How long is the flight from Chesapeake to Montego Bay?

A quick flight from Chesapeake to Montego Bay can take about 6h 36m. American Airlines provides one of the quickest options available for as low as $339. 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.

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.

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.

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).

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 16 days early can save you up to 99% on average compared to booking a flight this week. If booking 16 days before your flight isn’t an option for you, users have found flights from Chesapeake to Montego Bay for as little as $450 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 $450 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 $604. You can even find prices in January for less than $604, 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 48%.

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.

$136+ Flights from Chesapeake to Montego Bay

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

Airfare is below average for this route at the moment. Chesapeake to Montego Bay flights typically cost between $463 and $663 in December. The cheapest round-trip price found within the last 3 days was $319 on American Airlines (Dec 11-Dec 16).

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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

Cheap flight deals from Chesapeake to Montego Bay

Round-trip from	$319 (American Airlines)
One-way from	$136 (American Airlines)
Popular in	December
Cheapest in	January
Average price	$546

From Chesapeake to Montego Bay Sangster Intl

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One-way flight from Chesapeake to Montego Bay Sangster Intl

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Highest demand for flights based on searches. 9% potential increase in price ($65 potential increase over avg. RT price).

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Cheapest flight prices on average. 4% potential price decrease ($27 potential savings vs. average RT price).

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Average for round-trip flights in September 2025

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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 September 11, 2025.

Thu 12/117:29 pmORF - MBJ

1 stop14h 44mAmerican Airlines

Tue 12/1611:13 amMBJ - ORF

1 stop13h 15mAmerican Airlines

Deal found 9/10

$319

Thu 10/307:24 pmORF - MBJ

2 stops17h 36mAmerican Airlines

Tue 12/91:45 pmMBJ - ORF

2 stops9h 30mAmerican Airlines

Deal found 9/10

$323

Sun 10/55:24 amORF - MBJ

1 stop6h 36mSpirit Airlines

Sat 10/1112:09 pmMBJ - ORF

1 stop9h 37mSpirit Airlines

Deal found 9/10

$339

Sun 10/128:04 pmORF - MBJ

1 stop14h 09mAmerican Airlines

Thu 10/163:20 pmMBJ - ORF

1 stop6h 56mAmerican Airlines

Deal found 9/10

$344

Fri 9/267:27 pmORF - MBJ

1 stop18h 16mAmerican Airlines

Fri 10/33:54 pmMBJ - ORF

1 stop6h 21mAmerican Airlines

Deal found 9/10

$350

Sun 10/195:24 amORF - MBJ

1 stop6h 36mSpirit Airlines

Sat 10/2512:09 pmMBJ - ORF

1 stop9h 37mSpirit Airlines

Deal found 9/9

$363

Sat 10/45:20 amORF - MBJ

1 stop6h 45mSpirit Airlines

Fri 10/1012:09 pmMBJ - ORF

1 stop9h 37mSpirit Airlines

Deal found 9/10

$364

Sun 10/57:04 pmORF - MBJ

2 stops15h 09mAmerican Airlines

Sat 10/1112:27 pmMBJ - ORF

1 stop9h 49mAmerican Airlines

Deal found 9/10

$373

Sat 10/116:26 amORF - MBJ

1 stop8h 34mAmerican Airlines

Sat 10/182:05 pmMBJ - ORF

1 stop18h 23mAmerican Airlines

Deal found 9/11

$375

Sun 10/199:47 amORF - MBJ

2 stops26h 13mMultiple Airlines

Sat 10/2512:09 pmMBJ - ORF

1 stop9h 37mMultiple Airlines

Deal found 9/9

$382

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 September 11, 2025.

