Flights to Cayman Islands

Promo Code

Trending flight deals to and within Cayman Islands

$

New Orleans (MSY)to

Grand Cayman (GCM)
Depart: 11/18/2026
From
$154
Seen: 21 hrs ago
One-way
Basic

Orlando (MCO)to

Grand Cayman (GCM)
Depart: 11/18/2026
From
$156
Seen: 11 hrs ago
One-way
Basic

Washington D.C. Reagan National (DCA)to

Grand Cayman (GCM)
Depart: 11/15/2026
From
$162
Seen: 16 hrs ago
One-way
Basic

Houston Hobby (HOU)to

Grand Cayman (GCM)
Depart: 11/17/2026
From
$169
Seen: 8 hrs ago
One-way
Basic

Dallas-Love Field (DAL)to

Grand Cayman (GCM)
Depart: 11/17/2026
From
$169
Seen: 1 hour ago
One-way
Basic

Denver (DEN)to

Grand Cayman (GCM)
Depart: 11/17/2026
From
$169
Seen: 9 hrs ago
One-way
Basic

San Antonio (SAT)to

Grand Cayman (GCM)
Depart: 11/15/2026
From
$169
Seen: 6 hrs ago
One-way
Basic

Nashville (BNA)to

Grand Cayman (GCM)
Depart: 11/02/2026
From
$173
Seen: 22 hrs ago
One-way
Basic

Chicago-Midway (MDW)to

Grand Cayman (GCM)
Depart: 11/15/2026
From
$175
Seen: 6 hrs ago
One-way
Basic

Columbus (CMH)to

Grand Cayman (GCM)
Depart: 11/11/2026
From
$178
Seen: 19 hrs ago
One-way
Basic

Baltimore/Washington (BWI)to

Grand Cayman (GCM)
Depart: 11/01/2026
From
$207
Seen: 23 hrs ago
One-way
Basic

Fort Lauderdale (FLL)to

Grand Cayman (GCM)
Depart: 11/06/2026
From
$208
Seen: 3 hrs ago
One-way
Basic

Austin (AUS)to

Grand Cayman (GCM)
Depart: 11/14/2026
From
$213
Seen: 3 hrs ago
One-way
Basic

Atlanta (ATL)to

Grand Cayman (GCM)
Depart: 11/11/2026
From
$226
Seen: 18 hrs ago
One-way
Basic

St. Louis (STL)to

Grand Cayman (GCM)
Depart: 11/22/2026
From
$245
Seen: 3 hrs ago
One-way
Basic

Kansas City (MCI)to

Grand Cayman (GCM)
Depart: 10/31/2026
From
$250
Seen: 12 hrs ago
One-way
Basic

Indianapolis (IND)to

Grand Cayman (GCM)
Depart: 10/30/2026
From
$258
Seen: 23 hrs ago
One-way
Basic

Phoenix (PHX)to

Grand Cayman (GCM)
Depart: 11/14/2026
From
$268
Seen: 15 hrs ago
One-way
Basic

Milwaukee (MKE)to

Grand Cayman (GCM)
Depart: 11/10/2026
From
$285
Seen: 11 hrs ago
One-way
Choice

Tampa (TPA)to

Grand Cayman (GCM)
Depart: 11/18/2026
From
$403
Seen: 6 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: 11/28/2026

From

$138

Seen: 15 hrs ago

Atlanta (ATL)Grand Cayman (GCM)One-way
/
Basic		Depart: 01/20/2027

From

$139

Seen: 1 hour ago

Nashville (BNA)Grand Cayman (GCM)One-way
/
Basic		Depart: 12/16/2026

From

$154

Seen: 10 hrs ago

Raleigh/Durham (RDU)Grand Cayman (GCM)One-way
/
Basic		Depart: 01/12/2027

From

$154

Seen: 12 hrs ago

Orlando (MCO)Grand Cayman (GCM)One-way
/
Basic		Depart: 01/17/2027

From

$156

Seen: 11 hrs ago

Washington D.C. Reagan National (DCA)Grand Cayman (GCM)One-way
/
Basic		Depart: 11/27/2026

From

$162

Seen: 9 hrs ago

St. Louis (STL)Grand Cayman (GCM)One-way
/
Basic		Depart: 12/06/2026

From

$167

Seen: 9 hrs ago

Kansas City (MCI)Grand Cayman (GCM)One-way
/
Basic		Depart: 12/14/2026

From

$167

Seen: 15 hrs ago

Austin (AUS)Grand Cayman (GCM)One-way
/
Basic		Depart: 11/29/2026

From

$167

Seen: 17 hrs ago

Indianapolis (IND)Grand Cayman (GCM)One-way
/
Basic		Depart: 12/02/2026

From

$167

Seen: 12 hrs ago

Houston Hobby (HOU)Grand Cayman (GCM)One-way
/
Basic		Depart: 01/24/2027

From

$169

Seen: 13 hrs ago

Dallas-Love Field (DAL)Grand Cayman (GCM)One-way
/
Basic		Depart: 01/12/2027

From

$169

Seen: 20 hrs ago

Chicago-Midway (MDW)Grand Cayman (GCM)One-way
/
Basic		Depart: 01/12/2027

From

$169

Seen: 3 hrs ago

Milwaukee (MKE)Grand Cayman (GCM)One-way
/
Basic		Depart: 01/19/2027

From

$169

Seen: 13 hrs ago

San Antonio (SAT)Grand Cayman (GCM)One-way
/
Basic		Depart: 12/09/2026

From

$169

Seen: 21 hrs ago

Denver (DEN)Grand Cayman (GCM)One-way
/
Basic		Depart: 02/08/2027

From

$172

Seen: 9 hrs ago

Hartford/Springfield (BDL)Grand Cayman (GCM)One-way
/
Basic		Depart: 03/01/2027

From

$173

Seen: 7 hrs ago

Columbus (CMH)Grand Cayman (GCM)One-way
/
Basic		Depart: 12/29/2026

From

$178

Seen: 20 hrs ago

Pittsburgh (PIT)Grand Cayman (GCM)One-way
/
Basic		Depart: 01/31/2027

From

$181

Seen: 10 hrs ago

Phoenix (PHX)Grand Cayman (GCM)One-way
/
Basic		Depart: 01/17/2027

From

$196

Seen: 14 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.

Join Rapid Rewards, our award-winning frequent flyer program1.

Sign up now

No blackout dates.

You can use your points to book any seat, on any flight, no exceptions. Any day, any time, any flight, your points are ready to take you to where you want to go.

Your points don’t expire.

You can earn points on flights and on everyday purchases with our partners, which makes getting to your destination easy. No matter when, or where, you earn them, your points won’t expire.

Free inflight WiFi thanks to T-Mobile®.2

Rapid Rewards members can go online to check email, snag a dinner reservation, or browse social media from takeoff to landing. Learn more ›

12022–2023 Freddie Awards. 2Where available. Available only on WiFi-enabled designated aircraft. Free WiFi is only for Rapid Rewards® Members.

Discover the best flight deals to Cayman Islands

Explore Southwest Airlines popular destinations