Grand Cayman

$469+ Cheap flights from Chesapeake, VA 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 9/19. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — GCM
ago. 11 — ago. 181
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Cheap flight deals from Chesapeake to Grand Cayman

Keep the following information in mind while searching for Chesapeake to Grand Cayman flight deals. Data was last updated agosto 6, 2025.

Round-trip from

$469
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$548
From Chesapeake to Grand Cayman
Highest demand for flights based on searches. 10% potential increase in price ($68 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($25 potential savings vs. average RT price).
Average for round-trip flights in August 2025

Find flight deals from Chesapeake to Grand Cayman

Cheapest flights from Chesapeake to Grand Cayman
Explore the most affordable flight options available from Chesapeake to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on agosto 6, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/4. 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.
vie. 9/197:00 amORF - GCM
1 stop10h 05mMultiple Airlines
vie. 9/2611:25 amGCM - ORF
1 stop9h 53mMultiple Airlines
Deal found 8/4$469
This United Airlines deal was found by Cheapflights users on 8/6. 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.
jue. 12/48:10 pmORF - GCM
2 stops20h 20mUnited Airlines
lun. 12/85:45 pmGCM - ORF
2 stops20h 18mUnited Airlines
Deal found 8/6$504
This American Airlines deal was found by Cheapflights users on 8/6. 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.
vie. 10/108:04 pmORF - GCM
1 stop16h 21mAmerican Airlines
mar. 10/1412:25 pmGCM - ORF
1 stop7h 25mAmerican Airlines
Deal found 8/6$525
This American Airlines deal was found by Cheapflights users on 8/4. 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.
vie. 9/197:04 pmORF - GCM
2 stops17h 06mAmerican Airlines
vie. 9/2612:10 pmGCM - ORF
2 stops21h 06mAmerican Airlines
Deal found 8/4$529
This American Airlines deal was found by Cheapflights users on 8/5. 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.
mié. 9/176:00 amORF - GCM
1 stop6h 25mAmerican Airlines
dom. 9/2112:28 pmGCM - ORF
1 stop10h 31mAmerican Airlines
Deal found 8/5$530
This Kiwi.com deal was found by Cheapflights users on 8/6. 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.
jue. 12/47:00 amORF - GCM
1 stop10h 20mMultiple Airlines
lun. 12/812:40 pmGCM - ORF
1 stop9h 38mMultiple Airlines
Deal found 8/6$545
This Mytrip deal was found by Cheapflights users on 8/6. 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.
sáb. 9/205:38 pmORF - GCM
3 stops28h 42mMultiple Airlines
sáb. 9/271:45 pmGCM - ORF
2 stops32h 03mMultiple Airlines
Deal found 8/6$619
This American Airlines deal was found by Cheapflights users on 8/6. 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.
mié. 12/316:43 amORF - GCM
1 stop7h 17mAmerican Airlines
lun. 1/52:15 pmGCM - ORF
1 stop9h 46mAmerican Airlines
Deal found 8/6$625

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chesapeake 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 agosto 6, 2025.
Use the filters below to find and compare flights from Chesapeake to Grand Cayman that are best for you.

Fly from

Chesapeake

Fly to

Grand Cayman

Route

Depart

Return

Price

NorfolkGeorge Town

ORF - GCM

ORFGCM

Norfolk

vie. 9/19

7:00 am-4:05 pm

1 stop10h 05m

George Town Owen Roberts Intl

vie. 9/26

11:25 am-10:18 pm

1 stop9h 53m

$469

NorfolkGeorge Town

ORF - GCM

ORFGCM

Norfolk

jue. 12/4

8:10 pm-4:30 pm

2 stops20h 20m

George Town Owen Roberts Intl

lun. 12/8

5:45 pm-2:03 pm

2 stops20h 18m

$504

NorfolkGeorge Town

ORF - GCM

ORFGCM

Norfolk

vie. 10/10

8:04 pm-11:25 am

1 stop16h 21m

George Town Owen Roberts Intl

mar. 10/14

12:25 pm-8:50 pm

1 stop7h 25m

$525

NorfolkGeorge Town

ORF - GCM

ORFGCM

Norfolk

vie. 9/19

7:04 pm-11:10 am

2 stops17h 06m

George Town Owen Roberts Intl

vie. 9/26

12:10 pm-10:16 am

2 stops21h 06m

$529

NorfolkGeorge Town

ORF - GCM

ORFGCM

Norfolk

mié. 9/17

6:00 am-11:25 am

1 stop6h 25m

George Town Owen Roberts Intl

dom. 9/21

12:28 pm-11:59 pm

1 stop10h 31m

$530

NorfolkGeorge Town

ORF - GCM

ORFGCM

Norfolk

jue. 12/4

7:00 am-5:20 pm

1 stop10h 20m

George Town Owen Roberts Intl

lun. 12/8

12:40 pm-10:18 pm

1 stop9h 38m

$545

NorfolkGeorge Town

ORF - GCM

ORFGCM

Norfolk

sáb. 9/20

5:38 pm-9:20 pm

3 stops28h 42m

George Town Owen Roberts Intl

sáb. 9/27

1:45 pm-10:48 pm

2 stops32h 03m

$619

NorfolkGeorge Town

ORF - GCM

ORFGCM

Norfolk

mié. 12/31

6:43 am-2:00 pm

1 stop7h 17m

George Town Owen Roberts Intl

lun. 1/5

2:15 pm-12:01 am

1 stop9h 46m

$625

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/4

Best time to book a flight from Chesapeake to Grand Cayman

Have a flexible travel schedule? Discover the best time to fly to Grand Cayman from Chesapeake with our price prediction graph.
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 Chesapeake to Grand Cayman

What is the cheapest month to book a flight from Chesapeake to Grand Cayman?

Currently, January is the cheapest month in which you can book a flight from Chesapeake to Grand Cayman (average of $467). Flying from Chesapeake to Grand Cayman in March is currently the most expensive (average of $594). 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 agosto 6, 2025.
Read through reviews of airlines operating flights from Chesapeake to Grand Cayman, such as United Airlines and American Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Food

6.6

Overall

7.4

Entertainment

7.0

Boarding

7.7

Comfort

7.3

Crew

8.1

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

Food

6.6

Overall

7.4

Entertainment

7.0

Boarding

7.7

Comfort

7.3

Crew

8.1

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

Food

6.6

Overall

7.4

Entertainment

7.0

Boarding

7.7

Comfort

7.3

Crew

8.1

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

Related info for your journey

Find useful and relevant information for your journey from Chesapeake to Grand Cayman. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • Can I find deals for flights from Chesapeake to Grand Cayman that include hotel bookings?

    Yes. In addition to deals on Chesapeake to Grand Cayman flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chesapeake to Grand Cayman?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chesapeake to Grand Cayman.

  • Can I find deals for business class flights from Chesapeake to Grand Cayman?

    Yes. Cheapflights offers flight deals from Chesapeake to Grand Cayman by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chesapeake to Grand Cayman?

    Currently, January is the cheapest month in which you can book a flight from Chesapeake to Grand Cayman (average of $467). Flying from Chesapeake to Grand Cayman in March is currently the most expensive (average of $594). 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.

See more FAQs

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Top 2 airlines flying from Chesapeake to Grand Cayman

Discover the top 2 airlines that operate flights from Chesapeake 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 agosto 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$355Average$528FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$465Average$603FlexibilityNo cancel feeOn-time71%

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