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Madison

$296+ Cheap flights from Jamaica to Madison (MSN)

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 5/22. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — MSN
Apr 2 — Apr 91
Thu 4/2
Thu 4/9
1 adult, Economy
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Cheap flight deals from Jamaica to Madison

Cheapest flights from Jamaica to Madison
Explore the most affordable flight options available from Jamaica to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 3, 2026.

This American Airlines deal was found by Cheapflights users on 3/1. 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 5/222:30 pm
MBJ
-
MSN
1 stop17h 19m
American Airlines
Sat 9/58:26 pm
MSN
-
MBJ
1 stop16h 05m
American Airlines
Deal found 3/1$296
This American Airlines deal was found by Cheapflights users on 3/1. 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 5/2212:31 pm
MBJ
-
MSN
2 stops10h 48m
American Airlines
Mon 8/318:26 pm
MSN
-
MBJ
1 stop16h 05m
American Airlines
Deal found 3/1$301
This American Airlines deal was found by Cheapflights users on 3/2. 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 5/181:15 pm
MBJ
-
MSN
1 stop20h 33m
American Airlines
Sat 9/58:26 pm
MSN
-
MBJ
1 stop16h 05m
American Airlines
Deal found 3/2$302
This American Airlines deal was found by Cheapflights users on 3/1. 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 5/252:08 pm
MBJ
-
MSN
2 stops22h 29m
American Airlines
Tue 9/16:00 am
MSN
-
MBJ
1 stop6h 31m
American Airlines
Deal found 3/1$306
This American Airlines deal was found by Cheapflights users on 3/1. 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 5/245:17 pm
MBJ
-
MSN
2 stops19h 48m
American Airlines
Sun 8/308:26 pm
MSN
-
MBJ
1 stop16h 05m
American Airlines
Deal found 3/1$311
This American Airlines deal was found by Cheapflights users on 3/1. 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 5/232:08 pm
MBJ
-
MSN
2 stops9h 51m
American Airlines
Tue 9/16:00 am
MSN
-
MBJ
2 stops30h 20m
American Airlines
Deal found 3/1$312
This American Airlines deal was found by Cheapflights users on 3/1. 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 5/2512:47 pm
MBJ
-
MSN
1 stop21h 51m
American Airlines
Sun 8/309:52 am
MSN
-
MBJ
1 stop26h 39m
American Airlines
Deal found 3/1$314
This Delta deal was found by Cheapflights users on 3/1. 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 5/281:18 pm
MBJ
-
MSN
2 stops19h 31m
Delta
Mon 8/315:50 pm
MSN
-
MBJ
2 stops19h 14m
Delta
Deal found 3/1$322
This United Airlines deal was found by Cheapflights users on 3/1. 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 5/284:12 pm
MBJ
-
MSN
2 stops22h 45m
United Airlines
Fri 9/43:49 pm
MSN
-
MBJ
2 stops21h 41m
United Airlines
Deal found 3/1$344
This American Airlines deal was found by Cheapflights users on 3/1. 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 5/2612:47 pm
MBJ
-
MSN
1 stop10h 19m
American Airlines
Tue 9/16:46 am
MSN
-
MBJ
1 stop7h 34m
American Airlines
Deal found 3/1$346
This United Airlines deal was found by Cheapflights users on 3/1. 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 5/232:40 pm
MBJ
-
MSN
2 stops18h 15m
United Airlines
Fri 9/45:00 am
MSN
-
MBJ
2 stops32h 30m
United Airlines
Deal found 3/1$349

Find flight deals from Jamaica to Madison

Keep the following information in mind while searching for Jamaica to Madison flight deals. Data was last updated March 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$296
(American Airlines)
Provider with most accurate pricing for Montego Bay Sangster Intl-Madison Truax Field flight deals.
Search Deals
Provider most trusted by Cheapflights users for Montego Bay Sangster Intl-Madison Truax Field flights.
Search Deals
From Jamaica to Madison Truax Field
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Jamaica to Madison 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 March 3, 2026.
Use the filters below to find and compare flights from Jamaica to Madison that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Mon 5/18

4:37 pm-10:53 am

2 stops18h 16m

Madison Truax Field

Sat 9/5

6:45 pm-9:25 am

2 stops14h 40m

$301

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Thu 5/28

1:18 pm-8:49 am

2 stops19h 31m

Madison Truax Field

Sun 8/30

7:00 am-3:34 pm

2 stops8h 34m

$322

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Thu 5/28

4:59 pm-8:49 am

2 stops15h 50m

Madison Truax Field

Tue 9/1

5:45 am-1:04 pm

1 stop7h 19m

$322

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Sat 5/23

2:40 pm-8:55 am

2 stops18h 15m

Madison Truax Field

Fri 9/4

5:00 am-1:30 pm

2 stops32h 30m

$349

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Fri 5/22

2:40 pm-2:00 pm

2 stops23h 20m

Madison Truax Field

Fri 9/4

8:30 pm-1:30 pm

2 stops17h 00m

$370

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Mon 5/25

12:47 pm-10:38 am

1 stop21h 51m

Madison Truax Field

Wed 9/2

6:00 am-12:31 pm

1 stop6h 31m

$386

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Sun 5/17

10:17 am-7:54 pm

2 stops9h 37m

Madison Truax Field

Mon 5/18

8:24 pm-1:19 pm

2 stops16h 55m

$609

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Sun 5/24

2:21 pm-10:31 pm

1 stop8h 10m

Madison Truax Field

Tue 9/1

7:00 am-3:34 pm

2 stops8h 34m

$822

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Tue 5/26

4:59 pm-8:49 am

2 stops15h 50m

Madison Truax Field

Thu 9/3

7:00 am-3:34 pm

2 stops8h 34m

$1,109

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/2

Sorted by cheapest first

Best time to book a flight from Jamaica to Madison

Have a flexible travel schedule? Discover the best time to fly to Madison from Jamaica 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 Jamaica to Madison
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Madison

Get insights into the airlines that provide service to Madison. 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 Madison. Reviews last updated March 3, 2026.
Read through reviews of airlines operating flights from Jamaica to Madison, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.1
Good
11,375 reviews

Comfort

7.2

Crew

8.0

Entertainment

6.9

Overall

7.1

Boarding

7.5

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.1
Good
11,375 reviews
American Airlines
7.1
Good
11,375 reviews

Comfort

7.2

Crew

8.0

Entertainment

6.9

Overall

7.1

Boarding

7.5

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

Related info for your journey

Find useful and relevant information for your journey from Jamaica to Madison. 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 into for flights to Madison from Jamaica?

    If you book a flight to Madison from Jamaica, you will be flying to 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 Jamaica to Madison?

    There are many flights that can get you from Jamaica to Madison in 18h 15m. Fly via American Airlines, Delta, or United Airlines to get the fastest option. The distance from Jamaica to Madison is about 1826 mi. This flight may include one or multiple stops.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Jamaica to Madison 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

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Portage
Middleton
Baraboo
Fitchburg

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Jamaica to Madison

Discover the top airline that operate flights from Jamaica to Madison. 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 March 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$436Average$488FlexibilityNo cancel feeOn-time71%

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