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: 05/16/2026
From
$203
Seen: 17 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Fort Lauderdale (FLL)Depart: 04/22/2026
From
$238
Seen: 4 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Long Island/Islip MacArthur (ISP)Depart: 05/14/2026
From
$240
Seen: 4 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Manchester, NH (MHT)Depart: 04/28/2026
From
$240
Seen: 23 hrs ago
One-way
Basic
Grand Cayman (GCM)to
New York (LaGuardia) (LGA)Depart: 05/14/2026
From
$245
Seen: 4 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Dallas (Love Field) (DAL)Depart: 04/28/2026
From
$290
Seen: 4 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Austin (AUS)Depart: 04/22/2026
From
$290
Seen: 21 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Miami (MIA)Depart: 04/29/2026
From
$303
Seen: 21 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Norfolk/Virginia Beach (ORF)Depart: 05/22/2026
From
$309
Seen: 22 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Orlando (MCO)Depart: 05/13/2026
From
$316
Seen: 5 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Denver (DEN)Depart: 04/22/2026
From
$317
Seen: 16 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Indianapolis (IND)Depart: 05/13/2026
From
$328
Seen: 22 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Nashville (BNA)Depart: 04/28/2026
From
$330
Seen: 23 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Pittsburgh (PIT)Depart: 05/14/2026
From
$342
Seen: 23 hrs ago
One-way
Basic
Grand Cayman (GCM)to
New Orleans (MSY)Depart: 05/09/2026
From
$366
Seen: 7 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Chicago (Midway) (MDW)Depart: 05/05/2026
From
$386
Seen: 15 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Phoenix (PHX)Depart: 04/24/2026
From
$404
Seen: 4 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Atlanta (ATL)Depart: 05/09/2026
From
$406
Seen: 5 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Kansas City (MCI)Depart: 05/02/2026
From
$426
Seen: 18 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Chicago (O'Hare) (ORD)Depart: 05/04/2026
From
$426
Seen: 15 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) | Phoenix (PHX) | One-way / Basic | Depart: 05/28/2026 | From $233 Seen: 11 hrs ago |
| Grand Cayman (GCM) | Norfolk/Virginia Beach (ORF) | One-way / Basic | Depart: 05/26/2026 | From $258 Seen: 22 hrs ago |
| Grand Cayman (GCM) | Baltimore/Washington (BWI) | One-way / Basic | Depart: 05/27/2026 | From $292 Seen: 6 hrs ago |
| Grand Cayman (GCM) | Austin (AUS) | One-way / Basic | Depart: 07/23/2026 | From $313 Seen: 18 hrs ago |
| Grand Cayman (GCM) | Orlando (MCO) | One-way / Basic | Depart: 06/02/2026 | From $316 Seen: 23 hrs ago |
| Grand Cayman (GCM) | Tulsa (TUL) | One-way / Basic | Depart: 07/02/2026 | From $321 Seen: 2 hrs ago |
| Grand Cayman (GCM) | San Diego (SAN) | One-way / Basic | Depart: 06/29/2026 | From $330 Seen: 4 hrs ago |
| Grand Cayman (GCM) | Chicago (Midway) (MDW) | One-way / Basic | Depart: 06/03/2026 | From $342 Seen: 19 hrs ago |
| Grand Cayman (GCM) | Dallas (Love Field) (DAL) | One-way / Basic | Depart: 06/04/2026 | From $342 Seen: 16 hrs ago |
| Grand Cayman (GCM) | Fort Lauderdale (FLL) | One-way / Basic | Depart: 06/10/2026 | From $352 Seen: 1 hour ago |
| Grand Cayman (GCM) | Nashville (BNA) | One-way / Basic | Depart: 08/02/2026 | From $356 Seen: 8 hrs ago |
| Grand Cayman (GCM) | St. Louis (STL) | One-way / Basic | Depart: 06/10/2026 | From $356 Seen: 1 hour ago |
| Grand Cayman (GCM) | Louisville (SDF) | One-way / Basic | Depart: 07/30/2026 | From $356 Seen: 7 hrs ago |
| Grand Cayman (GCM) | Long Island/Islip MacArthur (ISP) | One-way / Basic | Depart: 07/02/2026 | From $356 Seen: 10 hrs ago |
| Grand Cayman (GCM) | West Palm Beach (PBI) | One-way / Basic | Depart: 06/10/2026 | From $361 Seen: 1 hour ago |
| Grand Cayman (GCM) | Fort Myers/Naples (RSW) | One-way / Basic | Depart: 07/29/2026 | From $361 Seen: 7 hrs ago |
| Grand Cayman (GCM) | Atlanta (ATL) | One-way / Basic | Depart: 07/23/2026 | From $366 Seen: 17 hrs ago |
| Grand Cayman (GCM) | Miami (MIA) | One-way / Basic | Depart: 06/10/2026 | From $373 Seen: 1 hour ago |
| Grand Cayman (GCM) | Tampa (TPA) | One-way / Basic | Depart: 07/20/2026 | From $401 Seen: 4 hrs ago |
| Grand Cayman (GCM) | Hartford/Springfield (BDL) | One-way / Basic | Depart: 06/01/2026 | From $405 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.
Explore Southwest Airlines popular destinations