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Grand Cayman

$485+ 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 6/17. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — GCM
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$485
(American Airlines)

Popular in

December

Cheapest in

January

Average price

$550
Provider with most accurate pricing for Norfolk-George Town Owen Roberts Intl flight deals.
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Provider most trusted by Cheapflights users for Norfolk-George Town Owen Roberts Intl flights.
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From Chesapeake to Grand Cayman
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Highest demand for flights based on searches. 6% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This American Airlines deal was found by Cheapflights users on 2/19. 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 6/178:24 pmORF - GCM
1 stop15h 36mAmerican Airlines
Fri 6/203:20 pmGCM - ORF
2 stops18h 04mAmerican Airlines
Deal found 2/19$485
This United Airlines deal was found by Cheapflights users on 2/19. 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.
Sun 5/255:05 pmORF - GCM
2 stops20h 25mUnited Airlines
Fri 5/301:35 pmGCM - ORF
2 stops31h 03mUnited Airlines
Deal found 2/19$676

Find flights from Chesapeake to Grand Cayman within your budget

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 February 20, 2025.

Fly from

Chesapeake

Fly to

Grand Cayman

Route

Depart

Return

Price

NorfolkGeorge Town

ORF - GCM

ORFGCM

Norfolk

Tue 6/17

8:24 pm-11:00 am

1 stop15h 36m

George Town Owen Roberts Intl

Fri 6/20

3:20 pm-10:24 am

2 stops18h 04m

$485

NorfolkGeorge Town

ORF - GCM

ORFGCM

Norfolk

Sun 5/25

5:05 pm-12:30 pm

2 stops20h 25m

George Town Owen Roberts Intl

Fri 5/30

1:35 pm-9:38 pm

2 stops31h 03m

$676

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

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.

Travel insights for flights from Chesapeake to Grand Cayman

Get recent, data-driven insights about flights from Chesapeake to Grand Cayman including ideal travel times, pricing trends, and more.

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 February 20, 2025.
United Airlines
7.4
Good
8,766 reviews

Food

6.7

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Reviews

1 / 20

2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

United Airlines
7.4
Good
8,766 reviews
United Airlines
7.4
Good
8,766 reviews

Food

6.7

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Reviews

1 / 20

2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,766 reviews

Food

6.7

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Reviews

1 / 20

2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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.

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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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$410Average$558FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$440Average$602FlexibilityNo cancel feeOn-time71%
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