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
Fort Lauderdale (FLL)Depart: 06/24/2026
From
$203
Seen: 19 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Houston (Hobby) (HOU)Depart: 06/03/2026
From
$203
Seen: 14 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Baltimore/Washington (BWI)Depart: 06/06/2026
From
$247
Seen: 16 hrs ago
One-way
Basic
Grand Cayman (GCM)to
New York (LaGuardia) (LGA)Depart: 06/03/2026
From
$289
Seen: 7 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Orlando (MCO)Depart: 06/26/2026
From
$316
Seen: 23 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Columbus (CMH)Depart: 06/02/2026
From
$328
Seen: 21 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Hartford/Springfield (BDL)Depart: 06/03/2026
From
$333
Seen: 7 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Nashville (BNA)Depart: 07/01/2026
From
$346
Seen: 8 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Birmingham (BHM)Depart: 06/02/2026
From
$351
Seen: 7 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Dallas (Love Field) (DAL)Depart: 06/09/2026
From
$377
Seen: 4 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Phoenix (PHX)Depart: 06/06/2026
From
$378
Seen: 15 hrs ago
One-way
Basic
Grand Cayman (GCM)to
San Antonio (SAT)Depart: 06/15/2026
From
$386
Seen: 5 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Las Vegas (LAS)Depart: 06/22/2026
From
$401
Seen: 3 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Oklahoma City (OKC)Depart: 06/08/2026
From
$441
Seen: 2 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Austin (AUS)Depart: 06/03/2026
From
$446
Seen: 4 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Minneapolis/St. Paul (MSP)Depart: 06/02/2026
From
$451
Seen: 20 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Oakland (OAK)Depart: 06/08/2026
From
$491
Seen: 6 hrs ago
One-way
Choice
Grand Cayman (GCM)to
San Juan (SJU)Depart: 06/12/2026
From
$565
Seen: 7 hrs ago
One-way
Choice
Grand Cayman (GCM)to
Atlanta (ATL)Depart: 06/12/2026
From
$616
Seen: 13 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) | Nashville (BNA) | One-way / Basic | Depart: 08/11/2026 | From $98 Seen: 7 hrs ago |
| Grand Cayman (GCM) | Orlando (MCO) | One-way / Basic | Depart: 08/31/2026 | From $227 Seen: 6 hrs ago |
| Grand Cayman (GCM) | Washington, D.C. (Reagan National) (DCA) | One-way / Basic | Depart: 08/29/2026 | From $311 Seen: 22 hrs ago |
| Grand Cayman (GCM) | Baltimore/Washington (BWI) | One-way / Basic | Depart: 08/29/2026 | From $321 Seen: 22 hrs ago |
| Grand Cayman (GCM) | Atlanta (ATL) | One-way / Basic | Depart: 07/29/2026 | From $321 Seen: 20 hrs ago |
| Grand Cayman (GCM) | Buffalo/Niagara Falls (BUF) | One-way / Basic | Depart: 12/11/2026 | From $339 Seen: 10 hrs ago |
| Grand Cayman (GCM) | Providence (PVD) | One-way / Basic | Depart: 07/23/2026 | From $342 Seen: 2 hrs ago |
| Grand Cayman (GCM) | Dallas (Love Field) (DAL) | One-way / Basic | Depart: 07/28/2026 | From $356 Seen: 3 hrs ago |
| Grand Cayman (GCM) | Kansas City (MCI) | One-way / Basic | Depart: 12/21/2026 | From $356 Seen: 4 hrs ago |
| Grand Cayman (GCM) | Grand Rapids (GRR) | One-way / Basic | Depart: 11/14/2026 | From $356 Seen: 7 hrs ago |
| Grand Cayman (GCM) | San Diego (SAN) | One-way / Basic | Depart: 12/17/2026 | From $359 Seen: 15 hrs ago |
| Grand Cayman (GCM) | Chicago (Midway) (MDW) | One-way / Basic | Depart: 07/24/2026 | From $366 Seen: 1 hour ago |
| Grand Cayman (GCM) | Phoenix (PHX) | One-way / Basic | Depart: 07/03/2026 | From $391 Seen: 7 hrs ago |
| Grand Cayman (GCM) | Austin (AUS) | One-way / Basic | Depart: 07/03/2026 | From $395 Seen: 21 hrs ago |
| Grand Cayman (GCM) | Reno/Tahoe (RNO) | One-way / Basic | Depart: 07/28/2026 | From $396 Seen: 3 hrs ago |
| Grand Cayman (GCM) | St. Louis (STL) | One-way / Basic | Depart: 09/26/2026 | From $412 Seen: 20 hrs ago |
| Grand Cayman (GCM) | Louisville (SDF) | One-way / Basic | Depart: 07/03/2026 | From $421 Seen: 6 hrs ago |
| Grand Cayman (GCM) | Pittsburgh (PIT) | One-way / Choice | Depart: 12/12/2026 | From $516 Seen: 4 hrs ago |
| Grand Cayman (GCM) | Boston (BOS) | One-way / Choice | Depart: 01/01/2027 | From $1,083 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.
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