$649+ Cheap flights from Portland (PDX) to Grand Cayman
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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — GCM
Jul 12 — Jul 191
Round-trip
1 adult, Economy
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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 June 12, 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 June 12, 2026.
This FlightHub deal was found by Cheapflights users on 6/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/163:30 pm
PDX
- GCM
2 stops18h 00m
Air Canada
Sun 10/2512:10 pm
GCM
- PDX
2 stops23h 16m
Air Canada
Deal found 6/12![Air Canada logo]()
$649
This Southwest deal was found by Cheapflights users on 6/10. 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 7/109:20 pm
PDX
- GCM
1 stop11h 10m
Southwest
Thu 7/1612:50 pm
GCM
- PDX
2 stops13h 05m
Southwest
Deal found 6/10![Southwest logo]()
$687
This FlightHub deal was found by Cheapflights users on 6/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/163:30 pm
PDX
- GCM
2 stops18h 00m
Air Canada
Thu 9/2412:25 pm
GCM
- PDX
2 stops23h 06m
Air Canada
Deal found 6/8![Air Canada logo]()
$698
This Southwest deal was found by Cheapflights users on 6/10. 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 7/269:20 pm
PDX
- GCM
2 stops12h 35m
Southwest
Sun 8/212:50 pm
GCM
- PDX
2 stops13h 25m
Southwest
Deal found 6/10![Southwest logo]()
$707
This Air Canada deal was found by Cheapflights users on 6/8. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:45 pm
PDX
- GCM
2 stops37h 45m
Air Canada
Thu 9/2412:25 pm
GCM
- PDX
2 stops23h 06m
Air Canada
Deal found 6/8![Air Canada logo]()
$712
This Kiwi.com deal was found by Cheapflights users on 6/7. 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.
Mon 8/176:19 am
PDX
- GCM
2 stops31h 46m
Multiple Airlines
Sat 8/224:00 pm
GCM
- PDX
1 stop21h 41m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$724
This Justfly.com deal was found by Cheapflights users on 6/10. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:45 pm
PDX
- GCM
2 stops37h 45m
Multiple Airlines
Sun 9/276:10 pm
GCM
- PDX
1 stop20h 49m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$743
This FlightHub deal was found by Cheapflights users on 6/7. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/310:00 am
PDX
- GCM
2 stops23h 00m
Air Canada
Wed 11/111:10 pm
GCM
- PDX
2 stops23h 16m
Air Canada
Deal found 6/7![Air Canada logo]()
$750
This Air Canada deal was found by Cheapflights users on 6/7. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2110:00 am
PDX
- GCM
2 stops23h 00m
Air Canada
Fri 11/271:10 pm
GCM
- PDX
2 stops23h 16m
Air Canada
Deal found 6/7![Air Canada logo]()
$756
This Southwest deal was found by Cheapflights users on 6/9. 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 7/17:40 pm
PDX
- GCM
2 stops14h 15m
Southwest
Tue 7/712:50 pm
GCM
- PDX
2 stops13h 20m
Southwest
Deal found 6/9![Southwest logo]()
$757
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 8/195:42 pm
PDX
- GCM
2 stops15h 53m
Multiple Airlines
Sat 8/224:00 pm
GCM
- PDX
1 stop21h 41m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$764
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 June 12, 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 June 12, 2026.
This Southwest deal was found by Cheapflights users on 6/11. 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 7/109:20 pm
PDX
- GCM
2 stops12h 50m
Southwest
Thu 7/1612:50 pm
GCM
- PDX
2 stops13h 05m
Southwest
Deal found 6/11![Southwest logo]()
$687
This American Airlines deal was found by Cheapflights users on 6/10. 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 8/143:00 pm
PDX
- GCM
2 stops17h 55m
American Airlines
Thu 8/272:10 pm
GCM
- PDX
2 stops23h 24m
American Airlines
Deal found 6/10![American Airlines logo]()
$796
This United Airlines deal was found by Cheapflights users on 6/9. 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 7/111:59 pm
PDX
- GCM
1 stop10h 31m
United Airlines
Tue 7/71:35 pm
GCM
- PDX
2 stops21h 59m
United Airlines
Deal found 6/9![United Airlines logo]()
$804
This Delta deal was found by Cheapflights users on 6/8. 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.
