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: 01/03/2026
From
$107
Seen: 2 hrs ago
One-way
Basic
Pittsburgh (PIT)to
Grand Cayman (GCM)Depart: 01/03/2026
From
$112
Seen: 2 hrs ago
One-way
Basic
Fort Lauderdale (FLL)to
Grand Cayman (GCM)Depart: 12/30/2025
From
$113
Seen: 12 hrs ago
One-way
Choice
New Orleans (MSY)to
Grand Cayman (GCM)Depart: 12/31/2025
From
$127
Seen: 18 hrs ago
One-way
Choice
Nashville (BNA)to
Grand Cayman (GCM)Depart: 01/19/2026
From
$138
Seen: 4 hrs ago
One-way
Basic
Austin (AUS)to
Grand Cayman (GCM)Depart: 01/05/2026
From
$138
Seen: 4 hrs ago
One-way
Choice
Houston (Hobby) (HOU)to
Grand Cayman (GCM)Depart: 01/14/2026
From
$151
Seen: 10 hrs ago
One-way
Basic
Columbus (CMH)to
Grand Cayman (GCM)Depart: 01/13/2026
From
$157
Seen: 13 hrs ago
One-way
Basic
Chicago (Midway) (MDW)to
Grand Cayman (GCM)Depart: 01/18/2026
From
$171
Seen: 9 hrs ago
One-way
Basic
St. Louis (STL)to
Grand Cayman (GCM)Depart: 01/14/2026
From
$171
Seen: 9 hrs ago
One-way
Basic
Orlando (MCO)to
Grand Cayman (GCM)Depart: 01/19/2026
From
$176
Seen: 12 hrs ago
One-way
Basic
Kansas City (MCI)to
Grand Cayman (GCM)Depart: 01/14/2026
From
$177
Seen: 3 hrs ago
One-way
Basic
Phoenix (PHX)to
Grand Cayman (GCM)Depart: 01/12/2026
From
$180
Seen: 6 hrs ago
One-way
Basic
Denver (DEN)to
Grand Cayman (GCM)Depart: 12/31/2025
From
$192
Seen: 15 hrs ago
One-way
Basic
Atlanta (ATL)to
Grand Cayman (GCM)Depart: 01/16/2026
From
$206
Seen: 2 hrs ago
One-way
Basic
Washington, D.C. (Reagan National) (DCA)to
Grand Cayman (GCM)Depart: 01/01/2026
From
$206
Seen: 20 hrs ago
One-way
Basic
Dallas (Love Field) (DAL)to
Grand Cayman (GCM)Depart: 01/15/2026
From
$227
Seen: 4 hrs ago
One-way
Basic
San Antonio (SAT)to
Grand Cayman (GCM)Depart: 01/03/2026
From
$260
Seen: 16 hrs ago
One-way
Basic
Indianapolis (IND)to
Grand Cayman (GCM)Depart: 12/22/2025
From
$261
Seen: 17 hrs ago
One-way
Basic
Milwaukee (MKE)to
Grand Cayman (GCM)Depart: 12/25/2025
From
$361
Seen: 15 hrs ago
One-way
Choice
*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 |
|---|---|---|---|---|
| New Orleans (MSY) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/22/2026 | From $92 Seen: 17 hrs ago |
| Baltimore/Washington (BWI) | Grand Cayman (GCM) | One-way / Basic | Depart: 04/18/2026 | From $98 Seen: 15 hrs ago |
| Columbus (CMH) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/28/2026 | From $134 Seen: 17 hrs ago |
| Orlando (MCO) | Grand Cayman (GCM) | One-way / Basic | Depart: 02/02/2026 | From $136 Seen: 15 hrs ago |
| Nashville (BNA) | Grand Cayman (GCM) | One-way / Basic | Depart: 04/28/2026 | From $138 Seen: 20 hrs ago |
| Atlanta (ATL) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/23/2026 | From $138 Seen: 5 hrs ago |
| Houston (Hobby) (HOU) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/09/2026 | From $151 Seen: 5 hrs ago |
| Chicago (Midway) (MDW) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/31/2026 | From $151 Seen: 15 hrs ago |
| St. Louis (STL) | Grand Cayman (GCM) | One-way / Basic | Depart: 02/02/2026 | From $151 Seen: 5 hrs ago |
| Kansas City (MCI) | Grand Cayman (GCM) | One-way / Basic | Depart: 02/23/2026 | From $151 Seen: 9 hrs ago |
| Denver (DEN) | Grand Cayman (GCM) | One-way / Basic | Depart: 02/18/2026 | From $151 Seen: 11 hrs ago |
| Washington, D.C. (Reagan National) (DCA) | Grand Cayman (GCM) | One-way / Basic | Depart: 02/23/2026 | From $151 Seen: 14 hrs ago |
| Albany (ALB) | Grand Cayman (GCM) | One-way / Basic | Depart: 02/09/2026 | From $151 Seen: 10 hrs ago |
| Fort Lauderdale (FLL) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/29/2026 | From $155 Seen: 12 hrs ago |
| Chicago (O'Hare) (ORD) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/30/2026 | From $157 Seen: 15 hrs ago |
| Dallas (Love Field) (DAL) | Grand Cayman (GCM) | One-way / Basic | Depart: 02/18/2026 | From $171 Seen: 7 hrs ago |
| Austin (AUS) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/19/2026 | From $171 Seen: 5 hrs ago |
| Indianapolis (IND) | Grand Cayman (GCM) | One-way / Basic | Depart: 02/23/2026 | From $171 Seen: 15 hrs ago |
| Pittsburgh (PIT) | Grand Cayman (GCM) | One-way / Basic | Depart: 02/03/2026 | From $171 Seen: 9 hrs ago |
| San Antonio (SAT) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/21/2026 | From $177 Seen: 13 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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