HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Jamaica

$172+ 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 6/19. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MBJ
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chesapeake to Jamaica with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 April 24, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$405
(Mytrip)

One-way from

$172
(Mytrip)

Popular in

December

Cheapest in

January

Average price

$551
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. 5% potential increase in price ($35 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals

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 April 24, 2025.

This Mytrip deal was found by Cheapflights users on 4/22. 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.
Sun 6/811:35 amORF - MBJ
1 stop24h 27mMultiple Airlines
Mon 6/1610:15 amMBJ - ORF
2 stops24h 56mMultiple Airlines
Deal found 4/22$405
This Mytrip deal was found by Cheapflights users on 4/22. 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.
Tue 5/2712:13 pmORF - KIN
2 stops25h 16mSpirit Airlines
Sun 6/151:34 pmKIN - ORF
1 stop24h 42mSpirit Airlines
Deal found 4/22$418
This Mytrip deal was found by Cheapflights users on 4/22. 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.
Sat 6/75:40 pmORF - KIN
1 stop19h 49mMultiple Airlines
Sat 6/141:34 pmKIN - ORF
1 stop20h 11mMultiple Airlines
Deal found 4/22$434
This CheapOair deal was found by Cheapflights users on 4/23. 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 5/233:11 pmORF - MBJ
1 stop20h 51mSpirit Airlines
Sun 5/2512:07 pmMBJ - ORF
1 stop25h 09mSpirit Airlines
Deal found 4/23$435
This American Airlines deal was found by Cheapflights users on 4/22. 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 4/296:00 amORF - MBJ
1 stop9h 20mAmerican Airlines
Tue 5/611:15 amMBJ - ORF
1 stop11h 21mAmerican Airlines
Deal found 4/22$463
This Delta deal was found by Cheapflights users on 4/23. 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 5/45:30 amORF - MBJ
1 stop6h 16mDelta
Wed 5/72:23 pmMBJ - ORF
1 stop6h 12mDelta
Deal found 4/23$483
This United Airlines deal was found by Cheapflights users on 4/22. 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.
Wed 6/46:15 amORF - MBJ
1 stop7h 55mUnited Airlines
Mon 6/92:17 pmMBJ - ORF
1 stop8h 27mUnited Airlines
Deal found 4/22$573
This American Airlines deal was found by Cheapflights users on 4/23. 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 7/155:46 amORF - KIN
2 stops15h 11mAmerican Airlines
Tue 7/226:00 amKIN - ORF
2 stops12h 40mAmerican Airlines
Deal found 4/23$577
This Delta deal was found by Cheapflights users on 4/22. 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 5/281:30 pmORF - KIN
1 stop7h 30mDelta
Sun 6/159:00 amKIN - ORF
1 stop7h 10mDelta
Deal found 4/22$585
This Southwest deal was found by Cheapflights users on 4/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/206:20 amORF - MBJ
2 stops7h 05mSouthwest
Sun 10/52:50 pmMBJ - ORF
2 stops17h 25mSouthwest
Deal found 4/22$688
This United Airlines deal was found by Cheapflights users on 4/23. 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.
Tue 7/156:00 amORF - KIN
3 stops56h 53mUnited Airlines
Tue 7/222:54 pmKIN - ORF
3 stops31h 42mUnited Airlines
Deal found 4/23$7,173

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 April 24, 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 6/8

