer

Our garage is one of our favorite places to hang o Our garage is one of our favorite places to hang out on the blazing summer days. We bought the house while it was still being built, so we had no idea just how big the garage was going to be. #Ad #TargetPartner
Once we saw it, we realized it would be much more fun to convert it into a rec room instead of just parking our cars in it. The latest addition has been an @Xbox. We got Xbox All Access from @Target , which got us an Xbox along with 100’s of games. Our kids are pretty new to gaming, so it was awesome, because there was no upfront cost, we get to keep the Xbox, and they can try out a bunch of games instead of me having to buy a bunch of different ones. Noah keeps changing his mind about which game is his favorite, from Forza to Minecraft, and now it’s Craftopia, so it’s already saving money 😂
#TargetPartner #xboxallaccess #xbox
#LTKmens #LTKkids #LTKfamily 

https://liketk.it/3LOFH
I’m trying to make our Florida house as easy to I’m trying to make our Florida house as easy to take care of as possible, so I bought a bunch of different smart home devices to help with the cleaning, lawn, thermostats, water leaks, lights, etc. This is the third house we’ve done this with, so we’re starting to finally figure out what works and what isn’t worth it. Check out my stories for our recommendations and to get links. #smarthome #florida #homeimprovement
It’s already heating up here in Texas, so we’v It’s already heating up here in Texas, so we’ve been splitting out time between the pool and the couch 😂 # ad. I’m always looking for things that both the kids and I both enjoy, so we naturally end up spending more time together. 
We signed up for Xbox All Access a couple months ago from @Target, and what’s nice about it is that you get a @Xbox as well as access to 100+ games for a just monthly price with no upfront cost, and it ends up being a good deal. It works out especially well for us, because Noah and Emma like very different types of games, so instead of us having to buy lots of games, there are over 100 already included for them to play.  It’s currently only available for purchase online, so I’ll link it in my stories. #TargetPartner #xboxallaccess #xbox 
https://liketk.it/3Inta
Father’s Day is about celebrating fathers, but I Father’s Day is about celebrating fathers, but I wanted to share appreciation for @LeeAnneBenjamin who gave me the privilege of being a father. Before I met Lee, my young, naive plan was that I wouldn’t be married until I was 30 and definitely wouldn’t be having children until I was at least 35. 
I was married to work and the idea of creating companies and wealth. I didn’t think I had time for both. 
Then Lee came along. I had no idea when I met her, but it was the luckiest moment of my life. I couldn’t dream of ending up with anyone better.  If there is such a thing as soulmates, I found mine. 
We’ve been together 17 years, almost half my life. And I couldn’t imagine my life without her. 
She’s the reason I get to be the father of two kids I’m obsessed with, and for that I’ll be forever grateful.
Happy Father’s Day!
We decided to have some fun this morning! The kids We decided to have some fun this morning! The kids have been getting into some games lately, so I thought we’d set it up all outside, because… why not! # ad 
We recently signed up for #xboxallaccess at @Target, where for a monthly price we got an Xbox Series X and access to hundreds of games. It’s been awesome for us because there are a ton of different games to try out. Noah seems to be into the racing and Minecraft games, while Emma’s been enjoying Paw Patrol 
Check out my stories to see what I’m talking about.

#TargetPartner #xboxallaccess #xbox @xbox 
#liketkit #LTKmens #LTKkids #LTKfamily
@shop.ltk
https://liketk.it/3GTA1
What's your favorite thing to cook on your grill? What's your favorite thing to cook on your grill? We go through a lot of burgers, but I love cooking thick ribeyes. If you can get enough heat on them for a good sear, I'm convinced there's nothing better. When we customized our new outdoor kitchen from @RTAOutdoorliving , we put in a grill from @coyoteoutdoor that has an infrared searing burner that IS AWESOME. Excited to share more details of our outdoor kitchen with you guys on stories. Lee's favorite part of the kitchen are the Corian Endura countertops from @coriandesign. Check out my stories for a video of some sweet sweet grilling action 😂
This week as part of @LeeAnneBenjamin 's and my go This week as part of @LeeAnneBenjamin 's and my goal to teach out kids something new or give them a unique experience every week this year, we're building @Lego Technic cars from @Target #Ad. I thought Noah would really be into them, but I was surprised by just how obsessed Emma has been with them too. They take a few days to make, so we've been doing a little bit most mornings or evenings. @Target has a bunch of different ones, and even has an exclusive on some of them like the green Mustang we're building, which is one of the less expensive ones. It's been an awesome way to get some good one on one time with both our kids. Check out my stories for more info and some links. #TargetPartner #TargetStyle 

Follow my shop @dylanbenjam on the @shop.LTK app to shop this post and get my exclusive app-only content!

