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Jamaica

$142+ 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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MBJ
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$348
(CheapOair)

One-way from

$143
(Priceline)

Popular in

December

Cheapest in

January

Average price

$597
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. 12% potential increase in price ($85 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($34 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 15, 2025.

This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/295:20 amORF - MBJ
1 stop6h 45mSpirit Airlines
Fri 10/312:10 pmMBJ - ORF
1 stop9h 38mSpirit Airlines
Deal found 9/14$318
This CheapOair deal was found by Cheapflights users on 9/13. 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.
Sun 10/125:24 amORF - MBJ
1 stop6h 36mSpirit Airlines
Thu 10/1612:09 pmMBJ - ORF
1 stop9h 37mSpirit Airlines
Deal found 9/13$348
This Delta deal was found by Cheapflights users on 9/12. 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.
Fri 9/268:06 amORF - KIN
1 stop12h 54mDelta
Tue 9/309:00 amKIN - ORF
1 stop14h 25mDelta
Deal found 9/12$361
This American Airlines deal was found by Cheapflights users on 9/12. 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.
Fri 9/267:27 pmORF - KIN
2 stops17h 25mAmerican Airlines
Tue 9/306:00 amKIN - ORF
2 stops16h 15mAmerican Airlines
Deal found 9/12$366
This Delta deal was found by Cheapflights users on 9/14. 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 9/233:36 pmORF - KIN
1 stop5h 24mDelta
Mon 10/69:00 amKIN - ORF
1 stop14h 20mDelta
Deal found 9/14$369
This American Airlines deal was found by Cheapflights users on 9/14. 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 9/235:30 amORF - KIN
2 stops15h 08mAmerican Airlines
Mon 10/67:00 amKIN - ORF
2 stops14h 33mAmerican Airlines
Deal found 9/14$374
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/305:24 amORF - MBJ
1 stop6h 36mSpirit Airlines
Thu 11/201:12 pmMBJ - ORF
1 stop9h 31mSpirit Airlines
Deal found 9/14$378
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/146:00 amORF - MBJ
1 stop6h 05mSpirit Airlines
Mon 11/171:12 pmMBJ - ORF
1 stop10h 28mSpirit Airlines
Deal found 9/15$395
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/251:22 pmORF - MBJ
1 stop26h 14mMultiple Airlines
Fri 10/313:30 pmMBJ - ORF
2 stops44h 46mMultiple Airlines
Deal found 9/13$397
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 11/156:00 amORF - MBJ
2 stops31h 54mSpirit Airlines
Tue 11/181:12 pmMBJ - ORF
1 stop10h 28mSpirit Airlines
Deal found 9/13$413
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/15:24 amORF - MBJ
1 stop6h 36mMultiple Airlines
Thu 11/61:12 pmMBJ - ORF
2 stops21h 36mMultiple Airlines
Deal found 9/14$416
This KAYAK deal was found by Cheapflights users on 9/13. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/305:38 pmORF - MBJ
2 stops18h 22mSpirit Airlines
Tue 12/91:12 pmMBJ - ORF
1 stop9h 31mSpirit Airlines
Deal found 9/13$430

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 September 15, 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

Sun 10/12

5:24 am-11:00 am

1 stop6h 36m

Montego Bay Sangster Intl

Thu 10/16

12:09 pm-10:46 pm

1 stop9h 37m

$348

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

Fri 9/26

8:06 am-8:00 pm

1 stop12h 54m

Kingston Norman Manley

Tue 9/30

9:00 am-12:25 am

1 stop14h 25m

$361

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

Thu 12/4

10:24 am-8:06 pm

1 stop9h 42m

Kingston Norman Manley

Sat 12/13

9:00 am-6:33 pm

1 stop9h 33m

$361

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

Fri 9/26

7:27 pm-11:52 am

2 stops17h 25m

Kingston Norman Manley

Tue 9/30

6:00 am-11:59 pm

1 stop16h 59m

$374

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

Wed 9/24

6:00 am-7:38 pm

2 stops14h 38m

Kingston Norman Manley

Tue 9/30

6:00 am-10:37 pm

2 stops15h 37m

$374

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

Mon 1/5

12:54 pm-11:10 pm

2 stops10h 16m

Kingston Norman Manley

Mon 1/19

1:50 pm-11:04 am

1 stop21h 14m

$401

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Sat 10/11

1:22 pm-11:00 am

2 stops22h 38m

Montego Bay Sangster Intl

Sat 10/18

12:09 pm-10:46 pm

1 stop9h 37m

$404

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

Wed 9/24

6:15 am-7:38 pm

1 stop14h 23m

Kingston Norman Manley

Mon 9/29

6:00 am-10:37 pm

2 stops15h 37m

$437

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

Sat 10/11

5:24 am-8:05 pm

1 stop15h 41m

Kingston Norman Manley

Sat 10/18

7:55 am-10:46 pm

1 stop13h 51m

$449

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Thu 12/11

8:09 pm-12:05 pm

1 stop15h 56m

Montego Bay Sangster Intl

Tue 12/16

1:12 pm-10:43 pm

1 stop9h 31m

$459

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 31 results
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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 $560). 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 September 15, 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 September 15, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines 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.
Southwest
8.0
Very good
4,245 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,956 reviews
Southwest
8.0
Very good
4,245 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,931 reviews
Southwest
8.0
Very good
4,245 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,245 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,016 reviews
Southwest
8.0
Very good
4,245 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Chesapeake to Jamaica?

    Airlines like Spirit Airlines, Delta, and American Airlines fly from Chesapeake to Jamaica in about 6h 36m. The time it takes to get you to your destination can typically vary by up to 10h 49m. Airlines will cover a distance of 1274 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $142. However, be on the lookout for offers from Spirit Airlines 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 $560). 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$258Average$438FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$359Average$602FlexibilityNo cancel feeOn-time69%
DeltaCheapest$361Average$542FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$367Average$702FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$414Average$630FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$471Average$740FlexibilityNo cancel feeOn-time63%

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