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Southwest® flights from and within Cayman Islands
Deals on flights from and within Cayman Islands
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$
Grand Cayman (GCM)to
Baltimore/Washington (BWI)Depart: 05/23/2026
From
$203
Seen: 3 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Oakland (OAK)Depart: 05/23/2026
From
$249
Seen: 3 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Washington, D.C. (Reagan National) (DCA)Depart: 05/19/2026
From
$267
Seen: 5 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Austin (AUS)Depart: 05/14/2026
From
$308
Seen: 3 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Boston (BOS)Depart: 05/12/2026
From
$313
Seen: 23 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Orlando (MCO)Depart: 06/05/2026
From
$316
Seen: 1 hour ago
One-way
Basic
Grand Cayman (GCM)to
Chicago (Midway) (MDW)Depart: 05/28/2026
From
$329
Seen: 17 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Chicago (O'Hare) (ORD)Depart: 05/13/2026
From
$329
Seen: 1 hour ago
One-way
Basic
Grand Cayman (GCM)to
Miami (MIA)Depart: 05/15/2026
From
$350
Seen: 6 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Dallas (Love Field) (DAL)Depart: 05/18/2026
From
$351
Seen: 19 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Houston (Hobby) (HOU)Depart: 05/15/2026
From
$351
Seen: 6 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Atlanta (ATL)Depart: 06/01/2026
From
$351
Seen: 18 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Charleston (CHS)Depart: 05/29/2026
From
$376
Seen: 12 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Kansas City (MCI)Depart: 05/26/2026
From
$386
Seen: 16 hrs ago
One-way
Basic
Grand Cayman (GCM)to
San Diego (SAN)Depart: 05/22/2026
From
$400
Seen: 19 hrs ago
One-way
Basic
Grand Cayman (GCM)to
San Juan (SJU)Depart: 05/22/2026
From
$463
Seen: 19 hrs ago
One-way
Choice
Grand Cayman (GCM)to
Tulsa (TUL)Depart: 05/30/2026
From
$516
Seen: 2 hrs ago
One-way
Choice
*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
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flight_land
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From | To | Fare Type | Dates | Price |
|---|---|---|---|---|
| Grand Cayman (GCM) | Orlando (MCO) | One-way / Basic | Depart: 11/26/2026 | From $247 Seen: 21 hrs ago |
| Grand Cayman (GCM) | Tampa (TPA) | One-way / Basic | Depart: 07/11/2026 | From $258 Seen: 18 hrs ago |
| Grand Cayman (GCM) | Fort Lauderdale (FLL) | One-way / Basic | Depart: 07/08/2026 | From $288 Seen: 11 hrs ago |
| Grand Cayman (GCM) | Baltimore/Washington (BWI) | One-way / Basic | Depart: 08/29/2026 | From $293 Seen: 23 hrs ago |
| Grand Cayman (GCM) | San Diego (SAN) | One-way / Basic | Depart: 07/15/2026 | From $297 Seen: 5 hrs ago |
| Grand Cayman (GCM) | Boston (BOS) | One-way / Basic | Depart: 12/28/2026 | From $313 Seen: 14 hrs ago |
| Grand Cayman (GCM) | Chicago (Midway) (MDW) | One-way / Basic | Depart: 07/08/2026 | From $329 Seen: 6 hrs ago |
| Grand Cayman (GCM) | Pittsburgh (PIT) | One-way / Basic | Depart: 07/09/2026 | From $342 Seen: 22 hrs ago |
| Grand Cayman (GCM) | Albuquerque (ABQ) | One-way / Basic | Depart: 06/24/2026 | From $347 Seen: 19 hrs ago |
| Grand Cayman (GCM) | Raleigh/Durham (RDU) | One-way / Basic | Depart: 07/09/2026 | From $351 Seen: 12 hrs ago |
| Grand Cayman (GCM) | Houston (Hobby) (HOU) | One-way / Basic | Depart: 07/13/2026 | From $356 Seen: 23 hrs ago |
| Grand Cayman (GCM) | Oakland (OAK) | One-way / Basic | Depart: 07/11/2026 | From $359 Seen: 2 hrs ago |
| Grand Cayman (GCM) | Birmingham (BHM) | One-way / Basic | Depart: 06/28/2026 | From $366 Seen: 4 hrs ago |
| Grand Cayman (GCM) | Albany (ALB) | One-way / Basic | Depart: 12/09/2026 | From $376 Seen: 6 hrs ago |
| Grand Cayman (GCM) | Sacramento (SMF) | One-way / Basic | Depart: 07/22/2026 | From $391 Seen: 20 hrs ago |
| Grand Cayman (GCM) | Miami (MIA) | One-way / Basic | Depart: 08/02/2026 | From $396 Seen: 23 hrs ago |
| Grand Cayman (GCM) | Phoenix (PHX) | One-way / Basic | Depart: 06/22/2026 | From $401 Seen: 18 hrs ago |
| Grand Cayman (GCM) | Denver (DEN) | One-way / Basic | Depart: 12/02/2026 | From $403 Seen: 17 hrs ago |
| Grand Cayman (GCM) | Austin (AUS) | One-way / Basic | Depart: 06/26/2026 | From $413 Seen: 3 hrs ago |
| Grand Cayman (GCM) | Atlanta (ATL) | One-way / Basic | Depart: 08/03/2026 | From $416 Seen: 1 hour 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.
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