Flights to Cayman Islands
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Trending flight deals to and within Cayman Islands
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Chicago (Midway) (MDW)to
Grand Cayman (GCM)Depart: 09/12/2026
From
$162
Seen: 21 hrs ago
One-way
Basic
Fort Lauderdale (FLL)to
Grand Cayman (GCM)Depart: 08/22/2026
From
$183
Seen: 21 hrs ago
One-way
Basic
Orlando (MCO)to
Grand Cayman (GCM)Depart: 09/12/2026
From
$192
Seen: 6 hrs ago
One-way
Basic
Baltimore/Washington (BWI)to
Grand Cayman (GCM)Depart: 09/05/2026
From
$203
Seen: 18 hrs ago
One-way
Basic
Houston (Hobby) (HOU)to
Grand Cayman (GCM)Depart: 09/12/2026
From
$207
Seen: 1 hour ago
One-way
Basic
Austin (AUS)to
Grand Cayman (GCM)Depart: 09/12/2026
From
$207
Seen: 23 hrs ago
One-way
Basic
Nashville (BNA)to
Grand Cayman (GCM)Depart: 09/04/2026
From
$229
Seen: 6 hrs ago
One-way
Basic
Columbus (CMH)to
Grand Cayman (GCM)Depart: 09/11/2026
From
$238
Seen: 21 hrs ago
One-way
Basic
Phoenix (PHX)to
Grand Cayman (GCM)Depart: 09/11/2026
From
$241
Seen: 12 hrs ago
One-way
Basic
Las Vegas (LAS)to
Grand Cayman (GCM)Depart: 09/12/2026
From
$241
Seen: 6 hrs ago
One-way
Basic
Buffalo/Niagara Falls (BUF)to
Grand Cayman (GCM)Depart: 09/11/2026
From
$245
Seen: 13 hrs ago
One-way
Basic
Washington, D.C. (Reagan National) (DCA)to
Grand Cayman (GCM)Depart: 09/12/2026
From
$246
Seen: 46 minutes ago
One-way
Basic
Dallas (Love Field) (DAL)to
Grand Cayman (GCM)Depart: 09/11/2026
From
$247
Seen: 20 hrs ago
One-way
Basic
Pittsburgh (PIT)to
Grand Cayman (GCM)Depart: 09/11/2026
From
$261
Seen: 11 hrs ago
One-way
Basic
St. Louis (STL)to
Grand Cayman (GCM)Depart: 09/04/2026
From
$281
Seen: 17 hrs ago
One-way
Basic
Indianapolis (IND)to
Grand Cayman (GCM)Depart: 09/04/2026
From
$285
Seen: 7 hrs ago
One-way
Basic
Los Angeles (LAX)to
Grand Cayman (GCM)Depart: 09/04/2026
From
$291
Seen: 21 hrs ago
One-way
Basic
New Orleans (MSY)to
Grand Cayman (GCM)Depart: 09/04/2026
From
$297
Seen: 11 hrs ago
One-way
Basic
New York (LaGuardia) (LGA)to
Grand Cayman (GCM)Depart: 09/18/2026
From
$307
Seen: 11 hrs ago
One-way
Basic
Atlanta (ATL)to
Grand Cayman (GCM)Depart: 09/06/2026
From
$336
Seen: 10 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 |
|---|---|---|---|---|
| Orlando (MCO) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/15/2026 | From $162 Seen: 21 hrs ago |
| Chicago (Midway) (MDW) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/06/2027 | From $162 Seen: 5 hrs ago |
| Denver (DEN) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/17/2027 | From $172 Seen: 22 hrs ago |
| Houston (Hobby) (HOU) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/10/2027 | From $177 Seen: 17 hrs ago |
| Dallas (Love Field) (DAL) | Grand Cayman (GCM) | One-way / Basic | Depart: 12/15/2026 | From $177 Seen: 6 hrs ago |
| Kansas City (MCI) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/17/2027 | From $177 Seen: 22 hrs ago |
| Austin (AUS) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/10/2027 | From $177 Seen: 9 hrs ago |
| Phoenix (PHX) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/10/2026 | From $183 Seen: 3 hrs ago |
| Nashville (BNA) | Grand Cayman (GCM) | One-way / Basic | Depart: 12/09/2026 | From $184 Seen: 20 hrs ago |
| Washington, D.C. (Reagan National) (DCA) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/24/2027 | From $186 Seen: 22 hrs ago |
| Buffalo/Niagara Falls (BUF) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/01/2026 | From $186 Seen: 15 hrs ago |
| Baltimore/Washington (BWI) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/17/2026 | From $187 Seen: 12 hrs ago |
| St. Louis (STL) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/17/2027 | From $187 Seen: 18 hrs ago |
| Indianapolis (IND) | Grand Cayman (GCM) | One-way / Basic | Depart: 12/13/2026 | From $187 Seen: 5 hrs ago |
| Louisville (SDF) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/18/2027 | From $187 Seen: 18 hrs ago |
| Philadelphia (PHL) | Grand Cayman (GCM) | One-way / Basic | Depart: 02/02/2027 | From $187 Seen: 3 hrs ago |
| Fort Lauderdale (FLL) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/21/2026 | From $189 Seen: 21 hrs ago |
| Pittsburgh (PIT) | Grand Cayman (GCM) | One-way / Basic | Depart: 02/22/2027 | From $197 Seen: 8 hrs ago |
| New Orleans (MSY) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/11/2027 | From $198 Seen: 23 hrs ago |
| Atlanta (ATL) | Grand Cayman (GCM) | One-way / Basic | Depart: 09/26/2026 | From $219 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.
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