The carrier is bringing back 28 seasonal routes and adding six new ones to its winter network — with a heavy focus on warm-weather Caribbean and Latin American destinations.
Southwest Airlines is making a major push back into the Caribbean and Mexico for the winter 2027 travel season.
The carrier has opened booking for its February 2027 flight schedule, with a notable expansion of warm-weather routes designed to capture the peak demand window between the holiday season and Spring Break — a stretch when travelers from the northern United States typically book heavily into Florida, California, Mexico and the Caribbean.
The schedule includes 28 seasonal routes returning to the Southwest network, alongside six new routes — a meaningful expansion at a moment when the airline has been steadily building out its Caribbean and Latin American presence.
For travelers heading to Mexico, the Caribbean and Central America, several of the new and returning routes stand out.
What’s New for the Caribbean and Latin America
Southwest is launching first-time service between Nashville and Liberia, Costa Rica, opening a new direct connection from the southeastern United States to the Guanacaste region — one of the most-talked-about luxury and beach destinations in Central America right now.
The airline is also launching first-time service between Columbus, Ohio and San Juan, Puerto Rico — a notable new route into the Caribbean from the Midwest, and one that adds meaningful airlift into Puerto Rico at a moment when the destination has been posting record tourism numbers.
Returning routes for the winter season include Nashville to San Jose, Costa Rica; Pittsburgh to Cancun, Mexico; and Indianapolis to San Juan, Puerto Rico. The Pittsburgh-Cancun service in particular is a meaningful return — connecting one of the largest US metro areas without direct Cancun service back to one of the busiest gateways in the Mexican Caribbean.
Why This Matters
The expansion lands at a notable moment for Caribbean and Mexican travel.
Cancun International Airport has continued to be one of the most-served airports in Latin America, with the broader Riviera Maya corridor functioning as one of the most aggressively expanding luxury and all-inclusive markets in the world. Puerto Rico has been posting record tourism numbers — including a 6.7 percent increase in first-quarter stayover arrivals — with strong forward booking data heading into 2027. Costa Rica’s Guanacaste region has emerged as one of the most-talked-about luxury beach destinations in Central America, with new resorts continuing to open across the corridor.
Across all three destinations, expanded Southwest service adds meaningful low-cost capacity from secondary US gateways that have historically been underserved on Caribbean and Latin American routes — particularly out of Nashville, Columbus, Indianapolis and Pittsburgh.
For destinations that have long depended on the major coastal gateways for US visitor traffic, the Southwest expansion opens up new source markets and meaningfully widens the airlift picture from the American interior.
The Bigger Picture
The new schedule reflects a continuing pattern at Southwest Airlines, which has been steadily building out its Caribbean and Latin American footprint over the past several years.
The airline now operates service to a wide range of destinations in the region, including Aruba, The Bahamas, Belize, Cancun, Cozumel, Costa Rica, the Dominican Republic, Jamaica, Liberia, Los Cabos, Mexico City, Montego Bay, Nassau, Puerto Rico, Punta Cana, San Jose and others — making it one of the more diversified low-cost carriers serving the Caribbean and broader Latin America market.
The February 2027 schedule includes five unique schedule structures designed to match peak and off-peak demand windows across the 64-day booking period. On lower-demand days, the airline will operate nearly 3,100 flights. On higher-demand days, the schedule expands to more than 4,300 flights. Overall, the carrier is offering more flights across each unique schedule compared to its January and February 2026 schedule.
Southwest has also continued to lean heavily into its Orlando International Airport operation, with up to 203 departures on high-demand Saturdays through the first two months of 2027 — reflecting both the strength of Florida as a winter travel market and Orlando’s role as a major connecting point for Caribbean and Latin American itineraries.
What It Means for Caribbean Travel
The new and returning routes give travelers from across the central and eastern United States new ways to reach some of the most-booked Caribbean and Latin American destinations next winter.
For Cancun and the broader Riviera Maya, the return of Pittsburgh service adds meaningful capacity from a major Midwestern metro that has been chronically underserved on direct Mexican Caribbean flights. For Puerto Rico, the new Columbus route and the returning Indianapolis service give the destination two new Midwestern gateways at a moment when the island has been actively diversifying its source markets. For Costa Rica, the new Nashville-Liberia route and the returning Nashville-San Jose service open up the Guanacaste corridor to travelers from the southeastern United States in a way that previously required connections.
Booking is now open for the full schedule through February 2027.
Caribbean Journal Staff
2026-06-11 15:03:00