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$59 Flights Available For Southwest’s Valentines Day Sale

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Big Price Drops On Domestic And Caribbean Destinations

Southwest has announced their newest Valentine's Day sale, with flights going for as low as $59 on some routes. The sale covers flights across the US and into the Caribbean.

wing southwest

The sale, which has been named “Small Fare. Big Heart” has hundreds of flights listed in the hopes of enticing some romantic getaways, or just those who like to grab a travel bargain.

The fares included in the sale must be booked before 11:59 PM on February 14th. Any flights purchased must fly between February 15th and May 18th. The dates give a sizable window for those looking to take advantage of the prices, especially those who already know they’ll be traveling domestically during that period.

vegas southwest

There is a 21-day advanced purchase rule in place, and the lowest prices are being marketed as Tuesdays and Wednesdays, so weekend getaways might be out of the question. The same routes over the weekend are coming in at over double the price in some cases.

Some notable flights in the sale come in the form of short-haul domestic flights. For example, a quick jaunt from New York, La Guardia to Baltimore is only $59 one-way. Those seeking a bit of sun or maybe a rollercoaster or two from the same airport can get to Orlando, Florida for just $84
Atlanta residents can think big and head to Austin, Texas for a few days with one-way flights coming in at $89.

southwest mountain

Chicago-based travelers can hit Austin, Boston, Houston, Kansas City, and Memphis for less than $100. One of the best domestic deals for Chicacgo however, is their $59 flight to Miami, letting those struggling with the cold grab some sun on South Beach.

Those in Hawaii can take advantage of some added exploration by using some of the $40 island hopper tickets going between islands like Honolulu and Maui.

cancun skyline

Of course, with it being a Valentine’s special, romantic getaways are a must for some. The sale does offer several great deals heading to the Caribbean lending plenty of opportunity for a couple to enjoy a really special break. Some of the deals aren’t as low as some recent airline specials, but it’s worth digging to find some gems.


LaGuardia and Boston both have flights heading to Nassau in the Bahamas for around $143 each way. If Fort Lauderdale’s sun isn’t quite enough, $107 flights to Turks and Caicos might be able to tempt some Floridians further South. For a little more, Fort Lauderdale offers flights to Cancun, Mexico and Havana, Cuba.

For $162 travelers can grab flights from Chicago to the Cayman Islands. Definitely, a tempting option considering the recent temperatures plaguing the North of the US.


For the full list of flights as well as the prices for individual dates, check out Southwest’s sale website. Simply navigate to your local airport and you’ll be shown all the applicable flights from your chosen location. Accommodation will need to be booked separately.

Southwest has a brand new CEO who has already indicated some potentially interesting changes to the company. The biggest shock was the suggestion that the airline may begin assigning seats. Southwest has long been known for its seat policy allowing anyone to grab a seat when they board the plane.

southwest landing

The carrier also announced they will be phasing alcohol sales back into their flights after a long pause during the pandemic. Most airlines suspended alcohol sales in an attempt to commit unruly passengers who took issue with some of the new rules surrounding COVID.

Those hoping to travel abroad with Southwest should keep on top of the latest restrictions to their chosen country. Rules can change quickly, so being prepared may help avert disappointment. 

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