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Montego Bay

$135+ 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 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
Fri 3/6
Fri 3/13
1 adult, Economy
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Cheap 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 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

Find 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 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.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-Montego Bay Sangster Intl flights.
Search Deals
From Chesapeake to Montego Bay Sangster Intl
Search Deals
One-way flight from Chesapeake to Montego Bay Sangster Intl
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($15 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 February 2026
Search Deals

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 February 4, 2026.
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

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

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Fri 2/27

7:31 pm-12:02 pm

1 stop16h 31m

$135

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Thu 2/26

7:31 pm-12:02 pm

1 stop16h 31m

$152

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/1

Showing 1-10 of 15 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 January 30, 2026.

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 $155). Flying from Chesapeake to Montego Bay 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 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 February 4, 2026.
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.
Southwest
8.0
Very good
4,272 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

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
8.0
Very good
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

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
8,138 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

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
9,236 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

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
11,216 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

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
8,407 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

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 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 18m. Spirit Airlines provides one of the quickest options available for as low as $248. Chesapeake and Montego Bay are separated by a distance of 1274 mi.

  • What are the cheapest airlines to fly from Chesapeake to Montego Bay one-way?

    The cheapest airlines for a one-way flight from Chesapeake to Montego Bay are Spirit Airlines ($106), American Airlines ($198), and Delta ($202).

  • 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 $155). Flying from Chesapeake to Montego Bay 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

Traveling to a place near Montego Bay?

Book flights to Montego Bay if you plan to visit one of these locations
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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 February 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$146Average$525FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$148Average$403FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$269Average$603FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$331Average$546FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$370Average$615FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$452Average$713FlexibilityNo cancel feeOn-time63%

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