Next article Southwest’s Big Shake-Up: What You Need to Know Before May 28th
Southwest just dropped a video update featuring Tony Roach, EVP of Customer & Brand, answering burning questions about the airline’s upcoming changes. While some details are still under wraps, here’s what we do know — and what savvy travelers should prepare for before May 28, 2025.
Let’s break it down:
🧳 Who Still Gets Free Checked Bags?
Southwest has always been known for its generous baggage policy. That’s changing — but some travelers will still keep the perk:
A-List Preferred: 2 free checked bags
A-List & Primary Cardholders: 1 free checked bag
Good news: These benefits now extend to up to 8 people on the same reservation — competitive with other airlines.
✈️ Pro tip: If you travel with family or groups, this is a major cost-saver if one person holds status or a Southwest credit card.
💰 What Will Checked Bags Cost?
They didn’t release exact prices yet, but Southwest says fees will be “in line with industry standards.” That likely means:
1st bag: ~$35
2nd bag: ~$45–$50
We’ll get final pricing closer to the May 28 launch. Until then, enjoy the free bags while they last.
🗓️ What If I Book My Flight Before May 28?
Flights booked before May 28 will still include the old benefits — including free bags — even if the travel date is later. But there’s a catch:
⚠️ If you change the flight after May 28, your booking will likely be reprocessed under the new rules. So saving $20 by rebooking could cost you $50 in bag fees.
👯 What About Companion Pass Flights?
Yes, your Companion Pass still gets free bags — but it’s clunky.
The companion ticket has a separate confirmation number
You’ll have to pay up front for their bags and get reimbursed later
That could mean skipping kiosks and standing in line
Not a deal-breaker, but it’s a disappointing IT hiccup.
🎯 What’s the Deal with Points Redemptions?
Here’s where it gets dicey.
Southwest is moving to variable point redemptions. The language was carefully chosen:
Low-demand flights will have lower points cost
Peak flights may cost more
Some flights will stay “similar” to today’s pricing
What worries me: this could be a multiplier on top of already high cash prices. If a peak flight in cash is $800 (versus $200 off-peak), and they now increase the points needed beyond today’s rates, the value of your Rapid Rewards could drop significantly.
❓ Open Questions Still Remain
Travelers (myself included) still want clarity on:
Will changing a pre-May 28 booking after May 28 forfeit old perks?
Will Basic fares be cheaper to reflect the unbundling?
How will the system track free bags for post-May 28 flights booked under the old rules?
How low will Rapid Rewards points go in value — is there a guaranteed floor?
Plus — we still haven’t heard anything about the new cardholder benefits. Why wait to announce them if they’re positive? Could be a red flag… or just more marketing suspense.
💡 Final Takeaway
Southwest is making its biggest changes in years — and May 28 is the date to watch. If you have Rapid Rewards points or travel booked (or plan to), you need to be strategic:
Book flights now to lock in legacy benefits
Avoid changing flights after May 28 unless you’re sure it makes financial sense
Watch for devaluation in points redemptions
Status and credit cards will be more valuable than ever
🔗 Need a Southwest credit card or looking to earn travel perks fast?
