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Jamaica

$193+ 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 7/12. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — MBJ
Mar 28 — Apr 41
Sat 3/28
Sat 4/4
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 February 26, 2026.

This American Airlines deal was found by Cheapflights users on 2/22. 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 5/98:24 pm
MSN
-
MBJ
1 stop15h 49m
American Airlines
Sat 5/163:20 pm
MBJ
-
MSN
1 stop8h 08m
American Airlines
Deal found 2/22$312
This American Airlines deal was found by Cheapflights users on 2/25. 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 9/58:26 pm
MSN
-
MBJ
1 stop16h 05m
American Airlines
Sat 9/1212:43 pm
MBJ
-
MSN
1 stop10h 40m
American Airlines
Deal found 2/25$321
This United Airlines deal was found by Cheapflights users on 2/24. 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 5/148:40 pm
MSN
-
MBJ
2 stops16h 50m
United Airlines
Fri 5/2212:52 pm
MBJ
-
MSN
2 stops20h 03m
United Airlines
Deal found 2/24$322
This American Airlines deal was found by Cheapflights users on 2/24. 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 4/108:24 pm
MSN
-
MBJ
1 stop15h 49m
American Airlines
Fri 4/174:37 pm
MBJ
-
MSN
2 stops18h 18m
American Airlines
Deal found 2/24$326
This American Airlines deal was found by Cheapflights users on 2/24. 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 5/64:12 pm
MSN
-
MBJ
2 stops17h 01m
American Airlines
Sat 5/94:37 pm
MBJ
-
MSN
2 stops18h 18m
American Airlines
Deal found 2/24$327
This American Airlines deal was found by Cheapflights users on 2/25. 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 4/1511:35 am
MSN
-
MBJ
1 stop21h 38m
American Airlines
Wed 4/222:29 pm
MBJ
-
MSN
1 stop9h 26m
American Airlines
Deal found 2/25$328
This United Airlines deal was found by Cheapflights users on 2/24. 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.
Tue 3/246:30 am
MSN
-
MBJ
1 stop6h 16m
United Airlines
Tue 3/314:12 pm
MBJ
-
MSN
2 stops17h 55m
United Airlines
Deal found 2/24$329
This United Airlines deal was found by Cheapflights users on 2/24. 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.
Mon 6/18:25 pm
MSN
-
MBJ
2 stops17h 05m
United Airlines
Mon 6/154:12 pm
MBJ
-
MSN
2 stops17h 47m
United Airlines
Deal found 2/24$389
This American Airlines deal was found by Cheapflights users on 2/24. 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 4/228:24 pm
MSN
-
MBJ
1 stop15h 49m
American Airlines
Tue 4/282:19 pm
MBJ
-
MSN
1 stop8h 42m
American Airlines
Deal found 2/24$423

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 February 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$312
(American Airlines)

One-way from

$193
(United Airlines)

Popular in

July

Cheapest in

May

Average price

$689
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. 7% potential increase in price ($54 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 26, 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

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sat 5/9

8:24 pm-12:13 pm

1 stop15h 49m

Montego Bay Sangster Intl

Sat 5/16

3:20 pm-11:28 pm

1 stop8h 08m

$312

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Thu 5/14

8:40 pm-1:30 pm

2 stops16h 50m

Montego Bay Sangster Intl

Fri 5/22

12:52 pm-8:55 am

2 stops20h 03m

$322

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Thu 5/14

4:12 pm-9:13 am

2 stops17h 01m

Montego Bay Sangster Intl

Fri 5/22

2:23 pm-7:45 am

1 stop17h 22m

$322

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Thu 5/14

4:12 pm-9:13 am

2 stops17h 01m

Montego Bay Sangster Intl

Thu 5/21

2:23 pm-7:45 am

1 stop17h 22m

$322

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Wed 4/15

5:08 pm-11:51 am

2 stops18h 43m

Montego Bay Sangster Intl

Wed 4/22

4:37 pm-10:55 am

2 stops18h 18m

$326

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Wed 5/6

4:12 pm-9:13 am

2 stops17h 01m

Montego Bay Sangster Intl

Sat 5/9

4:37 pm-10:55 am

2 stops18h 18m

$327

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Tue 3/24

3:54 pm-1:05 pm

2 stops21h 11m

Montego Bay Sangster Intl

Tue 3/31

4:12 pm-10:07 am

2 stops17h 55m

$427

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Mon 4/6

8:24 pm-3:37 pm

2 stops19h 13m

Montego Bay Sangster Intl

Fri 4/10

4:37 pm-9:48 am

2 stops17h 11m

$459

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sun 7/12

8:25 pm-3:10 pm

2 stops18h 45m

$193

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/23

Sorted by cheapest first

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 February 26, 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
8,237 reviews

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Crew

8.5

Overall

7.9

Food

7.2

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
8,237 reviews
Delta
7.9
Good
8,237 reviews

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Crew

8.5

Overall

7.9

Food

7.2

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
9,348 reviews
Delta
7.9
Good
8,237 reviews

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Crew

8.5

Overall

7.9

Food

7.2

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
11,352 reviews
Delta
7.9
Good
8,237 reviews

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Crew

8.5

Overall

7.9

Food

7.2

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 $322, American Airlines can have you in Jamaica from Madison in 16h 50m. 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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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 February 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$470Average$540FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$534Average$635FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$563Average$694FlexibilityNo cancel feeOn-time69%

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