How We Flew Our Family of 5 to Disney for Free
Disney trips are expensive enough. Here’s how we saved over $1,750 by flying Southwest — and how you can do it too with one simple strategy.
If you’ve ever priced out flights for a Disney trip as a family, you know how fast the costs add up. For us—two adults and three kids—the total came to $1,750 in flights alone.
But we paid $0 out of pocket for those tickets.
Thanks to a smart two-card strategy with Southwest and a few lesser-known perks, we not only covered the flights with points—we actually got 20,000 points back after we rebooked at a lower price.
💼 Real-World Savings Breakdown
Here’s how flying Southwest and using two credit card sign-up bonuses saved our family over $1,700 on flights:
Most Airlines
Roundtrip tickets for 5 people: $1,400
Repricing credit (fare dropped): No option to re-book for reduced price 😔
Checked bags (1 per person at $40/bag): $200
Seat selection fees: ~$150
✅ Total: $1,750+
Southwest (with 2-player strategy)
Roundtrip tickets: Fully covered with 100,000 points*
Repricing credit (fare dropped): Got 20,000 points back!
Checked bags: $0
Seat selection fees: $0
✅ Total saved: Over $1,750
*We each signed up for a Southwest credit card and earned 50,000 points apiece. Together, we had 100,000 points—enough to cover all five roundtrip tickets to Orlando.
💳 The Credit Card That Made It Happen
The secret? We each opened a Southwest credit card.
Each sign-up bonus gave us 50,000 points, worth about $700 in flight value. Combined, that was more than enough to cover our five roundtrip tickets—and every purchase we made for the trip earned us even more points.
Better still: those points also count toward earning the Southwest Companion Pass, which lets one of us fly free (plus taxes) every time we travel together.
👉 [Apply here to get your 50,000-point bonus »]
🧠 Why Southwest Is Perfect for Family Travel
✅ 2 free checked bags per person (note this is changing soon but credit card holders still get 1 free checked bag for up to 8 guests on their reservation!)
✅ No change or cancellation fees
✅ No seat selection fees—you can still sit together
✅ You can reprice flights when fares drop and get points back
✅ Lots of nonstop options to Disney (Orlando MCO)
This is the kind of flexibility we didn’t even know we needed until we started traveling with three kids.
💡 Pro Tip #1: Book Early, Rebook When Prices Drop
Southwest lets you rebook at a lower fare if prices drop. Before our trip, we saw a price drop of 5,000 points per ticket—and we were able to rebook with a few clicks and got 20,000 points back.
No fees. No penalties. Just more points for the next trip.
💡 Pro Tip #2: Maximize Points with a Referral Bonus
If you’re not in a rush to book, here’s a smart way to earn even more points:
One of you applies for the Southwest card first.
Once approved, you’ll get a referral link.
Your spouse then applies using that link—you’ll earn an extra 20,000 points just for the referral.
That’s on top of both of you earning your own 50,000-point bonuses.
It’s a great way to start building toward the Companion Pass even faster.
