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Jamaica

$206+ Cheap flights from Chesapeake, VA to Jamaica

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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MBJ
May 4 — May 111
Sun 5/4
Sun 5/11
1 adult, Economy
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Cheap flight deals from Chesapeake to Jamaica

Keep the following information in mind while searching for Chesapeake to Jamaica flight deals. Data was last updated April 29, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$341
(Kiwi.com)

One-way from

$206
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$551
Provider with most accurate pricing for Norfolk-Montego Bay Sangster Intl flight deals.
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Provider most trusted by Cheapflights users for Norfolk-Montego Bay Sangster Intl flights.
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From Chesapeake to Jamaica
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One-way flight from Chesapeake to Jamaica
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Highest demand for flights based on searches. 5% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Chesapeake to Jamaica

Cheapest flights from Chesapeake to Jamaica
Explore the most affordable flight options available from Chesapeake to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Thu 6/511:35 amORF - MBJ
1 stop24h 27mMultiple Airlines
Sat 6/712:07 pmMBJ - ORF
1 stop21h 38mMultiple Airlines
Deal found 4/28$341
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Sat 5/313:11 pmORF - MBJ
1 stop20h 51mSpirit Airlines
Fri 6/612:07 pmMBJ - ORF
1 stop27h 28mSpirit Airlines
Deal found 4/28$383
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 5/1412:13 pmORF - KIN
2 stops25h 16mSpirit Airlines
Fri 6/61:34 pmKIN - ORF
1 stop26h 01mSpirit Airlines
Deal found 4/27$418
This American Airlines deal was found by Cheapflights users on 4/28. 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 5/75:00 amORF - MBJ
1 stop7h 30mAmerican Airlines
Sat 5/102:41 pmMBJ - ORF
1 stop7h 47mAmerican Airlines
Deal found 4/28$491
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Tue 6/247:32 pmORF - KIN
1 stop17h 56mMultiple Airlines
Thu 6/267:05 amKIN - ORF
1 stop7h 11mMultiple Airlines
Deal found 4/27$517
This Delta deal was found by Cheapflights users on 4/28. 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 6/38:00 amORF - MBJ
1 stop5h 58mDelta
Wed 6/41:15 pmMBJ - ORF
1 stop9h 00mDelta
Deal found 4/28$531
This Southwest deal was found by Cheapflights users on 4/28. 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.
Mon 5/266:25 amORF - MBJ
2 stops8h 30mSouthwest
Sat 5/3112:05 pmMBJ - ORF
2 stops9h 50mSouthwest
Deal found 4/28$570
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Thu 7/36:23 amORF - KIN
2 stops14h 32mAmerican Airlines
Mon 8/256:00 amKIN - ORF
2 stops15h 02mAmerican Airlines
Deal found 4/28$605
This United Airlines deal was found by Cheapflights users on 4/28. 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.
Sat 5/318:05 pmORF - MBJ
1 stop20h 05mUnited Airlines
Tue 6/102:17 pmMBJ - ORF
1 stop8h 27mUnited Airlines
Deal found 4/28$611
This CheapOair deal was found by Cheapflights users on 4/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/2612:53 pmORF - MBJ
2 stops20h 05mFrontier
Tue 7/13:53 pmMBJ - ORF
2 stops41h 05mFrontier
Deal found 4/28$640
This Delta deal was found by Cheapflights users on 4/28. 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.
Sat 6/281:48 pmORF - KIN
1 stop7h 12mDelta
Mon 7/79:00 amKIN - ORF
1 stop8h 53mDelta
Deal found 4/28$650
This Copa Airlines deal was found by Cheapflights users on 4/28. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/258:00 pmORF - MBJ
2 stops15h 15mCopa Airlines
Sat 11/2912:15 pmMBJ - ORF
2 stops21h 20mCopa Airlines
Deal found 4/28$1,347

Cheapflights Fare Finder

Customize your flight search to find flights from Chesapeake to Jamaica 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 29, 2025.
Use the filters below to find and compare flights from Chesapeake to Jamaica that are best for you.

