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Jamaica

$158+ 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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Jul 22 — Jul 291
Wed 7/22
Wed 7/29
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 June 22, 2026.

This Super.com deal was found by Cheapflights users on 6/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/117:00 am
ORD
-
MBJ
1 stop6h 54m
JetBlue
Tue 11/173:59 pm
MBJ
-
ORD
1 stop8h 45m
JetBlue
Deal found 6/17$361
This Super.com deal was found by Cheapflights users on 6/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:00 am
ORD
-
MBJ
1 stop6h 54m
JetBlue
Tue 11/103:59 pm
MBJ
-
ORD
1 stop8h 45m
JetBlue
Deal found 6/21$364
This American Airlines deal was found by Cheapflights users on 6/18. 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.
Thu 8/276:20 am
MKE
-
MBJ
1 stop8h 03m
American Airlines
Mon 8/312:12 pm
MBJ
-
MKE
1 stop17h 32m
American Airlines
Deal found 6/18$372
This United Airlines deal was found by Cheapflights users on 6/17. 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.
Fri 12/45:00 am
MSN
-
MBJ
1 stop7h 46m
United Airlines
Thu 12/102:48 pm
MBJ
-
MSN
1 stop10h 24m
United Airlines
Deal found 6/17$372
This American Airlines deal was found by Cheapflights users on 6/20. 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 11/26:02 pm
LSE
-
MBJ
1 stop18h 12m
American Airlines
Thu 11/53:14 pm
MBJ
-
LSE
1 stop27h 18m
American Airlines
Deal found 6/20$374
This American Airlines deal was found by Cheapflights users on 6/21. 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 9/195:43 pm
MKE
-
MBJ
2 stops19h 10m
American Airlines
Sat 9/265:16 pm
MBJ
-
MKE
2 stops19h 32m
American Airlines
Deal found 6/21$377
This American Airlines deal was found by Cheapflights users on 6/21. 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 9/57:00 am
MSN
-
MBJ
1 stop9h 08m
American Airlines
Sat 9/125:16 pm
MBJ
-
MSN
2 stops17h 35m
American Airlines
Deal found 6/21$377
This American Airlines deal was found by Cheapflights users on 6/17. 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 12/48:08 pm
MSN
-
MBJ
1 stop16h 12m
American Airlines
Thu 12/103:12 pm
MBJ
-
MSN
1 stop19h 07m
American Airlines
Deal found 6/17$378
This Justfly.com deal was found by Cheapflights users on 6/21. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:00 am
ORD
-
MBJ
1 stop6h 54m
JetBlue
Tue 11/102:00 pm
MBJ
-
ORD
1 stop10h 44m
JetBlue
Deal found 6/21$384
This Super.com deal was found by Cheapflights users on 6/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/277:00 am
ORD
-
MBJ
1 stop6h 48m
JetBlue
Mon 11/22:00 pm
MBJ
-
ORD
1 stop10h 44m
JetBlue
Deal found 6/17$389
This Super.com deal was found by Cheapflights users on 6/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:00 am
ORD
-
MBJ
1 stop7h 47m
JetBlue
Tue 12/82:45 pm
MBJ
-
ORD
1 stop9h 59m
JetBlue
Deal found 6/21$390
This Super.com deal was found by Cheapflights users on 6/19. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:00 am
ORD
-
MBJ
1 stop6h 54m
JetBlue
Tue 11/172:00 pm
MBJ
-
ORD
1 stop10h 44m
JetBlue
Deal found 6/19$391

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 June 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$361
(Super.com)

One-way from

$158
(Super.com)

Popular in

March

Cheapest in

July

Average price

$640
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. 4% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 22, 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

