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Jamaica

$172+ Cheap flights from Wisconsin 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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Sep 1 — Sep 81
Tue 9/1
Tue 9/8
1 adult, Economy
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Cheap flight deals from Wisconsin to Jamaica

Cheapest flights from Wisconsin to Jamaica
Explore the most affordable flight options available from Wisconsin to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 2, 2026.

This American Airlines deal was found by Cheapflights users on 7/30. 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 10/247:14 am
MKE
-
MBJ
1 stop8h 58m
American Airlines
Wed 10/2812:16 pm
MBJ
-
MKE
1 stop9h 33m
American Airlines
Deal found 7/30$392
This American Airlines deal was found by Cheapflights users on 7/28. 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 9/117:17 am
MSN
-
MBJ
1 stop8h 59m
American Airlines
Fri 9/1812:05 pm
MBJ
-
MSN
1 stop10h 52m
American Airlines
Deal found 7/28$392
This United Airlines deal was found by Cheapflights users on 7/30. 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 10/243:10 pm
DLH
-
MBJ
2 stops20h 03m
United Airlines
Wed 10/282:01 pm
MBJ
-
DLH
1 stop20h 40m
United Airlines
Deal found 7/30$393
This American Airlines deal was found by Cheapflights users on 7/28. 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 9/66:00 am
MKE
-
MBJ
1 stop7h 12m
American Airlines
Sat 9/125:16 pm
MBJ
-
MKE
2 stops17h 51m
American Airlines
Deal found 7/28$397
This American Airlines deal was found by Cheapflights users on 7/30. 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 12/43:55 pm
MSN
-
MBJ
2 stops20h 05m
American Airlines
Thu 12/103:12 pm
MBJ
-
MSN
1 stop10h 00m
American Airlines
Deal found 7/30$397
This American Airlines deal was found by Cheapflights users on 7/28. 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 9/52:45 pm
MSN
-
MBJ
1 stop22h 27m
American Airlines
Sat 9/125:16 pm
MBJ
-
MSN
2 stops19h 40m
American Airlines
Deal found 7/28$402
This Air Canada deal was found by Cheapflights users on 7/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/283:45 pm
ORD
-
MBJ
2 stops20h 05m
Air Canada
Sun 11/12:20 pm
MBJ
-
ORD
1 stop25h 32m
Air Canada
Deal found 7/31$419
This Air Canada deal was found by Cheapflights users on 7/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/71:55 pm
ORD
-
MBJ
1 stop22h 30m
Air Canada
Sun 11/152:20 pm
MBJ
-
ORD
2 stops20h 03m
Air Canada
Deal found 7/31$420
This Air Canada deal was found by Cheapflights users on 8/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/68:50 pm
ORD
-
MBJ
1 stop19h 30m
Air Canada
Mon 11/96:20 pm
MBJ
-
ORD
1 stop16h 03m
Air Canada
Deal found 8/1$421
This Air Canada deal was found by Cheapflights users on 7/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/58:45 am
ORD
-
MBJ
1 stop7h 35m
Air Canada
Sat 12/121:50 pm
MBJ
-
ORD
1 stop20h 18m
Air Canada
Deal found 7/31$422
This Air Canada deal was found by Cheapflights users on 8/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:21 pm
ORD
-
MBJ
2 stops18h 04m
Air Canada
Sun 11/12:20 pm
MBJ
-
ORD
2 stops20h 03m
Air Canada
Deal found 8/1$423
This Air Canada deal was found by Cheapflights users on 7/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/283:45 pm
ORD
-
MBJ
2 stops20h 05m
Air Canada
Mon 11/26:20 pm
MBJ
-
ORD
1 stop16h 03m
Air Canada
Deal found 7/31$424

Find flight deals from Wisconsin to Jamaica

Keep the following information in mind while searching for Wisconsin to Jamaica flight deals. Data was last updated August 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$392
(American Airlines)

One-way from

$172
(Delta)

Popular in

December

Cheapest in

July

Average price

$623
Provider with most accurate pricing for Milwaukee-Mitchell-Montego Bay Sangster Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Montego Bay Sangster Intl flights.
Search Deals
From Wisconsin to Jamaica
Search Deals
One-way flight from Wisconsin to Jamaica
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin 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 August 2, 2026.
Use the filters below to find and compare flights from Wisconsin to Jamaica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Tue 12/8

