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Cheap flights from Madison to Jamaica from $352

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Madison to Jamaica departing on 9/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Madison to Jamaica

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
4:20 pm - 9:25 am
MSN
-
MBJ
17h 05m
1 stop
American Airlines Logo
12:43 pm - 11:23 pm
MBJ
-
MSN
10h 40m
1 stop
$352American Airlines
Sat, Sep 5 - Sat, Sep 12
American Airlines Logo
8:26 pm - 12:20 pm
MSN
-
MBJ
15h 54m
2 stops
American Airlines Logo
1:05 pm - 9:02 am
MBJ
-
MSN
19h 57m
2 stops
$357American Airlines
Sat, Sep 5 - Sat, Sep 12
American Airlines Logo
8:24 pm - 12:13 pm
MSN
-
MBJ
15h 49m
1 stop
American Airlines Logo
12:31 pm - 11:59 pm
MBJ
-
MSN
11h 28m
1 stop
$434American Airlines
Thu, May 14 - Thu, May 21
American Airlines Logo
8:24 pm - 1:25 pm
MSN
-
MBJ
17h 01m
2 stops
American Airlines Logo
5:17 pm - 11:36 am
MBJ
-
MSN
18h 19m
2 stops
$439American Airlines
Thu, May 14 - Thu, May 21
American Airlines Logo
11:35 am - 9:13 am
MSN
-
MBJ
21h 38m
1 stop
American Airlines Logo
12:31 pm - 11:59 pm
MBJ
-
MSN
11h 28m
1 stop
$444American Airlines
Thu, May 14 - Thu, May 21
American Airlines Logo
5:00 am - 1:23 pm
MSN
-
MBJ
8h 23m
1 stop
American Airlines Logo
2:23 pm - 10:40 pm
MBJ
-
MSN
8h 17m
1 stop
$472American Airlines
Tue, Jul 7 - Tue, Jul 21
American Airlines Logo
8:24 pm - 12:13 pm
MSN
-
MBJ
15h 49m
1 stop
American Airlines Logo
12:31 pm - 11:59 pm
MBJ
-
MSN
11h 28m
1 stop
$480American Airlines
Thu, May 14 - Thu, May 21
American Airlines Logo
8:24 pm - 1:25 pm
MSN
-
MBJ
17h 01m
2 stops
American Airlines Logo
12:31 pm - 11:59 pm
MBJ
-
MSN
11h 28m
1 stop
$485American Airlines
Thu, May 14 - Thu, May 21
United Airlines Logo
6:30 am - 12:50 pm
MSN
-
MBJ
6h 20m
1 stop
United Airlines Logo
2:40 pm - 3:00 pm
MBJ
-
MSN
24h 20m
2 stops
$487United Airlines
Sat, May 9 - Wed, May 13
American Airlines Logo
6:02 am - 1:55 pm
MSN
-
MBJ
7h 53m
1 stop
American Airlines Logo
2:55 pm - 12:03 pm
MBJ
-
MSN
21h 08m
1 stop
$491American Airlines
Fri, May 22 - Fri, May 29

United Airlines flights from Madison to Jamaica

Our best United Airlines deals on Madison to Jamaica flight tickets
United Airlines
May 9
MSN6:30 amMadison Truax Field
6h 20m
1 stop
MBJ12:50 pmMontego Bay Sangster Intl
May 13
MBJ2:40 pmMontego Bay Sangster Intl
24h 20m
2 stops
MSN3:00 pmMadison Truax Field
$487
United Airlines
May 3
MSN8:55 pmMadison Truax Field
18h 15m
2 stops
MBJ3:10 pmMontego Bay Sangster Intl
May 7
MBJ2:40 pmMontego Bay Sangster Intl
32h 14m
2 stops
MSN10:54 pmMadison Truax Field
$497
United Airlines
May 9
MSN6:30 amMadison Truax Field
6h 20m
1 stop
MBJ12:50 pmMontego Bay Sangster Intl
May 13
MBJ2:40 pmMontego Bay Sangster Intl
24h 20m
2 stops
MSN3:00 pmMadison Truax Field
$502

