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Jamaica

$155+ 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 2/15. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MBJ
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheap 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 December 15, 2025.

This Delta deal was found by Cheapflights users on 12/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/156:30 amORF - MBJ
1 stop7h 43mDelta
Fri 12/191:55 pmMBJ - ORF
1 stop9h 40mDelta
Deal found 12/13$377
This American Airlines deal was found by Cheapflights users on 12/14. 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.
Mon 12/155:51 amORF - MBJ
2 stops9h 58mAmerican Airlines
Fri 12/194:11 pmMBJ - ORF
1 stop8h 48mAmerican Airlines
Deal found 12/14$382
This Delta deal was found by Cheapflights users on 12/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/145:15 amORF - MBJ
1 stop7h 49mDelta
Sun 12/2112:30 pmMBJ - ORF
1 stop10h 26mDelta
Deal found 12/13$407
This American Airlines deal was found by Cheapflights users on 12/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:08 amORF - MBJ
1 stop27h 58mAmerican Airlines
Wed 12/3111:12 amMBJ - ORF
1 stop13h 47mAmerican Airlines
Deal found 12/13$438
This American Airlines deal was found by Cheapflights users on 12/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/145:08 amORF - MBJ
2 stops9h 31mAmerican Airlines
Sun 12/211:22 pmMBJ - ORF
1 stop6h 07mAmerican Airlines
Deal found 12/13$457
This Delta deal was found by Cheapflights users on 12/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:00 amORF - MBJ
1 stop12h 41mDelta
Wed 12/313:38 pmMBJ - ORF
1 stop8h 40mDelta
Deal found 12/15$472
This Delta deal was found by Cheapflights users on 12/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1612:37 pmORF - KIN
1 stop7h 29mDelta
Fri 12/269:00 amKIN - ORF
1 stop12h 52mDelta
Deal found 12/15$481
This American Airlines deal was found by Cheapflights users on 12/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/167:18 pmORF - KIN
2 stops18h 48mAmerican Airlines
Fri 12/263:48 pmKIN - ORF
2 stops16h 27mAmerican Airlines
Deal found 12/15$538
This American Airlines deal was found by Cheapflights users on 12/14. 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.
Sun 12/285:00 amORF - KIN
1 stop5h 12mAmerican Airlines
Mon 12/293:48 pmKIN - ORF
2 stops16h 27mAmerican Airlines
Deal found 12/14$661
This American Airlines deal was found by Cheapflights users on 12/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:37 pmORF - KIN
1 stop21h 32mAmerican Airlines
Mon 1/127:00 amKIN - ORF
1 stop11h 26mAmerican Airlines
Deal found 12/13$679
This Expedia deal was found by Cheapflights users on 12/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2812:35 pmORF - KIN
1 stop19h 35mJetBlue
Mon 12/297:32 pmKIN - ORF
1 stop16h 17mJetBlue
Deal found 12/13$714
This Kiwi.com deal was found by Cheapflights users on 12/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/243:01 pmORF - KIN
1 stop21h 13mMultiple Airlines
Sun 1/111:17 pmKIN - ORF
2 stops21h 28mMultiple Airlines
Deal found 12/12$739

Find flight deals from Chesapeake to Jamaica

Keep the following information in mind while searching for Chesapeake to Jamaica flight deals. Data was last updated December 15, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$308
(Priceline)

One-way from

$155
(Priceline)

Popular in

December

Cheapest in

January

Average price

$778
Provider with most accurate pricing for Norfolk-Montego Bay Sangster Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-Montego Bay Sangster Intl flights.
Search Deals
From Chesapeake to Jamaica
Search Deals
One-way flight from Chesapeake to Jamaica
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($21 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 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

Mon 1/19

5:30 pm-1:03 pm

1 stop19h 33m

Montego Bay Sangster Intl

Thu 1/22

12:57 pm-6:38 pm

1 stop5h 41m

$308

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Sat 2/28

8:34 pm-12:02 pm

1 stop15h 28m

Montego Bay Sangster Intl

Wed 3/4

1:00 pm-6:26 pm

1 stop5h 26m

$317

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Sun 2/8

5:30 pm-12:53 pm

1 stop19h 23m

Montego Bay Sangster Intl

Sun 2/15

1:58 pm-10:14 am

1 stop20h 16m

$345

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

Thu 1/29

10:15 am-8:00 pm

1 stop9h 45m

Kingston Norman Manley

Thu 2/5

9:00 am-12:16 am

1 stop15h 16m

$373

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Wed 3/4

4:55 pm-2:05 pm

2 stops21h 10m

Montego Bay Sangster Intl

Tue 3/17

2:55 pm-11:34 pm

1 stop7h 39m

$377

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Wed 3/4

6:25 am-3:19 pm

1 stop8h 54m

Montego Bay Sangster Intl

Tue 3/17

4:55 pm-12:25 am

1 stop6h 30m

$377

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Wed 3/4

7:45 am-3:19 pm

1 stop7h 34m

Montego Bay Sangster Intl

Tue 3/10

11:35 am-10:20 pm

1 stop9h 45m

$377

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Wed 1/28

7:45 am-3:20 pm

1 stop7h 35m

Montego Bay Sangster Intl

Wed 2/4

2:00 pm-11:02 pm

1 stop9h 02m

$377

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Wed 3/4

6:00 am-3:37 pm

2 stops9h 37m

Montego Bay Sangster Intl

Tue 3/10

10:07 am-10:58 pm

2 stops11h 51m

$382

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Mon 1/19

7:09 pm-12:58 pm

2 stops17h 49m

Montego Bay Sangster Intl

Thu 1/22

12:33 pm-6:41 pm

1 stop6h 08m

$382

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Showing 1-10 of 34 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 $155). 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 December 15, 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 December 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
7.9
Good
4,250 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,007 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,092 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,052 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,185 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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, Frontier, and JetBlue fly from Chesapeake to Jamaica in about 15h 28m. The time it takes to get you to your destination can typically vary by up to 10h 19m. 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 Spirit Airlines, with whom users have recently found tickets for as low as $106. However, be on the lookout for offers from American Airlines and United 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, October is the cheapest month in which you can book a flight from Chesapeake to Jamaica (average of $155). 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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$175Average$423FlexibilityNo cancel feeOn-time65%
DeltaCheapest$340Average$562FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$357Average$605FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$366Average$627FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$369Average$601FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$471Average$707FlexibilityNo cancel feeOn-time63%

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