Southwest® flights from and within Cayman Islands
Deals on flights from and within Cayman Islands
Grand Cayman (GCM)to
Austin (AUS)
Grand Cayman (GCM)to
Baltimore/Washington (BWI)
Grand Cayman (GCM)to
Charlotte (CLT)
Grand Cayman (GCM)to
Fort Lauderdale (FLL)
Grand Cayman (GCM)to
St. Louis (STL)
Grand Cayman (GCM)to
Raleigh/Durham (RDU)
Grand Cayman (GCM)to
New York (LaGuardia) (LGA)
Grand Cayman (GCM)to
Kansas City (MCI)
Grand Cayman (GCM)to
Los Angeles (LAX)
Grand Cayman (GCM)to
Dallas (Love Field) (DAL)
Grand Cayman (GCM)to
Indianapolis (IND)
Grand Cayman (GCM)to
Orlando (MCO)
Grand Cayman (GCM)to
Albany (ALB)
Grand Cayman (GCM)to
Miami (MIA)
Grand Cayman (GCM)to
Houston (Hobby) (HOU)
Grand Cayman (GCM)to
Nashville (BNA)
Grand Cayman (GCM)to
Long Island/Islip MacArthur (ISP)
Grand Cayman (GCM)to
Atlanta (ATL)
Grand Cayman (GCM)to
Las Vegas (LAS)
Grand Cayman (GCM)to
Columbus (CMH)*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.
Find popular low fares from and within Cayman Islands
From | To | Fare Type | Dates | Price |
|---|---|---|---|---|
| Grand Cayman (GCM) | Orlando (MCO) | One-way / Basic | Depart: 04/15/2026 | From $202 Seen: 12 hrs ago |
| Grand Cayman (GCM) | Baltimore/Washington (BWI) | One-way / Basic | Depart: 03/14/2026 | From $208 Seen: 10 hrs ago |
| Grand Cayman (GCM) | Washington, D.C. (Reagan National) (DCA) | One-way / Basic | Depart: 04/08/2026 | From $218 Seen: 12 hrs ago |
| Grand Cayman (GCM) | Omaha (OMA) | One-way / Basic | Depart: 05/22/2026 | From $257 Seen: 17 hrs ago |
| Grand Cayman (GCM) | Indianapolis (IND) | One-way / Basic | Depart: 05/09/2026 | From $266 Seen: 4 hrs ago |
| Grand Cayman (GCM) | Miami (MIA) | One-way / Basic | Depart: 03/25/2026 | From $277 Seen: 1 hour ago |
| Grand Cayman (GCM) | Dallas (Love Field) (DAL) | One-way / Basic | Depart: 03/04/2026 | From $283 Seen: 4 hrs ago |
| Grand Cayman (GCM) | Chicago (O'Hare) (ORD) | One-way / Basic | Depart: 05/06/2026 | From $283 Seen: 17 hrs ago |
| Grand Cayman (GCM) | Nashville (BNA) | One-way / Basic | Depart: 05/01/2026 | From $295 Seen: 10 hrs ago |
| Grand Cayman (GCM) | Austin (AUS) | One-way / Basic | Depart: 04/01/2026 | From $311 Seen: 23 hrs ago |
| Grand Cayman (GCM) | San Antonio (SAT) | One-way / Basic | Depart: 06/09/2026 | From $312 Seen: 5 hrs ago |
| Grand Cayman (GCM) | Fort Lauderdale (FLL) | One-way / Basic | Depart: 03/25/2026 | From $326 Seen: 1 hour ago |
| Grand Cayman (GCM) | New Orleans (MSY) | One-way / Basic | Depart: 03/11/2026 | From $326 Seen: 13 hrs ago |
| Grand Cayman (GCM) | Denver (DEN) | One-way / Basic | Depart: 06/04/2026 | From $327 Seen: 17 hrs ago |
| Grand Cayman (GCM) | Tampa (TPA) | One-way / Basic | Depart: 04/01/2026 | From $331 Seen: 17 hrs ago |
| Grand Cayman (GCM) | Richmond (RIC) | One-way / Basic | Depart: 03/25/2026 | From $333 Seen: 15 hrs ago |
| Grand Cayman (GCM) | Minneapolis/St. Paul (MSP) | One-way / Basic | Depart: 04/08/2026 | From $334 Seen: 13 hrs ago |
| Grand Cayman (GCM) | Cleveland (CLE) | One-way / Basic | Depart: 05/04/2026 | From $337 Seen: 13 hrs ago |
| Grand Cayman (GCM) | Detroit (DTW) | One-way / Basic | Depart: 07/16/2026 | From $337 Seen: 9 hrs ago |
| Grand Cayman (GCM) | Houston (Hobby) (HOU) | One-way / Basic | Depart: 04/01/2026 | From $346 Seen: 23 hrs ago |
*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.