Picture this: It’s the middle of winter, and you’ve just boarded a two- or three-hour flight to the Caribbean — and you don’t even need a passport.
That will soon be the reality for two U.S. cities that are set to get brand-new Southwest Airlines flights to the U.S. Virgin Islands.
Starting in February, Southwest will fly nonstop to St. Thomas’ Cyril E. King Airport (STT) from two of its busiest East Coast bases: Baltimore/Washington International Thurgood Marshall Airport (BWI) and Orlando International Airport (MCO).
Southwest’s new Orlando-St. Thomas service is first up, launching on Feb. 5. The new flight will make St. Thomas the first new destination for the Dallas-based carrier in almost five years; you have to go back to its 2021 Syracuse, New York, service (later canceled) to find the last time Southwest launched a new city.
And with all due respect to Syracuse, St. Thomas is a far more alluring mid-winter destination — one that boasts an array of resorts that you can book using points.
Marriott breathes new life into a beloved Caribbean resort: A review of The Westin Beach Resort & Spa at Frenchman’s Reef
Southwest’s 2 new St. Thomas flights
Southwest’s flights between Orlando and St. Thomas will run daily all year long.
The BWI flights to the USVI will launch on Feb. 7.
St. Thomas isn’t the end of Southwest’s expansion. Earlier this month, TPG reported the carrier had plans to announce two additional all-new cities as it begins expanding its route network, again, after uncharacteristic cuts last year. No word yet, however, on what or when those other two cities might be announced.
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Southwest assigned seats now for sale
The announcement of BWI and MCO flights to St. Thomas came on the same day Southwest started selling assigned seats for the first time, on Tuesday. Those seat assignments (including its brand-new extra legroom seats) will apply to bookings made from Jan. 27, 2026 onward — including these new Caribbean routes.
Keep in mind, Southwest’s basic fares do not come with complimentary seat selection, unless you have Rapid Rewards elite status or carry one of its cobranded credit cards.
Read more: 1 in 4 Southwest planes now have extra-legroom seats — Here’s how to snag one
Southwest’s new Choice fare comes with standard seat selection. Choice Preferred gives you access to a normal seat closer to the front of the plane. Choice Extra gets you access to the extra legroom seats (not to mention two free checked bags).
Keep in mind, all Southwest credit cards now come with some form of seat selection (even on basic fares) and a free checked bag for the primary cardholder and up to eight companions flying on the same reservation.
Read more: Southwest unveils big credit card refresh: 50% fee hikes, but new seating and boarding perks
Beach, warm weather and ski destinations highlight returning winter routes
Beyond announcing two new St. Thomas routes, Southwest opened up its schedule for booking through March 4, 2026, and confirmed the (expected) return of 24 seasonal routes, effective Jan. 27.
Those include:
- Chicago’s O’Hare International Airport (ORD) to Cancun international Airport (CUN)
- Chicago O’Hare to Denver International Airport (DEN)
- Chicago O’Hare to Fort Myers’ Southwest Florida International Airport (RSW)
- Fort Lauderdale-Hollywood International Airport (FLL) to Providence’s TF Green International Airport (PVD)
- Albany International Airport (ALB) to Fort Myers
- Albany to Sarasota Bradenton International Airport (SRQ)
- Austin Bergstrom International Airport (AUS) to San Juan, Puerto Rico’s Luis Munoz International Airport (SJU)
- Hartford’s Bradley International Airport (BDL) to Fort Myers
- Nashville International Airport (BNA) to Colorado’s Yampa Valley Regional Airport (HDN)
- Nashville to Punta Cana International Airport (PUJ)
- Boston Logan International Airport (BOS) to Orlando
- Buffalo Niagra Internatinal Airport (BUF) to Palm Beach International Airport (PBI)
- BWI to Providenciales International Airport (PLS) in Turks and Caicos
- Dallas Love Field (DAL) to Palm Springs International Airport (PSP)
- Detroit Wayne County Metropolitan Airport (DTW) to Phoenix Sky Harbor International Airport (PHX)
- Long Island MacArthur Airport (ISP) to Fort Lauderdale
- Houston Hobby Airport (HOU) to Sangster International Airport (MBJ) in Montego Bay, Jamaica
- Houston Hobby to Sarasota
- New York’s LaGuardia Airport (LGA) to Tampa International Airport (TPA)
- Portland International Jetport (PWM) in Maine to Orlando
- Salt Lake City International Airport (SLC) to Orlando
- Tulsa International Airport (TUL) to Orlando
- Chicago’s Midway Airport (MDW) to Palm Springs
- Milwaukee Mitchell International Airport (MKE) to Miami International Airport (MIA)
- Providence to West Palm Beach
- Frederick Douglass Greater Rochester International Airport (ROC) to Fort Myers
- Louisville International Airport (SDF) to Fort Myers
Many of these routes will operate with less-than-daily service to prime warm-weather, beach (and skiing) destinations during the cold winter months.
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