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
Orlando (MCO)Depart: 01/16/2026
From
$236
Seen: 4 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Raleigh/Durham (RDU)Depart: 12/23/2025
From
$237
Seen: 8 hrs ago
One-way
Choice
Grand Cayman (GCM)to
Baltimore/Washington (BWI)Depart: 01/13/2026
From
$248
Seen: 12 hrs ago
One-way
Basic
Grand Cayman (GCM)to
San Antonio (SAT)Depart: 01/16/2026
From
$256
Seen: 12 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Miami (MIA)Depart: 12/23/2025
From
$288
Seen: 11 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Fort Lauderdale (FLL)Depart: 01/12/2026
From
$293
Seen: 17 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Denver (DEN)Depart: 01/14/2026
From
$297
Seen: 16 hrs ago
One-way
Basic
Grand Cayman (GCM)to
New York (LaGuardia) (LGA)Depart: 01/21/2026
From
$312
Seen: 11 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Kansas City (MCI)Depart: 01/12/2026
From
$324
Seen: 5 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Chicago (Midway) (MDW)Depart: 01/08/2026
From
$376
Seen: 1 hour ago
One-way
Basic
Grand Cayman (GCM)to
Nashville (BNA)Depart: 12/24/2025
From
$405
Seen: 10 hrs ago
One-way
Choice
Grand Cayman (GCM)to
Dallas (Love Field) (DAL)Depart: 12/22/2025
From
$426
Seen: 8 hrs ago
One-way
Choice
Grand Cayman (GCM)to
Albuquerque (ABQ)Depart: 12/24/2025
From
$430
Seen: 17 hrs ago
One-way
Choice
Grand Cayman (GCM)to
West Palm Beach (PBI)Depart: 01/07/2026
From
$436
Seen: 14 hrs ago
One-way
Choice
Grand Cayman (GCM)to
St. Louis (STL)Depart: 01/19/2026
From
$476
Seen: 12 hrs ago
One-way
Choice
Grand Cayman (GCM)to
Seattle/Tacoma (SEA)Depart: 12/26/2025
From
$490
Seen: 23 hrs ago
One-way
Choice
Grand Cayman (GCM)to
Albany (ALB)Depart: 12/28/2025
From
$496
Seen: 16 hrs ago
One-way
Choice
Grand Cayman (GCM)to
Little Rock (LIT)Depart: 12/23/2025
From
$500
Seen: 13 hrs ago
One-way
Choice
Grand Cayman (GCM)to
Tampa (TPA)Depart: 12/27/2025
From
$530
Seen: 8 hrs ago
One-way
Choice
Grand Cayman (GCM)to
Long Beach (LGB)Depart: 01/04/2026
From
$570
Seen: 21 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
flight_takeoff
flight_land
$
From | To | Fare Type | Dates | Price |
|---|---|---|---|---|
| Grand Cayman (GCM) | Orlando (MCO) | One-way / Basic | Depart: 03/03/2026 | From $236 Seen: 17 hrs ago |
| Grand Cayman (GCM) | Baltimore/Washington (BWI) | One-way / Basic | Depart: 02/05/2026 | From $256 Seen: 44 minutes ago |
| Grand Cayman (GCM) | Chicago (Midway) (MDW) | One-way / Basic | Depart: 02/04/2026 | From $256 Seen: 9 hrs ago |
| Grand Cayman (GCM) | Dallas (Love Field) (DAL) | One-way / Basic | Depart: 01/22/2026 | From $256 Seen: 1 hour ago |
| Grand Cayman (GCM) | Fort Myers/Naples (RSW) | One-way / Basic | Depart: 02/13/2026 | From $267 Seen: 5 hrs ago |
| Grand Cayman (GCM) | Chicago (O'Hare) (ORD) | One-way / Basic | Depart: 02/03/2026 | From $276 Seen: 9 hrs ago |
| Grand Cayman (GCM) | New York (LaGuardia) (LGA) | One-way / Basic | Depart: 01/22/2026 | From $280 Seen: 13 hrs ago |
| Grand Cayman (GCM) | Fort Lauderdale (FLL) | One-way / Basic | Depart: 01/22/2026 | From $281 Seen: 7 hrs ago |
| Grand Cayman (GCM) | Phoenix (PHX) | One-way / Basic | Depart: 02/23/2026 | From $285 Seen: 6 hrs ago |
| Grand Cayman (GCM) | Kansas City (MCI) | One-way / Basic | Depart: 01/27/2026 | From $295 Seen: 11 hrs ago |
| Grand Cayman (GCM) | St. Louis (STL) | One-way / Basic | Depart: 01/30/2026 | From $295 Seen: 12 hrs ago |
| Grand Cayman (GCM) | San Diego (SAN) | One-way / Basic | Depart: 05/29/2026 | From $301 Seen: 1 hour ago |
| Grand Cayman (GCM) | Atlanta (ATL) | One-way / Basic | Depart: 04/01/2026 | From $311 Seen: 15 hrs ago |
| Grand Cayman (GCM) | Miami (MIA) | One-way / Basic | Depart: 03/07/2026 | From $318 Seen: 9 hrs ago |
| Grand Cayman (GCM) | Milwaukee (MKE) | One-way / Basic | Depart: 05/17/2026 | From $327 Seen: 9 hrs ago |
| Grand Cayman (GCM) | Buffalo/Niagara Falls (BUF) | One-way / Basic | Depart: 05/28/2026 | From $332 Seen: 6 hrs ago |
| Grand Cayman (GCM) | Rochester (ROC) | One-way / Basic | Depart: 05/28/2026 | From $336 Seen: 6 hrs ago |
| Grand Cayman (GCM) | Austin (AUS) | One-way / Basic | Depart: 03/07/2026 | From $346 Seen: 9 hrs ago |
| Grand Cayman (GCM) | New Orleans (MSY) | One-way / Basic | Depart: 05/02/2026 | From $346 Seen: 6 hrs ago |
| Grand Cayman (GCM) | Omaha (OMA) | One-way / Basic | Depart: 05/16/2026 | From $346 Seen: 12 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