Southwest winter flash sale: Get one-way flights for as low as $29

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If you have family members you want to visit or you’ve just been itching to take time off for a short winter trip, then book your flights with this Southwest deal. The airline is having a three-day winter flash sale where one-way fares start as low as $29.

Up until Oct. 6., Wanna Get Away fares are available for many cities in the continental U.S., along with routes to Hawaii, Puerto Rico and some international destinations.

The deal extends to travel that takes place from Nov. 19 to Feb. 15. However, the deal doesn’t apply to flights from Dec. 16 to Jan. 9, so you won’t have much luck booking cheap Christmas and New Year’s travel.

Also, there are certain travel restrictions in this deal. For example, these low fares do not apply to continental U.S. travel on Fridays and Sundays. Additionally, low fares for travel to international destinations are only valid from Sundays to Wednesdays; the same discounts only apply to travel from international destinations from Tuesdays to Fridays.

Deal basics

Airline: Southwest Airlines.
Routes: Houston; New Orleans; New York; Chicago; Nashville; Myrtle Beach, South Carolina; Baltimore; Boston; Denver; Long Beach, California; San Jose, California; Kona, Hawaii; and many other cities.
How to book: Directly through Southwest’s website.
Travel dates: Nov. 19 to Feb. 15, but blackout dates last from Dec. 16 to Jan. 9.
Book by: Oct. 6.

Sample flights

Across the board, Southwest has slashed the prices of many of its Wanna Get Away fares, with the cheapest possible fares costing $29 one-way.

Here are a few highlights:

  • William P. Hobby Airport (HOU) to Louis Armstrong New Orleans International Airport (MSY), starting at $29 one-way.
  • Nashville International Airport (BNA) to Myrtle Beach International Airport (MYR), starting at $29 one-way.
  • Baltimore/Washington International Thurgood Marshall Airport (BWI) to Boston Logan International Airport (BOS), starting at $29 one-way.
  • Denver International Airport (DEN) to Long Beach Airport (LGB), starting at $63 one-way.
  • LaGuardia Airport (LGA) to Midway International Airport (MDW), starting at $69 one-way.
  • DEN to Los Angeles International Airport (LAX), starting at $69 one-way.
  • MDW to Charleston International Airport (CHS), starting at $69 one-way.
  • Norman Y. Mineta San Jose International Airport (SJC) to Kona International Airport (KOA), starting at $99 one-way.

While many routes primarily in Southwest’s network qualify for discounts under this deal, we found that certain routes — like New York to Boston, for example — are not included in this deal.

Since this deal will only last for two more days, we recommend booking your tickets as quickly as possible. The seats on these flights could fill up quickly with such low prices.

Looking through calendar dates for flights between Baltimore and Boston, the majority of days in January after the blackout dates are priced at $29; only flights taking off on Fridays and Sundays cost more at $79.

BWI to BOS calendar flights

Southwest’s Wanna Get Away fare includes two free checked bags and two carry-ons. Southwest has open seating for all fares, so you can choose your seat once you board the flight.

For a Jan. 19 flight departing Baltimore for Boston, Southwest has four low-fare options. At the time of publication, the 6:55 p.m. flight had only one low-fare seat left, according to Southwest’s website.

January 19 flight options

The schedule for returning flights to Baltimore on Jan. 24 had the $29 fare option for every flight.

BOS to BWI flights

The total for a round-trip flight from Baltimore to Boston comes out to $58. If you’d like, you could pay $40 more to upgrade both flights to Wanna Get Away Plus. Wanna Get Away Plus allows for same-day confirmed changes and has transferable flight credits.

BWI to BOS flight
Wanna get away plus

Maximize your purchase

Use cards that earn bonus points on airfare purchases like The Platinum Card® from American Express (5 points per dollar on airfare booked directly with the airline or through American Express Travel, on up to $500,000 on these purchases per calendar year), Citi Prestige® Card (5 points per dollar on airfare), Citi Premier® Card, Chase Sapphire Reserve (3 points per dollar on airfare), American Express® Gold Card (3 points per dollar on airfare when booked directly with the airline or through Amex Travel) or the Chase Sapphire Preferred Card (2 points per dollar on travel). The Southwest Rapid Rewards Priority Credit Card also lets you earn 3 points per dollar on Southwest purchases. Check out this post for more on maximizing airfare purchases.

The information for the Citi Prestige Card has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

Bottom line

After searching through some of the routes in this Southwest deal, we found that the majority of low Wanna Get Away fares are still available. However, the lowest fares are mostly available from December to the beginning of February. Southwest’s Low Fare Calendar doesn’t have as much availability in November. There are also blackout dates around Christmas.

Given how some of these fares have been significantly discounted, flights are certain to fill up the longer you wait to book your flights. So, make sure to buy your tickets as soon as you can.

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