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Fri 12/4

5:00 am-1:46 pm

1 stop7h 46m

Montego Bay Sangster Intl

Thu 12/10

2:48 pm-12:12 am

1 stop10h 24m

$372

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Sat 9/19

5:43 pm-12:53 pm

2 stops19h 10m

Montego Bay Sangster Intl

Sat 9/26

5:16 pm-12:48 pm

2 stops19h 32m

$377

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Sat 10/3

8:14 pm-12:53 pm

2 stops16h 39m

Montego Bay Sangster Intl

Tue 10/13

5:00 pm-12:02 pm

2 stops19h 02m

$377

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Fri 12/4

8:08 pm-1:20 pm

1 stop16h 12m

Montego Bay Sangster Intl

Thu 12/10

4:23 pm-10:16 am

2 stops18h 53m

$377

La CrosseMontego Bay

LSE - MBJ

LSEMBJ

La Crosse

Mon 11/2

6:02 pm-12:42 pm

2 stops17h 40m

Montego Bay Sangster Intl

Thu 11/5

1:45 pm-9:20 am

2 stops20h 35m

$377

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Thu 9/10

4:21 pm-11:02 am

2 stops18h 41m

Montego Bay Sangster Intl

Sun 9/13

5:16 pm-12:56 pm

2 stops19h 40m

$382

DuluthMontego Bay

DLH - MBJ

DLHMBJ

Duluth Intl

Mon 11/9

6:23 pm-2:14 pm

2 stops18h 51m

Montego Bay Sangster Intl

Sat 11/14

5:21 pm-10:44 am

2 stops18h 23m

$416

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Sat 9/19

5:30 am-3:34 pm

1 stop10h 04m

Montego Bay Sangster Intl

Sat 9/26

4:59 pm-11:52 pm

1 stop6h 53m

$432

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Sat 12/5

6:00 am-1:46 pm

1 stop6h 46m

Montego Bay Sangster Intl

Mon 12/7

2:48 pm-10:39 pm

1 stop8h 51m

$432

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Sat 9/19

7:05 pm-11:43 am

1 stop16h 38m

Montego Bay Sangster Intl

Sat 9/26

2:40 pm-10:45 pm

1 stop8h 05m

$432

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

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, February is the cheapest month in which you can book a flight from Wisconsin to Jamaica (average of $213). Flying from Wisconsin to Jamaica in July is currently the most expensive (average of $516). 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?

    United Airlines, American Airlines, and Delta can get you from Wisconsin to Jamaica in just under 7h 46m. Your travel time can differ by up to 11h 24m. Airlines will cover a distance of 1826 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 Delta, which is currently one of the cheapest options available, starting at $180. Alaska Airlines flights start at $180 while deals on United Airlines start at $240 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, February is the cheapest month in which you can book a flight from Wisconsin to Jamaica (average of $213). Flying from Wisconsin to Jamaica in July is currently the most expensive (average of $516). 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.
John F Kennedy Intl to Santiago de los Caballeros flights
Newark to Luis Munoz Marin Intl flights
John F Kennedy Intl to Punta Cana flights
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John F Kennedy Intl to Luis Munoz Marin Intl flights
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John F Kennedy Intl to Oranjestad flights
LaGuardia to Luis Munoz Marin Intl flights
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John F Kennedy Intl to Montego Bay flights
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Newark to Santo Domingo flights
Boston to Luis Munoz Marin Intl flights
Tampa to Luis Munoz Marin Intl flights
Dallas/Fort Worth to Luis Munoz Marin Intl flights
Reagan-National to Luis Munoz Marin Intl flights
Atlanta to Luis Munoz Marin Intl flights
Boston to Punta Cana flights
Newark to Montego Bay flights
Hartford to Luis Munoz Marin Intl flights
Fort Lauderdale to Luis Munoz Marin Intl flights
Hobby to Luis Munoz Marin Intl flights
LaGuardia to Punta Cana flights
Atlanta to Punta Cana flights
LaGuardia to Santo Domingo flights
Dulles Intl to Punta Cana flights
George Bush Intcntl to Luis Munoz Marin Intl flights
Newark to Nassau flights
Atlanta to Montego Bay flights
Boston to Oranjestad flights
John F Kennedy Intl to Kingston flights
Orlando to Santo Domingo flights
LaGuardia to Santiago de los Caballeros flights
Newark to Providenciales flights
Charlotte to Luis Munoz Marin Intl flights
Raleigh to Luis Munoz Marin Intl flights
Newark to Simpson Bay flights
Orlando to Punta Cana flights
Fort Lauderdale to Montego Bay flights
Fort Lauderdale to Santo Domingo flights
John F Kennedy Intl to Bridgetown flights
Miami to Willemstad flights
Dulles Intl to Montego Bay flights

Top 3 airlines flying from Wisconsin to Jamaica

Discover the top 3 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 June 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$336Average$693FlexibilityNo cancel feeOn-time71%
DeltaCheapest$362Average$569FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$571Average$678FlexibilityNo cancel feeOn-time63%

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