Flights to Cayman Islands
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Trending flight deals to and within Cayman Islands
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$
Washington, D.C. (Reagan National) (DCA)to
Grand Cayman (GCM)Depart: 08/29/2026
From
$132
Seen: 13 hrs ago
One-way
Basic
Baltimore/Washington (BWI)to
Grand Cayman (GCM)Depart: 08/29/2026
From
$193
Seen: 16 hrs ago
One-way
Basic
Pittsburgh (PIT)to
Grand Cayman (GCM)Depart: 08/29/2026
From
$193
Seen: 9 hrs ago
One-way
Basic
Austin (AUS)to
Grand Cayman (GCM)Depart: 08/15/2026
From
$203
Seen: 6 hrs ago
One-way
Basic
Buffalo/Niagara Falls (BUF)to
Grand Cayman (GCM)Depart: 08/28/2026
From
$219
Seen: 6 hrs ago
One-way
Basic
Kansas City (MCI)to
Grand Cayman (GCM)Depart: 08/29/2026
From
$227
Seen: 21 hrs ago
One-way
Basic
Columbus (CMH)to
Grand Cayman (GCM)Depart: 08/08/2026
From
$234
Seen: 14 hrs ago
One-way
Basic
Houston (Hobby) (HOU)to
Grand Cayman (GCM)Depart: 08/29/2026
From
$251
Seen: 3 hrs ago
One-way
Basic
Fort Lauderdale (FLL)to
Grand Cayman (GCM)Depart: 08/22/2026
From
$253
Seen: 2 hrs ago
One-way
Basic
Indianapolis (IND)to
Grand Cayman (GCM)Depart: 08/02/2026
From
$255
Seen: 14 hrs ago
One-way
Basic
Dallas (Love Field) (DAL)to
Grand Cayman (GCM)Depart: 08/14/2026
From
$258
Seen: 8 hrs ago
One-way
Basic
Milwaukee (MKE)to
Grand Cayman (GCM)Depart: 08/07/2026
From
$258
Seen: 15 hrs ago
One-way
Basic
San Antonio (SAT)to
Grand Cayman (GCM)Depart: 08/02/2026
From
$296
Seen: 6 hrs ago
One-way
Basic
Orlando (MCO)to
Grand Cayman (GCM)Depart: 08/15/2026
From
$297
Seen: 1 hour ago
One-way
Basic
Denver (DEN)to
Grand Cayman (GCM)Depart: 08/07/2026
From
$298
Seen: 7 hrs ago
One-way
Basic
Atlanta (ATL)to
Grand Cayman (GCM)Depart: 08/08/2026
From
$311
Seen: 8 hrs ago
One-way
Basic
Phoenix (PHX)to
Grand Cayman (GCM)Depart: 08/02/2026
From
$311
Seen: 9 hrs ago
One-way
Choice
Nashville (BNA)to
Grand Cayman (GCM)Depart: 08/20/2026
From
$318
Seen: 20 hrs ago
One-way
Basic
St. Louis (STL)to
Grand Cayman (GCM)Depart: 08/08/2026
From
$331
Seen: 9 hrs ago
One-way
Basic
Chicago (Midway) (MDW)to
Grand Cayman (GCM)Depart: 08/22/2026
From
$411
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 |
|---|---|---|---|---|
| Fort Lauderdale (FLL) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/13/2027 | From $138 Seen: 44 minutes ago |
| Phoenix (PHX) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/02/2026 | From $147 Seen: 23 hrs ago |
| Providence (PVD) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/03/2026 | From $162 Seen: 14 hrs ago |
| Omaha (OMA) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/26/2027 | From $163 Seen: 17 hrs ago |
| Washington, D.C. (Reagan National) (DCA) | Grand Cayman (GCM) | One-way / Basic | Depart: 12/13/2026 | From $168 Seen: 3 hrs ago |
| Atlanta (ATL) | Grand Cayman (GCM) | One-way / Basic | Depart: 12/06/2026 | From $171 Seen: 14 hrs ago |
| Denver (DEN) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/01/2026 | From $171 Seen: 5 hrs ago |
| Nashville (BNA) | Grand Cayman (GCM) | One-way / Basic | Depart: 01/27/2027 | From $183 Seen: 23 hrs ago |
| Dallas (Love Field) (DAL) | Grand Cayman (GCM) | One-way / Basic | Depart: 02/01/2027 | From $188 Seen: 22 hrs ago |
| Philadelphia (PHL) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/09/2026 | From $188 Seen: 14 hrs ago |
| Orlando (MCO) | Grand Cayman (GCM) | One-way / Basic | Depart: 12/16/2026 | From $189 Seen: 17 hrs ago |
| Baltimore/Washington (BWI) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/04/2026 | From $193 Seen: 21 hrs ago |
| Hartford/Springfield (BDL) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/10/2026 | From $193 Seen: 6 hrs ago |
| Milwaukee (MKE) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/03/2026 | From $198 Seen: 19 hrs ago |
| New Orleans (MSY) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/04/2026 | From $198 Seen: 23 hrs ago |
| Austin (AUS) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/05/2026 | From $203 Seen: 11 hrs ago |
| Houston (Hobby) (HOU) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/01/2026 | From $207 Seen: 3 hrs ago |
| Chicago (Midway) (MDW) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/01/2026 | From $207 Seen: 15 hrs ago |
| St. Louis (STL) | Grand Cayman (GCM) | One-way / Basic | Depart: 11/15/2026 | From $207 Seen: 23 hrs ago |
| Kansas City (MCI) | Grand Cayman (GCM) | One-way / Basic | Depart: 02/03/2027 | From $207 Seen: 2 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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