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Jamaica

$509+ Cheap flights from Madison (MSN) to Jamaica

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 2/1. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — MBJ
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
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Cheap flight deals from Madison to Jamaica

Keep the following information in mind while searching for Madison to Jamaica flight deals. Data was last updated January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$509
(American Airlines)

Popular in

July

Cheapest in

October

Average price

$641
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.
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From Madison Truax Field to Jamaica
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Highest demand for flights based on searches. 9% potential increase in price ($64 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find 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 January 8, 2026.

This American Airlines deal was found by Cheapflights users on 1/7. 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 2/73:00 pmMSN - MBJ
2 stops19h 33mAmerican Airlines
Sat 2/142:33 pmMBJ - MSN
2 stops19h 44mAmerican Airlines
Deal found 1/7$509
This American Airlines deal was found by Cheapflights users on 1/6. 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.
Sun 2/11:16 pmMSN - MBJ
1 stop25h 11mAmerican Airlines
Sat 2/282:33 pmMBJ - MSN
2 stops20h 35mAmerican Airlines
Deal found 1/6$515
This Delta deal was found by Cheapflights users on 1/8. 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.
Sun 2/225:38 amMSN - MBJ
1 stop6h 15mDelta
Sun 3/14:05 pmMBJ - MSN
1 stop7h 43mDelta
Deal found 1/8$532
This Delta deal was found by Cheapflights users on 1/8. 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 3/56:20 amMSN - MBJ
1 stop7h 20mDelta
Tue 3/102:42 pmMBJ - MSN
1 stop8h 16mDelta
Deal found 1/8$538
This American Airlines deal was found by Cheapflights users on 1/6. 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 2/54:47 pmMSN - MBJ
2 stops19h 11mAmerican Airlines
Sat 2/142:33 pmMBJ - MSN
2 stops19h 44mAmerican Airlines
Deal found 1/6$539
This American Airlines deal was found by Cheapflights users on 1/8. 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.
Sun 2/228:24 pmMSN - MBJ
2 stops16h 09mAmerican Airlines
Sun 3/13:53 pmMBJ - MSN
1 stop19h 43mAmerican Airlines
Deal found 1/8$552
This American Airlines deal was found by Cheapflights users on 1/7. 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 3/265:00 amMSN - MBJ
1 stop7h 11mAmerican Airlines
Thu 4/23:04 pmMBJ - MSN
1 stop19h 32mAmerican Airlines
Deal found 1/7$564
This American Airlines deal was found by Cheapflights users on 1/7. 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 6/127:02 amMSN - MBJ
1 stop6h 11mAmerican Airlines
Thu 6/184:20 pmMBJ - MSN
1 stop7h 38mAmerican Airlines
Deal found 1/7$565

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 January 8, 2026.
Use the filters below to find and compare flights from Madison to Jamaica that are best for you.

Fly from

Madison

Fly to

Jamaica

Route

Depart

Return

Price

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sun 2/1

3:09 pm-11:33 am

2 stops19h 24m

Montego Bay Sangster Intl

Sat 2/28

2:33 pm-10:08 am

2 stops20h 35m

$509

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sat 2/7

3:00 pm-11:33 am

2 stops19h 33m

Montego Bay Sangster Intl

Sat 2/14

2:33 pm-9:17 am

2 stops19h 44m

$509

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sun 2/22

5:38 am-12:53 pm

1 stop6h 15m

Montego Bay Sangster Intl

Sun 3/1

4:05 pm-10:48 pm

1 stop7h 43m

$532

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Thu 3/5

6:20 am-2:40 pm

1 stop7h 20m

Montego Bay Sangster Intl

Tue 3/10

2:42 pm-10:58 pm

1 stop8h 16m

$538

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Thu 2/5

4:47 pm-12:58 pm

2 stops19h 11m

Montego Bay Sangster Intl

Sat 2/14

1:22 pm-11:40 pm

1 stop11h 18m

$539

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Thu 3/5

5:17 pm-1:33 pm

2 stops19h 16m

Montego Bay Sangster Intl

Tue 3/10

12:44 pm-9:04 pm

1 stop8h 20m

$543

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

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, October is the cheapest month in which you can book a flight from Madison to Jamaica (average of $312). Flying from Madison to Jamaica in July is currently the most expensive (average of $637). 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 January 8, 2026.
Get a feel of what it's like to fly with Delta, 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.
Delta
7.9
Good
8,025 reviews

Entertainment

7.8

Boarding

8.1

Food

7.2

Overall

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,025 reviews
Delta
7.9
Good
8,025 reviews

Entertainment

7.8

Boarding

8.1

Food

7.2

Overall

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,139 reviews
Delta
7.9
Good
8,025 reviews

Entertainment

7.8

Boarding

8.1

Food

7.2

Overall

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,095 reviews
Delta
7.9
Good
8,025 reviews

Entertainment

7.8

Boarding

8.1

Food

7.2

Overall

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 $532, American Airlines can have you in Jamaica from Madison in 6h 15m. The distance from Madison to Jamaica is about 1826 mi. This flight may include one or multiple stops.

  • 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, October is the cheapest month in which you can book a flight from Madison to Jamaica (average of $312). Flying from Madison to Jamaica in July is currently the most expensive (average of $637). 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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Alternative routes for Madison to Jamaica

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Madison to Jamaica

Discover the top 3 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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$531Average$540FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$534Average$628FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$563Average$718FlexibilityNo cancel feeOn-time69%

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