$223+ Cheap flights from San Diego (SAN) to the Cayman Islands
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — GCM
Dec 5 — Dec 121
Round-trip
1 adult, Economy
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Find cheap flights from San Diego to Cayman Islands with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from San Diego to Cayman Islands
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Cheapest flights from San Diego to Cayman IslandsExplore the most affordable flight options available from San Diego to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 5, 2026.
Explore the most affordable flight options available from San Diego to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 5, 2026.
This Southwest deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/48:05 pm -
2 stops13h 55m
Tue 12/81:30 pm -
2 stops12h 40m
Deal found 11/4![Southwest logo]()
$566
This American Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2610:35 pm -
1 stop10h 30m
Thu 12/312:21 pm -
1 stop12h 09m
Deal found 11/4![American Airlines logo]()
$572
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2612:37 pm -
2 stops24h 53m
Thu 12/35:45 pm -
2 stops20h 30m
Deal found 11/4![United Airlines logo]()
$576
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/74:01 pm -
2 stops21h 29m
Thu 12/105:45 pm -
2 stops19h 05m
Deal found 10/31![United Airlines logo]()
$686
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/77:41 pm -
3 stops17h 49m
Mon 12/145:45 pm -
3 stops27h 27m
Deal found 11/4![United Airlines logo]()
$706
This Mytrip deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/268:50 am -
2 stops23h 45m
Thu 12/34:45 pm -
3 stops42h 17m
Deal found 11/4![Multiple Airlines logo]()
$720
This American Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/610:20 pm -
1 stop12h 43m
Tue 11/1012:18 pm -
1 stop11h 27m
Deal found 11/4![American Airlines logo]()
$760
This Mytrip deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/256:30 am -
2 stops26h 40m
Sun 11/293:35 pm -
2 stops24h 05m
Deal found 11/1![Multiple Airlines logo]()
$790
This Southwest deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/610:35 pm -
2 stops11h 25m
Tue 11/101:30 pm -
2 stops12h 40m
Deal found 11/4![Southwest logo]()
$793
Best flights from San Diego to Cayman IslandsDiscover carefully curated flight deals from San Diego to Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 5, 2026.
Discover carefully curated flight deals from San Diego to Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 5, 2026.
This Southwest deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/48:05 pm -
2 stops13h 55m
Tue 12/81:30 pm -
2 stops12h 40m
Deal found 11/4![Southwest logo]()
$566
This United Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/177:41 pm -
2 stops15h 04m
Thu 1/212:55 pm -
1 stop10h 42m
Deal found 11/1![United Airlines logo]()
$682
This Southwest deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/175:40 pm -
2 stops16h 15m
Sun 1/241:50 pm -
2 stops21h 25m
Deal found 11/4![Southwest logo]()
$576
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/74:01 pm -
2 stops21h 29m
Thu 12/105:45 pm -
2 stops19h 05m
Deal found 10/31![United Airlines logo]()
$686
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:41 pm -
3 stops17h 19m
Tue 12/85:45 pm -
2 stops19h 05m
Deal found 11/4![United Airlines logo]()
$706
Last-minute flights from San Diego to Cayman IslandsDiscover last-minute flight deals from San Diego to Cayman Islands. Data last updated November 5, 2026 and is based on user searches.
Discover last-minute flight deals from San Diego to Cayman Islands. Data last updated November 5, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/610:20 pm -
1 stop12h 43m
Tue 11/1012:18 pm -
1 stop11h 27m
Deal found 11/4![American Airlines logo]()
$760
This Southwest deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/610:35 pm -
2 stops11h 25m
Tue 11/101:30 pm -
2 stops12h 40m
Deal found 11/4![Southwest logo]()
$793
This Mytrip deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/256:30 am -
2 stops26h 40m
Sun 11/293:35 pm -
2 stops24h 05m
Deal found 11/1![Multiple Airlines logo]()
$790
This American Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2610:35 pm -
1 stop10h 30m
Thu 12/312:21 pm -
1 stop12h 09m
Deal found 11/4![American Airlines logo]()
$572
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2612:37 pm -
2 stops24h 53m
Thu 12/35:45 pm -
2 stops20h 30m
Deal found 11/4![United Airlines logo]()
$576
This Mytrip deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/268:50 am -
2 stops23h 45m
Thu 12/34:45 pm -
3 stops42h 17m
Deal found 11/4![Multiple Airlines logo]()
$720
This Southwest deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/48:05 pm -
2 stops13h 55m
Tue 12/81:30 pm -
2 stops12h 40m
Deal found 11/4![Southwest logo]()
$566
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/74:01 pm -
2 stops21h 29m
Thu 12/105:45 pm -
2 stops19h 05m
Deal found 10/31![United Airlines logo]()
$686
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/77:41 pm -
3 stops17h 49m
Mon 12/145:45 pm -
2 stops21h 42m
Deal found 11/4![United Airlines logo]()
$706
One-way flights from San Diego to Cayman IslandsSearch for one-way flight options from San Diego to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated November 5, 2026.
Search for one-way flight options from San Diego to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated November 5, 2026.
