Flights to Cayman Islands
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Trending flight deals to and within Cayman Islands
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$
Fort Lauderdale (FLL)to
Grand Cayman (GCM)Depart: 02/15/2026
From
$88
Seen: 11 hrs ago
One-way
Basic
New Orleans (MSY)to
Grand Cayman (GCM)Depart: 02/10/2026
From
$92
Seen: 6 hrs ago
One-way
Basic
Baltimore/Washington (BWI)to
Grand Cayman (GCM)Depart: 03/01/2026
From
$113
Seen: 15 hrs ago
One-way
Basic
Washington, D.C. (Reagan National) (DCA)to
Grand Cayman (GCM)Depart: 02/23/2026
From
$113
Seen: 6 hrs ago
One-way
Basic
Dallas (Love Field) (DAL)to
Grand Cayman (GCM)Depart: 02/23/2026
From
$127
Seen: 15 hrs ago
One-way
Basic
Denver (DEN)to
Grand Cayman (GCM)Depart: 03/02/2026
From
$131
Seen: 12 hrs ago
One-way
Basic
Orlando (MCO)to
Grand Cayman (GCM)Depart: 03/03/2026
From
$138
Seen: 15 hrs ago
One-way
Basic
Atlanta (ATL)to
Grand Cayman (GCM)Depart: 02/25/2026
From
$139
Seen: 11 hrs ago
One-way
Basic
Kansas City (MCI)to
Grand Cayman (GCM)Depart: 02/15/2026
From
$140
Seen: 11 hrs ago
One-way
Basic
St. Louis (STL)to
Grand Cayman (GCM)Depart: 02/27/2026
From
$150
Seen: 2 hrs ago
One-way
Basic
Indianapolis (IND)to
Grand Cayman (GCM)Depart: 02/25/2026
From
$150
Seen: 5 hrs ago
One-way
Basic
Chicago (Midway) (MDW)to
Grand Cayman (GCM)Depart: 03/01/2026
From
$152
Seen: 1 hour ago
One-way
Basic
Columbus (CMH)to
Grand Cayman (GCM)Depart: 03/03/2026
From
$152
Seen: 16 hrs ago
One-way
Basic
Nashville (BNA)to
Grand Cayman (GCM)Depart: 02/24/2026
From
$160
Seen: 10 hrs ago
One-way
Basic
San Antonio (SAT)to
Grand Cayman (GCM)Depart: 03/02/2026
From
$171
Seen: 13 hrs ago
One-way
Basic
Pittsburgh (PIT)to
Grand Cayman (GCM)Depart: 03/03/2026
From
$177
Seen: 11 hrs ago
One-way
Basic
Phoenix (PHX)to
Grand Cayman (GCM)Depart: 02/24/2026
From
$181
Seen: 5 hrs ago
One-way
Basic
Austin (AUS)to
Grand Cayman (GCM)Depart: 02/23/2026
From
$190
Seen: 11 hrs ago
One-way
Basic
Milwaukee (MKE)to
Grand Cayman (GCM)Depart: 03/02/2026
From
$190
Seen: 6 hrs ago
One-way
Basic
Houston (Hobby) (HOU)to
Grand Cayman (GCM)Depart: 02/26/2026
From
$227
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
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From | To | Fare Type | Dates | Price |
|---|---|---|---|---|
| Austin (AUS) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/19/2026 | From $92 Seen: 9 hrs ago |
| New Orleans (MSY) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/12/2026 | From $92 Seen: 7 hrs ago |
| Albany (ALB) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/19/2026 | From $96 Seen: 18 hrs ago |
| Orlando (MCO) | Grand Cayman (GCM) | One-way / Basic | Depart: 04/27/2026 | From $103 Seen: 9 hrs ago |
| Nashville (BNA) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/12/2026 | From $104 Seen: 5 hrs ago |
| Denver (DEN) | Grand Cayman (GCM) | One-way / Basic | Depart: 04/27/2026 | From $106 Seen: 12 hrs ago |
| San Antonio (SAT) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/11/2026 | From $106 Seen: 16 hrs ago |
| Baltimore/Washington (BWI) | Grand Cayman (GCM) | One-way / Basic | Depart: 04/07/2026 | From $113 Seen: 12 hrs ago |
| Washington, D.C. (Reagan National) (DCA) | Grand Cayman (GCM) | One-way / Basic | Depart: 03/18/2026 | From $113 Seen: 19 hrs ago |
| Houston (Hobby) (HOU) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/10/2026 | From $127 Seen: 15 hrs ago |
| Chicago (Midway) (MDW) | Grand Cayman (GCM) | One-way / Basic | Depart: 03/04/2026 | From $127 Seen: 20 hrs ago |
| Kansas City (MCI) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/10/2026 | From $131 Seen: 4 hrs ago |
| Columbus (CMH) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/12/2026 | From $141 Seen: 13 hrs ago |
| St. Louis (STL) | Grand Cayman (GCM) | One-way / Basic | Depart: 04/27/2026 | From $152 Seen: 7 hrs ago |
| Louisville (SDF) | Grand Cayman (GCM) | One-way / Basic | Depart: 03/08/2026 | From $152 Seen: 19 hrs ago |
| Hartford/Springfield (BDL) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/04/2026 | From $152 Seen: 12 hrs ago |
| Indianapolis (IND) | Grand Cayman (GCM) | One-way / Basic | Depart: 03/12/2026 | From $156 Seen: 18 hrs ago |
| Tampa (TPA) | Grand Cayman (GCM) | One-way / Basic | Depart: 03/09/2026 | From $159 Seen: 16 hrs ago |
| Fort Lauderdale (FLL) | Grand Cayman (GCM) | One-way / Basic | Depart: 04/09/2026 | From $169 Seen: 9 hrs ago |
| Dallas (Love Field) (DAL) | Grand Cayman (GCM) | One-way / Basic | Depart: 03/09/2026 | From $178 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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