Southwest® flights from and within Cayman Islands
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Deals on flights from and within Cayman Islands
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Grand Cayman (GCM)to
Baltimore/Washington (BWI)Depart: 12/20/2025
From
$207
Seen: 4 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Indianapolis (IND)Depart: 01/14/2026
From
$233
Seen: 20 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Orlando (MCO)Depart: 01/16/2026
From
$236
Seen: 6 hrs ago
One-way
Basic
Grand Cayman (GCM)to
St. Louis (STL)Depart: 12/19/2025
From
$263
Seen: 10 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Kansas City (MCI)Depart: 01/15/2026
From
$276
Seen: 9 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Louisville (SDF)Depart: 01/16/2026
From
$276
Seen: 10 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Boston (BOS)Depart: 12/23/2025
From
$283
Seen: 23 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Dallas (Love Field) (DAL)Depart: 12/19/2025
From
$311
Seen: 15 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Miami (MIA)Depart: 12/19/2025
From
$311
Seen: 19 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Fort Lauderdale (FLL)Depart: 12/20/2025
From
$331
Seen: 12 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Atlanta (ATL)Depart: 01/17/2026
From
$356
Seen: 23 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Denver (DEN)Depart: 01/08/2026
From
$356
Seen: 18 hrs ago
One-way
Basic
Grand Cayman (GCM)to
West Palm Beach (PBI)Depart: 01/09/2026
From
$366
Seen: 27 minutes ago
One-way
Basic
Grand Cayman (GCM)to
Washington, D.C. (Reagan National) (DCA)Depart: 01/11/2026
From
$384
Seen: 19 hrs ago
One-way
Basic
Grand Cayman (GCM)to
New York (LaGuardia) (LGA)Depart: 12/20/2025
From
$397
Seen: 19 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Houston (Hobby) (HOU)Depart: 12/19/2025
From
$426
Seen: 21 hrs ago
One-way
Choice
Grand Cayman (GCM)to
San Diego (SAN)Depart: 12/23/2025
From
$481
Seen: 8 hrs ago
One-way
Choice
Grand Cayman (GCM)to
Nashville (BNA)Depart: 12/28/2025
From
$620
Seen: 22 hrs ago
One-way
Choice
Grand Cayman (GCM)to
Tampa (TPA)Depart: 12/29/2025
From
$660
Seen: 4 hrs ago
One-way
Choice
Grand Cayman (GCM)to
Chicago (Midway) (MDW)Depart: 01/03/2026
From
$768
Seen: 4 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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From | To | Fare Type | Dates | Price |
|---|---|---|---|---|
| Grand Cayman (GCM) | Orlando (MCO) | One-way / Basic | Depart: 01/28/2026 | From $236 Seen: 9 hrs ago |
| Grand Cayman (GCM) | Baltimore/Washington (BWI) | One-way / Basic | Depart: 02/05/2026 | From $256 Seen: 8 hrs ago |
| Grand Cayman (GCM) | Dallas (Love Field) (DAL) | One-way / Basic | Depart: 02/18/2026 | From $256 Seen: 10 hrs ago |
| Grand Cayman (GCM) | Indianapolis (IND) | One-way / Basic | Depart: 01/21/2026 | From $256 Seen: 20 hrs ago |
| Grand Cayman (GCM) | Atlanta (ATL) | One-way / Basic | Depart: 04/28/2026 | From $261 Seen: 6 hrs ago |
| Grand Cayman (GCM) | Nashville (BNA) | One-way / Basic | Depart: 02/13/2026 | From $261 Seen: 8 hrs ago |
| Grand Cayman (GCM) | New Orleans (MSY) | One-way / Basic | Depart: 05/01/2026 | From $261 Seen: 22 hrs ago |
| Grand Cayman (GCM) | Washington, D.C. (Reagan National) (DCA) | One-way / Basic | Depart: 02/06/2026 | From $276 Seen: 4 hrs ago |
| Grand Cayman (GCM) | Pittsburgh (PIT) | One-way / Basic | Depart: 01/21/2026 | From $276 Seen: 8 hrs ago |
| Grand Cayman (GCM) | Las Vegas (LAS) | One-way / Basic | Depart: 01/29/2026 | From $289 Seen: 8 hrs ago |
| Grand Cayman (GCM) | St. Louis (STL) | One-way / Basic | Depart: 01/30/2026 | From $295 Seen: 1 hour ago |
| Grand Cayman (GCM) | Chicago (Midway) (MDW) | One-way / Basic | Depart: 04/27/2026 | From $309 Seen: 15 hrs ago |
| Grand Cayman (GCM) | Phoenix (PHX) | One-way / Basic | Depart: 04/17/2026 | From $310 Seen: 10 hrs ago |
| Grand Cayman (GCM) | Louisville (SDF) | One-way / Basic | Depart: 05/29/2026 | From $324 Seen: 8 hrs ago |
| Grand Cayman (GCM) | Milwaukee (MKE) | One-way / Basic | Depart: 06/11/2026 | From $327 Seen: 1 hour ago |
| Grand Cayman (GCM) | Boston (BOS) | One-way / Basic | Depart: 05/02/2026 | From $332 Seen: 10 hrs ago |
| Grand Cayman (GCM) | Raleigh/Durham (RDU) | One-way / Basic | Depart: 05/25/2026 | From $356 Seen: 20 hrs ago |
| Grand Cayman (GCM) | San Jose, CA (SJC) | One-way / Basic | Depart: 02/01/2026 | From $384 Seen: 4 hrs ago |
| Grand Cayman (GCM) | Chicago (O'Hare) (ORD) | One-way / Basic | Depart: 01/31/2026 | From $389 Seen: 31 minutes ago |
| Grand Cayman (GCM) | San Antonio (SAT) | One-way / Choice | Depart: 01/19/2026 | From $446 Seen: 4 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.
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