$247+ Cheap flights from Portland (PDX) to Grand Cayman
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — GCM
Sep 25 — Oct 21
Round-trip
1 adult, Economy
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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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Best
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One-way
Cheapest flights from Portland to Grand CaymanExplore the most affordable flight options available from Portland to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 26, 2026.
Explore the most affordable flight options available from Portland to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 26, 2026.
This Southwest deal was found by Cheapflights users on 8/24. 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.
Sat 12/121:40 pm -
2 stops19h 55m
Thu 12/171:30 pm -
2 stops23h 45m
Deal found 8/24![Southwest logo]()
$637
This Priceline deal was found by Cheapflights users on 8/24. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1210:00 am -
2 stops23h 10m
Thu 12/177:00 am -
1 stop16h 39m
Deal found 8/24![Multiple Airlines logo]()
$726
This American Airlines deal was found by Cheapflights users on 8/24. 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.
Sat 12/1211:03 pm -
1 stop17h 55m
Thu 12/1712:36 pm -
1 stop14h 23m
Deal found 8/24![American Airlines logo]()
$781
This American Airlines deal was found by Cheapflights users on 8/24. 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 10/86:09 pm -
2 stops15h 21m
Thu 10/1512:35 pm -
1 stop10h 09m
Deal found 8/24![American Airlines logo]()
$786
This Gotogate deal was found by Cheapflights users on 8/22. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/153:30 pm -
2 stops41h 55m
Sun 9/206:10 pm -
1 stop20h 49m
Deal found 8/22![Multiple Airlines logo]()
$810
This American Airlines deal was found by Cheapflights users on 8/22. 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 9/1511:06 pm -
1 stop10h 21m
Sun 9/2012:36 pm -
1 stop10h 23m
Deal found 8/22![American Airlines logo]()
$824
This Priceline deal was found by Cheapflights users on 8/24. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/75:07 am -
2 stops14h 08m
Thu 9/1012:25 pm -
2 stops23h 06m
Deal found 8/24![Multiple Airlines logo]()
$863
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Sat 10/109:44 pm -
1 stop11h 46m
Sat 10/173:15 pm -
1 stop10h 24m
Deal found 8/25![American Airlines logo]()
$881
Best flights from Portland to Grand CaymanDiscover carefully curated flight deals from Portland to Grand Cayman that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 26, 2026.
Discover carefully curated flight deals from Portland to Grand Cayman that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 26, 2026.
This Southwest deal was found by Cheapflights users on 8/24. 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.
Sat 12/121:40 pm -
2 stops19h 55m
Thu 12/171:30 pm -
2 stops23h 45m
Deal found 8/24![Southwest logo]()
$637
This Priceline deal was found by Cheapflights users on 8/23. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/910:00 am -
2 stops23h 10m
Sat 1/231:10 pm -
2 stops23h 16m
Deal found 8/23![Air Canada logo]()
$649
This Priceline deal was found by Cheapflights users on 8/25. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/153:15 pm -
2 stops17h 55m
Mon 1/184:45 pm -
1 stop30h 47m
Deal found 8/25![Multiple Airlines logo]()
$754
This American Airlines deal was found by Cheapflights users on 8/22. 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 9/1511:06 pm -
1 stop10h 21m
Sun 9/2012:36 pm -
1 stop10h 23m
Deal found 8/22![American Airlines logo]()
$824
This Delta deal was found by Cheapflights users on 8/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/810:57 pm -
1 stop10h 43m
Thu 9/171:00 pm -
1 stop10h 47m
Deal found 8/24![Delta logo]()
$902
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Tue 10/272:34 pm -
2 stops22h 56m
Thu 10/294:45 pm -
2 stops21h 07m
Deal found 8/21![United Airlines logo]()
$982
This Gotogate deal was found by Cheapflights users on 8/22. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/153:30 pm -
2 stops41h 55m
Sun 9/206:10 pm -
1 stop20h 49m
Deal found 8/22![Multiple Airlines logo]()
$810
This Delta deal was found by Cheapflights users on 8/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/711:01 pm -
1 stop10h 39m
Thu 9/101:00 pm -
1 stop10h 47m
Deal found 8/24![Delta logo]()
$947
Last-minute flights from Portland to Grand CaymanDiscover last-minute flight deals from Portland to Grand Cayman. Data last updated August 26, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Grand Cayman. Data last updated August 26, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/21. 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 9/111:34 pm -
2 stops11h 36m
Wed 9/3012:36 pm -
2 stops24h 19m
Deal found 8/21![American Airlines logo]()
$911
This Priceline deal was found by Cheapflights users on 8/24. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/75:07 am -
2 stops14h 08m
Thu 9/1012:25 pm -
2 stops23h 06m
Deal found 8/24![Multiple Airlines logo]()
$863
This American Airlines deal was found by Cheapflights users on 8/24. 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.