7:00 am-4:35 pm

1 stop8h 35m

Montego Bay Sangster Intl

Tue 12/15

6:00 pm-11:54 pm

1 stop6h 54m

$392

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Wed 12/2

6:00 am-1:46 pm

1 stop6h 46m

Montego Bay Sangster Intl

Wed 12/9

3:36 pm-11:27 pm

1 stop8h 51m

$392

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Fri 12/4

7:00 am-4:35 pm

1 stop8h 35m

Montego Bay Sangster Intl

Wed 12/9

6:00 pm-11:54 pm

1 stop6h 54m

$392

DuluthMontego Bay

DLH - MBJ

DLHMBJ

Duluth Intl

Sat 10/24

3:10 pm-11:13 am

2 stops20h 03m

Montego Bay Sangster Intl

Wed 10/28

2:01 pm-10:41 am

1 stop20h 40m

$393

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Fri 10/9

6:27 pm-12:54 pm

2 stops18h 27m

Montego Bay Sangster Intl

Wed 10/14

12:18 pm-9:52 pm

1 stop9h 34m

$397

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Tue 1/26

7:19 pm-2:13 pm

2 stops17h 54m

Montego Bay Sangster Intl

Tue 2/9

2:19 pm-10:58 pm

1 stop9h 39m

$397

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sun 9/13

4:21 pm-11:03 am

2 stops18h 42m

Montego Bay Sangster Intl

Sat 9/19

5:16 pm-10:51 am

2 stops17h 35m

$397

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sat 12/5

6:06 pm-12:55 pm

2 stops17h 49m

Montego Bay Sangster Intl

Fri 12/11

6:00 pm-9:05 am

2 stops16h 05m

$397

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Fri 12/4

3:55 pm-1:00 pm

2 stops20h 05m

Montego Bay Sangster Intl

Thu 12/10

2:02 pm-8:06 am

2 stops19h 04m

$397

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Tue 9/15

4:06 pm-11:43 am

2 stops19h 37m

Montego Bay Sangster Intl

Tue 9/22

12:52 pm-10:14 am

1 stop21h 22m

$435

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Wisconsin to Jamaica

Have a flexible travel schedule? Discover the best time to fly to Jamaica from Wisconsin 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 Wisconsin to Jamaica

What is the cheapest month to book a flight from Wisconsin to Jamaica?

Currently, May is the cheapest month in which you can book a flight from Wisconsin to Jamaica (average of $539). Flying from Wisconsin to Jamaica in November is currently the most expensive (average of $689). 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.

Related info for your journey

Find useful and relevant information for your journey from Wisconsin to Jamaica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Wisconsin to Jamaica?

    American Airlines, United Airlines, and Delta can get you from Wisconsin to Jamaica in just under 6h 31m. Your travel time can differ by up to 13h 32m. Airlines will cover a distance of 1786 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Wisconsin to Jamaica one-way?

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $174. Delta flights start at $180 while deals on Alaska Airlines start at $180 one-way.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Wisconsin 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 Wisconsin to Jamaica?

    Currently, May is the cheapest month in which you can book a flight from Wisconsin to Jamaica (average of $539). Flying from Wisconsin to Jamaica in November is currently the most expensive (average of $689). 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 Wisconsin to Jamaica

See prices for flight routes from nearby airports that may be better suited for you.
Newark to Luis Munoz Marin Intl flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santiago de los Caballeros flights
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Newark to Santiago de los Caballeros flights
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O'Hare Intl to Luis Munoz Marin Intl flights
Newark to Montego Bay flights
Boston to Luis Munoz Marin Intl flights
Dulles Intl to Luis Munoz Marin Intl flights
Reagan-National to Luis Munoz Marin Intl flights
LaGuardia to Punta Cana flights
Atlanta to Luis Munoz Marin Intl flights
Dallas/Fort Worth to Luis Munoz Marin Intl flights
John F Kennedy Intl to Kingston flights
Hartford to Luis Munoz Marin Intl flights
LaGuardia to Santo Domingo flights
Boston to Oranjestad flights
Hobby to Luis Munoz Marin Intl flights
Tampa to Luis Munoz Marin Intl flights
Fort Lauderdale to Luis Munoz Marin Intl flights
Newark to Nassau flights
John F Kennedy Intl to Willemstad flights
George Bush Intcntl to Luis Munoz Marin Intl flights
LaGuardia to Montego Bay flights
Boston to Punta Cana flights
John F Kennedy Intl to Port of Spain flights
Dulles Intl to Punta Cana flights
Atlanta to Montego Bay flights
John F Kennedy Intl to Bridgetown flights
O'Hare Intl to Punta Cana flights
John F Kennedy Intl to Nassau flights
Newark to Simpson Bay flights
Philadelphia to Punta Cana flights
Orlando to Punta Cana flights
LaGuardia to Santiago de los Caballeros flights
Newark to Providenciales flights
Atlanta to Punta Cana flights
Boston to Santo Domingo flights

Top 4 airlines flying from Wisconsin to Jamaica

Discover the top 4 airlines that operate flights from Wisconsin 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 August 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$336Average$696FlexibilityNo cancel feeOn-time71%
DeltaCheapest$362Average$587FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$390Average$665FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$615Average$716FlexibilityNo cancel feeOn-time63%

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