Flights to Cayman Islands
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Trending flight deals to and within Cayman Islands
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$
Baltimore/Washington (BWI)to
Grand Cayman (GCM)Depart: 05/16/2026
From
$104
Seen: 7 hrs ago
One-way
Basic
Pittsburgh (PIT)to
Grand Cayman (GCM)Depart: 05/16/2026
From
$104
Seen: 11 hrs ago
One-way
Basic
Fort Lauderdale (FLL)to
Grand Cayman (GCM)Depart: 04/26/2026
From
$113
Seen: 5 hrs ago
One-way
Basic
Denver (DEN)to
Grand Cayman (GCM)Depart: 05/10/2026
From
$135
Seen: 21 hrs ago
One-way
Basic
Washington, D.C. (Reagan National) (DCA)to
Grand Cayman (GCM)Depart: 04/27/2026
From
$135
Seen: 7 hrs ago
One-way
Basic
Dallas (Love Field) (DAL)to
Grand Cayman (GCM)Depart: 05/04/2026
From
$185
Seen: 8 hrs ago
One-way
Basic
Austin (AUS)to
Grand Cayman (GCM)Depart: 05/08/2026
From
$213
Seen: 9 hrs ago
One-way
Basic
Atlanta (ATL)to
Grand Cayman (GCM)Depart: 04/24/2026
From
$224
Seen: 7 hrs ago
One-way
Basic
Nashville (BNA)to
Grand Cayman (GCM)Depart: 05/04/2026
From
$225
Seen: 13 hrs ago
One-way
Basic
St. Louis (STL)to
Grand Cayman (GCM)Depart: 05/14/2026
From
$237
Seen: 6 hrs ago
One-way
Basic
Columbus (CMH)to
Grand Cayman (GCM)Depart: 05/15/2026
From
$237
Seen: 8 hrs ago
One-way
Basic
Orlando (MCO)to
Grand Cayman (GCM)Depart: 05/08/2026
From
$247
Seen: 11 hrs ago
One-way
Basic
Houston (Hobby) (HOU)to
Grand Cayman (GCM)Depart: 05/24/2026
From
$251
Seen: 2 hrs ago
One-way
Basic
Indianapolis (IND)to
Grand Cayman (GCM)Depart: 05/16/2026
From
$251
Seen: 13 hrs ago
One-way
Basic
Chicago (Midway) (MDW)to
Grand Cayman (GCM)Depart: 05/24/2026
From
$261
Seen: 10 hrs ago
One-way
Basic
New Orleans (MSY)to
Grand Cayman (GCM)Depart: 04/24/2026
From
$261
Seen: 3 hrs ago
One-way
Basic
Kansas City (MCI)to
Grand Cayman (GCM)Depart: 05/08/2026
From
$281
Seen: 23 hrs ago
One-way
Basic
Phoenix (PHX)to
Grand Cayman (GCM)Depart: 05/23/2026
From
$291
Seen: 8 hrs ago
One-way
Basic
Milwaukee (MKE)to
Grand Cayman (GCM)Depart: 05/09/2026
From
$301
Seen: 21 hrs ago
One-way
Basic
San Antonio (SAT)to
Grand Cayman (GCM)Depart: 05/07/2026
From
$311
Seen: 4 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
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From | To | Fare Type | Dates | Price |
|---|---|---|---|---|
| Baltimore/Washington (BWI) | Grand Cayman (GCM) | One-way / Basic | Depart: 08/01/2026 | From $104 Seen: 13 hrs ago |
| Denver (DEN) | Grand Cayman (GCM) | One-way / Basic | Depart: 07/13/2026 | From $104 Seen: 5 hrs ago |
| Pittsburgh (PIT) | Grand Cayman (GCM) | One-way / Basic | Depart: 06/26/2026 | From $104 Seen: 20 hrs ago |
| Austin (AUS) | Grand Cayman (GCM) | One-way / Basic | Depart: 07/21/2026 | From $127 Seen: 7 hrs ago |
| Nashville (BNA) | Grand Cayman (GCM) | One-way / Basic | Depart: 07/09/2026 | From $139 Seen: 9 hrs ago |
| Dallas (Love Field) (DAL) | Grand Cayman (GCM) | One-way / Basic | Depart: 07/21/2026 | From $153 Seen: 7 hrs ago |
| St. Louis (STL) | Grand Cayman (GCM) | One-way / Basic | Depart: 08/02/2026 | From $176 Seen: 5 hrs ago |
| Fort Lauderdale (FLL) | Grand Cayman (GCM) | One-way / Basic | Depart: 07/07/2026 | From $183 Seen: 12 hrs ago |
| New Orleans (MSY) | Grand Cayman (GCM) | One-way / Basic | Depart: 06/09/2026 | From $197 Seen: 5 hrs ago |
| Columbus (CMH) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/25/2026 | From $211 Seen: 4 hrs ago |
| Atlanta (ATL) | Grand Cayman (GCM) | One-way / Basic | Depart: 07/08/2026 | From $216 Seen: 6 hrs ago |
| Birmingham (BHM) | Grand Cayman (GCM) | One-way / Basic | Depart: 06/15/2026 | From $216 Seen: 22 hrs ago |
| Orlando (MCO) | Grand Cayman (GCM) | One-way / Basic | Depart: 07/07/2026 | From $217 Seen: 22 hrs ago |
| Kansas City (MCI) | Grand Cayman (GCM) | One-way / Basic | Depart: 06/02/2026 | From $217 Seen: 11 hrs ago |
| Indianapolis (IND) | Grand Cayman (GCM) | One-way / Basic | Depart: 07/14/2026 | From $223 Seen: 4 hrs ago |
| Phoenix (PHX) | Grand Cayman (GCM) | One-way / Basic | Depart: 06/16/2026 | From $228 Seen: 6 hrs ago |
| Tampa (TPA) | Grand Cayman (GCM) | One-way / Basic | Depart: 06/05/2026 | From $231 Seen: 1 hour ago |
| Houston (Hobby) (HOU) | Grand Cayman (GCM) | One-way / Basic | Depart: 07/19/2026 | From $237 Seen: 18 hrs ago |
| Chicago (Midway) (MDW) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/01/2026 | From $237 Seen: 12 hrs ago |
| Washington, D.C. (Reagan National) (DCA) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/11/2026 | From $237 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.
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