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Jamaica

$156+ 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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MBJ
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
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 October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$314
(Priceline)

One-way from

$156
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$573
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. 9% potential increase in price ($61 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 October 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 October 29, 2025.

This Priceline deal was found by Cheapflights users on 10/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/88:11 pmORF - MBJ
1 stop15h 59mSpirit Airlines
Thu 12/111:05 pmMBJ - ORF
1 stop6h 11mSpirit Airlines
Deal found 10/28$342
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1710:24 amORF - KIN
1 stop9h 36mDelta
Sun 12/79:00 amKIN - ORF
1 stop9h 34mDelta
Deal found 10/29$362
This American Airlines deal was found by Cheapflights users on 10/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/186:00 amORF - KIN
2 stops16h 13mAmerican Airlines
Sat 12/63:06 pmKIN - ORF
1 stop8h 53mAmerican Airlines
Deal found 10/29$366
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1212:00 pmORF - MBJ
1 stop27h 51mMultiple Airlines
Tue 12/161:05 pmMBJ - ORF
1 stop6h 11mMultiple Airlines
Deal found 10/29$396
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Mon 12/88:10 pmORF - MBJ
2 stops15h 57mUnited Airlines
Thu 12/113:36 pmMBJ - ORF
1 stop7h 51mUnited Airlines
Deal found 10/28$419
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/243:01 pmORF - MBJ
1 stop21h 04mSpirit Airlines
Mon 1/261:12 pmMBJ - ORF
1 stop6h 02mSpirit Airlines
Deal found 10/29$420
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/118:38 amORF - MBJ
2 stops26h 36mMultiple Airlines
Tue 12/161:05 pmMBJ - ORF
1 stop6h 11mMultiple Airlines
Deal found 10/28$421
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/47:53 pmORF - KIN
1 stop16h 08mSpirit Airlines
Wed 11/121:06 pmKIN - ORF
1 stop5h 52mSpirit Airlines
Deal found 10/27$421
This American Airlines deal was found by Cheapflights users on 10/26. 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 11/279:56 amORF - MBJ
2 stops24h 21mAmerican Airlines
Wed 12/32:27 pmMBJ - ORF
1 stop6h 24mAmerican Airlines
Deal found 10/26$424
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/127:53 pmORF - MBJ
1 stop16h 09mMultiple Airlines
Sat 11/151:07 pmMBJ - ORF
2 stops23h 09mMultiple Airlines
Deal found 10/29$427
This American Airlines deal was found by Cheapflights users on 10/26. 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 12/26:00 amORF - MBJ
2 stops8h 50mAmerican Airlines
Sun 12/711:13 amMBJ - ORF
1 stop12h 46mAmerican Airlines
Deal found 10/26$429
This American Airlines deal was found by Cheapflights users on 10/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/115:08 amORF - KIN
2 stops17h 26mAmerican Airlines
Thu 12/183:48 pmKIN - ORF
2 stops16h 27mAmerican Airlines
Deal found 10/27$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 October 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

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

Mon 11/17

10:24 am-8:00 pm

1 stop9h 36m

Kingston Norman Manley

Sun 12/7

9:00 am-6:34 pm

1 stop9h 34m

$362

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

Tue 11/18

6:00 am-10:13 pm

1 stop16h 13m

Kingston Norman Manley

Sat 12/6

3:06 pm-11:59 pm

1 stop8h 53m

$362

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

Wed 2/4

5:00 pm-2:26 pm

2 stops21h 26m

Kingston Norman Manley

Sun 2/8

3:32 pm-9:32 am

2 stops18h 00m

$383

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

Fri 1/9

7:06 pm-12:07 pm

1 stop17h 01m

Kingston Norman Manley

Mon 1/12

7:00 am-11:10 pm

2 stops16h 10m

$385

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Mon 2/2

8:09 pm-12:05 pm

1 stop15h 56m

Montego Bay Sangster Intl

Thu 2/5

1:12 pm-7:37 pm

3 stops30h 25m

$387

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

Mon 3/9

6:44 am-6:20 pm

1 stop12h 36m

Kingston Norman Manley

Mon 3/16

5:20 am-11:41 pm

2 stops17h 21m

$394

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Fri 12/12

12:00 pm-3:51 pm

1 stop27h 51m

Montego Bay Sangster Intl

Tue 12/16

1:05 pm-7:16 pm

1 stop6h 11m

$395

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Mon 12/8

8:38 am-12:10 pm

3 stops27h 32m

Montego Bay Sangster Intl

Thu 12/11

1:05 pm-7:16 pm

1 stop6h 11m

$412

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Mon 12/8

8:10 pm-12:07 pm

2 stops15h 57m

Montego Bay Sangster Intl

Thu 12/11

3:36 pm-11:27 pm

1 stop7h 51m

$419

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

Thu 12/11

8:11 pm-12:14 pm

1 stop16h 03m

Kingston Norman Manley

Thu 12/18

1:19 pm-2:06 pm

1 stop24h 47m

$421

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 32 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, October is the cheapest month in which you can book a flight from Chesapeake to Jamaica (average of $157). Flying from Chesapeake to Jamaica in July is currently the most expensive (average of $416). 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 October 29, 2025.

A simple way to save on the total cost of your ticket is to fly from Chesapeake to Jamaica in the evening. If you’re flexible enough to do this you can expect to save up to 29% on your trip compared to booking a flight in the morning.

What is the cheapest day to fly from Chesapeake to Jamaica?

Use this chart to determine the cheapest time to fly round-trip from Chesapeake to Jamaica. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chesapeake to Jamaica flight should consider departing on Saturday evenings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 October 29, 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
4,241 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

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
7.9
Good
7,992 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

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
8,999 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

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
11,032 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

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
8,114 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

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 Delta, American Airlines, and Spirit Airlines fly from Chesapeake to Jamaica in about 9h 36m. The time it takes to get you to your destination can typically vary by up to 6h 37m. Airlines will cover a distance of 1310 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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, October is the cheapest month in which you can book a flight from Chesapeake to Jamaica (average of $157). Flying from Chesapeake to Jamaica in July is currently the most expensive (average of $416). 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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$177Average$439FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$357Average$604FlexibilityNo cancel feeOn-time69%
DeltaCheapest$361Average$555FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$377Average$690FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$389Average$616FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$471Average$734FlexibilityNo cancel feeOn-time63%

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