Southwest’s Winter Sale Has Fares As Low As $29 — but You’ll Have to Book by Tomorrow

Travelers must book by 11:59 p.m. CT on Oct. 6.

Southwest Airlines kicked off a a winter sale offering travelers the chance to book flights across the United States and beyond starting at just $29. 

The sale, which the airline called “one of its largest and most iconic sales of the year,” has great deals across the country and even to Hawaii, Mexico, and several Caribbean destinations for travel from Nov. 29 through Feb. 15, 2023. To take advantage, travelers must book by 11:59 p.m. CT on Oct. 6.

“We’re making it easier for Customers to book their winter getaway with confidence,” Bill Tierney, the vice president of marketing and digital experience at Southwest Airlines, said in a statement. “Our low fares, combined with our enhanced Customer Experience… [ensure] we’re ready to serve our Customers and take them where and when they need to go.”

Travelers can fly between Houston and New Orleans, between Nashville and Myrtle Beach, and between Baltimore and Boston starting at just $29 one-way. Splurge a bit with a warm-weather getaway to Kona on Hawaii’s Big Island from San Jose in California starting at just $99 one-way. Or book a trip to Charleston from chilly Chicago starting as low as $69 one-way.

Southwest Airlines Boeing 737-7H4 arrives at Los Angeles international Airport

AaronP/Bauer-Griffin/Getty Images

The sale includes several blackout dates from Dec. 16 through Jan. 9, 2023. Typically, continental U.S. travel is not valid on Fridays or Sundays. Travel from the continental U.S. to Hawaii is valid on Sunday through Wednesday, travel from Hawaii to the continental U.S. is valid on Monday through Thursday, and interisland Hawaii travel is not valid on Fridays or Sundays.

Travel to international destinations is valid on Sundays through Wednesdays, while travel from international destinations is valid on Tuesdays through Fridays.

Beyond the sale itself, Southwest made it easier to island hop in Hawaii by extending its $39 offer for inter-island flights through the end of the year.

Southwest allows two checked bags for free and doesn’t charge change or cancellation fees for flights. Earlier this year, the airline also eliminated expiration dates on flight credits, started allowing customers to purchase a boarding upgrade online ahead of their flight, and introduced a new fare class, the Wanna Get Away Plus fare, which allows passengers to transfer eligible unused flight credits to someone for future use.

Southwest has also recently made plans to upgrade its flight experience with personal chargers, larger overhead bins, and upgraded Wi-Fi. 

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