HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Grand Cayman

$490+ 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 6/10. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — GCM
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chesapeake to Grand Cayman with Cheapflights

1. Tell us where you want to go

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

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

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 Chesapeake to Grand Cayman

Keep the following information in mind while searching for Chesapeake to Grand Cayman flight deals. Data was last updated April 17, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$490
(Delta)

Popular in

December

Cheapest in

October

Average price

$607
Provider with most accurate pricing for Norfolk-George Town Owen Roberts Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-George Town Owen Roberts Intl flights.
Search Deals
From Chesapeake to Grand Cayman
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($48 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals

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 April 17, 2025.

This Delta deal was found by Cheapflights users on 4/16. 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 6/105:23 amORF - GCM
1 stop7h 02mDelta
Wed 6/1812:40 pmGCM - ORF
1 stop7h 58mDelta
Deal found 4/16$490
This American Airlines deal was found by Cheapflights users on 4/16. 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 6/108:17 pmORF - GCM
2 stops15h 47mAmerican Airlines
Wed 6/1812:25 pmGCM - ORF
1 stop8h 11mAmerican Airlines
Deal found 4/16$494
This United Airlines deal was found by Cheapflights users on 4/17. 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 7/18:10 pmORF - GCM
2 stops17h 20mUnited Airlines
Tue 7/81:35 pmGCM - ORF
3 stops24h 39mUnited Airlines
Deal found 4/17$584
This Mytrip deal was found by Cheapflights users on 4/15. 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.
Mon 6/95:40 pmORF - GCM
3 stops23h 30mMultiple Airlines
Fri 6/1311:25 amGCM - ORF
3 stops22h 11mMultiple Airlines
Deal found 4/15$1,325

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 April 17, 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

Tue 6/10

5:23 am-11:25 am

1 stop7h 02m

George Town Owen Roberts Intl

Wed 6/18

12:40 pm-9:38 pm

1 stop7h 58m

$490

NorfolkGeorge Town

ORF - GCM

ORFGCM

Norfolk

Tue 6/10

7:55 pm-11:04 am

2 stops16h 09m

George Town Owen Roberts Intl

Wed 6/18

2:05 pm-11:59 pm

2 stops8h 54m

$494

NorfolkGeorge Town

ORF - GCM

ORFGCM

Norfolk

Tue 7/1

8:10 pm-12:30 pm

2 stops17h 20m

George Town Owen Roberts Intl

Tue 7/8

1:35 pm-3:14 pm

3 stops24h 39m

$584

NorfolkGeorge Town

ORF - GCM

ORFGCM

Norfolk

Mon 6/9

5:40 pm-4:10 pm

3 stops23h 30m

George Town Owen Roberts Intl

Fri 6/13

11:25 am-10:36 am

3 stops22h 11m

$1,325

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

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 April 17, 2025.
Delta
8.0
Very good
7,916 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,916 reviews
Delta
8.0
Very good
7,916 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,667 reviews
Delta
8.0
Very good
7,916 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,916 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$355Average$538FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$444Average$595FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.