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Jamaica

$117+ 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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MBJ
ago. 4 — ago. 111
lun. 8/4
lun. 8/11
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 julio 30, 2025.

Round-trip from

$283
(CheapOair)

One-way from

$117
(CheapOair)

Popular in

December

Cheapest in

January

Average price

$607
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. 8% potential increase in price ($53 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in July 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 julio 30, 2025.

This CheapOair deal was found by Cheapflights users on 7/29. 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.
sáb. 9/135:45 amORF - MBJ
1 stop6h 20mSpirit Airlines
jue. 9/1812:10 pmMBJ - ORF
1 stop9h 38mSpirit Airlines
Deal found 7/29$283
This Delta deal was found by Cheapflights users on 7/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/1011:43 amORF - KIN
1 stop9h 42mDelta
mié. 9/249:00 amKIN - ORF
1 stop11h 08mDelta
Deal found 7/27$361
This American Airlines deal was found by Cheapflights users on 7/30. 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.
sáb. 10/46:01 pmORF - KIN
2 stops18h 51mAmerican Airlines
sáb. 10/117:00 amKIN - ORF
1 stop15h 16mAmerican Airlines
Deal found 7/30$366
This Mytrip deal was found by Cheapflights users on 7/29. 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.
vie. 9/125:38 pmORF - KIN
2 stops18h 24mSpirit Airlines
vie. 9/1912:08 pmKIN - ORF
1 stop9h 40mSpirit Airlines
Deal found 7/29$421
This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/115:45 amORF - MBJ
1 stop8h 35mMultiple Airlines
jue. 9/1812:10 pmMBJ - ORF
1 stop9h 38mMultiple Airlines
Deal found 7/28$442
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
sáb. 12/137:30 amORF - KIN
1 stop13h 05mMultiple Airlines
mar. 12/167:05 amKIN - ORF
1 stop15h 38mMultiple Airlines
Deal found 7/28$548
This Expedia deal was found by Cheapflights users on 7/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/410:41 amORF - KIN
2 stops30h 23mJetBlue
vie. 10/102:10 amKIN - ORF
2 stops29h 25mJetBlue
Deal found 7/30$605
This United Airlines deal was found by Cheapflights users on 7/29. 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.
lun. 12/226:00 amORF - KIN
3 stops32h 02mUnited Airlines
mié. 12/313:02 pmKIN - ORF
2 stops18h 53mUnited Airlines
Deal found 7/29$1,596

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 julio 30, 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

sáb. 9/13

5:45 am-11:05 am

1 stop6h 20m

Montego Bay Sangster Intl

jue. 9/18

12:10 pm-10:48 pm

1 stop9h 38m

$283

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

mié. 9/10

11:43 am-8:25 pm

1 stop9h 42m

Kingston Norman Manley

mié. 9/24

9:00 am-9:08 pm

1 stop11h 08m

$361

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

sáb. 10/4

6:01 pm-11:52 am

2 stops18h 51m

Kingston Norman Manley

sáb. 10/11

7:00 am-11:16 pm

1 stop15h 16m

$366

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

vie. 9/12

5:38 pm-11:02 am

2 stops18h 24m

Kingston Norman Manley

vie. 9/19

12:08 pm-10:48 pm

1 stop9h 40m

$421

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

jue. 9/11

5:45 am-1:20 pm

1 stop8h 35m

Montego Bay Sangster Intl

jue. 9/18

12:10 pm-10:48 pm

1 stop9h 38m

$442

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

dom. 8/17

5:34 pm-11:27 am

2 stops18h 53m

Kingston Norman Manley

lun. 9/8

12:08 pm-1:27 pm

2 stops24h 19m

$562

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

sáb. 10/4

10:41 am-4:04 pm

2 stops30h 23m

Kingston Norman Manley

vie. 10/10

2:10 am-8:35 am

2 stops29h 25m

$605

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

mié. 9/10

6:00 am-1:53 pm

3 stops56h 53m

Kingston Norman Manley

mié. 9/24

2:59 pm-11:32 pm

3 stops31h 33m

$7,122

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

sáb. 9/13

5:45 am-11:05 am

1 stop6h 20m

$117

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

lun. 8/25

5:30 am-11:27 am

1 stop6h 57m

$155

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 11 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 $562). 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 julio 30, 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.

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 julio 30, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and JetBlue from Chesapeake to Jamaica. 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
7,980 reviews

Comfort

7.9

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

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
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Comfort

7.9

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

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
8,896 reviews
Delta
8.0
Very good
7,980 reviews

Comfort

7.9

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

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!
JetBlue
7.3
Good
2,913 reviews
Delta
8.0
Very good
7,980 reviews

Comfort

7.9

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

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
7,980 reviews

Comfort

7.9

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

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!
Spirit Airlines
6.3
Okay
8,048 reviews
Delta
8.0
Very good
7,980 reviews

Comfort

7.9

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

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 Jamaica. 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 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 $562). 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.

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 julio 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$258Average$453FlexibilityNo cancel feeOn-time65%
DeltaCheapest$292Average$539FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$367Average$644FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$369Average$607FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$394Average$598FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$415Average$719FlexibilityNo cancel feeOn-time63%

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