Fly from

Chesapeake

Fly to

Jamaica

Route

Depart

Return

Price

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Thu 6/5

11:35 am-11:02 am

1 stop24h 27m

Montego Bay Sangster Intl

Sat 6/7

12:07 pm-10:45 am

1 stop21h 38m

$341

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Sat 5/31

3:11 pm-11:02 am

1 stop20h 51m

Montego Bay Sangster Intl

Fri 6/6

12:07 pm-4:35 pm

1 stop27h 28m

$383

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

Wed 5/14

12:13 pm-12:29 pm

2 stops25h 16m

Kingston Norman Manley

Fri 6/6

1:34 pm-4:35 pm

1 stop26h 01m

$418

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Sun 5/11

5:35 am-12:58 pm

1 stop8h 23m

Montego Bay Sangster Intl

Sat 5/17

1:02 pm-11:24 pm

1 stop9h 22m

$491

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Mon 5/26

5:38 am-1:35 pm

2 stops8h 57m

Montego Bay Sangster Intl

Sat 5/31

3:40 pm-11:28 pm

1 stop6h 48m

$495

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

Tue 6/24

7:32 pm-12:28 pm

1 stop17h 56m

Kingston Norman Manley

Thu 6/26

7:05 am-3:16 pm

1 stop7h 11m

$517

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Mon 5/26

6:25 am-1:55 pm

2 stops8h 30m

Montego Bay Sangster Intl

Sat 5/31

12:05 pm-10:55 pm

2 stops9h 50m

$570

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

Thu 7/3

6:23 am-7:55 pm

2 stops14h 32m

Kingston Norman Manley

Mon 8/25

6:00 am-10:02 pm

2 stops15h 02m

$605

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Sat 5/31

8:05 pm-3:10 pm

1 stop20h 05m

Montego Bay Sangster Intl

Tue 6/10

2:17 pm-11:44 pm

1 stop8h 27m

$611

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Thu 6/26

12:53 pm-7:58 am

2 stops20h 05m

Montego Bay Sangster Intl

Tue 7/1

3:53 pm-9:58 am

2 stops41h 05m

$640

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/27

Showing 1-10 of 17 results
1
2

Best time to book a flight from Chesapeake to Jamaica

Have a flexible travel schedule? Discover the best time to fly to Jamaica 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 Jamaica

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

Currently, January is the cheapest month in which you can book a flight from Chesapeake to Jamaica (average of $403). Flying from Chesapeake to Jamaica in July is currently the most expensive (average of $569). 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.

What is the cheapest time of day to fly from C6E to JM?

Find hourly flight availability from Chesapeake to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 29, 2025.

When flying from Chesapeake to Jamaica, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Jamaica by month

Plan your trip to Jamaica by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Jamaica ranges from 1.6 - 7.1 inches per month. October is typically the wettest month, when rainfall can reach 7.1 in. February is typically the driest time to visit Jamaica when rainfall is around 1.6 in.

Temperature in Jamaica by month

Plan your trip to Jamaica by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Jamaica, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Jamaica

Get insights into the airlines that provide service to Jamaica. 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 Jamaica. Reviews last updated April 29, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and United Airlines from Chesapeake to Jamaica to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,929 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Air Canada
7.0
Good
9,242 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

Related info for your journey

Find useful and relevant information for your journey from Chesapeake to Jamaica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Chesapeake to Jamaica one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $206. However, be on the lookout for offers from Delta and American Airlines, as they are both options that can get you from Chesapeake to Jamaica for a low price.

  • Can I find deals for flights from Chesapeake to Jamaica that include hotel bookings?

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

  • How can I find direct flights from Chesapeake to Jamaica?

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

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

    Yes. Cheapflights offers flight deals from Chesapeake to Jamaica 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 Jamaica?

    Currently, January is the cheapest month in which you can book a flight from Chesapeake to Jamaica (average of $403). Flying from Chesapeake to Jamaica in July is currently the most expensive (average of $569). 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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Alternative routes for Chesapeake to Jamaica

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Chesapeake to Jamaica

Discover the top 6 airlines that operate flights from Chesapeake to Jamaica. 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 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$252Average$457FlexibilityNo cancel feeOn-time65%
DeltaCheapest$292Average$525FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$367Average$643FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$368Average$703FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$375Average$579FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$383Average$637FlexibilityNo cancel feeOn-time69%

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