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
Fort Lauderdale (FLL)Depart: 11/18/2026
From
$244
Seen: 6 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Orlando (MCO)Depart: 11/17/2026
From
$255
Seen: 21 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Kansas City (MCI)Depart: 11/13/2026
From
$275
Seen: 17 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Raleigh/Durham (RDU)Depart: 11/05/2026
From
$289
Seen: 19 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Las Vegas (LAS)Depart: 10/26/2026
From
$299
Seen: 18 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Dallas-Love Field (DAL)Depart: 11/10/2026
From
$363
Seen: 22 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Houston Hobby (HOU)Depart: 11/04/2026
From
$407
Seen: 23 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Miami (MIA)Depart: 11/15/2026
From
$537
Seen: 15 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) | Fort Lauderdale (FLL) | One-way / Basic | Depart: 01/21/2027 | From $244 Seen: 2 hrs ago |
| Grand Cayman (GCM) | Hartford/Springfield (BDL) | One-way / Basic | Depart: 01/21/2027 | From $252 Seen: 1 hour ago |
| Grand Cayman (GCM) | Orlando (MCO) | One-way / Basic | Depart: 12/03/2026 | From $255 Seen: 59 minutes ago |
| Grand Cayman (GCM) | Washington D.C. Reagan National (DCA) | One-way / Basic | Depart: 01/08/2027 | From $268 Seen: 5 hrs ago |
| Grand Cayman (GCM) | St. Louis (STL) | One-way / Basic | Depart: 12/09/2026 | From $275 Seen: 3 hrs ago |
| Grand Cayman (GCM) | Indianapolis (IND) | One-way / Basic | Depart: 12/02/2026 | From $275 Seen: 4 hrs ago |
| Grand Cayman (GCM) | Milwaukee (MKE) | One-way / Basic | Depart: 01/27/2027 | From $275 Seen: 23 hrs ago |
| Grand Cayman (GCM) | Chicago-Midway (MDW) | One-way / Basic | Depart: 12/15/2026 | From $279 Seen: 11 hrs ago |
| Grand Cayman (GCM) | Houston Hobby (HOU) | One-way / Basic | Depart: 01/07/2027 | From $285 Seen: 4 hrs ago |
| Grand Cayman (GCM) | Manchester, NH (MHT) | One-way / Basic | Depart: 12/22/2026 | From $286 Seen: 4 hrs ago |
| Grand Cayman (GCM) | Fort Myers/Naples (RSW) | One-way / Basic | Depart: 02/10/2027 | From $287 Seen: 2 hrs ago |
| Grand Cayman (GCM) | Baltimore/Washington (BWI) | One-way / Basic | Depart: 12/26/2026 | From $302 Seen: 15 hrs ago |
| Grand Cayman (GCM) | Sacramento (SMF) | One-way / Basic | Depart: 02/19/2027 | From $309 Seen: 12 hrs ago |
| Grand Cayman (GCM) | Nashville (BNA) | One-way / Basic | Depart: 12/26/2026 | From $329 Seen: 4 hrs ago |
| Grand Cayman (GCM) | Omaha (OMA) | One-way / Basic | Depart: 11/22/2026 | From $330 Seen: 15 hrs ago |
| Grand Cayman (GCM) | Denver (DEN) | One-way / Basic | Depart: 04/15/2027 | From $334 Seen: 3 hrs ago |
| Grand Cayman (GCM) | Oklahoma City (OKC) | One-way / Basic | Depart: 12/04/2026 | From $349 Seen: 4 hrs ago |
| Grand Cayman (GCM) | Atlanta (ATL) | One-way / Basic | Depart: 02/27/2027 | From $357 Seen: 8 hrs ago |
| Grand Cayman (GCM) | Long Island/Islip MacArthur (ISP) | One-way / Basic | Depart: 02/18/2027 | From $391 Seen: 7 hrs ago |
| Grand Cayman (GCM) | Midland/Odessa (MAF) | One-way / Basic | Depart: 11/22/2026 | From $391 Seen: 8 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