Southwest Expands Caribbean Network With New Puerto Rico Connections

MundoTrip | Travel News | September 24, 2026

Southwest Airlines is expanding its Caribbean network, giving U.S. travellers more ways to reach destinations including Puerto Rico, St. Thomas and St. Maarten. The airline has added new routes to its network during 2026 while continuing to operate services to several established Caribbean destinations.

The expansion gives travellers more options when planning Caribbean holidays from different parts of the United States, with Puerto Rico receiving particular attention through new and expanded connections.

New Southwest Flights Strengthen Puerto Rico Connectivity

Southwest added a new Indianapolis–San Juan service in 2026 and has also opened bookings for a new Columbus–San Juan route. The Columbus service is scheduled to begin in January 2027, operating once a week on Saturdays.

San Juan is already connected to several cities across the United States through Southwest's network, including Fort Lauderdale, Orlando, Tampa, Chicago, Baltimore, St. Louis, Nashville, Austin and Houston.

The additional services give travellers in more U.S. cities another option for reaching Puerto Rico without having to rely on existing departure points.

Southwest Continues Expanding Across the Caribbean

Southwest Adds More Caribbean Destinations

Puerto Rico is part of Southwest's wider Caribbean expansion.

The airline currently serves several Caribbean destinations, including Aruba, Grand Cayman, Montego Bay, Nassau, Punta Cana, Turks and Caicos, and St. Maarten.

Southwest also added St. Thomas in the U.S. Virgin Islands to its network in 2026. Service to the island began earlier this year, providing another Caribbean option for travellers flying from the United States.

The airline also launched service to St. Maarten in April 2026, adding another international destination to its network.

More Choices for U.S. Caribbean Travellers

For U.S. travellers, the expanded network means more choices when selecting both a Caribbean destination and a departure airport.

Puerto Rico can be particularly convenient for travellers looking for a Caribbean getaway with connections from multiple U.S. cities, while destinations such as St. Thomas and St. Maarten provide additional options for beach holidays and island trips.

Travellers should check the operating schedule for their specific route before booking, as some Caribbean services may operate on selected days or according to seasonal schedules.

Southwest Continues to Grow Its Caribbean Network

Southwest's latest additions show the airline's continued development across the Caribbean, with new services complementing its existing network.

As more routes become available, travellers can compare different departure cities, destinations and travel dates when planning future Caribbean trips.

For the latest airline route announcements, schedule changes and international travel developments, MundoTrip keeps travellers informed to help them plan their next journey.