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Montego Bay

$357+ Cheap flights from Madison (MSN) to Montego Bay (MBJ)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — MBJ
Jun 27 — Jul 41
Sat 6/27
Sat 7/4
1 adult, Economy
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Cheap flight deals from Madison to Montego Bay

Cheapest flights from Madison to Montego Bay
Explore the most affordable flight options available from Madison to Montego Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 28, 2026.

This American Airlines deal was found by Cheapflights users on 5/27. 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.
Sat 9/56:53 pm
MSN
-
MBJ
2 stops18h 41m
American Airlines
Sat 9/125:16 pm
MBJ
-
MSN
2 stops19h 10m
American Airlines
Deal found 5/27$357
This American Airlines deal was found by Cheapflights users on 5/27. 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.
Fri 12/43:55 pm
MSN
-
MBJ
1 stop17h 17m
American Airlines
Thu 12/102:30 pm
MBJ
-
MSN
1 stop19h 49m
American Airlines
Deal found 5/27$358
This American Airlines deal was found by Cheapflights users on 5/26. 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.
Wed 8/194:26 pm
MSN
-
MBJ
2 stops19h 16m
American Airlines
Sun 8/235:08 pm
MBJ
-
MSN
2 stops17h 32m
American Airlines
Deal found 5/26$367
This American Airlines deal was found by Cheapflights users on 5/27. 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 9/104:21 pm
MSN
-
MBJ
2 stops18h 41m
American Airlines
Sun 9/135:16 pm
MBJ
-
MSN
2 stops20h 17m
American Airlines
Deal found 5/27$376
This American Airlines deal was found by Cheapflights users on 5/27. 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.
Wed 9/92:48 pm
MSN
-
MBJ
2 stops20h 14m
American Airlines
Sun 9/135:16 pm
MBJ
-
MSN
2 stops20h 17m
American Airlines
Deal found 5/27$381
This United Airlines deal was found by Cheapflights users on 5/23. 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.
Thu 10/298:25 pm
MSN
-
MBJ
1 stop16h 21m
United Airlines
Mon 11/22:48 pm
MBJ
-
MSN
1 stop10h 24m
United Airlines
Deal found 5/23$395
This United Airlines deal was found by Cheapflights users on 5/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:45 am
MSN
-
MBJ
1 stop6h 01m
United Airlines
Wed 12/92:48 pm
MBJ
-
MSN
1 stop10h 24m
United Airlines
Deal found 5/26$472

Find flight deals from Madison to Montego Bay

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Montego Bay (MBJ). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$357
(American Airlines)

Popular in

September

Cheapest in

March

Average price

$681
Provider with most accurate pricing for Madison Truax Field-Montego Bay Sangster Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-Montego Bay Sangster Intl flights.
Search Deals
From Madison Truax Field 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 ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison 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 May 28, 2026.
Use the filters below to find and compare flights from Madison to Montego Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sat 9/5

5:46 pm-11:34 am

2 stops17h 48m

Montego Bay Sangster Intl

Sat 9/12

5:16 pm-12:10 pm

2 stops18h 54m

$357

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Thu 10/29

3:47 pm-9:05 am

2 stops17h 18m

Montego Bay Sangster Intl

Mon 11/2

2:19 pm-9:21 am

1 stop20h 02m

$362

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Wed 9/9

2:48 pm-11:02 am

2 stops20h 14m

Montego Bay Sangster Intl

Sun 9/13

5:16 pm-1:33 pm

2 stops20h 17m

$381
Quickest round-trip

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sat 7/11

5:00 am-12:50 pm

1 stop7h 50m

Montego Bay Sangster Intl

Sat 7/18

1:52 pm-8:57 pm

1 stop7h 05m

$604

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Thu 6/11

8:05 am-3:10 pm

2 stops31h 05m

Montego Bay Sangster Intl

Fri 6/19

12:52 pm-8:39 am

2 stops19h 47m

$618

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Wed 6/24

6:30 am-3:10 pm

2 stops8h 40m

Montego Bay Sangster Intl

Wed 7/1

2:40 pm-11:49 am

2 stops21h 09m

$672

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Wed 6/24

6:46 am-4:16 pm

1 stop9h 30m

Montego Bay Sangster Intl

Wed 7/1

12:48 pm-11:06 pm

1 stop10h 18m

$723

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/26

Sorted by cheapest first

Compare providers for flights from Madison to Montego Bay

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Madison to Montego Bay in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Madison-Montego Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-Montego Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Madison-Montego Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Madison-Montego Bay flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Madison-Montego Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Madison to Montego Bay

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

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

Currently, March is the cheapest month in which you can book a flight from Madison to Montego Bay (average of $564). Flying from Madison to Montego Bay in September is currently the most expensive (average of $937). 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.

How much does it cost to fly round-trip from Madison 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 May 28, 2026.
Read reviews from past customers who have flown United Airlines and American Airlines from Madison to Montego Bay. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,751 reviews

Comfort

7.3

Overall

7.4

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
United Airlines
7.4
Good
9,751 reviews
United Airlines
7.4
Good
9,751 reviews

Comfort

7.3

Overall

7.4

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
American Airlines
7.1
Good
11,639 reviews
United Airlines
7.4
Good
9,751 reviews

Comfort

7.3

Overall

7.4

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.

Related info for your journey

Find useful and relevant information for your journey from Madison to Montego Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    For as low as $357, American Airlines can have you in Montego Bay from Madison in 17h 48m. The distance between Madison and Montego Bay is about 1826 mi.

  • What are the cheapest airlines flying from Madison to Montego Bay round-trip?

    Cheapflights users have booked flights from Madison to Montego Bay round-trip from $390. Another airline that can offer you cheap pricing is American Airlines. You may be able to fly from Madison to Montego Bay for 42% less than the average price by searching for these airlines.

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

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

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

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

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

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

    Currently, March is the cheapest month in which you can book a flight from Madison to Montego Bay (average of $564). Flying from Madison to Montego Bay in September is currently the most expensive (average of $937). 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
Lucea

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Top 2 airlines flying from Madison to Montego Bay

Discover the top 2 airlines that operate flights from Madison 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 May 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$390Average$689FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$518Average$632FlexibilityNo cancel feeOn-time71%

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