American Airlines flights from Madison to Jamaica

Our best American Airlines deals on Madison to Jamaica flight tickets
American Airlines
Sep 5
MSN4:20 pmMadison Truax Field
17h 05m
1 stop
MBJ9:25 amMontego Bay Sangster Intl
Sep 12
MBJ12:43 pmMontego Bay Sangster Intl
10h 40m
1 stop
MSN11:23 pmMadison Truax Field
$352
American Airlines
Sep 5
MSN6:45 pmMadison Truax Field
14h 40m
2 stops
MBJ9:25 amMontego Bay Sangster Intl
Sep 12
MBJ12:43 pmMontego Bay Sangster Intl
10h 40m
1 stop
MSN11:23 pmMadison Truax Field
$357
American Airlines
May 14
MSN8:24 pmMadison Truax Field
15h 49m
1 stop
MBJ12:13 pmMontego Bay Sangster Intl
May 21
MBJ12:31 pmMontego Bay Sangster Intl
11h 28m
1 stop
MSN11:59 pmMadison Truax Field
$434

momondo 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, momondo users made 832,500 searches. Data last updated April 9, 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

4:20 pm-9:25 am

1 stop17h 05m

Montego Bay Sangster Intl

Sat 9/12

12:43 pm-11:23 pm

1 stop10h 40m

$352

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sat 9/5

8:26 pm-12:20 pm

2 stops15h 54m

Montego Bay Sangster Intl

Sat 9/12

1:05 pm-9:02 am

2 stops19h 57m

$357

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Thu 5/14

8:24 pm-12:13 pm

1 stop15h 49m

Montego Bay Sangster Intl

Thu 5/21

12:31 pm-11:59 pm

1 stop11h 28m

$434

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Thu 5/14

8:24 pm-1:25 pm

2 stops17h 01m

Montego Bay Sangster Intl

Thu 5/21

5:17 pm-11:36 am

2 stops18h 19m

$439

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Thu 5/14

11:35 am-9:13 am

1 stop21h 38m

Montego Bay Sangster Intl

Thu 5/21

12:31 pm-11:59 pm

1 stop11h 28m

$444
Quickest round-trip

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Tue 7/7

5:00 am-1:23 pm

1 stop8h 23m

Montego Bay Sangster Intl

Tue 7/21

2:23 pm-10:40 pm

1 stop8h 17m

$472

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Thu 5/14

8:24 pm-12:13 pm

1 stop15h 49m

Montego Bay Sangster Intl

Thu 5/21

12:31 pm-11:59 pm

1 stop11h 28m

$480

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Thu 5/14

8:24 pm-1:25 pm

2 stops17h 01m

Montego Bay Sangster Intl

Thu 5/21

12:31 pm-11:59 pm

1 stop11h 28m

$485

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sat 5/9

6:30 am-12:50 pm

1 stop6h 20m

Montego Bay Sangster Intl

Wed 5/13

2:40 pm-3:00 pm

2 stops24h 20m

$487

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Fri 5/22

6:02 am-1:55 pm

1 stop7h 53m

Montego Bay Sangster Intl

Fri 5/29

2:55 pm-12:03 pm

1 stop21h 08m

$491

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to Jamaica from

How to get the cheapest flight ticket from Madison to Jamaica

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Jamaica?

The cheapest month to fly to Jamaica from Madison is in March. Flight prices, which tend to average around $582, are often lower during this time because this is during the off-season. If you aren’t able to travel to Jamaica during the month of March, then flying in December is also cheap. Prices for this month can be found on momondo for an average of $604.

Can stopping save me money on Madison to Jamaica flights?

You could potentially save up to 31% on your flight if you consider stops on a Madison to Jamaica flight.

Cheap Madison to Jamaica flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Madison to Jamaica

Fastest flight time

6h 20m

Direct flights

None
The fastest flight from Madison to Jamaica takes 6h 20m
There are no direct flights from Madison to Jamaica. There are no popular flight routes from Madison to Jamaica.
Search flight deals

Frequently asked questions about flying from Madison to Jamaica

  • When did momondo last update prices for flights from Madison Truax Field Airport to Jamaica?

    Prices for flights from Madison Truax Field Airport to Jamaica were last updated today.

  • How many operators does momondo search for flights from Madison Truax Field Airport to Jamaica?

  • How old do you have to be to fly from Madison Truax Field Airport to Jamaica?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Madison Truax Field Airport to Jamaica.

  • What documentation or ID do you need to fly to Jamaica?

    The required travel and health documents for your Jamaica trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Jamaica. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Madison to Jamaica

Compare and see reviews for airlines that fly from Madison to Jamaica with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $518Free CancellationRating
7.1
11,563 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Madison to Jamaica?

It is quick and easy to find Madison to Jamaica flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Jamaica that suits you.

Can I find flights from Madison to Jamaica with flexible booking policies on momondo?

Yes. All flights to Jamaica from Madison on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Madison to Jamaica?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Madison to Jamaica.

I’m not ready to book a flight from Madison to Jamaica right now. Can momondo alert me if prices change?

Price alerts on flights to Jamaica from Madison are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Jamaica trip

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