This Southwest deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/108:45 pm -
2 stops12h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Southwest logo]()
$223
This Southwest deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/98:45 pm -
2 stops12h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Southwest logo]()
$228
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/265:10 pm -
1 stop17h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![United Airlines logo]()
$232
This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/210:45 pm -
1 stop9h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![American Airlines logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/98:57 am -
3 stops33h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Multiple Airlines logo]()
$251
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/98:00 am -
1 stop29h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![United Airlines logo]()
$252
This Mytrip deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/212:32 pm -
3 stops25h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Multiple Airlines logo]()
$253
This American Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:15 am -
2 stops10h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![American Airlines logo]()
$273
This United Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/107:41 pm -
3 stops17h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![United Airlines logo]()
$288
This Mytrip deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/248:11 pm -
3 stops36h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Multiple Airlines logo]()
$306
This United Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/296:20 am -
2 stops31h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![United Airlines logo]()
$315
Find flight deals from San Diego to Cayman Islands
Keep the following information in mind while searching for San Diego to Cayman Islands flight deals. Data was last updated November 5, 2026.
Round-trip from | $566 (Southwest) |
|---|---|
One-way from | $223 (Southwest) |
Popular in | October |
Cheapest in | December |
Average price | $850 |
Cheapflights Fare Finder
Customize your flight search to find flights from San Diego to Cayman Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated November 5, 2026.
Use the filters below to find and compare flights from San Diego to the Cayman Islands that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San DiegoGeorge Town
SAN San Diego - GCM George Town Owen Roberts Intl
SANGCM
San Diego
Thu 12/10
8:45 pm-12:35 pm
2 stops12h 50m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$223
Quickest round-trip
San DiegoGeorge Town
SAN San Diego - GCM George Town Owen Roberts Intl
SANGCM
San Diego
Thu 12/10
10:45 pm-11:26 am
1 stop9h 41m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$223
San DiegoGeorge Town
SAN San Diego - GCM George Town Owen Roberts Intl
SANGCM
San Diego
Wed 12/2
8:45 pm-12:35 pm
2 stops12h 50m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$223
San DiegoGeorge Town
SAN San Diego - GCM George Town Owen Roberts Intl
SANGCM
San Diego
Sun 11/29
10:45 pm-8:06 pm
1 stop18h 21m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$223
San DiegoGeorge Town
SAN San Diego - GCM George Town Owen Roberts Intl
SANGCM
San Diego
Wed 12/9
8:45 pm-12:35 pm
2 stops12h 50m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$228
San DiegoGeorge Town
SAN San Diego - GCM George Town Owen Roberts Intl
SANGCM
San Diego
Fri 3/26
5:10 pm-12:25 pm
1 stop17h 15m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$232
San DiegoGeorge Town
SAN San Diego - GCM George Town Owen Roberts Intl
SANGCM
San Diego
Wed 12/9
8:00 am-4:30 pm
1 stop29h 30m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$252
San DiegoGeorge Town
SAN San Diego - GCM George Town Owen Roberts Intl
SANGCM
San Diego
Thu 12/10
7:41 pm-4:30 pm
3 stops17h 49m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$288
San DiegoGeorge Town
SAN San Diego - GCM George Town Owen Roberts Intl
SANGCM
San Diego
Sun 11/29
6:20 am-4:30 pm
2 stops31h 10m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$315
San DiegoGeorge Town
SAN San Diego - GCM George Town Owen Roberts Intl
SANGCM
San Diego
Sun 11/29
1:30 pm-2:35 pm
3 stops22h 05m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$438
Showing 1-10 of 16 resultsSorted by cheapest first
Best time to book a flight from San Diego to Cayman Islands
Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from San Diego with our price prediction graph.
SAN-GCM
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from San Diego to the Cayman Islands
SAN-KY0
SAN-GCM
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing Cayman Islands
Get insights into the airlines that provide service to Cayman Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Cayman Islands. Reviews last updated November 5, 2026.
Get a feel of what it's like to fly with United Airlines and American Airlines from San Diego to the Cayman Islands by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.3
Crew
8.1
Entertainment
7.1
Boarding
7.7
Food
6.7
Overall
7.3
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Comfort
7.3
Crew
8.1
Entertainment
7.1
Boarding
7.7
Food
6.7
Overall
7.3
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Comfort
7.3
Crew
8.1
Entertainment
7.1
Boarding
7.7
Food
6.7
Overall
7.3
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Related info for your journey
Find useful and relevant information for your journey from San Diego to Cayman Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Complete your trip
Complete your trip to Cayman Islands by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from San Diego to Cayman Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
San Diego and Cayman Islands flights
Browse other San Diego and Cayman Islands flight options. Last updated on November 5, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Cayman Islands regions
Consider these flights traveling to Cayman Islands regions.
Top 2 airlines flying from San Diego to Cayman Islands
Discover the top 2 airlines that operate flights from San Diego to Cayman Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated November 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$493 | Average$684 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$496 | Average$693 | FlexibilityNo cancel fee | On-time69% |