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
Orlando (MCO)Depart: 10/05/2026
From
$312
Seen: 20 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Houston Hobby (HOU)Depart: 09/29/2026
From
$331
Seen: 5 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Pittsburgh (PIT)Depart: 10/03/2026
From
$366
Seen: 16 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Phoenix (PHX)Depart: 09/26/2026
From
$446
Seen: 11 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) | Baltimore/Washington (BWI) | One-way / Basic | Depart: 10/29/2026 | From $169 Seen: 23 hrs ago |
| Grand Cayman (GCM) | Orlando (MCO) | One-way / Basic | Depart: 10/29/2026 | From $171 Seen: 19 hrs ago |
| Grand Cayman (GCM) | Fort Lauderdale (FLL) | One-way / Basic | Depart: 11/21/2026 | From $213 Seen: 1 hour ago |
| Grand Cayman (GCM) | Chicago-Midway (MDW) | One-way / Basic | Depart: 12/11/2026 | From $267 Seen: 19 hrs ago |
| Grand Cayman (GCM) | New Orleans (MSY) | One-way / Basic | Depart: 01/06/2027 | From $268 Seen: 4 hrs ago |
| Grand Cayman (GCM) | Denver (DEN) | One-way / Basic | Depart: 12/16/2026 | From $277 Seen: 13 hrs ago |
| Grand Cayman (GCM) | Miami (MIA) | One-way / Basic | Depart: 10/10/2026 | From $288 Seen: 10 hrs ago |
| Grand Cayman (GCM) | St. Louis (STL) | One-way / Basic | Depart: 11/20/2026 | From $292 Seen: 23 hrs ago |
| Grand Cayman (GCM) | Las Vegas (LAS) | One-way / Basic | Depart: 01/11/2027 | From $292 Seen: 7 hrs ago |
| Grand Cayman (GCM) | Philadelphia (PHL) | One-way / Basic | Depart: 01/28/2027 | From $292 Seen: 20 hrs ago |
| Grand Cayman (GCM) | New York LaGuardia (LGA) | One-way / Basic | Depart: 11/16/2026 | From $295 Seen: 14 hrs ago |
| Grand Cayman (GCM) | Dallas-Love Field (DAL) | One-way / Basic | Depart: 11/19/2026 | From $302 Seen: 2 hrs ago |
| Grand Cayman (GCM) | Los Angeles (LAX) | One-way / Basic | Depart: 11/11/2026 | From $327 Seen: 12 hrs ago |
| Grand Cayman (GCM) | Houston Hobby (HOU) | One-way / Basic | Depart: 10/14/2026 | From $331 Seen: 13 hrs ago |
| Grand Cayman (GCM) | Buffalo/Niagara Falls (BUF) | One-way / Basic | Depart: 01/16/2027 | From $406 Seen: 9 hrs ago |
| Grand Cayman (GCM) | Indianapolis (IND) | One-way / Basic | Depart: 04/01/2027 | From $473 Seen: 15 hrs ago |
| Grand Cayman (GCM) | Phoenix (PHX) | One-way / Choice | Depart: 01/04/2027 | From $616 Seen: 16 hrs ago |
| Grand Cayman (GCM) | Kansas City (MCI) | One-way / Choice | Depart: 04/03/2027 | From $788 Seen: 10 hrs ago |
| Grand Cayman (GCM) | Oakland (OAK) | One-way / Choice | Depart: 12/31/2026 | From $798 Seen: 10 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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