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: 08/09/2026
From
$183
Seen: 19 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Baltimore/Washington (BWI)Depart: 08/04/2026
From
$193
Seen: 40 minutes ago
One-way
Basic
Grand Cayman (GCM)to
Atlanta (ATL)Depart: 08/09/2026
From
$261
Seen: 19 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Orlando (MCO)Depart: 08/29/2026
From
$346
Seen: 17 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Nashville (BNA)Depart: 08/02/2026
From
$436
Seen: 8 hrs ago
One-way
Basic
Grand Cayman (GCM)to
Houston (Hobby) (HOU)Depart: 08/02/2026
From
$516
Seen: 7 hrs ago
One-way
Choice
Grand Cayman (GCM)to
Boston (BOS)Depart: 08/02/2026
From
$521
Seen: 17 hrs ago
One-way
Choice
Grand Cayman (GCM)to
New Orleans (MSY)Depart: 08/02/2026
From
$546
Seen: 22 hrs ago
One-way
Choice
Grand Cayman (GCM)to
Austin (AUS)Depart: 08/03/2026
From
$586
Seen: 18 hrs ago
One-way
Choice
Grand Cayman (GCM)to
Washington, D.C. (Reagan National) (DCA)Depart: 08/03/2026
From
$636
Seen: 4 hrs ago
One-way
Choice
Grand Cayman (GCM)to
Chicago (Midway) (MDW)Depart: 08/08/2026
From
$863
Seen: 20 hrs ago
One-way
Choice
Grand Cayman (GCM)to
Dallas (Love Field) (DAL)Depart: 08/08/2026
From
$953
Seen: 53 minutes ago
One-way
Choice
Grand Cayman (GCM)to
St. Louis (STL)Depart: 08/08/2026
From
$953
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: 09/05/2026 | From $203 Seen: 14 hrs ago |
| Grand Cayman (GCM) | Miami (MIA) | One-way / Basic | Depart: 09/12/2026 | From $278 Seen: 49 minutes ago |
| Grand Cayman (GCM) | Orlando (MCO) | One-way / Basic | Depart: 11/03/2026 | From $288 Seen: 22 minutes ago |
| Grand Cayman (GCM) | Denver (DEN) | One-way / Basic | Depart: 12/02/2026 | From $302 Seen: 17 hrs ago |
| Grand Cayman (GCM) | Los Angeles (LAX) | One-way / Basic | Depart: 01/16/2027 | From $305 Seen: 17 hrs ago |
| Grand Cayman (GCM) | Dallas (Love Field) (DAL) | One-way / Basic | Depart: 12/08/2026 | From $312 Seen: 11 hrs ago |
| Grand Cayman (GCM) | Kansas City (MCI) | One-way / Basic | Depart: 12/08/2026 | From $312 Seen: 5 hrs ago |
| Grand Cayman (GCM) | Atlanta (ATL) | One-way / Basic | Depart: 11/02/2026 | From $336 Seen: 1 hour ago |
| Grand Cayman (GCM) | Des Moines (DSM) | One-way / Basic | Depart: 11/10/2026 | From $347 Seen: 11 hrs ago |
| Grand Cayman (GCM) | Washington, D.C. (Reagan National) (DCA) | One-way / Basic | Depart: 01/19/2027 | From $350 Seen: 14 hrs ago |
| Grand Cayman (GCM) | Spokane (GEG) | One-way / Basic | Depart: 02/12/2027 | From $358 Seen: 2 hrs ago |
| Grand Cayman (GCM) | Baltimore/Washington (BWI) | One-way / Basic | Depart: 01/19/2027 | From $366 Seen: 16 hrs ago |
| Grand Cayman (GCM) | New Orleans (MSY) | One-way / Basic | Depart: 11/25/2026 | From $392 Seen: 15 hrs ago |
| Grand Cayman (GCM) | Austin (AUS) | One-way / Basic | Depart: 12/28/2026 | From $397 Seen: 8 hrs ago |
| Grand Cayman (GCM) | Chicago (Midway) (MDW) | One-way / Basic | Depart: 01/19/2027 | From $421 Seen: 3 minutes ago |
| Grand Cayman (GCM) | Nashville (BNA) | One-way / Basic | Depart: 12/30/2026 | From $441 Seen: 17 hrs ago |
| Grand Cayman (GCM) | St. Louis (STL) | One-way / Choice | Depart: 01/18/2027 | From $556 Seen: 10 hrs ago |
| Grand Cayman (GCM) | San Diego (SAN) | One-way / Choice | Depart: 01/01/2027 | From $556 Seen: 56 minutes ago |
| Grand Cayman (GCM) | Raleigh/Durham (RDU) | One-way / Choice | Depart: 01/04/2027 | From $586 Seen: 5 hrs ago |
| Grand Cayman (GCM) | Pittsburgh (PIT) | One-way / Choice | Depart: 03/22/2027 | From $636 Seen: 11 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