Sun 8/1610:55 pm
PDX
- GCM
1 stop10h 44m
Delta
Sat 8/221:04 pm
GCM
- PDX
1 stop10h 40m
Delta
Deal found 6/8![Delta logo]()
$807
This Southwest deal was found by Cheapflights users on 6/10. 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 7/269:20 pm
PDX
- GCM
2 stops12h 35m
Southwest
Sun 8/212:50 pm
GCM
- PDX
2 stops13h 25m
Southwest
Deal found 6/10![Southwest logo]()
$707
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Sun 8/165:59 pm
PDX
- GCM
2 stops15h 01m
American Airlines
Sat 8/2212:30 pm
GCM
- PDX
2 stops13h 28m
American Airlines
Deal found 6/10![American Airlines logo]()
$812
This Southwest deal was found by Cheapflights users on 6/9. 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 7/17:40 pm
PDX
- GCM
2 stops14h 15m
Southwest
Tue 7/712:50 pm
GCM
- PDX
2 stops13h 20m
Southwest
Deal found 6/9![Southwest logo]()
$757
Last-minute flights from Portland to Grand CaymanDiscover last-minute flight deals from Portland to Grand Cayman. Data last updated June 12, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Grand Cayman. Data last updated June 12, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/9. 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 7/17:40 pm
PDX
- GCM
2 stops14h 15m
Southwest
Tue 7/712:50 pm
GCM
- PDX
2 stops13h 20m
Southwest
Deal found 6/9![Southwest logo]()
$757
This United Airlines deal was found by Cheapflights users on 6/9. 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 7/111:59 pm
PDX
- GCM
1 stop10h 31m
United Airlines
Tue 7/71:35 pm
GCM
- PDX
2 stops21h 59m
United Airlines
Deal found 6/9![United Airlines logo]()
$804
This American Airlines deal was found by Cheapflights users on 6/9. 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 7/19:47 pm
PDX
- GCM
1 stop11h 38m
American Airlines
Tue 7/712:33 pm
GCM
- PDX
1 stop13h 22m
American Airlines
Deal found 6/9![American Airlines logo]()
$845
This American Airlines deal was found by Cheapflights users on 6/10. 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 7/79:47 pm
PDX
- GCM
1 stop11h 38m
American Airlines
Sun 7/1212:33 pm
GCM
- PDX
1 stop13h 22m
American Airlines
Deal found 6/10![American Airlines logo]()
$874
This American Airlines deal was found by Cheapflights users on 6/9. 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 7/89:47 pm
PDX
- GCM
1 stop11h 38m
American Airlines
Sun 7/1212:33 pm
GCM
- PDX
1 stop13h 22m
American Airlines
Deal found 6/9![American Airlines logo]()
$871
This Southwest deal was found by Cheapflights users on 6/10. 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 7/109:20 pm
PDX
- GCM
1 stop11h 10m
Southwest
Thu 7/1612:50 pm
GCM
- PDX
2 stops13h 05m
Southwest
Deal found 6/10![Southwest logo]()
$687
This American Airlines deal was found by Cheapflights users on 6/11. 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 7/109:47 pm
PDX
- GCM
1 stop15h 16m
American Airlines
Thu 7/162:41 pm
GCM
- PDX
1 stop10h 10m
American Airlines
Deal found 6/11![American Airlines logo]()
$781
This Southwest deal was found by Cheapflights users on 6/10. 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 7/269:20 pm
PDX
- GCM
2 stops12h 35m
Southwest
Sun 8/212:50 pm
GCM
- PDX
2 stops13h 25m
Southwest
Deal found 6/10![Southwest logo]()
$707
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Sun 7/269:47 pm
PDX
- GCM
1 stop11h 38m
American Airlines
Sun 8/22:41 pm
GCM
- PDX
1 stop10h 10m
American Airlines
Deal found 6/10![American Airlines logo]()
$786
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 June 12, 2026.
Round-trip from | $687 (Southwest) |
|---|---|
Popular in | March |
Cheapest in | January |
Average price | $922 |
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 2,558,603 searches. Data last updated June 12, 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 - GCM
PDXGCM
Portland
Fri 7/10
9:20 pm-12:10 pm
2 stops12h 50m
George Town Owen Roberts Intl
Thu 7/16
12:50 pm-11:55 pm
2 stops13h 05m
$687
PortlandGeorge Town
PDX - GCM
PDXGCM
Portland
Sun 7/26
9:20 pm-11:55 am
2 stops12h 35m
George Town Owen Roberts Intl
Sun 8/2
12:50 pm-12:15 am
2 stops13h 25m
$707
PortlandGeorge Town
PDX - GCM
PDXGCM
Portland
Wed 7/1
7:40 pm-11:55 am
2 stops14h 15m
George Town Owen Roberts Intl
Tue 7/7
12:50 pm-12:10 am
2 stops13h 20m
$757
PortlandGeorge Town
PDX - GCM
PDXGCM
Portland
Fri 8/14
3:00 pm-10:55 am
2 stops17h 55m
George Town Owen Roberts Intl
Thu 8/27
2:10 pm-11:34 am
2 stops23h 24m
$796
PortlandGeorge Town
PDX - GCM
PDXGCM
Portland
Wed 7/1
11:59 pm-12:30 pm
1 stop10h 31m
George Town Owen Roberts Intl
Tue 7/7
1:35 pm-9:34 am
2 stops21h 59m
$804
Quickest round-trip
PortlandGeorge Town
PDX - GCM
PDXGCM
Portland
Sun 8/16
10:55 pm-11:39 am
1 stop10h 44m
George Town Owen Roberts Intl
Sat 8/22
1:04 pm-9:44 pm
1 stop10h 40m
$807
PortlandGeorge Town
PDX - GCM
PDXGCM
Portland
Sun 8/16
5:59 pm-11:00 am
2 stops15h 01m
George Town Owen Roberts Intl
Sat 8/22
12:30 pm-11:58 pm
2 stops13h 28m
$812
Sorted 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 October is currently the most expensive (average of $948). 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 June 12, 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
Overall
7.1
Crew
7.9
Entertainment
6.9
Boarding
7.5
Food
6.4
Reviews
1 / 20
2.0
MediocreAnonymous,Apr 2026
DFW - BDL
Comfort
7.2
Overall
7.1
Crew
7.9
Entertainment
6.9
Boarding
7.5
Food
6.4
Reviews
1 / 20
2.0
MediocreAnonymous,Apr 2026
DFW - BDL
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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Portland and Grand Cayman flights
Browse other Portland and Grand Cayman flight options. Last updated on June 12, 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 2,558,603 searches. Data last updated June 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$666 | Average$799 | FlexibilityNo cancel fee | On-time71% |