#liketkit #LTKunder50 #LTKkids #LTKfamily
@shop.ltk
https://liketk.it/3DBQt
We’ve got a new project! I want to get the kids We’ve got a new project! I want to get the kids out fishing on the lake, but the boat slips here are either on a waitlist or too expensive to be worth it. Instead we’re going to transform this one into something we can drop in the water ourselves and spend less than we would on an annual boat slip. 
It’s not as big of a project as some we’ve done in the last, but this one should get done quickly. 
I’ve got a lot of ideas of what to add to it so we can have “Champaign taste on a beer budget.”
First up is a motor we can drive by a remote and eliminates the need for an anchor by using GPS. Check out my stories for more info

#fishingboat #fishing #smallboats #smarthomes #austinblogger #smarthometech #austintx #guyswithlonghair #casualman #styleoftheday #mensfashion
Spring's finally here, so we've finally been able Spring's finally here, so we've finally been able to get back outside. We've made a lot of changes to our backyard and are excited to share it all. One of our kids favorites is definitely the outdoor ping pong table from @Ledgelounger. It's made from high-quality resin just like their signature chairs, so it's going to stand up to just about anything the weather is going to throw at it, so we can simply enjoy it. Check out @leeannebenjamin 's stories for more info. #ad
We’re buying this house in Florida and Noah and We’re buying this house in Florida and Noah and Emma still don’t know :)
If you haven’t been following along on @leeannebenjamin ‘s stories, we’ve been looking for a Florida home for quite a while. 
In this crazy real estate market, even if you put an offer in a house above asking the asking price, there is a good chance you won’t get it. 
We had our offer accepted on this one a couple days ago, and today was the first time we got to see it in person. I shared a walkthrough of the house on @leeannebenjamin ‘s stories, so you can see more there. 
I’m super excited to let the kids know, but we’re going to wait until the closing is done, so we can bring them both to Florida and surprise them! I can’t wait to see their faces!

#newhouse #florida #smarthomes #austinblogger #smarthometech #austintx #guyswithlonghair #menwithstyle #mensfashiontips #casualman #styleoftheday #mensfashion
Happy Tuesday guys! Thanks for the love on my unde Happy Tuesday guys! Thanks for the love on my underwater shenanigans. Let me know what I should do next! Wearing this comfortable slub crew neck sweatshirt & my favorite pair of @express jeans today. The weather is finally cooling off enough in Austin! Linking this outfit from @express today with http://liketk.it/3nFNb

#ExpressPartner #liketkit #LTKmens #LTKstyletip #LTKunder100
@shop.ltk
Did I redeem myself @leeannebenjamin ? Did I redeem myself @leeannebenjamin ?
I liked the @Denizen jeans so much, we got some fo I liked the @Denizen jeans so much, we got some for Noah too. Can you guess if he likes them? 😂
They have some added stretch to them that makes them comfortable all day, even for a kid as active as Noah.
The Boys' Skinny Fit jeans he's wearing are only $19 and my 216 Slim Fit jeans are only $29. Check out my stories for the links. #ad #denizenyourway
When I wear jeans, I never sacrifice comfort. Thes When I wear jeans, I never sacrifice comfort. These Men's 216 Slim Fit Straight Knit from @denizen are only $29! The soft knit fabric makes it feel like it would cost so much more! They have just enough stretch to keep them comfortable all day and a skinny without being too skinny. Check out more and where you can find your @denizen in my stories! #denizenyourway #ad

Copyright © 2025 · Life By Dylan

  • Home
  • About Dylan
  • Categories
    • Business
    • Life
    • Travel
    • Home
      • Smart Home
    • Fashion
  • Shop
  • Contact
  • Lee’s Blog
 

Loading Comments...