Flights to Cayman Islands

Promo Code

Trending flight deals to and within Cayman Islands

$

Orlando (MCO)to

Grand Cayman (GCM)
Depart: 11/01/2026
From
$188
Seen: 19 hrs ago
One-way
Basic

Dallas-Love Field (DAL)to

Grand Cayman (GCM)
Depart: 11/01/2026
From
$205
Seen: 54 minutes ago
One-way
Basic

Chicago-Midway (MDW)to

Grand Cayman (GCM)
Depart: 11/01/2026
From
$205
Seen: 20 hrs ago
One-way
Basic

Fort Lauderdale (FLL)to

Grand Cayman (GCM)
Depart: 10/03/2026
From
$208
Seen: 22 hrs ago
One-way
Basic

Denver (DEN)to

Grand Cayman (GCM)
Depart: 10/02/2026
From
$208
Seen: 23 hrs ago
One-way
Basic

Los Angeles (LAX)to

Grand Cayman (GCM)
Depart: 11/01/2026
From
$208
Seen: 21 hrs ago
One-way
Basic

Pittsburgh (PIT)to

Grand Cayman (GCM)
Depart: 11/01/2026
From
$215
Seen: 17 hrs ago
One-way
Basic

Austin (AUS)to

Grand Cayman (GCM)
Depart: 10/17/2026
From
$223
Seen: 8 hrs ago
One-way
Basic

Indianapolis (IND)to

Grand Cayman (GCM)
Depart: 10/03/2026
From
$228
Seen: 1 hour ago
One-way
Basic

Nashville (BNA)to

Grand Cayman (GCM)
Depart: 10/09/2026
From
$229
Seen: 17 minutes ago
One-way
Basic

Columbus (CMH)to

Grand Cayman (GCM)
Depart: 10/09/2026
From
$265
Seen: 21 hrs ago
One-way
Basic

Baltimore/Washington (BWI)to

Grand Cayman (GCM)
Depart: 10/03/2026
From
$275
Seen: 5 hrs ago
One-way
Basic

San Antonio (SAT)to

Grand Cayman (GCM)
Depart: 10/02/2026
From
$296
Seen: 11 hrs ago
One-way
Basic

Las Vegas (LAS)to

Grand Cayman (GCM)
Depart: 10/02/2026
From
$296
Seen: 12 hrs ago
One-way
Basic

Kansas City (MCI)to

Grand Cayman (GCM)
Depart: 10/09/2026
From
$300
Seen: 10 hrs ago
One-way
Basic

Atlanta (ATL)to

Grand Cayman (GCM)
Depart: 10/10/2026
From
$321
Seen: 17 hrs ago
One-way
Basic

St. Louis (STL)to

Grand Cayman (GCM)
Depart: 10/23/2026
From
$341
Seen: 6 hrs ago
One-way
Basic

Houston Hobby (HOU)to

Grand Cayman (GCM)
Depart: 10/02/2026
From
$351
Seen: 14 hrs ago
One-way
Basic

Philadelphia (PHL)to

Grand Cayman (GCM)
Depart: 10/03/2026
From
$351
Seen: 4 hrs ago
One-way
Basic

New Orleans (MSY)to

Grand Cayman (GCM)
Depart: 10/09/2026
From
$413
Seen: 17 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

$
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: 01/08/2027

From

$122

Seen: 16 hrs ago

Pittsburgh (PIT)Grand Cayman (GCM)One-way
/
Basic		Depart: 12/14/2026

From

$133

Seen: 2 hrs ago

Fort Lauderdale (FLL)Grand Cayman (GCM)One-way
/
Basic		Depart: 12/13/2026

From

$138

Seen: 2 hrs ago

Washington D.C. Reagan National (DCA)Grand Cayman (GCM)One-way
/
Basic		Depart: 12/04/2026

From

$142

Seen: 11 hrs ago

Nashville (BNA)Grand Cayman (GCM)One-way
/
Basic		Depart: 01/09/2027

From

$153

Seen: 18 hrs ago

Austin (AUS)Grand Cayman (GCM)One-way
/
Basic		Depart: 11/11/2026

From

$153

Seen: 4 hrs ago

New Orleans (MSY)Grand Cayman (GCM)One-way
/
Basic		Depart: 11/11/2026

From

$153

Seen: 5 hrs ago

Phoenix (PHX)Grand Cayman (GCM)One-way
/
Basic		Depart: 11/15/2026

From

$158

Seen: 19 hrs ago

Denver (DEN)Grand Cayman (GCM)One-way
/
Basic		Depart: 05/25/2027

From

$172

Seen: 1 hour ago

Kansas City (MCI)Grand Cayman (GCM)One-way
/
Basic		Depart: 11/15/2026

From

$175

Seen: 4 hrs ago

Las Vegas (LAS)Grand Cayman (GCM)One-way
/
Basic		Depart: 01/23/2027

From

$187

Seen: 1 minutes ago

Orlando (MCO)Grand Cayman (GCM)One-way
/
Basic		Depart: 11/29/2026

From

$188

Seen: 17 hrs ago

Indianapolis (IND)Grand Cayman (GCM)One-way
/
Basic		Depart: 11/04/2026

From

$194

Seen: 1 hour ago

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

From

$194

Seen: 14 hrs ago

Providence (PVD)Grand Cayman (GCM)One-way
/
Basic		Depart: 01/31/2027

From

$203

Seen: 17 hrs ago

Houston Hobby (HOU)Grand Cayman (GCM)One-way
/
Basic		Depart: 11/02/2026

From

$205

Seen: 20 hrs ago

Chicago-Midway (MDW)Grand Cayman (GCM)One-way
/
Basic		Depart: 11/03/2026

From

$205

Seen: 10 hrs ago

Milwaukee (MKE)Grand Cayman (GCM)One-way
/
Basic		Depart: 11/29/2026

From

$205

Seen: 17 hrs ago

Atlanta (ATL)Grand Cayman (GCM)One-way
/
Basic		Depart: 12/21/2026

From

$209

Seen: 7 hrs ago

Boston (BOS)Grand Cayman (GCM)One-way
/
Basic		Depart: 05/01/2027

From

$213

Seen: 3 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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