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: 12/09/2025
From
$217
Seen: 46 minutes ago
One-way
Basic
Grand Cayman (GCM)to
Raleigh/Durham (RDU)Depart: 12/17/2025
From
$252
Seen: 7 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Milwaukee (MKE)Depart: 12/18/2025
From
$259
Seen: 9 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Dallas (Love Field) (DAL)Depart: 12/17/2025
From
$264
Seen: 1 minute ago
One-way
Basic
Grand Cayman (GCM)to
San Antonio (SAT)Depart: 12/12/2025
From
$271
Seen: 2 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Austin (AUS)Depart: 12/16/2025
From
$281
Seen: 6 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Fort Lauderdale (FLL)Depart: 12/08/2025
From
$293
Seen: 18 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Denver (DEN)Depart: 12/18/2025
From
$297
Seen: 7 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Orlando (MCO)Depart: 01/01/2026
From
$306
Seen: 9 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Chicago (Midway) (MDW)Depart: 12/22/2025
From
$309
Seen: 13 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Los Angeles (LAX)Depart: 12/20/2025
From
$310
Seen: 10 hrs ago
One-way
Basic
Grand Cayman (GCM)to
St. Louis (STL)Depart: 12/05/2025
From
$311
Seen: 9 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Washington, D.C. (Reagan National) (DCA)Depart: 12/17/2025
From
$311
Seen: 8 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Indianapolis (IND)Depart: 12/18/2025
From
$311
Seen: 6 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Atlanta (ATL)Depart: 12/26/2025
From
$326
Seen: 9 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Nashville (BNA)Depart: 12/26/2025
From
$326
Seen: 10 hrs ago
One-way
Basic
Grand Cayman (GCM)to
New Orleans (MSY)Depart: 12/11/2025
From
$326
Seen: 14 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Pittsburgh (PIT)Depart: 12/11/2025
From
$328
Seen: 12 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Houston (Hobby) (HOU)Depart: 12/26/2025
From
$332
Seen: 9 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Columbus (CMH)Depart: 12/21/2025
From
$351
Seen: 10 hrs ago
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.
Find popular low fares from and within Cayman Islands
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From | To | Fare Type | Dates | Price |
|---|---|---|---|---|
| Grand Cayman (GCM) | Fort Lauderdale (FLL) | One-way / Choice | Depart: 01/21/2026 | From $213 Seen: 11 hrs ago |
| Grand Cayman (GCM) | New York (LaGuardia) (LGA) | One-way / Basic | Depart: 01/16/2026 | From $229 Seen: 12 hrs ago |
| Grand Cayman (GCM) | Denver (DEN) | One-way / Basic | Depart: 02/05/2026 | From $231 Seen: 14 hrs ago |
| Grand Cayman (GCM) | Orlando (MCO) | One-way / Basic | Depart: 01/08/2026 | From $236 Seen: 4 hrs ago |
| Grand Cayman (GCM) | Indianapolis (IND) | One-way / Basic | Depart: 01/27/2026 | From $241 Seen: 13 hrs ago |
| Grand Cayman (GCM) | Nashville (BNA) | One-way / Basic | Depart: 01/20/2026 | From $243 Seen: 23 hrs ago |
| Grand Cayman (GCM) | Baltimore/Washington (BWI) | One-way / Basic | Depart: 03/04/2026 | From $248 Seen: 14 hrs ago |
| Grand Cayman (GCM) | Dallas (Love Field) (DAL) | One-way / Basic | Depart: 01/21/2026 | From $256 Seen: 4 hrs ago |
| Grand Cayman (GCM) | Kansas City (MCI) | One-way / Basic | Depart: 03/06/2026 | From $256 Seen: 4 hrs ago |
| Grand Cayman (GCM) | Columbus (CMH) | One-way / Basic | Depart: 03/06/2026 | From $256 Seen: 12 hrs ago |
| Grand Cayman (GCM) | Pittsburgh (PIT) | One-way / Basic | Depart: 01/29/2026 | From $256 Seen: 4 hrs ago |
| Grand Cayman (GCM) | Miami (MIA) | One-way / Basic | Depart: 02/11/2026 | From $260 Seen: 14 hrs ago |
| Grand Cayman (GCM) | Los Angeles (LAX) | One-way / Basic | Depart: 01/27/2026 | From $273 Seen: 6 hrs ago |
| Grand Cayman (GCM) | Hartford/Springfield (BDL) | One-way / Basic | Depart: 03/03/2026 | From $295 Seen: 8 hrs ago |
| Grand Cayman (GCM) | San Antonio (SAT) | One-way / Basic | Depart: 04/15/2026 | From $299 Seen: 16 hrs ago |
| Grand Cayman (GCM) | Chicago (Midway) (MDW) | One-way / Basic | Depart: 03/18/2026 | From $309 Seen: 11 hrs ago |
| Grand Cayman (GCM) | Chicago (O'Hare) (ORD) | One-way / Basic | Depart: 02/02/2026 | From $309 Seen: 13 hrs ago |
| Grand Cayman (GCM) | Atlanta (ATL) | One-way / Basic | Depart: 01/26/2026 | From $310 Seen: 23 hrs ago |
| Grand Cayman (GCM) | New Orleans (MSY) | One-way / Basic | Depart: 02/04/2026 | From $310 Seen: 6 hrs ago |
| Grand Cayman (GCM) | Raleigh/Durham (RDU) | One-way / Basic | Depart: 04/15/2026 | From $310 Seen: 13 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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