Last week I flew from Dallas to Colorado Springs to… see a movie.
I’ll start by acknowledging the privilege and frivolity involved here. The idea of flying to another state, spending the night, watching a movie, and then turning around and flying home sounds pretty ridiculous on its face.
So why did I do it?
Chasing Another Companion Pass
The Southwest Companion Pass has been called one of the best deals in the travel hacking world, and for Katie and me it has certainly lived up to that reputation. One or the other of us has had a pass for most of the past ten years, and we have probably gotten more than 100 free flights from it.
I’ve never tried very hard to calculate how much money we “saved” because that isn’t really how we used it. Many of those were trips we never would have taken if we had needed to buy a second ticket. The Companion Pass gave us the freedom to take more trips, add a weekend somewhere, or have Katie tag along when I was already traveling for work.
Looking ahead, though, I’m not sure it will continue to be as valuable for us. I’m flying less for work, which means fewer opportunities to bring Katie along on a reimbursed ticket, and changes to Southwest and the associated Chase credit card programs have made earning the pass more difficult and using it less attractive.
That made a recent Southwest promotion interesting. The rules were pretty simple. Register for the promotion, book a qualifying round trip or two one-way flights by August 6, and complete the travel by November 18. In return, I could earn a promotional Companion Pass valid from January 5 through March 3, 2027.
The math seemed pretty straightforward. If I could complete a relatively inexpensive trip now and save more than that amount on Katie’s flights next year, I would come out ahead.
We already have several trips in mind for early 2027, including Hawaii, so finding more than $200 of value from the pass shouldn’t be difficult.
Now I just needed somewhere to go.
The Mileage Run
I started by looking for a simple mileage run from Dallas Love Field. Houston? Austin? Lubbock? Fly somewhere, turn around, and come home.
Unfortunately, last-minute fares on the shortest routes were higher than I expected.
Then I found Colorado Springs.
I could fly there for about $250 and come straight home, but if I stayed overnight and returned the next day, the airfare dropped to about $200. Normally the cost of a hotel would wipe out the savings, but I had a free-night certificate that was about to expire anyway.
Suddenly, I had an overnight trip to Colorado Springs.
Now I just needed something to do.
Wait… There’s an IMAX Theater?
Katie and I had just visited Colorado Springs, so I wasn’t particularly interested in repeating the tourist stops we had done a few weeks earlier. It was also really hot, and with less than a day to acclimate to the altitude, a long hike didn’t sound particularly appealing.
Then I remembered something a local had told me during our previous visit.
Colorado Springs has one of only 26 theaters in the United States capable of showing movies in 70mm IMAX. Dallas has one too, but tickets for The Odyssey had been sold out for months. Our son managed to get one, but he was sitting in the corner of the front row for a 2:30 AM showing!
On a whim, I checked Colorado Springs. Plenty of seats. Apparently, when you live next to mountains, hiking trails, and the Garden of the Gods, sitting inside a movie theater isn’t quite as exciting. 🙂
For my purposes, though, it was perfect.
So What Did This Actually Cost?
Here was the damage:
- Round-trip flight from Dallas to Colorado Springs: $200
- Hotel: free with an expiring certificate
- Lyft between the airport, hotel, and theater: $39, minus a $10 Sapphire Reserve credit
- Movie ticket: $25
That put my out-of-pocket cost at about $254.
In exchange, I earned a promotional Companion Pass that I should be able to use for several flights during the first two months of 2027. Based on the trips we are considering, I estimate that Katie’s tickets during that period could easily cost $1,500 to $1,800.
Of course, that doesn’t mean I “made” $1,500 by going to a movie. We have to actually take those flights for the savings to be real, and there was still a very real $254 charged to our credit card this week.
But I like my odds. 🙂
Was This Really About Saving Money?
I am certainly not recommending that everyone start flying to other states to see movies in the name of financial responsibility.
There were other factors at play.
It is August in Texas. Temperatures are routinely over 100 degrees, school has started again, and even our local pool has reduced its hours. I had been home for a while and was getting restless waiting for our Fall travels to start.
So I spent $254, got a quick adventure, used a hotel certificate before it expired, saw a movie in a format I couldn’t easily see at home, and potentially unlocked $1,500 or more of future travel.
That seems like a pretty good trade to me.
It also illustrates a few things I enjoy about financial independence and travel hacking. One is simple arbitrage. Sometimes spending a little money today creates an opportunity to save considerably more later. Another is learning how the programs you use actually work and looking for opportunities around the edges. Promotions, points, credits, certificates, and loyalty programs can be stacked together in ways that create some pretty interesting possibilities.
Most importantly, though, financial independence has given us the freedom to occasionally do something just because it sounds fun.
Years ago, taking a random overnight trip in the middle of the week would have required vacation days, schedule juggling, and probably more justification than I was willing to give it. Today, I can see an interesting opportunity, do the math, check my calendar, and occasionally say, “Why not?”
Was flying to Colorado Springs to see a movie necessary?
Absolutely not.
Was it the most efficient possible use of $254?
Probably not that either.
But I had a great little adventure, and if Katie ends up flying to Hawaii for free because of it, I suspect I’ll feel even better about the decision. 🙂

