Book One Southwest Roundtrip By Thursday, Earn Two Months Of Companion Pass — Bring Someone Free This Winter

Southwest Airlines is back with a familiar offer: register and book just one roundtrip—or two one-way flights—by Thursday, August 6, and you’ll earn a promotional Companion Pass valid January 5 – March 3, 2027 after completing the travel by November 18.

A Companion Pass lets you designate someone to travel with you for just the cost of taxes and fees, starting at $5.60 each way. It works whether you buy your own ticket with cash or redeem Rapid Rewards points, and there’s no limit to how many times you can use it during the promotional period as long as there’s a seat available.

Here are the details:

• Register before booking.
• Book one roundtrip or two one-way Southwest flights by 11:59 p.m. Central on August 6.
• Complete the qualifying travel by November 18.
• Cash, Rapid Rewards points and Cash + Points bookings all qualify.
• All four fare types qualify, including Basic Economy which was excluded from last August’s version of this promotion.
• Existing reservations don’t count, though you can cancel and rebook after registering if the fare hasn’t gone up too much. (I literally booked a Southwest flight hours before this promo came out)
• Changes made after August 6 may eliminate eligibility, so don’t plan on repeatedly repricing or moving these tickets.
• Companion Pass, charter, group and Getaways by Southwest travel doesn’t qualify.

A connection still counts as one one-way flight, not two. You can change your designated companion three times during the promotional pass period. However, those changes count against your 2027 allowance if you later earn a regular Companion Pass that year.

This Can Be A Huge Offer If Both Travel Windows Work

If you already have Southwest travel planned through November 18, register and check whether cancelling and rebooking leaves you no worse off. In that case, you’re earning something valuable for almost nothing.

I took advantage of the February version of this offer. My wife and I each earned promotional Companion Passes and our kids are our companions. When a family of four can travel for the price or points of two tickets, this gets valuable very quickly.

The pass is only valid for 58 days, and it expires before most spring breaks. I wouldn’t buy an unnecessary expensive trip this fall just to qualify unless I was reasonably certain the companion travel would be worth more than the qualifying fare and my time.

Why Southwest Keeps Doing This

By running a short-term promotion like this, Southwest generates incremental ticket sales immediately. Then it limits Companion Pass use to a period when it expects to have plenty of empty seats.

• Qualifying travel runs through November 18, ending before Thanksgiving.
• Companion travel begins January 5, after the holidays.
• It ends March 3, before most spring break travel.

Southwest is giving away inventory when the marginal cost of adding a passenger is low. But the member still has to buy a ticket or redeem points, and may choose Southwest for a trip that otherwise would have gone to a competitor. Some customers will qualify and never use the pass at all.

The promotion also creates two Southwest trips out of one: travel this fall to earn it, then return during the winter to use it. And it lets new Rapid Rewards members experience what is arguably the single best domestic airline loyalty benefit.

Southwest has run a late-summer version of this offer every year since 2021. It ran another version this past February, and in 2024 even restricted one to Hawaii travel when those flights were underperforming. And after eliminating open seating and universal free checked bags, Companion Pass is one of the few pieces of the old Southwest value proposition that remains unique.