11:35 am-11:02 am

1 stop24h 27m

Montego Bay Sangster Intl

Mon 6/16

10:15 am-12:11 pm

2 stops24h 56m

$405

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

Tue 5/27

12:13 pm-12:29 pm

2 stops25h 16m

Kingston Norman Manley

Sun 6/15

1:34 pm-3:16 pm

1 stop24h 42m

$418

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

Sat 6/7

5:40 pm-12:29 pm

1 stop19h 49m

Kingston Norman Manley

Sat 6/14

1:34 pm-10:45 am

1 stop20h 11m

$434

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Fri 5/23

3:11 pm-11:02 am

1 stop20h 51m

Montego Bay Sangster Intl

Sun 5/25

12:07 pm-2:16 pm

1 stop25h 09m

$435

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Tue 4/29

6:00 am-2:20 pm

1 stop9h 20m

Montego Bay Sangster Intl

Tue 5/6

11:15 am-11:36 pm

1 stop11h 21m

$463

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Sun 5/4

5:30 am-10:46 am

1 stop6h 16m

Montego Bay Sangster Intl

Wed 5/7

2:23 pm-9:35 pm

1 stop6h 12m

$483

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Wed 6/4

6:15 am-1:10 pm

1 stop7h 55m

Montego Bay Sangster Intl

Mon 6/9

2:17 pm-11:44 pm

1 stop8h 27m

$573

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

Tue 7/15

5:46 am-7:57 pm

2 stops15h 11m

Kingston Norman Manley

Tue 7/22

6:00 am-7:40 pm

2 stops12h 40m

$577

NorfolkKingston

ORF - KIN

ORFKIN

Norfolk

Wed 5/28

1:30 pm-8:00 pm

1 stop7h 30m

Kingston Norman Manley

Sun 6/15

9:00 am-5:10 pm

1 stop7h 10m

$585

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Mon 6/23

5:40 am-1:00 pm

1 stop8h 20m

Montego Bay Sangster Intl

Mon 6/30

12:45 pm-11:35 pm

2 stops9h 50m

$882

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 16 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 $569). 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 April 24, 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.

Rainfall in Jamaica by month

Plan your trip to Jamaica by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Jamaica ranges from 1.6 - 7.1 inches per month. October is typically the wettest month, when rainfall can reach 7.1 in. February is typically the driest time to visit Jamaica when rainfall is around 1.6 in.

Temperature in Jamaica by month

Plan your trip to Jamaica by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Jamaica, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 April 24, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and United Airlines from Chesapeake to Jamaica to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Crew

8.6

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Crew

8.6

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Crew

8.6

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,685 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Crew

8.6

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Crew

8.6

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
WestJet
7.2
Good
2,816 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Crew

8.6

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 $569). 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.
Dulles Intl to Luis Munoz Marin Intl flights
Reagan-National to Luis Munoz Marin Intl flights
Dulles Intl to Punta Cana flights
Dulles Intl to Montego Bay flights
Raleigh to Luis Munoz Marin Intl flights
Dulles Intl to Oranjestad flights
Dulles Intl to Saint Thomas Island flights
Reagan-National to Montego Bay flights
Reagan-National to Punta Cana flights
Reagan-National to Nassau flights
Dulles Intl to Nassau flights
Dulles Intl to Providenciales flights
Reagan-National to Saint Thomas Island flights
Richmond to Luis Munoz Marin Intl flights
Reagan-National to Oranjestad flights
Dulles Intl to Simpson Bay flights
Dulles Intl to Santo Domingo flights
Dulles Intl to Castries flights
Dulles Intl to Willemstad flights
Raleigh to Saint Thomas Island flights
Reagan-National to Providenciales flights
Norfolk to Montego Bay flights
Dulles Intl to Bridgetown flights
Reagan-National to Bridgetown flights
Norfolk to Luis Munoz Marin Intl flights
Reagan-National to Simpson Bay flights
Richmond to Montego Bay flights
Dulles Intl to Port of Spain flights
Reagan-National to Willemstad flights
Dulles Intl to George Town flights
Reagan-National to Santo Domingo flights
Reagan-National to Port of Spain flights
Raleigh to Punta Cana flights
Reagan-National to Castries flights
Dulles Intl to Ponce flights
Raleigh to Bridgetown flights
Raleigh to Montego Bay flights
Richmond to Punta Cana flights
Reagan-National to Puerto Plata flights
Reagan-National to George Town flights
Greensboro to Luis Munoz Marin Intl flights
Norfolk to Saint Thomas Island flights
Dulles Intl to St. John's flights
Raleigh to Oranjestad flights
Reagan-National to Christiansted flights
Raleigh to Simpson Bay flights
Raleigh to Christiansted flights
Raleigh to Nassau flights
Dulles Intl to Santiago de los Caballeros flights
Dulles Intl to Kingston flights

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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$167Average$455FlexibilityNo cancel feeOn-time65%
DeltaCheapest$292Average$521FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$367Average$640FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$368Average$714FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$373Average$578FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$383Average$657FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.