Thu 12/117:29 pmORF - MBJ

1 stop14h 44mAmerican Airlines

Tue 12/1611:13 amMBJ - ORF

1 stop13h 15mAmerican Airlines

Deal found 9/10

$319

Sun 10/55:24 amORF - MBJ

1 stop6h 36mSpirit Airlines

Sat 10/1112:09 pmMBJ - ORF

1 stop9h 37mSpirit Airlines

Deal found 9/10

$339

Sat 10/111:22 pmORF - MBJ

2 stops22h 38mMultiple Airlines

Sat 10/1812:09 pmMBJ - ORF

1 stop9h 37mMultiple Airlines

Deal found 9/11

$430

Mon 10/278:05 pmORF - MBJ

2 stops16h 02mUnited Airlines

Mon 11/33:36 pmMBJ - ORF

1 stop7h 51mUnited Airlines

Deal found 9/11

$484

Fri 9/267:27 pmORF - MBJ

2 stops17h 38mAmerican Airlines

Fri 10/311:35 amMBJ - ORF

2 stops10h 02mAmerican Airlines

Deal found 9/10

$348

Thu 11/206:15 amORF - MBJ

1 stop8h 38mAmerican Airlines

Tue 11/2511:17 amMBJ - ORF

1 stop12h 58mAmerican Airlines

Deal found 9/10

$411

Thu 12/118:09 pmORF - MBJ

1 stop15h 56mSpirit Airlines

Tue 12/161:12 pmMBJ - ORF

1 stop9h 31mSpirit Airlines

Deal found 9/11

$459

Fri 10/105:38 pmORF - MBJ

3 stops42h 22mSpirit Airlines

Fri 10/1712:09 pmMBJ - ORF

1 stop9h 37mSpirit Airlines

Deal found 9/10

$478

Sat 12/139:56 amORF - MBJ

1 stop6h 25mAmerican Airlines

Thu 12/182:19 pmMBJ - ORF

1 stop10h 40mAmerican Airlines

Deal found 9/9

$436

Thu 12/117:29 pmORF - MBJ

1 stop14h 44mAmerican Airlines

Mon 12/1511:13 amMBJ - ORF

2 stops10h 57mAmerican Airlines

Deal found 9/10

$469

Last-minute flights from Chesapeake to Montego Bay
Discover last-minute flight deals from Chesapeake to Montego Bay. Data last updated September 11, 2025 and is based on user searches.

Fri 9/267:27 pmORF - MBJ

1 stop18h 16mAmerican Airlines

Fri 10/33:54 pmMBJ - ORF

1 stop6h 21mAmerican Airlines

Deal found 9/10

$350

Sat 10/45:20 amORF - MBJ

1 stop6h 45mSpirit Airlines

Fri 10/1012:09 pmMBJ - ORF

1 stop9h 37mSpirit Airlines

Deal found 9/10

$364

Sun 10/55:24 amORF - MBJ

1 stop6h 36mSpirit Airlines

Sat 10/1112:09 pmMBJ - ORF

1 stop9h 37mSpirit Airlines

Deal found 9/10

$339

Sun 10/57:04 pmORF - MBJ

2 stops15h 09mAmerican Airlines

Sat 10/1112:27 pmMBJ - ORF

1 stop9h 49mAmerican Airlines

Deal found 9/10

$373

Sat 10/116:26 amORF - MBJ

1 stop8h 34mAmerican Airlines

Sat 10/182:05 pmMBJ - ORF

1 stop18h 23mAmerican Airlines

Deal found 9/11

$375

Sun 10/128:04 pmORF - MBJ

1 stop14h 09mAmerican Airlines

Thu 10/163:20 pmMBJ - ORF

1 stop6h 56mAmerican Airlines

Deal found 9/10

$344

Sun 10/195:24 amORF - MBJ

1 stop6h 36mSpirit Airlines

Sat 10/2512:09 pmMBJ - ORF

1 stop9h 37mSpirit Airlines

Deal found 9/9

$363

Sun 10/199:47 amORF - MBJ

2 stops26h 13mMultiple Airlines

Sat 10/2512:09 pmMBJ - ORF

1 stop9h 37mMultiple Airlines

Deal found 9/9

$382

Thu 10/307:24 pmORF - MBJ

2 stops17h 36mAmerican Airlines

Tue 12/91:45 pmMBJ - ORF

2 stops9h 30mAmerican Airlines

Deal found 9/10

$323

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 September 11, 2025.