Mon 9/710:59 pm -
2 stops12h 11m
Wed 9/1612:00 pm -
2 stops13h 23m
Deal found 8/24![American Airlines logo]()
$907
This Delta deal was found by Cheapflights users on 8/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/711:01 pm -
1 stop10h 39m
Thu 9/101:00 pm -
1 stop10h 47m
Deal found 8/24![Delta logo]()
$947
This American Airlines deal was found by Cheapflights users on 8/24. 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.
Mon 9/710:59 pm -
1 stop10h 28m
Thu 9/1012:00 pm -
2 stops24h 55m
Deal found 8/24![American Airlines logo]()
$952
This Priceline deal was found by Cheapflights users on 8/24. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:07 am -
2 stops32h 58m
Thu 9/1712:25 pm -
2 stops23h 06m
Deal found 8/24![Multiple Airlines logo]()
$899
This Delta deal was found by Cheapflights users on 8/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/810:57 pm -
1 stop10h 43m
Thu 9/171:00 pm -
1 stop10h 47m
Deal found 8/24![Delta logo]()
$902
This Gotogate deal was found by Cheapflights users on 8/22. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/153:30 pm -
2 stops41h 55m
Sun 9/206:10 pm -
1 stop20h 49m
Deal found 8/22![Multiple Airlines logo]()
$810
This American Airlines deal was found by Cheapflights users on 8/22. 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 9/1511:06 pm -
1 stop10h 21m
Sun 9/2012:36 pm -
1 stop10h 23m
Deal found 8/22![American Airlines logo]()
$824
One-way flights from Portland to Grand CaymanSearch for one-way flight options from Portland to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated August 26, 2026.
Search for one-way flight options from Portland to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated August 26, 2026.
This Southwest deal was found by Cheapflights users on 8/23. 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.
Sat 12/121:40 pm -
2 stops19h 55m
Deal found 8/23![Southwest logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 8/23. 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.
Sat 12/127:25 am -
3 stops28h 10m
Deal found 8/23![Multiple Airlines logo]()
$351
This American Airlines deal was found by Cheapflights users on 8/23. 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.
Sat 12/1211:03 pm -
1 stop12h 42m
Deal found 8/23![American Airlines logo]()
$376
Find flight deals from Portland to Grand Cayman
Keep the following information in mind while searching for Portland to Grand Cayman flight deals. Data was last updated August 26, 2026.
Round-trip from | $637 (Southwest) |
|---|---|
One-way from | $247 (Southwest) |
Popular in | March |
Cheapest in | December |
Average price | $909 |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to Grand Cayman 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 August 26, 2026.
