Southwest® flights from and within Cayman Islands
expand_more
1 Passenger
expand_morePromo Code
expand_moretoday
today
Deals on flights from and within Cayman Islands
flight_takeoff
flight_land
$
Grand Cayman (GCM)to
Baltimore/Washington (BWI)Depart: 03/14/2026
From
$223
Seen: 22 hrs ago
One-way
Basic
Grand Cayman (GCM)to
New Orleans (MSY)Depart: 02/24/2026
From
$282
Seen: 2 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Fort Lauderdale (FLL)Depart: 03/04/2026
From
$288
Seen: 14 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Orlando (MCO)Depart: 03/13/2026
From
$306
Seen: 21 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Columbus (CMH)Depart: 02/27/2026
From
$307
Seen: 32 minutes ago
One-way
Basic
Grand Cayman (GCM)to
Washington, D.C. (Reagan National) (DCA)Depart: 02/20/2026
From
$322
Seen: 4 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Las Vegas (LAS)Depart: 02/20/2026
From
$343
Seen: 23 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Miami (MIA)Depart: 02/20/2026
From
$348
Seen: 15 hrs ago
One-way
Basic
Grand Cayman (GCM)to
St. Louis (STL)Depart: 03/17/2026
From
$356
Seen: 13 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Raleigh/Durham (RDU)Depart: 02/24/2026
From
$360
Seen: 23 minutes ago
One-way
Basic
Grand Cayman (GCM)to
Los Angeles (LAX)Depart: 02/20/2026
From
$361
Seen: 12 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Hartford/Springfield (BDL)Depart: 03/03/2026
From
$365
Seen: 23 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Destin/Fort Walton Beach (VPS)Depart: 03/10/2026
From
$382
Seen: 14 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Nashville (BNA)Depart: 03/02/2026
From
$396
Seen: 8 minutes ago
One-way
Basic
Grand Cayman (GCM)to
Houston (Hobby) (HOU)Depart: 02/26/2026
From
$416
Seen: 18 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Kansas City (MCI)Depart: 02/20/2026
From
$426
Seen: 18 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Providence (PVD)Depart: 03/21/2026
From
$426
Seen: 2 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Long Island/Islip MacArthur (ISP)Depart: 02/26/2026
From
$426
Seen: 4 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Albuquerque (ABQ)Depart: 02/20/2026
From
$466
Seen: 16 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Fresno (FAT)Depart: 02/28/2026
From
$471
Seen: 13 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
flight_takeoff
flight_land
$
From | To | Fare Type | Dates | Price |
|---|---|---|---|---|
| Grand Cayman (GCM) | Orlando (MCO) | One-way / Basic | Depart: 04/14/2026 | From $212 Seen: 19 hrs ago |
| Grand Cayman (GCM) | Baltimore/Washington (BWI) | One-way / Basic | Depart: 05/16/2026 | From $223 Seen: 13 hrs ago |
| Grand Cayman (GCM) | Chicago (O'Hare) (ORD) | One-way / Basic | Depart: 05/07/2026 | From $242 Seen: 21 hrs ago |
| Grand Cayman (GCM) | Denver (DEN) | One-way / Basic | Depart: 05/21/2026 | From $267 Seen: 16 hrs ago |
| Grand Cayman (GCM) | Hartford/Springfield (BDL) | One-way / Basic | Depart: 04/08/2026 | From $267 Seen: 20 hrs ago |
| Grand Cayman (GCM) | Los Angeles (LAX) | One-way / Basic | Depart: 05/02/2026 | From $277 Seen: 13 hrs ago |
| Grand Cayman (GCM) | Fort Lauderdale (FLL) | One-way / Basic | Depart: 04/01/2026 | From $293 Seen: 14 hrs ago |
| Grand Cayman (GCM) | Chicago (Midway) (MDW) | One-way / Basic | Depart: 05/15/2026 | From $293 Seen: 20 hrs ago |
| Grand Cayman (GCM) | Washington, D.C. (Reagan National) (DCA) | One-way / Basic | Depart: 04/08/2026 | From $293 Seen: 18 hrs ago |
| Grand Cayman (GCM) | Minneapolis/St. Paul (MSP) | One-way / Basic | Depart: 04/08/2026 | From $298 Seen: 12 hrs ago |
| Grand Cayman (GCM) | Houston (Hobby) (HOU) | One-way / Basic | Depart: 09/15/2026 | From $301 Seen: 17 hrs ago |
| Grand Cayman (GCM) | Providence (PVD) | One-way / Basic | Depart: 05/06/2026 | From $303 Seen: 17 hrs ago |
| Grand Cayman (GCM) | Austin (AUS) | One-way / Basic | Depart: 05/27/2026 | From $308 Seen: 18 hrs ago |
| Grand Cayman (GCM) | Nashville (BNA) | One-way / Basic | Depart: 06/13/2026 | From $311 Seen: 17 hrs ago |
| Grand Cayman (GCM) | Miami (MIA) | One-way / Basic | Depart: 05/31/2026 | From $331 Seen: 15 hrs ago |
| Grand Cayman (GCM) | Columbus (CMH) | One-way / Basic | Depart: 04/08/2026 | From $332 Seen: 5 hrs ago |
| Grand Cayman (GCM) | Louisville (SDF) | One-way / Basic | Depart: 06/04/2026 | From $332 Seen: 18 hrs ago |
| Grand Cayman (GCM) | Manchester, NH (MHT) | One-way / Basic | Depart: 03/25/2026 | From $337 Seen: 4 hrs ago |
| Grand Cayman (GCM) | Buffalo/Niagara Falls (BUF) | One-way / Basic | Depart: 05/25/2026 | From $342 Seen: 19 hrs ago |
| Grand Cayman (GCM) | Dallas (Love Field) (DAL) | One-way / Basic | Depart: 03/25/2026 | From $346 Seen: 18 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.
Explore Southwest Airlines popular destinations