Thu 10/307:24 pmORF - MBJ

2 stops17h 36mAmerican Airlines

Deal found 9/10

$136

Thu 10/305:24 amORF - MBJ

1 stop6h 36mSpirit Airlines

Deal found 9/11

$159

Sat 11/15:00 pmORF - MBJ

2 stops18h 12mAmerican Airlines

Deal found 9/10

$167

Thu 10/301:06 pmORF - MBJ

3 stops22h 54mMultiple Airlines

Deal found 9/10

$228

Fri 9/195:38 pmORF - MBJ

2 stops18h 27mSpirit Airlines

Deal found 9/9

$235

Thu 9/185:12 pmORF - MBJ

3 stops42h 05mMultiple Airlines

Deal found 9/9

$246

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

Thu 12/11

7:29 pm-10:13 am

1 stop14h 44m

Montego Bay Sangster Intl

Tue 12/16

11:13 am-12:28 am

1 stop13h 15m

$319

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Sun 10/5

5:24 am-11:00 am

1 stop6h 36m

Montego Bay Sangster Intl

Sat 10/11

12:09 pm-10:46 pm

1 stop9h 37m

$339

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Fri 9/26

7:27 pm-12:05 pm

2 stops17h 38m

Montego Bay Sangster Intl

Fri 10/3

11:35 am-10:37 pm

2 stops10h 02m

$348

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Thu 11/20

6:15 am-2:53 pm

1 stop8h 38m

Montego Bay Sangster Intl

Tue 11/25

11:17 am-12:15 am

1 stop12h 58m

$411

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Sat 10/11

1:22 pm-11:00 am

2 stops22h 38m

Montego Bay Sangster Intl

Sat 10/18

12:09 pm-10:46 pm

1 stop9h 37m

$430

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Sat 12/13

9:56 am-4:21 pm

1 stop6h 25m

Montego Bay Sangster Intl

Thu 12/18

2:19 pm-12:59 am

1 stop10h 40m

$436

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Thu 12/11

8:09 pm-12:05 pm

1 stop15h 56m

Montego Bay Sangster Intl

Tue 12/16

1:12 pm-10:43 pm

1 stop9h 31m

$459

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Thu 12/11

7:29 pm-10:13 am

1 stop14h 44m

Montego Bay Sangster Intl

Mon 12/15

11:13 am-10:10 pm

2 stops10h 57m

$469

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Fri 10/10

5:38 pm-11:00 am

3 stops42h 22m

Montego Bay Sangster Intl

Fri 10/17

12:09 pm-10:46 pm

1 stop9h 37m

$478

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Mon 10/27

8:05 pm-11:07 am

2 stops16h 02m

Montego Bay Sangster Intl

Mon 11/3

3:36 pm-11:27 pm

1 stop7h 51m

$484

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 15 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 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, 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 $560). 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.

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

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

4,248 reviews

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

Southwest

8.0

Very good

4,248 reviews

Southwest

8.0

Very good

4,248 reviews

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

Delta

8.0

Very good

7,960 reviews

Southwest

8.0

Very good

4,248 reviews

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

United Airlines

7.4

Good

8,937 reviews

Southwest

8.0

Very good

4,248 reviews

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

American Airlines

7.2

Good

10,000 reviews

Southwest

8.0

Very good

4,248 reviews

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

Spirit Airlines

6.3

Okay

8,023 reviews

Southwest

8.0

Very good

4,248 reviews

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

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 6h 36m. American Airlines provides one of the quickest options available for as low as $339. 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, 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 $560). 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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Top 6 airlines flying from Chesapeake to Montego Bay

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$258	Average$415	FlexibilityNo cancel fee	On-time65%
United Airlines	Cheapest$359	Average$599	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$367	Average$638	FlexibilityNo cancel fee	On-time71%
Delta	Cheapest$374	Average$535	FlexibilityNo cancel fee	On-timeN/A
JetBlue	Cheapest$415	Average$593	FlexibilityNo cancel fee	On-time62%
Southwest	Cheapest$471	Average$728	FlexibilityNo cancel fee	On-time63%

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$136+ 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 10/30. 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 March, booked 15 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 September 11, 2025.

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 September 11, 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 September 11, 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 August 29, 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 September 11, 2025.

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

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?

How long is the flight from Chesapeake to Montego Bay?

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 Montego Bay?

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Alternative routes for Chesapeake to Montego Bay

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Top 6 airlines flying from Chesapeake to Montego Bay

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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 September 11, 2025.