In pursuit of financial independence and personal fulfillment

How I got $4,000 in free flights in just six months

I opened my first travel rewards credit card just six months ago with visions of free travel dancing in my head. Although I have yet to take my first points-purchased flight, I already have 10 booked for the next seven months.

How much did that save me? A lot!

The 10 flights would have cost just over $4,300 if I paid all cash. Instead, I’ve spent 160,000 points and $340 — almost $4,000 saved!

How I earned all those travel rewards points

My wife and I have opened four new cards to get all the points and perks I’m going to talk about. (If this interests you, please use my link to sign up for your own card and I’ll get a 10,000 point referral bonus.)

In August, I wrote about my plans for starting my travel rewards journey. I held to that strategy, but on an accelerated schedule.

First, I opened a Chase Sapphire Preferred card. I spent $4,000 in three months and earned 60,000 bonus points on top of the 4,000 spending points.

Next, my wife opened the Chase Sapphire Reserve, with the same spending and bonus numbers. While the $450 annual fee initially turned me off, since looking more into the added perks that come with the Reserve and the included annual refunds for travel, I would suggest opening that one first.

With those two cards, we earned just over 128,000 Chase Ultimate Rewards points that can be used with many different airline and hotel companies.

After that, I had my sights set on earning the Southwest companion pass, which allows me to bring a named companion on any Southwest flight for a nominal fee of usually $5.60 each way.

I had intended to wait until just after January to start accruing points, because you have to earn 110,000 Rapid Rewards in a calendar year to qualify for the companion pass. The Premier card was offering a 60,000 point bonus when I first looked into it and the Plus card was offering 40,000, but in September Southwest cards started offering 60,000 point bonuses on both.

I signed up for both the Premier and Plus cards on Oct. 2, and got a confirmation from Chase that I had to meet my three-month, $2,000 spending threshold by Jan. 25, 2018 because of the way the billing cycle fell. So I spent up to about $1,900 on each of the cards before Jan. 1, then finished off the spending just after the new year.

That gave me enough points on my January statements to trigger the companion pass three months earlier than I had anticipated, and without spending the extra $10,000 I was planning to spend.

Now I had another 125,000 Southwest Rapid Rewards points, plus a free flight for my wife on every flight I went on.

Booking my travel

Armed with 125,000 Southwest points and 128,000 Chase Ultimate Rewards points, I started booking our vacation flights.

Because of the Companion Pass, my wife’s ticket is a nominal fee on any flight where I’ve purchased a ticket, even with points.

A weeklong trip to Cabo San Lucas, Mexico, would cost us $515 per ticket if we were paying cash for everyone like we would had I not been travel hacking. Instead, I bought a ticket each for me and my daughter at 21,600 points per person, and my wife’s is covered. We each paid $91 in fees (much of it due to it being a foreign flight), for a grand total of $270 for all of us.

That’s a savings of $1,265.

Our long weekend trip for my brother-in-law’s 40th birthday in Nashville would be $417 a ticket. Instead, I bought two round trip tickets for 22,908 each. For just less than 46,000 points and $34 we’re heading to Nashville with an extra $1,200 in our pockets.

Another trip to Michigan cost less than 50,000 points and saved another $1,200. That drained our Rapid Rewards balance, and I opted to transfer 13,000 Chase points to make up the difference. (Yes, I gave up some buying power there in that the Chase points would have been worth 1.5x through the Chase portal, but are only worth 1x after transferring to Southwest.)

And, finally, my flight to FinCon in September is paid for entirely by 22,000 Chase points, saving me $290.

That’s how I have managed to get 10 flights for $340 and a bucketful of travel points I earned by putting my expected spending on cards with lucrative sign-up bonuses. We still have more than 110,000 Ultimate Rewards points left, and I’m starting to think about my next rewards card.


  1. Allyson

    Congrats on your success with travel hacking! The Southwest companion pass sounds like the way to go if you typically travel together. Do you have any travel hacks in the works for your lodging? Thanks for sharing about your flight success!

  2. Nick

    Hey, Scott! This is awesome! When it comes to traveling with multiple people, how would you recommend handling? Should I consider trying to get a companion pass for both my wife AND me so that two of our three kids fly for free?

    • I Dream of FIRE

      If you can swing two companion passes, that’s an amazing way to go. Not only will you get two flights free, but you’ll have double the points to buy the three tickets you still need.

      Explore your options for the two cards. Right now the Plus and Premier offer 50K bonuses after you meet the required $2K spend on each, which would leave you in the neighborhood of $6,000 more per person to hit 110,000 points and earn the Companion Pass. That’s $10,000ish in total spending to get the pass.

      However, the Business version of the card offers 60,000 points when you spend $3K. If you get a Plus and a Business, you could have 115,000+ points after just $5K in total spend. If you can do that for both you and your wife, that’s more than double the points for the same amount of spend in total! Just remember that business cards are available for almost anything you can call a business — selling stuff on eBay, running a blog, any side hustle. Chase isn’t the IRS 🙂

  3. Michelle

    This is the definition of thrifty! I am intrigued by this for later when the twins will be bigger and it will be easier to fly with them. I wouldn’t attempt it now. We would have a flight full of angry co-passengers, I think.

    I do have a business that I could get a business card with though! I’ll have to keep that tip in my back pocket. Thank you!

  4. Nick

    Great tips!!!
    You said “I’m starting to think about my next rewards card.”. So I’m curious; do you keep opening new cards to take advantage of sign up bonus points? Do you close the old cards at all?

    • I Dream of FIRE

      You’re curious? Way to be on brand! 🙂 I don’t intend to open a new card every month like some people do, but I’ll definitely be opening cards as they make sense for what we want to do travel-wise. I’ll close the old cards, probably around the time the annual fee is due. With most cards, including the Chase ones I opened already, you can get the point bonuses again every two years. So you want to close those cards for several months and then reapply just after your two-year mark to get the bonus again.

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