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
Kansas City (MCI)Depart: 10/03/2026
From
$335
Seen: 10 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Orlando (MCO)Depart: 10/31/2026
From
$336
Seen: 17 hrs ago
One-way
Basic
Grand Cayman (GCM)to
New York LaGuardia (LGA)Depart: 10/24/2026
From
$358
Seen: 4 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Nashville (BNA)Depart: 10/10/2026
From
$388
Seen: 19 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Baltimore/Washington (BWI)Depart: 10/24/2026
From
$403
Seen: 13 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Philadelphia (PHL)Depart: 10/24/2026
From
$483
Seen: 3 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 / Basic | Depart: 11/26/2026 | From $169 Seen: 16 hrs ago |
| Grand Cayman (GCM) | Nashville (BNA) | One-way / Basic | Depart: 01/16/2027 | From $258 Seen: 2 hrs ago |
| Grand Cayman (GCM) | Baltimore/Washington (BWI) | One-way / Basic | Depart: 12/19/2026 | From $277 Seen: 15 hrs ago |
| Grand Cayman (GCM) | Orlando (MCO) | One-way / Basic | Depart: 02/11/2027 | From $287 Seen: 11 hrs ago |
| Grand Cayman (GCM) | Atlanta (ATL) | One-way / Basic | Depart: 11/05/2026 | From $293 Seen: 8 hrs ago |
| Grand Cayman (GCM) | Austin (AUS) | One-way / Basic | Depart: 01/31/2027 | From $299 Seen: 22 hrs ago |
| Grand Cayman (GCM) | Chicago-Midway (MDW) | One-way / Basic | Depart: 11/17/2026 | From $310 Seen: 17 hrs ago |
| Grand Cayman (GCM) | Houston Hobby (HOU) | One-way / Basic | Depart: 12/03/2026 | From $310 Seen: 15 hrs ago |
| Grand Cayman (GCM) | Fort Myers/Naples (RSW) | One-way / Basic | Depart: 12/09/2026 | From $325 Seen: 13 hrs ago |
| Grand Cayman (GCM) | Kansas City (MCI) | One-way / Basic | Depart: 11/23/2026 | From $331 Seen: 14 hrs ago |
| Grand Cayman (GCM) | Washington D.C. Reagan National (DCA) | One-way / Basic | Depart: 12/19/2026 | From $347 Seen: 15 hrs ago |
| Grand Cayman (GCM) | Omaha (OMA) | One-way / Basic | Depart: 02/05/2027 | From $376 Seen: 2 minutes ago |
| Grand Cayman (GCM) | Miami (MIA) | One-way / Basic | Depart: 11/25/2026 | From $380 Seen: 15 hrs ago |
| Grand Cayman (GCM) | Milwaukee (MKE) | One-way / Basic | Depart: 03/23/2027 | From $397 Seen: 12 hrs ago |
| Grand Cayman (GCM) | Raleigh/Durham (RDU) | One-way / Basic | Depart: 12/28/2026 | From $407 Seen: 15 hrs ago |
| Grand Cayman (GCM) | St. Louis (STL) | One-way / Basic | Depart: 12/26/2026 | From $416 Seen: 22 hrs ago |
| Grand Cayman (GCM) | Pittsburgh (PIT) | One-way / Basic | Depart: 12/26/2026 | From $424 Seen: 15 hrs ago |
| Grand Cayman (GCM) | Las Vegas (LAS) | One-way / Basic | Depart: 01/23/2027 | From $471 Seen: 2 hrs ago |
| Grand Cayman (GCM) | Oakland (OAK) | One-way / Basic | Depart: 01/04/2027 | From $486 Seen: 13 hrs ago |
| Grand Cayman (GCM) | Oklahoma City (OKC) | One-way / Choice | Depart: 03/18/2027 | From $526 Seen: 17 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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