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Jamaica

$158+ Cheap flights from Madison (MSN) to Jamaica

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 8/16. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — MBJ
Jun 14 — Jun 211
Sun 6/14
Sun 6/21
1 adult, Economy
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Cheap flight deals from Madison to Jamaica

Cheapest flights from Madison to Jamaica
Explore the most affordable flight options available from Madison to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 15, 2026.

This American Airlines deal was found by Cheapflights users on 5/13. 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 9/56:52 pm
MSN
-
MBJ
2 stops18h 42m
American Airlines
Sat 9/121:05 pm
MBJ
-
MSN
2 stops11h 16m
American Airlines
Deal found 5/13$357
This American Airlines deal was found by Cheapflights users on 5/13. 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 5/13$358
This American Airlines deal was found by Cheapflights users on 5/11. 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 9/96:23 pm
MSN
-
MBJ
2 stops18h 22m
American Airlines
Sun 9/133:15 pm
MBJ
-
MSN
2 stops20h 46m
American Airlines
Deal found 5/11$449
This American Airlines deal was found by Cheapflights users on 5/11. 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 5/148:24 pm
MSN
-
MBJ
1 stop15h 49m
American Airlines
Thu 5/2112:31 pm
MBJ
-
MSN
1 stop11h 28m
American Airlines
Deal found 5/11$469
This American Airlines deal was found by Cheapflights users on 5/11. 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 7/146:00 am
MSN
-
MBJ
1 stop8h 02m
American Airlines
Tue 7/2812:47 pm
MBJ
-
MSN
1 stop10h 06m
American Airlines
Deal found 5/11$477
This Delta deal was found by Cheapflights users on 5/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:43 am
MSN
-
MBJ
1 stop9h 51m
Delta
Thu 5/214:59 pm
MBJ
-
MSN
2 stops15h 50m
Delta
Deal found 5/10$478
This American Airlines deal was found by Cheapflights users on 5/14. 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.
Mon 6/295:52 pm
MSN
-
MBJ
2 stops17h 27m
American Airlines
Fri 7/312:25 pm
MBJ
-
MSN
1 stop11h 28m
American Airlines
Deal found 5/14$482
This United Airlines deal was found by Cheapflights users on 5/12. 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.
Wed 5/275:00 am
MSN
-
MBJ
2 stops10h 10m
United Airlines
Sat 5/304:33 pm
MBJ
-
MSN
2 stops15h 33m
United Airlines
Deal found 5/12$484

Find flight deals from Madison to Jamaica

Keep the following information in mind while searching for Madison to Jamaica flight deals. Data was last updated May 15, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$357
(American Airlines)

One-way from

$158
(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.
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Provider most trusted by Cheapflights users for Madison Truax Field-Montego Bay Sangster Intl flights.
Search Deals
From Madison Truax Field to Jamaica
Search Deals
One-way flight from Madison Truax Field to Jamaica
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 Jamaica 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 15, 2026.
Use the filters below to find and compare flights from Madison to Jamaica 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

5:47 pm-11:19 am

2 stops17h 32m

Montego Bay Sangster Intl

Sat 9/12

1:05 pm-9:02 am

2 stops19h 57m

$357
Quickest round-trip

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sun 6/28

5:52 pm-11:19 am

2 stops17h 27m

Montego Bay Sangster Intl

Fri 7/3

12:25 pm-11:53 pm

1 stop11h 28m

$482

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Tue 7/14

5:52 pm-11:47 am

2 stops17h 55m

Montego Bay Sangster Intl

Tue 7/28

12:25 pm-11:42 pm

1 stop11h 17m

$482

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Mon 6/29

5:52 pm-11:19 am

2 stops17h 27m

Montego Bay Sangster Intl

Fri 7/3

12:25 pm-11:53 pm

1 stop11h 28m

$482
Cheapest one-way

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sun 8/16

4:20 pm-11:42 am

2 stops19h 22m

$158
Quickest one-way

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Fri 9/4

7:03 am-4:13 pm

1 stop9h 10m

$280

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Fri 6/26

8:10 am-12:50 pm

1 stop28h 40m

$388

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Wed 7/29

6:29 am-11:43 am

1 stop29h 14m

$394

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Thu 6/25

8:10 am-3:10 pm

2 stops31h 00m

$446

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Fri 9/4

2:50 pm-1:30 pm

3 stops22h 40m

$1,820

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/11

Showing 1-10 of 11 resultsSorted by cheapest first
1
2

Best time to book a flight from Madison to Jamaica

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

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

Currently, February is the cheapest month in which you can book a flight from Madison to Jamaica (average of $213). Flying from Madison to Jamaica in November is currently the most expensive (average of $689). 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 Jamaica

Get insights into the airlines that provide service to Jamaica. 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 Jamaica. Reviews last updated May 15, 2026.
Get a feel of what it's like to fly with United Airlines and American Airlines from Madison to Jamaica by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,717 reviews

Crew

8.1

Overall

7.4

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Food

6.6

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
9,717 reviews
United Airlines
7.4
Good
9,717 reviews

Crew

8.1

Overall

7.4

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Food

6.6

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
11,662 reviews
United Airlines
7.4
Good
9,717 reviews

Crew

8.1

Overall

7.4

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Food

6.6

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 Jamaica. 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 from for flights from Madison to Jamaica?

    If you book a flight to Jamaica from Madison, you will be flying from Truax Field, which is the city’s only airport. Madison Truax Field (MSN) is located 5.4 mi from the center of Madison.

  • How long is the flight from Madison to Jamaica?

    For as low as $357, American Airlines can have you in Jamaica from Madison in 17h 32m. The distance from Madison to Jamaica is about 1826 mi.

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

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

  • How can I find direct flights from Madison to Jamaica?

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

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

    Yes. Cheapflights offers flight deals from Madison to Jamaica 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 Jamaica?

    Currently, February is the cheapest month in which you can book a flight from Madison to Jamaica (average of $213). Flying from Madison to Jamaica in November is currently the most expensive (average of $689). 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

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from Madison to Jamaica

Discover the top 2 airlines that operate flights from Madison to Jamaica. 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 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$390Average$689FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$518Average$632FlexibilityNo cancel feeOn-time71%

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