What is the cheapest day to fly from Chesapeake to Montego Bay?

Travelers seeking maximum savings on their Chesapeake to Montego Bay flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

What are the most popular airlines that fly from Chesapeake to Montego Bay?

Before booking your flight from Chesapeake to Montego Bay check out the most popular airlines for this route: American Airlines, JetBlue or Delta.

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

Users have found that booking a flight from Chesapeake to Montego Bay at least 26 days early can save you up to 73% on average compared to booking a flight this week. If booking 26 days before your flight isn’t an option for you, users have found flights from Chesapeake to Montego Bay for as little as $444 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $530 for flights departing within the next 3 days.

What is the cheapest month to fly from Chesapeake to Montego Bay?

The best pricing can be found in the month of January. Prices to Montego Bay from Chesapeake average $597. You can even find prices in January for less than $597, as users have found deals to Montego Bay from as low as $403. The month of December appears to be one of the more expensive times to travel to Montego Bay from Chesapeake. Flying in the targeted month can save you up to 35%.

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.

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.

$172+ Flights from Chesapeake to Montego Bay

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights from Chesapeake to Montego Bay 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.

Cheapflights Tip: The best prices from Chesapeake to Montego Bay Sangster Intl are usually found in January or February, booked 25 days in advance, depart on a Saturday or Tuesday and return on a Saturday

Cheap flight deals from Chesapeake to Montego Bay

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 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. 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 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 April 24, 2025.

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

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

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

Sun 5/45:30 amORF - MBJ

1 stop6h 16mDelta

Wed 5/72:23 pmMBJ - ORF

1 stop6h 12mDelta

Deal found 4/23

$483

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

Sat 9/206:20 amORF - MBJ

2 stops7h 05mSouthwest

Sun 10/52:50 pmMBJ - ORF

2 stops17h 25mSouthwest

Deal found 4/22

$688

Best flights from Chesapeake to Montego Bay
Discover carefully curated flight deals from Chesapeake to Montego Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 24, 2025.

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

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

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

Sun 5/45:30 amORF - MBJ

1 stop6h 16mDelta

Wed 5/72:23 pmMBJ - ORF

1 stop6h 12mDelta

Deal found 4/23

$483

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

Mon 6/235:40 amORF - MBJ

1 stop8h 20mSouthwest

Mon 6/3012:45 pmMBJ - ORF

2 stops9h 50mSouthwest

Deal found 4/22

$882

Tue 4/292:50 pmORF - MBJ

3 stops21h 20mAir Canada

Tue 5/612:10 pmMBJ - ORF

3 stops24h 46mAir Canada

Deal found 4/22

$1,774

Sat 4/265:30 amORF - MBJ

2 stops13h 53mWestJet

Sat 5/37:25 pmMBJ - ORF

2 stops15h 17mWestJet

Deal found 4/22

$4,118

Last-minute flights from Chesapeake to Montego Bay
Discover last-minute flight deals from Chesapeake to Montego Bay. Data last updated April 24, 2025 and is based on user searches.

