Flights to Cayman Islands
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Trending flight deals to and within Cayman Islands
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New Orleans (MSY)to
Grand Cayman (GCM)Depart: 01/01/2026
From
$126
Seen: 3 hrs ago
One-way
Choice
Columbus (CMH)to
Grand Cayman (GCM)Depart: 01/03/2026
From
$128
Seen: 6 hrs ago
One-way
Basic
Fort Lauderdale (FLL)to
Grand Cayman (GCM)Depart: 12/16/2025
From
$137
Seen: 8 hrs ago
One-way
Basic
Nashville (BNA)to
Grand Cayman (GCM)Depart: 01/04/2026
From
$138
Seen: 14 hrs ago
One-way
Basic
Baltimore/Washington (BWI)to
Grand Cayman (GCM)Depart: 01/01/2026
From
$143
Seen: 22 hrs ago
One-way
Basic
Dallas (Love Field) (DAL)to
Grand Cayman (GCM)Depart: 01/04/2026
From
$159
Seen: 11 hrs ago
One-way
Basic
Chicago (Midway) (MDW)to
Grand Cayman (GCM)Depart: 12/31/2025
From
$174
Seen: 23 hrs ago
One-way
Basic
Austin (AUS)to
Grand Cayman (GCM)Depart: 01/04/2026
From
$190
Seen: 6 hrs ago
One-way
Basic
San Antonio (SAT)to
Grand Cayman (GCM)Depart: 01/04/2026
From
$190
Seen: 10 hrs ago
One-way
Basic
Milwaukee (MKE)to
Grand Cayman (GCM)Depart: 12/07/2025
From
$194
Seen: 3 hrs ago
One-way
Basic
St. Louis (STL)to
Grand Cayman (GCM)Depart: 01/01/2026
From
$206
Seen: 2 hrs ago
One-way
Basic
Atlanta (ATL)to
Grand Cayman (GCM)Depart: 12/31/2025
From
$206
Seen: 12 hrs ago
One-way
Basic
Indianapolis (IND)to
Grand Cayman (GCM)Depart: 12/30/2025
From
$206
Seen: 1 hour ago
One-way
Basic
Washington, D.C. (Reagan National) (DCA)to
Grand Cayman (GCM)Depart: 12/13/2025
From
$206
Seen: 7 hrs ago
One-way
Basic
Pittsburgh (PIT)to
Grand Cayman (GCM)Depart: 12/08/2025
From
$206
Seen: 11 hrs ago
One-way
Basic
Orlando (MCO)to
Grand Cayman (GCM)Depart: 01/01/2026
From
$236
Seen: 10 hrs ago
One-way
Basic
Phoenix (PHX)to
Grand Cayman (GCM)Depart: 12/14/2025
From
$246
Seen: 9 hrs ago
One-way
Basic
Denver (DEN)to
Grand Cayman (GCM)Depart: 12/11/2025
From
$260
Seen: 6 hrs ago
One-way
Basic
Kansas City (MCI)to
Grand Cayman (GCM)Depart: 12/05/2025
From
$310
Seen: 16 hrs ago
One-way
Choice
Houston (Hobby) (HOU)to
Grand Cayman (GCM)Depart: 12/14/2025
From
$311
Seen: 7 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 |
|---|---|---|---|---|
| Baltimore/Washington (BWI) | Grand Cayman (GCM) | One-way / Basic | Depart: 02/04/2026 | From $103 Seen: 8 hrs ago |
| Washington, D.C. (Reagan National) (DCA) | Grand Cayman (GCM) | One-way / Basic | Depart: 03/01/2026 | From $103 Seen: 5 hrs ago |
| Albany (ALB) | Grand Cayman (GCM) | One-way / Basic | Depart: 03/18/2026 | From $103 Seen: 8 hrs ago |
| Hartford/Springfield (BDL) | Grand Cayman (GCM) | One-way / Basic | Depart: 02/23/2026 | From $110 Seen: 7 hrs ago |
| Fort Lauderdale (FLL) | Grand Cayman (GCM) | One-way / Basic | Depart: 03/01/2026 | From $120 Seen: 2 hrs ago |
| Denver (DEN) | Grand Cayman (GCM) | One-way / Basic | Depart: 02/18/2026 | From $126 Seen: 13 hrs ago |
| New Orleans (MSY) | Grand Cayman (GCM) | One-way / Choice | Depart: 01/27/2026 | From $126 Seen: 6 hrs ago |
| Indianapolis (IND) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/07/2026 | From $136 Seen: 10 hrs ago |
| Columbus (CMH) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/05/2026 | From $136 Seen: 12 hrs ago |
| Nashville (BNA) | Grand Cayman (GCM) | One-way / Basic | Depart: 02/22/2026 | From $138 Seen: 13 hrs ago |
| Birmingham (BHM) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/09/2026 | From $138 Seen: 6 minutes ago |
| Los Angeles (LAX) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/19/2026 | From $142 Seen: 9 hrs ago |
| Houston (Hobby) (HOU) | Grand Cayman (GCM) | One-way / Basic | Depart: 02/09/2026 | From $151 Seen: 2 hrs ago |
| Dallas (Love Field) (DAL) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/21/2026 | From $151 Seen: 2 hrs ago |
| Chicago (Midway) (MDW) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/14/2026 | From $151 Seen: 2 hrs ago |
| St. Louis (STL) | Grand Cayman (GCM) | One-way / Basic | Depart: 02/08/2026 | From $151 Seen: 2 hrs ago |
| Kansas City (MCI) | Grand Cayman (GCM) | One-way / Basic | Depart: 02/24/2026 | From $151 Seen: 41 minutes ago |
| Milwaukee (MKE) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/19/2026 | From $151 Seen: 20 minutes ago |
| San Antonio (SAT) | Grand Cayman (GCM) | One-way / Basic | Depart: 02/01/2026 | From $151 Seen: 1 hour ago |
| Chicago (O'Hare) (ORD) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/19/2026 | From $151 Seen: 22 minutes 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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