Flights to Cayman Islands
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Trending flight deals to and within Cayman Islands
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$
Columbus (CMH)to
Grand Cayman (GCM)Depart: 04/07/2026
From
$126
Seen: 48 minutes ago
One-way
Basic
Baltimore/Washington (BWI)to
Grand Cayman (GCM)Depart: 03/24/2026
From
$137
Seen: 16 hrs ago
One-way
Basic
Washington, D.C. (Reagan National) (DCA)to
Grand Cayman (GCM)Depart: 04/09/2026
From
$169
Seen: 19 hrs ago
One-way
Basic
Austin (AUS)to
Grand Cayman (GCM)Depart: 03/26/2026
From
$173
Seen: 20 hrs ago
One-way
Basic
Dallas (Love Field) (DAL)to
Grand Cayman (GCM)Depart: 04/07/2026
From
$181
Seen: 23 hrs ago
One-way
Basic
Denver (DEN)to
Grand Cayman (GCM)Depart: 04/12/2026
From
$181
Seen: 17 hrs ago
One-way
Basic
Fort Lauderdale (FLL)to
Grand Cayman (GCM)Depart: 03/31/2026
From
$183
Seen: 20 hrs ago
One-way
Basic
St. Louis (STL)to
Grand Cayman (GCM)Depart: 04/07/2026
From
$212
Seen: 29 minutes ago
One-way
Basic
Nashville (BNA)to
Grand Cayman (GCM)Depart: 04/06/2026
From
$215
Seen: 20 hrs ago
One-way
Basic
Atlanta (ATL)to
Grand Cayman (GCM)Depart: 04/06/2026
From
$216
Seen: 16 hrs ago
One-way
Basic
Orlando (MCO)to
Grand Cayman (GCM)Depart: 04/11/2026
From
$217
Seen: 11 hrs ago
One-way
Basic
Houston (Hobby) (HOU)to
Grand Cayman (GCM)Depart: 04/10/2026
From
$237
Seen: 14 hrs ago
One-way
Basic
San Antonio (SAT)to
Grand Cayman (GCM)Depart: 04/09/2026
From
$251
Seen: 4 hrs ago
One-way
Basic
Indianapolis (IND)to
Grand Cayman (GCM)Depart: 04/05/2026
From
$261
Seen: 9 hrs ago
One-way
Basic
Phoenix (PHX)to
Grand Cayman (GCM)Depart: 04/10/2026
From
$272
Seen: 13 minutes ago
One-way
Basic
Milwaukee (MKE)to
Grand Cayman (GCM)Depart: 04/12/2026
From
$301
Seen: 1 hour ago
One-way
Basic
Chicago (Midway) (MDW)to
Grand Cayman (GCM)Depart: 03/19/2026
From
$321
Seen: 22 hrs ago
One-way
Basic
Kansas City (MCI)to
Grand Cayman (GCM)Depart: 03/18/2026
From
$331
Seen: 3 hrs ago
One-way
Basic
Pittsburgh (PIT)to
Grand Cayman (GCM)Depart: 03/19/2026
From
$371
Seen: 18 hrs ago
One-way
Basic
New Orleans (MSY)to
Grand Cayman (GCM)Depart: 03/14/2026
From
$431
Seen: 3 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 |
|---|---|---|---|---|
| Baltimore/Washington (BWI) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/14/2026 | From $111 Seen: 18 hrs ago |
| Denver (DEN) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/18/2026 | From $121 Seen: 19 hrs ago |
| Austin (AUS) | Grand Cayman (GCM) | One-way / Basic | Depart: 06/10/2026 | From $127 Seen: 16 hrs ago |
| Tampa (TPA) | Grand Cayman (GCM) | One-way / Basic | Depart: 04/19/2026 | From $133 Seen: 16 hrs ago |
| St. Louis (STL) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/05/2026 | From $136 Seen: 16 hrs ago |
| Nashville (BNA) | Grand Cayman (GCM) | One-way / Basic | Depart: 04/20/2026 | From $139 Seen: 15 hrs ago |
| Columbus (CMH) | Grand Cayman (GCM) | One-way / Basic | Depart: 04/27/2026 | From $151 Seen: 20 hrs ago |
| Fort Lauderdale (FLL) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/08/2026 | From $164 Seen: 17 hrs ago |
| Orlando (MCO) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/19/2026 | From $166 Seen: 13 hrs ago |
| Raleigh/Durham (RDU) | Grand Cayman (GCM) | One-way / Basic | Depart: 04/15/2026 | From $166 Seen: 14 hrs ago |
| New Orleans (MSY) | Grand Cayman (GCM) | One-way / Basic | Depart: 06/15/2026 | From $173 Seen: 20 hrs ago |
| Pittsburgh (PIT) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/10/2026 | From $179 Seen: 5 hrs ago |
| Dallas (Love Field) (DAL) | Grand Cayman (GCM) | One-way / Basic | Depart: 04/20/2026 | From $181 Seen: 17 hrs ago |
| Chicago (Midway) (MDW) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/03/2026 | From $181 Seen: 16 hrs ago |
| Milwaukee (MKE) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/04/2026 | From $181 Seen: 16 hrs ago |
| Phoenix (PHX) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/05/2026 | From $181 Seen: 18 hrs ago |
| San Antonio (SAT) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/10/2026 | From $181 Seen: 2 hrs ago |
| Chicago (O'Hare) (ORD) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/17/2026 | From $181 Seen: 21 hrs ago |
| Kansas City (MCI) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/18/2026 | From $208 Seen: 20 hrs ago |
| Hartford/Springfield (BDL) | Grand Cayman (GCM) | One-way / Basic | Depart: 05/14/2026 | From $208 Seen: 2 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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