Fri 4/2512:22 pmORF - MBJ

2 stops29h 33mWestJet

Sat 5/37:25 pmMBJ - ORF

2 stops26h 20mWestJet

Deal found 4/22

$1,831

Sat 4/266:30 amORF - MBJ

1 stop7h 19mUnited Airlines

Fri 5/212:52 pmMBJ - ORF

2 stops9h 54mUnited Airlines

Deal found 4/22

$590

Sat 4/266:00 amORF - MBJ

1 stop9h 00mSouthwest

Mon 4/283:35 pmMBJ - ORF

1 stop6h 20mSouthwest

Deal found 4/22

$703

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

Tue 4/296:17 amORF - MBJ

2 stops9h 53mUnited Airlines

Tue 5/62:40 pmMBJ - ORF

2 stops17h 41mUnited Airlines

Deal found 4/22

$495

Tue 4/292:50 pmORF - MBJ

3 stops21h 20mAir Canada

Tue 5/612:10 pmMBJ - ORF

3 stops24h 46mAir Canada

Deal found 4/22

$1,774

Thu 5/18:56 pmORF - MBJ

2 stops14h 59mSpirit Airlines

Mon 5/512:00 pmMBJ - ORF

2 stops27h 11mSpirit Airlines

Deal found 4/23

$639

Thu 5/111:21 amORF - MBJ

2 stops24h 34mMultiple Airlines

Mon 5/512:00 pmMBJ - ORF

1 stop11h 19mMultiple Airlines

Deal found 4/23

$643

Sun 5/46:00 amORF - MBJ

1 stop5h 55mMultiple Airlines

Wed 5/712:07 pmMBJ - ORF

2 stops21h 24mMultiple Airlines

Deal found 4/23

$460

Sun 5/45:30 amORF - MBJ

1 stop6h 16mDelta

Wed 5/72:23 pmMBJ - ORF

1 stop6h 12mDelta

Deal found 4/23

$483

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

One-way flights from Chesapeake to Montego Bay
Search for one-way flight options from Chesapeake to Montego Bay. Find affordable one-way fares based on user searches. Data last updated April 24, 2025.

Thu 6/194:11 pmORF - MBJ

1 stop17h 59mSpirit Airlines

Deal found 4/22

$172

Sun 5/411:21 amORF - MBJ

2 stops24h 34mMultiple Airlines

Deal found 4/23

$211

Sun 5/46:55 amORF - MBJ

1 stop9h 36mDelta

Deal found 4/23

$218

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chesapeake to Montego Bay that are best for you.

Fly from

Fly to

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

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

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

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Tue 4/29

2:50 pm-11:10 am

3 stops21h 20m

Montego Bay Sangster Intl

Tue 5/6

12:10 pm-1:56 pm

3 stops24h 46m

$1,774

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Sat 4/26

5:30 am-6:23 pm

2 stops13h 53m

Montego Bay Sangster Intl

Sat 5/3

7:25 pm-11:42 am

2 stops15h 17m

$4,118

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Thu 6/19

4:11 pm-9:10 am

1 stop17h 59m

$172

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Sun 5/4

11:21 am-10:55 am

2 stops24h 34m

$211

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 11 results

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?

To ensure you get the cheapest price possible for a flight from Chesapeake to Montego Bay, you should look to book at least 25 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, January is the cheapest month in which you can book a flight from Chesapeake to Montego Bay (average of $403). Flying from Chesapeake to Montego Bay 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 MBJ?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chesapeake to Montego Bay as you normally would.

Rainfall in Montego Bay by month

In terms of precipitation, rainfall in Montego Bay 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 Montego Bay when rainfall is around 1.6 in.

Temperature in Montego Bay by month

If weather is an important factor for your trip to Montego Bay, 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 Montego Bay

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

4,286 reviews

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

4,286 reviews

Southwest

8.0

Very good

4,286 reviews

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

4,286 reviews

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

4,286 reviews

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

4,286 reviews

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

4,286 reviews

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

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.
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, January is the cheapest month in which you can book a flight from Chesapeake to Montego Bay (average of $403). Flying from Chesapeake to Montego Bay 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

Whitehouse

Lucea

Browse thousands of different options on Cheapflights for your next trip

Top 6 airlines flying from Chesapeake to Montego Bay

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$167	Average$419	FlexibilityNo cancel fee	On-time65%
American Airlines	Cheapest$367	Average$567	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$368	Average$714	FlexibilityNo cancel fee	On-time63%
JetBlue	Cheapest$373	Average$571	FlexibilityNo cancel fee	On-time62%
Delta	Cheapest$374	Average$516	FlexibilityNo cancel fee	On-timeN/A
United Airlines	Cheapest$383	Average$657	FlexibilityNo cancel fee	On-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.

$172+ 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 6/19. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chesapeake to Montego Bay with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Chesapeake to Montego Bay Sangster Intl are usually found in January or February, booked 25 days in advance, depart on a Saturday or Tuesday and return on a Saturday

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 April 24, 2025.

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Chesapeake to Montego Bay

Cheapest flights from Chesapeake to Montego BayExplore 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 April 24, 2025.

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 April 24, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chesapeake to Montego Bay that are best for you.

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.

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 April 18, 2025.

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

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 April 24, 2025.

Rainfall in Montego Bay by month

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

Temperature in Montego Bay by month

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

Reviews of airlines servicing Montego Bay

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.

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?

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

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

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

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

Traveling to a place near Chesapeake?

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 Montego Bay

See prices for flight routes from nearby airports that may be better suited for you.

Top 6 airlines flying from Chesapeake to Montego Bay

100% Free

Book with Flexibility

Travel Smart

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 April 24, 2025.