Montego Bay

$156+ Cheap flights from Chesapeake, VA to Montego Bay (MBJ)

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
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Cheapflights Tip: The best prices from Chesapeake to Montego Bay Sangster Intl are usually found in January or March, booked 15 days in advance, depart on a Saturday or Tuesday and return on a Saturday

Find flight deals from Chesapeake to Montego Bay

Cheapest flights from Chesapeake to Montego Bay
Explore the most affordable flight options available from Chesapeake to Montego Bay. 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 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 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 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 04mMultiple Airlines
Wed 1/281:12 pmMBJ - ORF
2 stops23h 03mMultiple Airlines
Deal found 10/29$434
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
Thu 1/291:12 pmMBJ - ORF
2 stops30h 25mSpirit Airlines
Deal found 10/29$435

Cheap flight deals from Chesapeake to Montego Bay

Keep the following information in mind while searching for Chesapeake to Montego Bay 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.
Provider most trusted by Cheapflights users for Norfolk-Montego Bay Sangster Intl flights.
From Chesapeake to Montego Bay Sangster Intl
One-way flight from Chesapeake to Montego Bay Sangster Intl
Highest demand for flights based on searches. 9% potential increase in price ($61 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($25 potential savings vs. average RT price).
Average for round-trip flights in October 2025

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chesapeake to Montego Bay 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 Montego Bay that are best for you.

Fly from

Chesapeake

Fly to

Montego Bay

Route

Depart

Return

Price

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

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

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Thu 11/27

9:56 am-10:17 am

2 stops24h 21m

Montego Bay Sangster Intl

Wed 12/3

4:23 pm-11:59 pm

1 stop7h 36m

$424

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Fri 12/12

8:10 pm-4:12 pm

1 stop20h 02m

Montego Bay Sangster Intl

Fri 12/19

5:14 pm-11:41 pm

1 stop6h 27m

$425

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Thu 12/11

8:38 am-11:14 am

2 stops26h 36m

Montego Bay Sangster Intl

Sun 12/14

1:05 pm-7:16 pm

1 stop6h 11m

$439

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Fri 12/12

7:29 pm-10:13 am

1 stop14h 44m

Montego Bay Sangster Intl

Thu 12/18

3:14 pm-12:07 am

1 stop8h 53m

$455

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Mon 11/10

7:53 pm-12:02 pm

1 stop16h 09m

$156

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Fri 11/7

7:53 pm-12:02 pm

1 stop16h 09m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 16 results
1
2

Best time to book a flight from Chesapeake to Montego Bay

Have a flexible travel schedule? Discover the best time to fly to Montego Bay 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 Montego Bay

How far ahead should I book a flight from Chesapeake to Montego Bay?

Use this chart to determine the optimal time to book a round-trip flight from Chesapeake to Montego Bay. Price data was last updated on October 24, 2025.

To ensure you get the cheapest price possible for a flight from Chesapeake to Montego Bay, you should look to book at least 15 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chesapeake to Montego Bay?

Currently, October is the cheapest month in which you can book a flight from Chesapeake to Montego Bay (average of $157). Flying from Chesapeake to Montego Bay 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 MBJ?

Find hourly flight availability from Chesapeake to Montego Bay. 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.

It’s optimal to fly from Chesapeake to Montego Bay in the afternoon. By choosing this option you can save up to 23% on the cost of your flight, compared to a flight in the morning.

How much does it cost to fly round-trip from Chesapeake to Montego Bay?

Reviews of airlines servicing Montego Bay

Get insights into the airlines that provide service to Montego Bay. 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 Montego Bay. Reviews last updated October 29, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Chesapeake to Montego Bay to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

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

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

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

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

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

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

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

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

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

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

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 Montego Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • What airport do you fly into for flights to Montego Bay from Chesapeake?

    Montego Bay Sangster Intl (MBJ), located 2.3 mi from the city center, is the airport you fly into when you book flights from Chesapeake to Montego Bay. 6 airlines have flights to Sangster Intl from Chesapeake on a regular basis. Booking flights from Chesapeake to Montego Bay Sangster Intl should not be difficult; the airport handles an average of 0 inbound flights from Chesapeake per day.

  • How long is the flight from Chesapeake to Montego Bay?

    A quick flight from Chesapeake to Montego Bay can take about 15h 56m. Spirit Airlines provides one of the quickest options available for as low as $387. Chesapeake and Montego Bay are separated by a distance of 1274 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from Chesapeake to Montego Bay that include hotel bookings?

    Yes. In addition to deals on Chesapeake to Montego Bay flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chesapeake to Montego Bay?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chesapeake to Montego Bay.

  • Can I find deals for business class flights from Chesapeake to Montego Bay?

    Yes. Cheapflights offers flight deals from Chesapeake to Montego Bay 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 Montego Bay?

    Currently, October is the cheapest month in which you can book a flight from Chesapeake to Montego Bay (average of $157). Flying from Chesapeake to Montego Bay 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

Traveling to a place near Montego Bay?

Book flights to Montego Bay if you plan to visit one of these locations
Whitehouse
Lucea

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Top 6 airlines flying from Chesapeake to Montego Bay

Discover the top 6 airlines that operate flights from Chesapeake to Montego Bay. 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$411FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$357Average$604FlexibilityNo cancel feeOn-time69%
DeltaCheapest$367Average$539FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$388Average$667FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$389Average$571FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$471Average$734FlexibilityNo cancel feeOn-time63%

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