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: 09/03/2026
From
$201
Seen: 23 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Miami (MIA)Depart: 08/22/2026
From
$408
Seen: 2 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Chicago (Midway) (MDW)Depart: 08/22/2026
From
$446
Seen: 16 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Baltimore/Washington (BWI)Depart: 08/22/2026
From
$521
Seen: 33 minutes 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) | Dallas (Love Field) (DAL) | One-way / Basic | Depart: 10/26/2026 | From $187 Seen: 1 hour ago |
| Grand Cayman (GCM) | Fort Lauderdale (FLL) | One-way / Basic | Depart: 11/13/2026 | From $203 Seen: 8 hrs ago |
| Grand Cayman (GCM) | Chicago (Midway) (MDW) | One-way / Basic | Depart: 01/20/2027 | From $267 Seen: 22 hrs ago |
| Grand Cayman (GCM) | Orlando (MCO) | One-way / Basic | Depart: 11/06/2026 | From $279 Seen: 11 hrs ago |
| Grand Cayman (GCM) | Phoenix (PHX) | One-way / Basic | Depart: 12/09/2026 | From $288 Seen: 9 hrs ago |
| Grand Cayman (GCM) | New Orleans (MSY) | One-way / Basic | Depart: 11/17/2026 | From $293 Seen: 6 hrs ago |
| Grand Cayman (GCM) | Raleigh/Durham (RDU) | One-way / Basic | Depart: 11/03/2026 | From $294 Seen: 14 hrs ago |
| Grand Cayman (GCM) | Nashville (BNA) | One-way / Basic | Depart: 02/01/2027 | From $299 Seen: 11 hrs ago |
| Grand Cayman (GCM) | St. Louis (STL) | One-way / Basic | Depart: 11/06/2026 | From $302 Seen: 15 hrs ago |
| Grand Cayman (GCM) | Sarasota/Bradenton (SRQ) | One-way / Basic | Depart: 02/22/2027 | From $325 Seen: 7 hrs ago |
| Grand Cayman (GCM) | Houston (Hobby) (HOU) | One-way / Basic | Depart: 11/24/2026 | From $327 Seen: 6 hrs ago |
| Grand Cayman (GCM) | Baltimore/Washington (BWI) | One-way / Basic | Depart: 10/10/2026 | From $338 Seen: 14 hrs ago |
| Grand Cayman (GCM) | Kansas City (MCI) | One-way / Basic | Depart: 03/08/2027 | From $342 Seen: 8 hrs ago |
| Grand Cayman (GCM) | Denver (DEN) | One-way / Basic | Depart: 11/09/2026 | From $371 Seen: 3 hrs ago |
| Grand Cayman (GCM) | Indianapolis (IND) | One-way / Basic | Depart: 01/29/2027 | From $390 Seen: 1 hour ago |
| Grand Cayman (GCM) | Los Angeles (LAX) | One-way / Basic | Depart: 10/24/2026 | From $417 Seen: 13 hrs ago |
| Grand Cayman (GCM) | San Diego (SAN) | One-way / Choice | Depart: 01/01/2027 | From $556 Seen: 5 hrs ago |
| Grand Cayman (GCM) | Pittsburgh (PIT) | One-way / Choice | Depart: 10/17/2026 | From $616 Seen: 10 minutes ago |
| Grand Cayman (GCM) | Austin (AUS) | One-way / Choice | Depart: 03/28/2027 | From $738 Seen: 17 hrs ago |
| Grand Cayman (GCM) | Las Vegas (LAS) | One-way / Choice | Depart: 01/04/2027 | From $738 Seen: 7 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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