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: 12/01/2026
From
$244
Seen: 19 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Baltimore/Washington (BWI)Depart: 12/03/2026
From
$253
Seen: 19 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Nashville (BNA)Depart: 11/14/2026
From
$284
Seen: 8 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Orlando (MCO)Depart: 12/03/2026
From
$299
Seen: 18 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Denver (DEN)Depart: 12/03/2026
From
$303
Seen: 11 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Kansas City (MCI)Depart: 12/08/2026
From
$306
Seen: 15 hrs ago
One-way
Basic
Grand Cayman (GCM)to
New Orleans (MSY)Depart: 11/20/2026
From
$337
Seen: 19 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Los Angeles (LAX)Depart: 11/09/2026
From
$347
Seen: 14 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Hartford/Springfield (BDL)Depart: 11/22/2026
From
$360
Seen: 5 hrs ago
One-way
Basic
Grand Cayman (GCM)to
St. Louis (STL)Depart: 11/23/2026
From
$412
Seen: 21 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Las Vegas (LAS)Depart: 11/09/2026
From
$436
Seen: 9 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Washington D.C. Reagan National (DCA)Depart: 11/09/2026
From
$439
Seen: 8 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Birmingham (BHM)Depart: 11/10/2026
From
$462
Seen: 6 minutes ago
One-way
Basic
Grand Cayman (GCM)to
Chicago-Midway (MDW)Depart: 11/09/2026
From
$472
Seen: 17 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Dallas-Love Field (DAL)Depart: 11/10/2026
From
$472
Seen: 20 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Houston Hobby (HOU)Depart: 11/10/2026
From
$472
Seen: 21 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Oklahoma City (OKC)Depart: 11/13/2026
From
$472
Seen: 18 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Atlanta (ATL)Depart: 11/29/2026
From
$622
Seen: 18 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Austin (AUS)Depart: 11/29/2026
From
$768
Seen: 20 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Jackson (JAN)Depart: 11/27/2026
From
$818
Seen: 14 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) | Fort Lauderdale (FLL) | One-way / Basic | Depart: 12/11/2026 | From $244 Seen: 12 hrs ago |
| Grand Cayman (GCM) | Baltimore/Washington (BWI) | One-way / Basic | Depart: 12/11/2026 | From $253 Seen: 15 hrs ago |
| Grand Cayman (GCM) | Hartford/Springfield (BDL) | One-way / Basic | Depart: 01/22/2027 | From $262 Seen: 1 hour ago |
| Grand Cayman (GCM) | New Orleans (MSY) | One-way / Basic | Depart: 01/21/2027 | From $284 Seen: 14 hrs ago |
| Grand Cayman (GCM) | Miami (MIA) | One-way / Basic | Depart: 01/15/2027 | From $299 Seen: 23 hrs ago |
| Grand Cayman (GCM) | Orlando (MCO) | One-way / Basic | Depart: 01/15/2027 | From $299 Seen: 23 hrs ago |
| Grand Cayman (GCM) | Denver (DEN) | One-way / Basic | Depart: 01/10/2027 | From $303 Seen: 7 hrs ago |
| Grand Cayman (GCM) | Chicago-Midway (MDW) | One-way / Basic | Depart: 02/04/2027 | From $323 Seen: 11 hrs ago |
| Grand Cayman (GCM) | Dallas-Love Field (DAL) | One-way / Basic | Depart: 12/16/2026 | From $323 Seen: 7 hrs ago |
| Grand Cayman (GCM) | Los Angeles (LAX) | One-way / Basic | Depart: 03/01/2027 | From $343 Seen: 10 hrs ago |
| Grand Cayman (GCM) | San Diego (SAN) | One-way / Basic | Depart: 03/02/2027 | From $343 Seen: 5 hrs ago |
| Grand Cayman (GCM) | Louisville (SDF) | One-way / Basic | Depart: 05/14/2027 | From $348 Seen: 8 hrs ago |
| Grand Cayman (GCM) | Salt Lake City (SLC) | One-way / Basic | Depart: 04/14/2027 | From $366 Seen: 8 hrs ago |
| Grand Cayman (GCM) | Santa Barbara (SBA) | One-way / Basic | Depart: 02/26/2027 | From $366 Seen: 4 hrs ago |
| Grand Cayman (GCM) | Long Island/Islip MacArthur (ISP) | One-way / Basic | Depart: 03/10/2027 | From $368 Seen: 10 hrs ago |
| Grand Cayman (GCM) | Columbus (CMH) | One-way / Basic | Depart: 07/09/2027 | From $381 Seen: 11 hrs ago |
| Grand Cayman (GCM) | Kansas City (MCI) | One-way / Basic | Depart: 06/18/2027 | From $414 Seen: 5 hrs ago |
| Grand Cayman (GCM) | Las Vegas (LAS) | One-way / Basic | Depart: 06/07/2027 | From $415 Seen: 6 hrs ago |
| Grand Cayman (GCM) | Seattle/Tacoma (SEA) | One-way / Basic | Depart: 03/05/2027 | From $421 Seen: 18 hrs ago |
| Grand Cayman (GCM) | Boise (BOI) | One-way / Basic | Depart: 12/30/2026 | From $427 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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