Southwest® flights to the Caribbean

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Visit the Caribbean.

When you visit the Caribbean, you’ll quickly recognize that no two islands are alike—though they may all have gorgeous sugar-sand beaches in common. From dancehall beats and reggae vibes to infectious salsa sounds, vibrant communities lure you to their island homes. Enjoy and discover vibrant histories, burgeoning modern urban settings, authentic foods, art unlike anything you’ve encountered before, and, of course, the unparalleled beaches. What are you waiting for? Your flight to the Caribbean is ready to be booked.

St. Thomas

Featured destination.

St. Thomas

Experience St. Thomas, a top U.S. Virgin Islands getaway with over 40 beaches. Unwind on Magens Bay, Sapphire Beach, and Coki Beach, then explore Charlotte Amalie and take in views from Drake’s Seat for the perfect mix of beaches, history, and island charm.

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Caribbean destinations

Aruba

Aruba

Grand Cayman

Grand Cayman

Havana

Havana

Montego Bay

Montego Bay

Nassau

Nassau

Punta Cana

Punta Cana

Turks and Caicos

Turks and Caicos

St. Maarten

St. Maarten

Low Fares to the Caribbean

Baltimore/Washington (BWI)to

Grand Cayman (GCM)
Depart: 01/03/2026
From
$98
One-way
Basic

Fort Lauderdale (FLL)to

San Juan (SJU)
Depart: 01/27/2026
From
$100
One-way
Basic

Washington, D.C. (Reagan National) (DCA)to

Grand Cayman (GCM)
Depart: 03/01/2026
From
$103
One-way
Basic

Orlando (MCO)to

Nassau (NAS)
Depart: 03/03/2026
From
$103
One-way
Basic

Fort Lauderdale (FLL)to

Nassau (NAS)
Depart: 12/11/2025
From
$104
One-way
Basic

Buffalo/Niagara Falls (BUF)to

San Juan (SJU)
Depart: 01/27/2026
From
$106
One-way
Basic

Rochester (ROC)to

San Juan (SJU)
Depart: 05/04/2026
From
$106
One-way
Basic

New Orleans (MSY)to

Grand Cayman (GCM)
Depart: 01/01/2026
From
$108
One-way
Basic

Nashville (BNA)to

San Juan (SJU)
Depart: 02/02/2026
From
$108
One-way
Basic

Chicago (Midway) (MDW)to

San Juan (SJU)
Depart: 01/22/2026
From
$113
One-way
Basic

Chicago (O'Hare) (ORD)to

San Juan (SJU)
Depart: 01/28/2026
From
$113
One-way
Basic

Washington, D.C. (Reagan National) (DCA)to

San Juan (SJU)
Depart: 03/09/2026
From
$113
One-way
Basic

*Fares displayed have been collected within the last 24 hours and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply. Modifying this information may result in a different fare. To find the most updated fare, please visit Southwest.com. Fares listed are Basic, which are subject to additional terms and conditions.

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