Use the filters below to find and compare flights from Portland to Grand Cayman that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandGeorge Town
PDX Portland - GCM George Town Owen Roberts Intl
PDXGCM
Portland
Sat 12/12
1:40 pm-12:35 pm
2 stops19h 55m
George Town Owen Roberts Intl
Thu 12/17
1:30 pm-10:15 am
2 stops23h 45m
$637
PortlandGeorge Town
PDX Portland - GCM George Town Owen Roberts Intl
PDXGCM
Portland
Sat 1/9
10:00 am-12:10 pm
2 stops23h 10m
George Town Owen Roberts Intl
Sat 1/23
1:10 pm-9:26 am
2 stops23h 16m
$649
PortlandGeorge Town
PDX Portland - GCM George Town Owen Roberts Intl
PDXGCM
Portland
Fri 1/15
3:15 pm-12:10 pm
2 stops17h 55m
George Town Owen Roberts Intl
Mon 1/18
4:45 pm-8:32 pm
1 stop30h 47m
$754
PortlandGeorge Town
PDX Portland - GCM George Town Owen Roberts Intl
PDXGCM
Portland
Tue 9/15
3:30 pm-11:25 am
2 stops41h 55m
George Town Owen Roberts Intl
Sun 9/20
6:10 pm-12:59 pm
1 stop20h 49m
$810
Quickest round-trip
PortlandGeorge Town
PDX Portland - GCM George Town Owen Roberts Intl
PDXGCM
Portland
Tue 9/15
11:06 pm-11:27 am
1 stop10h 21m
George Town Owen Roberts Intl
Sun 9/20
12:36 pm-8:59 pm
1 stop10h 23m
$824
PortlandGeorge Town
PDX Portland - GCM George Town Owen Roberts Intl
PDXGCM
Portland
Tue 9/8
10:57 pm-11:40 am
1 stop10h 43m
George Town Owen Roberts Intl
Thu 9/17
1:00 pm-9:47 pm
1 stop10h 47m
$902
PortlandGeorge Town
PDX Portland - GCM George Town Owen Roberts Intl
PDXGCM
Portland
Mon 9/7
11:01 pm-11:40 am
1 stop10h 39m
George Town Owen Roberts Intl
Thu 9/10
1:00 pm-9:47 pm
1 stop10h 47m
$947
PortlandGeorge Town
PDX Portland - GCM George Town Owen Roberts Intl
PDXGCM
Portland
Tue 10/27
2:34 pm-3:30 pm
2 stops22h 56m
George Town Owen Roberts Intl
Thu 10/29
4:45 pm-11:52 am
2 stops21h 07m
$982
Cheapest one-way
PortlandGeorge Town
PDX Portland - GCM George Town Owen Roberts Intl
PDXGCM
Portland
Sat 12/12
1:40 pm-12:35 pm
2 stops19h 55m
$247
PortlandGeorge Town
PDX Portland - GCM George Town Owen Roberts Intl
PDXGCM
Portland
Sat 12/12
7:25 am-2:35 pm
3 stops28h 10m
$351
Showing 1-10 of 11 resultsSorted by cheapest first
Best time to book a flight from Portland to Grand Cayman
Have a flexible travel schedule? Discover the best time to fly to Grand Cayman from Portland with our price prediction graph.
PDX-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 Portland to Grand Cayman
PDX-zzLAW
PDX-GCM
What is the cheapest month to book a flight from Portland to Grand Cayman?
Currently, December is the cheapest month in which you can book a flight from Portland to Grand Cayman (average of $665). Flying from Portland to Grand Cayman in March is currently the most expensive (average of $1,211). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Reviews of airlines servicing Grand Cayman
Get insights into the airlines that provide service to Grand Cayman. 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 Grand Cayman. Reviews last updated August 26, 2026.
Get a feel of what it's like to fly with American Airlines from Portland to Grand Cayman by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.2
Food
6.4
Entertainment
6.8
Crew
7.9
Overall
7.1
Boarding
7.5
Reviews
1 / 20
10.0
ExcellentLinda,Jul 2026
ROA - CLT
Comfort
7.2
Food
6.4
Entertainment
6.8
Crew
7.9
Overall
7.1
Boarding
7.5
Reviews
1 / 20
10.0
ExcellentLinda,Jul 2026
ROA - CLT
Related info for your journey
Find useful and relevant information for your journey from Portland to Grand Cayman. 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
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Find flights from Portland to Grand Cayman, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Portland and Grand Cayman flights
Browse other Portland and Grand Cayman flight options. Last updated on August 26, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Portland to Grand Cayman
Discover the top airline that operate flights from Portland to Grand Cayman. 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 August 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$666 | Average$787 | FlexibilityNo cancel fee | On-time71% |