Jamaica

$135+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MBJ
Mar 6 — Mar 131
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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 February 4, 2026.

This Expedia deal was found by Cheapflights users on 2/2. 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.
Sat 2/218:44 pm
ORF
-
MBJ
1 stop15h 18m
Spirit Airlines
Wed 2/251:00 pm
MBJ
-
ORF
1 stop5h 26m
Spirit Airlines
Deal found 2/2$248
This Travelocity deal was found by Cheapflights users on 2/1. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/78:44 pm
ORF
-
MBJ
1 stop14h 18m
Spirit Airlines
Wed 3/1111:57 am
MBJ
-
ORF
1 stop5h 29m
Spirit Airlines
Deal found 2/1$266
This FlightHub deal was found by Cheapflights users on 2/3. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/78:44 pm
ORF
-
MBJ
1 stop14h 18m
Spirit Airlines
Tue 3/1011:57 am
MBJ
-
ORF
1 stop5h 29m
Spirit Airlines
Deal found 2/3$281
This FlightHub deal was found by Cheapflights users on 2/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:44 pm
ORF
-
MBJ
1 stop15h 18m
Spirit Airlines
Wed 3/41:00 pm
MBJ
-
ORF
1 stop5h 26m
Spirit Airlines
Deal found 2/2$286
This FlightHub deal was found by Cheapflights users on 2/3. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/78:44 pm
ORF
-
MBJ
1 stop14h 18m
Spirit Airlines
Thu 3/1212:00 pm
MBJ
-
ORF
1 stop6h 46m
Spirit Airlines
Deal found 2/3$295
This CheapOair deal was found by Cheapflights users on 2/2. 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 2/227:31 pm
ORF
-
MBJ
1 stop16h 31m
Spirit Airlines
Sat 2/281:00 pm
MBJ
-
ORF
1 stop6h 49m
Spirit Airlines
Deal found 2/2$299
This CheapOair deal was found by Cheapflights users on 2/2. 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.
Fri 2/207:31 pm
ORF
-
MBJ
1 stop16h 31m
Spirit Airlines
Tue 2/241:00 pm
MBJ
-
ORF
1 stop5h 26m
Spirit Airlines
Deal found 2/2$306
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Sun 2/2211:32 am
ORF
-
MBJ
2 stops24h 30m
Multiple Airlines
Sat 2/2812:40 pm
MBJ
-
ORF
1 stop21h 57m
Multiple Airlines
Deal found 2/2$318
This Cheapflightsfares deal was found by Cheapflights users on 2/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/117:31 pm
ORF
-
KIN
1 stop17h 04m
Spirit Airlines
Tue 3/1712:32 pm
KIN
-
ORF
1 stop6h 14m
Spirit Airlines
Deal found 2/4$353
This American Airlines deal was found by Cheapflights users on 2/3. 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 3/27:41 pm
ORF
-
KIN
1 stop14h 41m
American Airlines
Tue 3/1010:12 am
KIN
-
ORF
1 stop12h 39m
American Airlines
Deal found 2/3$374
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/318:41 pm
ORF
-
KIN
1 stop15h 54m
Spirit Airlines
Thu 4/3012:00 pm
KIN
-
ORF
1 stop6h 29m
Spirit Airlines
Deal found 2/2$375
This American Airlines deal was found by Cheapflights users on 2/4. 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.
Sat 3/146:15 pm
ORF
-
KIN
2 stops16h 07m
American Airlines
Tue 3/1710:12 am
KIN
-
ORF
2 stops11h 46m
American Airlines
Deal found 2/4$379

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 February 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$248
(FlightHub)

One-way from

$135
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$527
Provider with most accurate pricing for Norfolk-Montego Bay Sangster Intl flight deals.
Provider most trusted by Cheapflights users for Norfolk-Montego Bay Sangster Intl flights.
From Chesapeake to Jamaica
One-way flight from Chesapeake to Jamaica
Highest demand for flights based on searches. 2% potential increase in price ($15 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Average for round-trip flights in February 2026

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 February 4, 2026.
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

Sat 2/21

8:44 pm-12:02 pm

1 stop15h 18m

Montego Bay Sangster Intl

Wed 2/25

1:00 pm-6:26 pm

1 stop5h 26m

$248

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Thu 3/12

8:41 pm-11:05 am

1 stop15h 24m

Montego Bay Sangster Intl

Tue 3/24

12:00 pm-7:46 pm

1 stop6h 46m

$292

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Sat 2/28

8:44 pm-12:02 pm

1 stop15h 18m

Montego Bay Sangster Intl

Wed 3/4

1:00 pm-6:26 pm

1 stop5h 26m

$292

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Tue 3/3

7:31 pm-12:02 pm

1 stop16h 31m

Montego Bay Sangster Intl

Tue 3/17

12:00 pm-7:46 pm

1 stop6h 46m

$299

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Sun 2/22

7:31 pm-12:02 pm

1 stop16h 31m

Montego Bay Sangster Intl

Sat 2/28

1:00 pm-7:49 pm

1 stop6h 49m

$299

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Fri 2/20

7:31 pm-12:02 pm

1 stop16h 31m

Montego Bay Sangster Intl

Tue 2/24

1:00 pm-6:26 pm

1 stop5h 26m

$306

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Sat 3/7

8:44 pm-11:02 am

1 stop14h 18m

Montego Bay Sangster Intl

Thu 3/12

12:00 pm-7:46 pm

1 stop6h 46m

$308

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Sat 3/7

6:45 am-11:02 am

2 stops28h 17m

Montego Bay Sangster Intl

Wed 3/11

11:57 am-6:26 pm

1 stop5h 29m

$337

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

Mon 3/2

7:41 pm-10:22 am

1 stop14h 41m

Kingston Norman Manley

Tue 3/10

10:12 am-11:51 pm

1 stop12h 39m

$374

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

Wed 3/11

6:00 am-7:12 pm

2 stops14h 12m

Kingston Norman Manley

Tue 3/17

2:34 pm-11:51 pm

1 stop8h 17m

$379

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/1

Showing 1-10 of 28 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 $415). 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.

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 February 4, 2026.
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.

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

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

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

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

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

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

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

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

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

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

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

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 and American Airlines fly from Chesapeake to Jamaica in about 14h 41m. The time it takes to get you to your destination can typically vary by up to 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.

  • 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 Delta, 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 $415). 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.

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 February 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$146Average$532FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$148Average$418FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$269Average$603FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$331Average$596FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$366Average$668FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$452Average$713FlexibilityNo cancel feeOn-time63%

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