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
$
Fort Lauderdale (FLL)to
Grand Cayman (GCM)Depart: 08/15/2026
From
$183
Seen: 23 hrs ago
One-way
Basic
Baltimore/Washington (BWI)to
Grand Cayman (GCM)Depart: 08/15/2026
From
$193
Seen: 4 hrs ago
One-way
Basic
Nashville (BNA)to
Grand Cayman (GCM)Depart: 08/14/2026
From
$213
Seen: 19 hrs ago
One-way
Basic
Austin (AUS)to
Grand Cayman (GCM)Depart: 08/03/2026
From
$213
Seen: 8 hrs ago
One-way
Basic
Chicago (Midway) (MDW)to
Grand Cayman (GCM)Depart: 08/28/2026
From
$217
Seen: 22 hrs ago
One-way
Basic
Pittsburgh (PIT)to
Grand Cayman (GCM)Depart: 08/01/2026
From
$219
Seen: 10 hrs ago
One-way
Basic
Orlando (MCO)to
Grand Cayman (GCM)Depart: 08/29/2026
From
$227
Seen: 10 hrs ago
One-way
Basic
Washington, D.C. (Reagan National) (DCA)to
Grand Cayman (GCM)Depart: 08/22/2026
From
$231
Seen: 23 hrs ago
One-way
Basic
Dallas (Love Field) (DAL)to
Grand Cayman (GCM)Depart: 08/07/2026
From
$258
Seen: 8 hrs ago
One-way
Basic
Atlanta (ATL)to
Grand Cayman (GCM)Depart: 08/15/2026
From
$261
Seen: 11 hrs ago
One-way
Basic
New Orleans (MSY)to
Grand Cayman (GCM)Depart: 08/01/2026
From
$261
Seen: 7 hrs ago
One-way
Basic
Raleigh/Durham (RDU)to
Grand Cayman (GCM)Depart: 08/03/2026
From
$290
Seen: 14 hrs ago
One-way
Basic
Columbus (CMH)to
Grand Cayman (GCM)Depart: 08/08/2026
From
$294
Seen: 23 hrs ago
One-way
Basic
Houston (Hobby) (HOU)to
Grand Cayman (GCM)Depart: 08/22/2026
From
$301
Seen: 10 hrs ago
One-way
Basic
Phoenix (PHX)to
Grand Cayman (GCM)Depart: 08/01/2026
From
$311
Seen: 13 hrs ago
One-way
Choice
Denver (DEN)to
Grand Cayman (GCM)Depart: 08/01/2026
From
$330
Seen: 17 hrs ago
One-way
Basic
San Antonio (SAT)to
Grand Cayman (GCM)Depart: 08/07/2026
From
$331
Seen: 5 hrs ago
One-way
Basic
Milwaukee (MKE)to
Grand Cayman (GCM)Depart: 08/02/2026
From
$333
Seen: 17 hrs ago
One-way
Basic
Kansas City (MCI)to
Grand Cayman (GCM)Depart: 08/01/2026
From
$341
Seen: 22 hrs ago
One-way
Basic
Los Angeles (LAX)to
Grand Cayman (GCM)Depart: 08/21/2026
From
$357
Seen: 11 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 |
|---|---|---|---|---|
| Fort Lauderdale (FLL) | Grand Cayman (GCM) | One-way / Basic | Depart: 12/01/2026 | From $98 Seen: 7 hrs ago |
| Washington, D.C. (Reagan National) (DCA) | Grand Cayman (GCM) | One-way / Basic | Depart: 12/14/2026 | From $132 Seen: 10 hrs ago |
| Pittsburgh (PIT) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/30/2026 | From $167 Seen: 19 hrs ago |
| Nashville (BNA) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/17/2026 | From $173 Seen: 14 hrs ago |
| Atlanta (ATL) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/02/2026 | From $176 Seen: 4 hrs ago |
| Denver (DEN) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/16/2026 | From $176 Seen: 13 hrs ago |
| New Orleans (MSY) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/03/2026 | From $178 Seen: 12 hrs ago |
| Dallas (Love Field) (DAL) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/01/2026 | From $188 Seen: 7 hrs ago |
| Orlando (MCO) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/01/2026 | From $189 Seen: 19 hrs ago |
| Birmingham (BHM) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/16/2026 | From $189 Seen: 10 hrs ago |
| Baltimore/Washington (BWI) | Grand Cayman (GCM) | One-way / Basic | Depart: 02/09/2027 | From $193 Seen: 21 hrs ago |
| Louisville (SDF) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/01/2026 | From $197 Seen: 4 hrs ago |
| Milwaukee (MKE) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/03/2026 | From $198 Seen: 3 hrs ago |
| Phoenix (PHX) | Grand Cayman (GCM) | One-way / Basic | Depart: 03/09/2027 | From $198 Seen: 7 hrs ago |
| Raleigh/Durham (RDU) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/10/2026 | From $198 Seen: 11 hrs ago |
| Providence (PVD) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/13/2026 | From $199 Seen: 17 hrs ago |
| Austin (AUS) | Grand Cayman (GCM) | One-way / Basic | Depart: 09/19/2026 | From $203 Seen: 17 hrs ago |
| Philadelphia (PHL) | Grand Cayman (GCM) | One-way / Basic | Depart: 03/05/2027 | From $206 Seen: 13 hrs ago |
| Houston (Hobby) (HOU) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/18/2027 | From $207 Seen: 11 hrs ago |
| Chicago (Midway) (MDW) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/10/2026 | From $207 Seen: 5 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