Southwest Airlines is preparing to make a major policy shift that will affect millions of travelers. Beginning Tuesday, May 28, 2025, the airline will start charging passengers for checked bags, ending its decades-long promise of allowing two free checked bags per customer. This move positions Southwest more closely with its domestic competitors, many of whom have long implemented baggage fees as part of standard fare structures.

Until now, Southwest’s generous baggage policy has stood out as a key selling point — particularly for families, frequent flyers, and budget-conscious travelers. But rising operating costs and industry-wide financial pressures have prompted the carrier to reconsider how it balances service perks with profitability.

Last Chance to Secure Free Bags for Future Trips

There’s a silver lining for those who act fast: passengers who complete their flight bookings by 11:59 PM on Monday, May 27, will retain the two free checked bags benefit, no matter when they travel. That means any flights scheduled for the remainder of 2025 and even into early 2026 can still qualify for the complimentary baggage policy — as long as the ticket is purchased before the deadline.

With Southwest’s booking schedule open through mid-January 2026, travelers looking ahead to winter holidays, New Year getaways, or spring trips have a clear incentive to finalize their plans immediately.

Booking Date, Not Travel Date, Determines Eligibility

A crucial detail in Southwest’s updated policy is that the new baggage fees apply only to bookings made on or after May 28. In other words, passengers flying in December or January who book before the May 27 cutoff will still enjoy the airline’s two-bag allowance. This makes the next few days a strategic moment to secure savings for the long term.

The announcement is expected to trigger a spike in last-minute bookings, especially from loyal Southwest customers hoping to avoid future fees.

Why Southwest Is Introducing Bag Fees Now

For years, Southwest has built its brand around simplicity and value — no change fees, no hidden charges, and free checked luggage. However, the airline industry has undergone major shifts, with increased fuel prices, inflationary trends, and growing labor and maintenance costs placing pressure on carriers to find new revenue streams.

By adopting a baggage fee model, Southwest is following in the footsteps of most other major US airlines, which have long capitalized on checked bag charges as a lucrative income source. While exact pricing has yet to be announced, estimates suggest fees could range from thirty to forty dollars for the first bag, with higher charges for additional or oversized items.

Memorial Day Timing Signals Strategic Intent

The timing of the policy change is no coincidence. By implementing the new fees immediately after the Memorial Day weekend, Southwest avoids disrupting one of the busiest travel periods of the year — while also creating a sense of urgency for travelers to book now. The decision aligns with seasonal booking patterns, when many Americans solidify their summer travel plans.

This strategy not only boosts short-term bookings but also softens the potential backlash from customers who associate the brand with cost-free benefits.

Customer Loyalty Could Be Tested

The phrase “Bags Fly Free” has become synonymous with Southwest Airlines and has served as a strong brand differentiator in a crowded marketplace. Removing that benefit introduces a risk — especially for loyal customers who have long praised the airline’s customer-friendly policies.

To preserve goodwill, Southwest may need to introduce alternative benefits or promotional fare structures to offset the policy shift. How the airline handles this transition — from communication to customer support — will play a major role in determining the long-term impact on brand perception.

How to Avoid Paying Baggage Fees

For travelers who want to continue enjoying Southwest’s two free checked bags, the path is clear:

• Book Before the Deadline: Purchase your flights by the end of May 27 to lock in the free bag allowance.
• Plan Ahead for Future Travel: Take advantage of the open booking window through January 2026 to secure winter and holiday travel now.
• Use Change-Friendly Policies: Since Southwest doesn’t charge for flight changes, there’s minimal risk in booking early.
• Look Out for Sale Fares: Combining discounted tickets with free luggage offers a chance to maximize overall savings.

A New Chapter in Southwest’s Evolution

The move to implement checked baggage fees marks a significant turning point in Southwest’s operational strategy. Though the airline has long resisted many of the fee-driven practices common across the industry, the economic landscape has made such adjustments difficult to avoid.

Yet for now, Southwest is offering travelers one last opportunity to benefit from its hallmark perk. By acting before May 28, customers can protect themselves from added costs and continue enjoying the convenience of free checked bags, even months down the line.

The post Southwest Airlines Announces End of Its Popular Free Bag Policy With New Fees Taking Effect May 28, Creating a Final Opportunity for Travelers to Book and Keep the Benefit appeared first on Travel And Tour World.