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
Chicago (Midway) (MDW)Depart: 07/11/2026
From
$293
Seen: 21 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Houston (Hobby) (HOU)Depart: 07/11/2026
From
$325
Seen: 23 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Nashville (BNA)Depart: 07/14/2026
From
$325
Seen: 5 hrs ago
One-way
Basic
Grand Cayman (GCM)to
New Orleans (MSY)Depart: 07/14/2026
From
$326
Seen: 1 hour ago
One-way
Basic
Grand Cayman (GCM)to
Austin (AUS)Depart: 07/13/2026
From
$328
Seen: 17 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Baltimore/Washington (BWI)Depart: 07/13/2026
From
$338
Seen: 4 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Denver (DEN)Depart: 07/13/2026
From
$339
Seen: 6 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Albany (ALB)Depart: 07/12/2026
From
$344
Seen: 14 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Boston (BOS)Depart: 07/15/2026
From
$358
Seen: 7 hrs ago
One-way
Basic
Grand Cayman (GCM)to
San Diego (SAN)Depart: 07/12/2026
From
$387
Seen: 40 minutes ago
One-way
Basic
Grand Cayman (GCM)to
Fort Lauderdale (FLL)Depart: 07/25/2026
From
$393
Seen: 22 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Miami (MIA)Depart: 07/13/2026
From
$408
Seen: 24 minutes ago
One-way
Basic
Grand Cayman (GCM)to
Orlando (MCO)Depart: 07/14/2026
From
$416
Seen: 4 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Atlanta (ATL)Depart: 07/17/2026
From
$416
Seen: 20 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Washington, D.C. (Reagan National) (DCA)Depart: 07/16/2026
From
$434
Seen: 11 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Orange County/Santa Ana (SNA)Depart: 07/14/2026
From
$437
Seen: 7 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Little Rock (LIT)Depart: 07/12/2026
From
$441
Seen: 46 minutes ago
One-way
Basic
Grand Cayman (GCM)to
Buffalo/Niagara Falls (BUF)Depart: 07/13/2026
From
$446
Seen: 34 minutes ago
One-way
Basic
Grand Cayman (GCM)to
Minneapolis/St. Paul (MSP)Depart: 07/12/2026
From
$451
Seen: 7 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Dallas (Love Field) (DAL)Depart: 07/24/2026
From
$473
Seen: 23 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) | Philadelphia (PHL) | One-way / Basic | Depart: 08/24/2026 | From $234 Seen: 7 hrs ago |
| Grand Cayman (GCM) | Orlando (MCO) | One-way / Basic | Depart: 11/17/2026 | From $243 Seen: 23 hrs ago |
| Grand Cayman (GCM) | Providence (PVD) | One-way / Basic | Depart: 01/20/2027 | From $246 Seen: 4 hrs ago |
| Grand Cayman (GCM) | St. Louis (STL) | One-way / Basic | Depart: 12/11/2026 | From $262 Seen: 19 hrs ago |
| Grand Cayman (GCM) | Fort Lauderdale (FLL) | One-way / Basic | Depart: 11/06/2026 | From $268 Seen: 13 hrs ago |
| Grand Cayman (GCM) | Hartford/Springfield (BDL) | One-way / Basic | Depart: 11/04/2026 | From $272 Seen: 3 hrs ago |
| Grand Cayman (GCM) | Houston (Hobby) (HOU) | One-way / Basic | Depart: 08/22/2026 | From $293 Seen: 4 hrs ago |
| Grand Cayman (GCM) | Miami (MIA) | One-way / Basic | Depart: 03/08/2027 | From $323 Seen: 1 hour ago |
| Grand Cayman (GCM) | Chicago (Midway) (MDW) | One-way / Basic | Depart: 03/01/2027 | From $325 Seen: 17 hrs ago |
| Grand Cayman (GCM) | Columbus (CMH) | One-way / Basic | Depart: 12/24/2026 | From $342 Seen: 23 hrs ago |
| Grand Cayman (GCM) | Los Angeles (LAX) | One-way / Basic | Depart: 01/16/2027 | From $342 Seen: 22 hrs ago |
| Grand Cayman (GCM) | West Palm Beach (PBI) | One-way / Basic | Depart: 03/08/2027 | From $376 Seen: 1 hour ago |
| Grand Cayman (GCM) | Phoenix (PHX) | One-way / Basic | Depart: 12/19/2026 | From $396 Seen: 3 hrs ago |
| Grand Cayman (GCM) | Baltimore/Washington (BWI) | One-way / Basic | Depart: 11/25/2026 | From $434 Seen: 9 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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