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Grand Cayman

$198+ Cheap flights from Chesapeake, VA 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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — GCM
Jun 10 — Jun 171
Tue 6/10
Tue 6/17
1 adult, Economy
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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 June 5, 2025.

Round-trip from

$490
(American Airlines)

One-way from

$198
(Delta)

Popular in

December

Cheapest in

October

Average price

$579
From Chesapeake to Grand Cayman
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One-way flight from Chesapeake to Grand Cayman
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Highest demand for flights based on searches. 7% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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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 June 5, 2025.

This American Airlines deal was found by Cheapflights users on 6/2. 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 7/26:26 amORF - GCM
1 stop7h 44mAmerican Airlines
Wed 7/92:10 pmGCM - ORF
1 stop8h 35mAmerican Airlines
Deal found 6/2$490
This United Airlines deal was found by Cheapflights users on 6/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/188:10 pmORF - GCM
2 stops18h 20mUnited Airlines
Tue 7/221:35 pmGCM - ORF
1 stop7h 52mUnited Airlines
Deal found 6/5$525
This Delta deal was found by Cheapflights users on 6/3. 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
Tue 6/1712:40 pmGCM - ORF
1 stop7h 58mDelta
Deal found 6/3$686
This Mytrip deal was found by Cheapflights users on 6/2. 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 7/23:29 pmORF - GCM
3 stops21h 26mMultiple Airlines
Wed 7/911:30 amGCM - ORF
3 stops29h 05mMultiple Airlines
Deal found 6/2$999

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 June 5, 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

Wed 7/2

6:26 am-1:10 pm

1 stop7h 44m

George Town Owen Roberts Intl

Wed 7/9

2:10 pm-11:45 pm

1 stop8h 35m

$490

NorfolkGeorge Town

ORF - GCM

ORFGCM

Norfolk

Fri 7/18

8:10 pm-1:30 pm

2 stops18h 20m

George Town Owen Roberts Intl

Tue 7/22

1:35 pm-10:27 pm

1 stop7h 52m

$525

NorfolkGeorge Town

ORF - GCM

ORFGCM

Norfolk

Wed 7/2

3:29 pm-11:55 am

3 stops21h 26m

George Town Owen Roberts Intl

Wed 7/9

11:30 am-5:35 pm

3 stops29h 05m

$999

NorfolkGeorge Town

ORF - GCM

ORFGCM

Norfolk

Tue 7/29

6:27 am-11:22 am

1 stop5h 55m

$198

NorfolkGeorge Town

ORF - GCM

ORFGCM

Norfolk

Tue 7/29

5:50 am-4:10 pm

3 stops35h 20m

$434

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/5

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 June 5, 2025.
Read reviews from past customers who have flown Delta, United Airlines and American Airlines from Chesapeake to Grand Cayman. 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.
Delta
8.0
Very good
7,956 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,956 reviews
Delta
8.0
Very good
7,956 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,774 reviews
Delta
8.0
Very good
7,956 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,956 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 June 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$192Average$534FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$444Average$609FlexibilityNo cancel feeOn-time71%

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