Southwest Companion Pass Success: Two Passes, Multiple Trips

Thanks to @thatjacobsongirl for sharing her family’s success with traveling all over the U.S. with two earned Southwest Companion Passes!

My entry-level travel points example isn’t jaw-dropping to most but it was certainly valuable to our family. All costs/savings mentioned are estimates as I didn’t track these details and can only access a portion of our Rapid Rewards records.

In the Summer of 2021, we started with the Southwest Rapid Rewards card in my hubby’s name. We quickly earned the sign up bonus with regular spending and received the bonus in time to earn the Companion Pass for a family trip to Maui September of 2021 and we used those points to pay for our 3 tickets. A few weeks before our trip, my hubby referred me for the same Southwest card. The referral bonus he earned gave him enough points to achieve a Companion Pass for the remainder of 2021 plus all of 2022. I canceled our son’s Maui ticket I paid with points and added him as my husband’s companion instead and re-booked his ticket. We chose to fly to LA first then out to Maui the following day.
ESTIMATED COST FOR 3 RT TICKETS FROM KC TO LAX TO MAUI $1434 ($478 EACH); OUR COST $67.20 PLUS ABOUT 72,000 POINTS

We used the new Southwest card I got for our expenses on our trip and I was able to earn my signup bonus just in time before the end of the bonus period. My bonus had not been as good as one they offered a few weeks after I opened my card so I called Southwest and they gave me a chance to earn the difference with an additional spend. That extra bonus didn’t hit my account until 2022. In March of 2022, my hubby and I went to Maui again by ourselves using Southwest points and his Companion Pass which he switched to my name. I believe Southwest was running a promo for deeply discounted tickets to Hawaii at the time which explains why it didn’t cost us much in points!
ESTIMATED COST FOR 2 RT TICKETS FROM KC TO MAUI $578 ($289 EACH); OUR COST $22.40 PLUS 21,774 POINTS

Southwest ran a special promo in the Spring of 2022 if you booked a cash ticket and traveled by the end of May, you’d get bonus points that were Companion Pass eligible. I had already planned a 2-night trip to NYC in late May to celebrate my oldest daughter graduating college and to visit my middle kiddo who lives in Brooklyn. I had originally booked our 2 tickets for 24,458 points each but canceled both to take advantage of the promo. I re-booked by paying cash for my ticket and used Southwest points for my daughter’s ticket and upon our return, I received the promo bonus and that gave me enough to earn the Companion Pass on my account for the remainder of 2022 plus all of 2023.
ESTIMATED COST FOR 2 RT TICKETS FROM KC TO NYC $536 ($268 EACH); OUR COST $279.20 PLUS 18,436 POINTS

Just a couple weeks later, my husband used his Southwest points and Companion Pass to take our son to DC for their annual father/son trip to catch a Major League Baseball game.
ESTIMATED COST FOR 2 RT TICKETS FROM KC TO DC $544 ($272 EACH); OUR COST $22.40 PLUS 20,491 POINTS

Then, in October 2022, we took our son and his girlfriend on a family trip to San Diego using Southwest points and both of our Companion Passes.
ESTIMATED COST FOR 4 RT TICKETS FROM KC TO SAN DIEGO $1436 ($359 EACH); OUR COST $44.80 PLUS 54,012 POINTS

In total, we used approximately 186,713 Southwest Rapid Reward points and spent $574 ($436 for tickets/taxes/fees plus annual fee for 2 cards) for a trip to Maui for 3, a trip to Maui for 2, a trip to NYC for 2, a trip to DC for 2, and a trip to San Diego for 4.

Now that I’ve learned better strategies from Katie, I wouldn’t necessarily recommend the method in which we earned our Southwest Companion Passes, because we could’ve timed it to earn them earlier in the year. That being said, our method still worked for us perfectly because we didn’t overspend to meet sign-up bonuses, didn’t travel more than we would have normally and most importantly, we paid off our balances monthly to make the extras we earned really free.

Credit Cards You Can Use to Get Companion Pass