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: 04/14/2026
From
$113
Seen: 3 hrs ago
One-way
Basic

Baltimore/Washington (BWI)to

Grand Cayman (GCM)
Depart: 05/02/2026
From
$133
Seen: 4 hrs ago
One-way
Basic

Orlando (MCO)to

Grand Cayman (GCM)
Depart: 04/26/2026
From
$163
Seen: 3 hrs ago
One-way
Basic

Denver (DEN)to

Grand Cayman (GCM)
Depart: 04/10/2026
From
$169
Seen: 21 hrs ago
One-way
Basic

Nashville (BNA)to

Grand Cayman (GCM)
Depart: 04/27/2026
From
$185
Seen: 5 hrs ago
One-way
Basic

Chicago (Midway) (MDW)to

Grand Cayman (GCM)
Depart: 05/04/2026
From
$188
Seen: 6 hrs ago
One-way
Basic

Tampa (TPA)to

Grand Cayman (GCM)
Depart: 04/25/2026
From
$203
Seen: 8 hrs ago
One-way
Basic

Phoenix (PHX)to

Grand Cayman (GCM)
Depart: 04/23/2026
From
$206
Seen: 2 hrs ago
One-way
Basic

Dallas (Love Field) (DAL)to

Grand Cayman (GCM)
Depart: 04/25/2026
From
$208
Seen: 23 hrs ago
One-way
Basic

Atlanta (ATL)to

Grand Cayman (GCM)
Depart: 04/08/2026
From
$208
Seen: 21 hrs ago
One-way
Basic

Kansas City (MCI)to

Grand Cayman (GCM)
Depart: 05/03/2026
From
$213
Seen: 7 hrs ago
One-way
Basic

Milwaukee (MKE)to

Grand Cayman (GCM)
Depart: 04/26/2026
From
$230
Seen: 6 hrs ago
One-way
Basic

St. Louis (STL)to

Grand Cayman (GCM)
Depart: 05/02/2026
From
$237
Seen: 22 hrs ago
One-way
Basic

Houston (Hobby) (HOU)to

Grand Cayman (GCM)
Depart: 05/01/2026
From
$251
Seen: 4 hrs ago
One-way
Basic

New Orleans (MSY)to

Grand Cayman (GCM)
Depart: 04/24/2026
From
$251
Seen: 2 hrs ago
One-way
Basic

Pittsburgh (PIT)to

Grand Cayman (GCM)
Depart: 04/24/2026
From
$251
Seen: 48 minutes ago
One-way
Basic

Austin (AUS)to

Grand Cayman (GCM)
Depart: 04/04/2026
From
$253
Seen: 9 hrs ago
One-way
Basic

Indianapolis (IND)to

Grand Cayman (GCM)
Depart: 04/04/2026
From
$326
Seen: 13 hrs ago
One-way
Basic

Columbus (CMH)to

Grand Cayman (GCM)
Depart: 04/29/2026
From
$331
Seen: 8 hrs ago
One-way
Basic

San Antonio (SAT)to

Grand Cayman (GCM)
Depart: 04/04/2026
From
$331
Seen: 1 hour 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: 05/16/2026

From

$107

Seen: 9 hrs ago

Austin (AUS)Grand Cayman (GCM)One-way
/
Basic		Depart: 05/19/2026

From

$117

Seen: 10 hrs ago

Nashville (BNA)Grand Cayman (GCM)One-way
/
Basic		Depart: 05/12/2026

From

$129

Seen: 11 hrs ago

Kansas City (MCI)Grand Cayman (GCM)One-way
/
Basic		Depart: 08/02/2026

From

$178

Seen: 11 hrs ago

Denver (DEN)Grand Cayman (GCM)One-way
/
Basic		Depart: 05/26/2026

From

$188

Seen: 5 hrs ago

San Antonio (SAT)Grand Cayman (GCM)One-way
/
Basic		Depart: 05/19/2026

From

$188

Seen: 23 hrs ago

Dallas (Love Field) (DAL)Grand Cayman (GCM)One-way
/
Basic		Depart: 05/25/2026

From

$208

Seen: 3 hrs ago

Fort Lauderdale (FLL)Grand Cayman (GCM)One-way
/
Basic		Depart: 06/07/2026

From

$208

Seen: 20 hrs ago

Tampa (TPA)Grand Cayman (GCM)One-way
/
Basic		Depart: 05/18/2026

From

$209

Seen: 11 minutes ago

Orlando (MCO)Grand Cayman (GCM)One-way
/
Basic		Depart: 06/15/2026

From

$217

Seen: 8 hrs ago

Houston (Hobby) (HOU)Grand Cayman (GCM)One-way
/
Basic		Depart: 08/02/2026

From

$223

Seen: 12 hrs ago

Milwaukee (MKE)Grand Cayman (GCM)One-way
/
Basic		Depart: 05/18/2026

From

$223

Seen: 1 hour ago

Chicago (Midway) (MDW)Grand Cayman (GCM)One-way
/
Basic		Depart: 08/03/2026

From

$230

Seen: 22 hrs ago

Atlanta (ATL)Grand Cayman (GCM)One-way
/
Basic		Depart: 05/18/2026

From

$231

Seen: 8 hrs ago

New Orleans (MSY)Grand Cayman (GCM)One-way
/
Basic		Depart: 06/19/2026

From

$231

Seen: 2 hrs ago

St. Louis (STL)Grand Cayman (GCM)One-way
/
Basic		Depart: 07/06/2026

From

$237

Seen: 14 hrs ago

Washington, D.C. (Reagan National) (DCA)Grand Cayman (GCM)One-way
/
Basic		Depart: 05/14/2026

From

$237

Seen: 8 hrs ago

Columbus (CMH)Grand Cayman (GCM)One-way
/
Basic		Depart: 05/31/2026

From

$237

Seen: 9 hrs ago

Chicago (O'Hare) (ORD)Grand Cayman (GCM)One-way
/
Basic		Depart: 05/25/2026

From

$237

Seen: 20 hrs ago

Phoenix (PHX)Grand Cayman (GCM)One-way
/
Basic		Depart: 07/20/2026

From

$242

Seen: 19 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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