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Jamaica

$152+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — MBJ
Aug 11 — Aug 181
Tue 8/11
Tue 8/18
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 July 12, 2026.

This American Airlines deal was found by Cheapflights users on 7/9. 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 8/246:00 am
MSN
-
MBJ
1 stop8h 23m
American Airlines
Fri 8/282:12 pm
MBJ
-
MSN
1 stop9h 58m
American Airlines
Deal found 7/9$352
This American Airlines deal was found by Cheapflights users on 7/9. 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 12/47:05 pm
MSN
-
MBJ
2 stops18h 07m
American Airlines
Thu 12/103:12 pm
MBJ
-
MSN
1 stop17h 54m
American Airlines
Deal found 7/9$367
This Delta deal was found by Cheapflights users on 7/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/136:00 am
MSN
-
MBJ
1 stop5h 48m
Delta
Sat 9/192:26 pm
MBJ
-
MSN
1 stop8h 27m
Delta
Deal found 7/11$372
This American Airlines deal was found by Cheapflights users on 7/9. 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 9/134:21 pm
MSN
-
MBJ
2 stops18h 41m
American Airlines
Sat 9/1912:05 pm
MBJ
-
MSN
1 stop22h 46m
American Airlines
Deal found 7/9$374
This American Airlines deal was found by Cheapflights users on 7/8. 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.
Sat 9/55:46 pm
MSN
-
MBJ
2 stops17h 48m
American Airlines
Sat 9/125:16 pm
MBJ
-
MSN
2 stops17h 35m
American Airlines
Deal found 7/8$377
This United Airlines deal was found by Cheapflights users on 7/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:30 am
MSN
-
MBJ
1 stop6h 18m
United Airlines
Sat 11/72:54 pm
MBJ
-
MSN
1 stop6h 55m
United Airlines
Deal found 7/8$410
This United Airlines deal was found by Cheapflights users on 7/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:30 am
MSN
-
MBJ
2 stops8h 49m
United Airlines
Sat 11/215:21 pm
MBJ
-
MSN
2 stops17h 23m
United Airlines
Deal found 7/8$415

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 July 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$352
(American Airlines)

One-way from

$152
(American Airlines)

Popular in

September

Cheapest in

August
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 Jamaica
Search Deals
One-way flight from Madison Truax Field to Jamaica
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($92 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($57 potential savings vs. average RT price).
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 July 12, 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

Sun 11/8

3:55 pm-12:55 pm

2 stops20h 00m

Montego Bay Sangster Intl

Thu 11/12

10:56 am-10:50 pm

2 stops12h 54m

$377
Quickest round-trip

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Mon 11/2

6:30 am-1:48 pm

1 stop6h 18m

Montego Bay Sangster Intl

Sat 11/7

2:54 pm-8:49 pm

1 stop6h 55m

$410

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sat 11/14

6:30 am-4:19 pm

2 stops8h 49m

Montego Bay Sangster Intl

Sat 11/21

5:21 pm-9:44 am

2 stops17h 23m

$415

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Fri 12/4

6:00 am-2:55 pm

1 stop7h 55m

Montego Bay Sangster Intl

Thu 12/10

3:12 pm-8:06 am

1 stop17h 54m

$437

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sun 9/13

7:17 am-4:16 pm

1 stop8h 59m

Montego Bay Sangster Intl

Sat 9/19

12:05 pm-10:51 am

1 stop22h 46m

$452
Cheapest one-way
Quickest one-way

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Mon 8/31

5:00 am-1:12 pm

1 stop8h 12m

$162

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sat 9/5

5:00 am-1:12 pm

1 stop8h 12m

$162

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Mon 7/20

5:00 am-3:10 pm

2 stops10h 10m

$201

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Wed 9/2

6:00 am-2:23 pm

1 stop8h 23m

$239

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sun 8/2

6:43 pm-1:31 pm

2 stops18h 48m

$243

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/11

Showing 1-10 of 13 resultsSorted by cheapest first
1
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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
No data available for this route at this time. Please check back soon.

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 July 12, 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
9,980 reviews

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Overall

7.4

Crew

8.1

Food

6.7

Reviews

1 / 20
6.0
Good

ROHIT,Jun 2026

IND - EWR

It should not be delayed by 2 hours. I missed the important event due to this
United Airlines
7.4
Good
9,980 reviews
United Airlines
7.4
Good
9,980 reviews

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Overall

7.4

Crew

8.1

Food

6.7

Reviews

1 / 20
6.0
Good

ROHIT,Jun 2026

IND - EWR

It should not be delayed by 2 hours. I missed the important event due to this
American Airlines
7.1
Good
11,804 reviews
United Airlines
7.4
Good
9,980 reviews

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Overall

7.4

Crew

8.1

Food

6.7

Reviews

1 / 20
6.0
Good

ROHIT,Jun 2026

IND - EWR

It should not be delayed by 2 hours. I missed the important event due to this

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 $410, American Airlines can have you in Jamaica from Madison in 6h 18m. 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.

See more FAQs

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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 July 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$390Average$689FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$484Average$632FlexibilityNo cancel feeOn-time71%

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