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: 02/25/2026
From
$93
Seen: 12 hrs ago
One-way
Basic
New Orleans (MSY)to
Grand Cayman (GCM)Depart: 02/27/2026
From
$97
Seen: 6 hrs ago
One-way
Basic
Pittsburgh (PIT)to
Grand Cayman (GCM)Depart: 02/25/2026
From
$127
Seen: 10 hrs ago
One-way
Basic
Baltimore/Washington (BWI)to
Grand Cayman (GCM)Depart: 03/17/2026
From
$128
Seen: 2 hrs ago
One-way
Basic
Columbus (CMH)to
Grand Cayman (GCM)Depart: 03/18/2026
From
$198
Seen: 22 hrs ago
One-way
Basic
Nashville (BNA)to
Grand Cayman (GCM)Depart: 03/17/2026
From
$206
Seen: 5 hrs ago
One-way
Basic
Atlanta (ATL)to
Grand Cayman (GCM)Depart: 03/19/2026
From
$206
Seen: 17 hrs ago
One-way
Basic
Austin (AUS)to
Grand Cayman (GCM)Depart: 03/18/2026
From
$213
Seen: 9 hrs ago
One-way
Basic
Chicago (Midway) (MDW)to
Grand Cayman (GCM)Depart: 03/17/2026
From
$215
Seen: 23 hrs ago
One-way
Basic
Orlando (MCO)to
Grand Cayman (GCM)Depart: 03/22/2026
From
$217
Seen: 3 hrs ago
One-way
Basic
Denver (DEN)to
Grand Cayman (GCM)Depart: 03/11/2026
From
$217
Seen: 21 hrs ago
One-way
Basic
Washington, D.C. (Reagan National) (DCA)to
Grand Cayman (GCM)Depart: 02/22/2026
From
$217
Seen: 12 hrs ago
One-way
Basic
St. Louis (STL)to
Grand Cayman (GCM)Depart: 03/17/2026
From
$227
Seen: 18 hrs ago
One-way
Basic
Kansas City (MCI)to
Grand Cayman (GCM)Depart: 03/17/2026
From
$227
Seen: 3 hrs ago
One-way
Basic
Indianapolis (IND)to
Grand Cayman (GCM)Depart: 02/22/2026
From
$242
Seen: 18 hrs ago
One-way
Basic
Houston (Hobby) (HOU)to
Grand Cayman (GCM)Depart: 03/11/2026
From
$271
Seen: 22 hrs ago
One-way
Basic
Dallas (Love Field) (DAL)to
Grand Cayman (GCM)Depart: 03/16/2026
From
$291
Seen: 18 hrs ago
One-way
Basic
Milwaukee (MKE)to
Grand Cayman (GCM)Depart: 02/20/2026
From
$295
Seen: 23 hrs ago
One-way
Basic
San Antonio (SAT)to
Grand Cayman (GCM)Depart: 03/04/2026
From
$317
Seen: 4 hrs ago
One-way
Basic
Phoenix (PHX)to
Grand Cayman (GCM)Depart: 02/21/2026
From
$381
Seen: 14 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: 04/25/2026 | From $97 Seen: 20 hrs ago |
| Orlando (MCO) | Grand Cayman (GCM) | One-way / Basic | Depart: 04/27/2026 | From $113 Seen: 22 hrs ago |
| Denver (DEN) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/05/2026 | From $116 Seen: 20 hrs ago |
| Baltimore/Washington (BWI) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/16/2026 | From $124 Seen: 3 hrs ago |
| Hartford/Springfield (BDL) | Grand Cayman (GCM) | One-way / Basic | Depart: 04/28/2026 | From $125 Seen: 6 hrs ago |
| Washington, D.C. (Reagan National) (DCA) | Grand Cayman (GCM) | One-way / Basic | Depart: 04/07/2026 | From $128 Seen: 3 hrs ago |
| Houston (Hobby) (HOU) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/10/2026 | From $137 Seen: 23 hrs ago |
| Chicago (O'Hare) (ORD) | Grand Cayman (GCM) | One-way / Basic | Depart: 04/27/2026 | From $137 Seen: 18 hrs ago |
| Austin (AUS) | Grand Cayman (GCM) | One-way / Basic | Depart: 06/16/2026 | From $147 Seen: 23 hrs ago |
| Tampa (TPA) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/18/2026 | From $159 Seen: 4 hrs ago |
| Phoenix (PHX) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/04/2026 | From $164 Seen: 21 hrs ago |
| Los Angeles (LAX) | Grand Cayman (GCM) | One-way / Basic | Depart: 04/26/2026 | From $171 Seen: 23 hrs ago |
| Fort Lauderdale (FLL) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/07/2026 | From $176 Seen: 7 hrs ago |
| Pittsburgh (PIT) | Grand Cayman (GCM) | One-way / Basic | Depart: 04/27/2026 | From $178 Seen: 18 hrs ago |
| Chicago (Midway) (MDW) | Grand Cayman (GCM) | One-way / Basic | Depart: 04/22/2026 | From $188 Seen: 20 hrs ago |
| Raleigh/Durham (RDU) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/10/2026 | From $188 Seen: 1 hour ago |
| Kansas City (MCI) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/25/2026 | From $193 Seen: 19 hrs ago |
| Indianapolis (IND) | Grand Cayman (GCM) | One-way / Basic | Depart: 04/01/2026 | From $193 Seen: 18 hrs ago |
| St. Louis (STL) | Grand Cayman (GCM) | One-way / Basic | Depart: 03/25/2026 | From $198 Seen: 22 hrs ago |
| Columbus (CMH) | Grand Cayman (GCM) | One-way / Basic | Depart: 04/02/2026 | From $198 Seen: 18 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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