Spirit Airlines Customers: Southwest has options for Customers holding Spirit reservations. We’re here to help you continue your journey. Learn more.
Flights to Cayman Islands
expand_more
1 Passenger
expand_morePromo Code
expand_moretoday
today
Trending flight deals to and within Cayman Islands
flight_takeoff
flight_land
$
Austin (AUS)to
Grand Cayman (GCM)Depart: 06/02/2026
From
$98
Seen: 5 hrs ago
One-way
Basic
Fort Lauderdale (FLL)to
Grand Cayman (GCM)Depart: 06/10/2026
From
$133
Seen: 3 hrs ago
One-way
Basic
Baltimore/Washington (BWI)to
Grand Cayman (GCM)Depart: 05/16/2026
From
$148
Seen: 9 hrs ago
One-way
Basic
Houston (Hobby) (HOU)to
Grand Cayman (GCM)Depart: 05/19/2026
From
$185
Seen: 4 hrs ago
One-way
Basic
Columbus (CMH)to
Grand Cayman (GCM)Depart: 06/02/2026
From
$185
Seen: 6 hrs ago
One-way
Basic
Nashville (BNA)to
Grand Cayman (GCM)Depart: 05/26/2026
From
$205
Seen: 3 minutes ago
One-way
Basic
Pittsburgh (PIT)to
Grand Cayman (GCM)Depart: 06/04/2026
From
$206
Seen: 14 hrs ago
One-way
Basic
Washington, D.C. (Reagan National) (DCA)to
Grand Cayman (GCM)Depart: 05/28/2026
From
$207
Seen: 8 hrs ago
One-way
Basic
Orlando (MCO)to
Grand Cayman (GCM)Depart: 06/09/2026
From
$217
Seen: 3 hrs ago
One-way
Basic
Chicago (Midway) (MDW)to
Grand Cayman (GCM)Depart: 05/24/2026
From
$224
Seen: 1 hour ago
One-way
Basic
Kansas City (MCI)to
Grand Cayman (GCM)Depart: 06/03/2026
From
$237
Seen: 12 hrs ago
One-way
Basic
St. Louis (STL)to
Grand Cayman (GCM)Depart: 06/10/2026
From
$243
Seen: 1 hour ago
One-way
Basic
Dallas (Love Field) (DAL)to
Grand Cayman (GCM)Depart: 06/01/2026
From
$246
Seen: 1 hour ago
One-way
Basic
Atlanta (ATL)to
Grand Cayman (GCM)Depart: 06/02/2026
From
$246
Seen: 1 hour ago
One-way
Basic
San Antonio (SAT)to
Grand Cayman (GCM)Depart: 06/09/2026
From
$251
Seen: 4 hrs ago
One-way
Basic
Indianapolis (IND)to
Grand Cayman (GCM)Depart: 06/06/2026
From
$261
Seen: 1 hour ago
One-way
Basic
Phoenix (PHX)to
Grand Cayman (GCM)Depart: 05/19/2026
From
$273
Seen: 23 hrs ago
One-way
Basic
Denver (DEN)to
Grand Cayman (GCM)Depart: 05/14/2026
From
$277
Seen: 14 hrs ago
One-way
Basic
New Orleans (MSY)to
Grand Cayman (GCM)Depart: 05/15/2026
From
$331
Seen: 5 hrs ago
One-way
Basic
Milwaukee (MKE)to
Grand Cayman (GCM)Depart: 05/14/2026
From
$341
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 to Cayman Islands with Southwest Airlines
flight_takeoff
flight_land
$
From | To | Fare Type | Dates | Price |
|---|---|---|---|---|
| Pittsburgh (PIT) | Grand Cayman (GCM) | One-way / Basic | Depart: 07/05/2026 | From $91 Seen: 14 hrs ago |
| Dallas (Love Field) (DAL) | Grand Cayman (GCM) | One-way / Basic | Depart: 08/03/2026 | From $98 Seen: 17 hrs ago |
| Baltimore/Washington (BWI) | Grand Cayman (GCM) | One-way / Basic | Depart: 07/21/2026 | From $108 Seen: 22 hrs ago |
| Austin (AUS) | Grand Cayman (GCM) | One-way / Basic | Depart: 07/28/2026 | From $133 Seen: 9 hrs ago |
| Nashville (BNA) | Grand Cayman (GCM) | One-way / Basic | Depart: 07/15/2026 | From $179 Seen: 1 hour ago |
| Fort Lauderdale (FLL) | Grand Cayman (GCM) | One-way / Basic | Depart: 06/23/2026 | From $199 Seen: 10 hrs ago |
| Tampa (TPA) | Grand Cayman (GCM) | One-way / Basic | Depart: 07/12/2026 | From $209 Seen: 2 hrs ago |
| Birmingham (BHM) | Grand Cayman (GCM) | One-way / Basic | Depart: 07/15/2026 | From $216 Seen: 1 hour ago |
| Orlando (MCO) | Grand Cayman (GCM) | One-way / Basic | Depart: 07/14/2026 | From $217 Seen: 16 hrs ago |
| St. Louis (STL) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/02/2026 | From $217 Seen: 1 hour ago |
| Denver (DEN) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/04/2026 | From $217 Seen: 10 hrs ago |
| Houston (Hobby) (HOU) | Grand Cayman (GCM) | One-way / Basic | Depart: 07/07/2026 | From $224 Seen: 10 hrs ago |
| Chicago (Midway) (MDW) | Grand Cayman (GCM) | One-way / Basic | Depart: 09/12/2026 | From $224 Seen: 16 hrs ago |
| Indianapolis (IND) | Grand Cayman (GCM) | One-way / Basic | Depart: 07/11/2026 | From $224 Seen: 14 hrs ago |
| Columbus (CMH) | Grand Cayman (GCM) | One-way / Basic | Depart: 09/26/2026 | From $224 Seen: 7 hrs ago |
| New Orleans (MSY) | Grand Cayman (GCM) | One-way / Basic | Depart: 07/23/2026 | From $231 Seen: 1 hour ago |
| Buffalo/Niagara Falls (BUF) | Grand Cayman (GCM) | One-way / Basic | Depart: 07/08/2026 | From $234 Seen: 10 hrs ago |
| Kansas City (MCI) | Grand Cayman (GCM) | One-way / Basic | Depart: 07/31/2026 | From $237 Seen: 8 hrs ago |
| Washington, D.C. (Reagan National) (DCA) | Grand Cayman (GCM) | One-way / Basic | Depart: 06/29/2026 | From $237 Seen: 15 hrs ago |
| San Antonio (SAT) | Grand Cayman (GCM) | One-way / Basic | Depart: 07/07/2026 | From $237 Seen: 2 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.
Join Rapid Rewards, our award-winning frequent flyer program1.
Sign up nowNo blackout dates.
You can use your points to book any seat, on any flight, no exceptions. Any day, any time, any flight, your points are ready to take you to where you want to go.
Your points don’t expire.
You can earn points on flights and on everyday purchases with our partners, which makes getting to your destination easy. No matter when, or where, you earn them, your points won’t expire.
Free inflight WiFi thanks to T-Mobile®.2
Rapid Rewards members can go online to check email, snag a dinner reservation, or browse social media from takeoff to landing. Learn more ›
12022–2023 Freddie Awards. 2Where available. Available only on WiFi-enabled designated aircraft. Free WiFi is only for Rapid Rewards® Members.
Discover the best flight deals to Cayman Islands
Explore Southwest Airlines popular destinations