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: 12/06/2026
From
$138
Seen: 13 hrs ago
One-way
Basic

Baltimore/Washington (BWI)to

Grand Cayman (GCM)
Depart: 12/14/2026
From
$147
Seen: 22 hrs ago
One-way
Basic

Nashville (BNA)to

Grand Cayman (GCM)
Depart: 12/01/2026
From
$178
Seen: 11 hrs ago
One-way
Basic

Austin (AUS)to

Grand Cayman (GCM)
Depart: 12/14/2026
From
$178
Seen: 17 hrs ago
One-way
Basic

New Orleans (MSY)to

Grand Cayman (GCM)
Depart: 12/08/2026
From
$178
Seen: 2 hrs ago
One-way
Basic

Columbus (CMH)to

Grand Cayman (GCM)
Depart: 12/08/2026
From
$183
Seen: 6 hrs ago
One-way
Basic

Pittsburgh (PIT)to

Grand Cayman (GCM)
Depart: 11/15/2026
From
$186
Seen: 55 minutes ago
One-way
Basic

Washington D.C. Reagan National (DCA)to

Grand Cayman (GCM)
Depart: 12/14/2026
From
$197
Seen: 19 hrs ago
One-way
Basic

Orlando (MCO)to

Grand Cayman (GCM)
Depart: 12/08/2026
From
$200
Seen: 14 hrs ago
One-way
Basic

Kansas City (MCI)to

Grand Cayman (GCM)
Depart: 12/14/2026
From
$200
Seen: 9 hrs ago
One-way
Basic

Denver (DEN)to

Grand Cayman (GCM)
Depart: 12/07/2026
From
$208
Seen: 14 hrs ago
One-way
Basic

Houston Hobby (HOU)to

Grand Cayman (GCM)
Depart: 12/14/2026
From
$217
Seen: 13 hrs ago
One-way
Basic

Dallas-Love Field (DAL)to

Grand Cayman (GCM)
Depart: 12/09/2026
From
$217
Seen: 4 hrs ago
One-way
Basic

Chicago-Midway (MDW)to

Grand Cayman (GCM)
Depart: 12/09/2026
From
$217
Seen: 17 hrs ago
One-way
Basic

Indianapolis (IND)to

Grand Cayman (GCM)
Depart: 11/14/2026
From
$223
Seen: 3 hrs ago
One-way
Basic

Phoenix (PHX)to

Grand Cayman (GCM)
Depart: 12/10/2026
From
$238
Seen: 21 hrs ago
One-way
Basic

St. Louis (STL)to

Grand Cayman (GCM)
Depart: 12/07/2026
From
$240
Seen: 17 hrs ago
One-way
Basic

Atlanta (ATL)to

Grand Cayman (GCM)
Depart: 12/11/2026
From
$256
Seen: 10 hrs ago
One-way
Basic

San Antonio (SAT)to

Grand Cayman (GCM)
Depart: 12/07/2026
From
$262
Seen: 9 minutes ago
One-way
Basic

Milwaukee (MKE)to

Grand Cayman (GCM)
Depart: 12/09/2026
From
$274
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

$
Find popular low fares to Cayman Islands with Southwest Airlines
From
To
Fare Type
Dates
Price
Baltimore/Washington (BWI)Grand Cayman (GCM)One-way
/
Basic		Depart: 01/02/2027

From

$143

Seen: 23 hrs ago

Tampa (TPA)Grand Cayman (GCM)One-way
/
Basic		Depart: 02/08/2027

From

$153

Seen: 23 hrs ago

Pittsburgh (PIT)Grand Cayman (GCM)One-way
/
Basic		Depart: 02/08/2027

From

$158

Seen: 13 hrs ago

Nashville (BNA)Grand Cayman (GCM)One-way
/
Basic		Depart: 01/18/2027

From

$178

Seen: 18 hrs ago

Austin (AUS)Grand Cayman (GCM)One-way
/
Basic		Depart: 12/15/2026

From

$178

Seen: 17 hrs ago

New Orleans (MSY)Grand Cayman (GCM)One-way
/
Basic		Depart: 02/19/2027

From

$178

Seen: 21 hrs ago

Columbus (CMH)Grand Cayman (GCM)One-way
/
Basic		Depart: 01/12/2027

From

$183

Seen: 20 hrs ago

Fort Lauderdale (FLL)Grand Cayman (GCM)One-way
/
Basic		Depart: 02/16/2027

From

$185

Seen: 16 hrs ago

Indianapolis (IND)Grand Cayman (GCM)One-way
/
Basic		Depart: 12/23/2026

From

$188

Seen: 16 hrs ago

Boston (BOS)Grand Cayman (GCM)One-way
/
Basic		Depart: 02/04/2027

From

$189

Seen: 10 hrs ago

Raleigh/Durham (RDU)Grand Cayman (GCM)One-way
/
Basic		Depart: 01/20/2027

From

$192

Seen: 1 hour ago

Denver (DEN)Grand Cayman (GCM)One-way
/
Basic		Depart: 05/10/2027

From

$197

Seen: 14 hrs ago

Washington D.C. Reagan National (DCA)Grand Cayman (GCM)One-way
/
Basic		Depart: 03/02/2027

From

$197

Seen: 15 hrs ago

Orlando (MCO)Grand Cayman (GCM)One-way
/
Basic		Depart: 01/20/2027

From

$200

Seen: 18 hrs ago

Kansas City (MCI)Grand Cayman (GCM)One-way
/
Basic		Depart: 01/11/2027

From

$200

Seen: 16 hrs ago

Birmingham (BHM)Grand Cayman (GCM)One-way
/
Basic		Depart: 01/31/2027

From

$200

Seen: 22 hrs ago

Albany (ALB)Grand Cayman (GCM)One-way
/
Basic		Depart: 03/02/2027

From

$208

Seen: 13 hrs ago

Hartford/Springfield (BDL)Grand Cayman (GCM)One-way
/
Basic		Depart: 01/11/2027

From

$211

Seen: 8 hrs ago

Houston Hobby (HOU)Grand Cayman (GCM)One-way
/
Basic		Depart: 02/15/2027

From

$217

Seen: 23 hrs ago

Dallas-Love Field (DAL)Grand Cayman (GCM)One-way
/
Basic		Depart: 12/15/2026

From

$217

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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