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Jamaica

$147+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Jun 4 — Jun 111
Thu 6/4
Thu 6/11
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 May 5, 2026.

This United Airlines deal was found by Cheapflights users on 4/30. 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.
Fri 5/16:00 am
ORD
-
MBJ
1 stop9h 10m
United Airlines
Fri 5/84:12 pm
MBJ
-
ORD
1 stop7h 32m
United Airlines
Deal found 4/30$332
This American Airlines deal was found by Cheapflights users on 5/4. 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 11/38:05 am
ORD
-
MBJ
Nonstop4h 09m
American Airlines
Tue 11/103:14 pm
MBJ
-
ORD
Nonstop4h 41m
American Airlines
Deal found 5/4$338
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Sun 12/138:10 am
ORD
-
MBJ
Nonstop4h 10m
American Airlines
Sun 12/204:27 pm
MBJ
-
ORD
Nonstop4h 37m
American Airlines
Deal found 4/30$343
This American Airlines deal was found by Cheapflights users on 5/5. 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 5/115:00 am
ORD
-
MBJ
1 stop6h 24m
American Airlines
Wed 5/2010:17 am
MBJ
-
ORD
1 stop7h 41m
American Airlines
Deal found 5/5$344
This American Airlines deal was found by Cheapflights users on 5/4. 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 5/188:05 am
ORD
-
MBJ
Nonstop4h 08m
American Airlines
Fri 5/222:08 pm
MBJ
-
ORD
1 stop10h 16m
American Airlines
Deal found 5/4$348
This United Airlines deal was found by Cheapflights users on 5/4. 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.
Tue 12/16:00 am
MKE
-
MBJ
1 stop6h 46m
United Airlines
Tue 12/82:48 pm
MBJ
-
MKE
1 stop10h 21m
United Airlines
Deal found 5/4$352
This American Airlines deal was found by Cheapflights users on 5/2. 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.
Sat 5/165:08 pm
MSN
-
MBJ
1 stop16h 05m
American Airlines
Fri 5/2212:31 pm
MBJ
-
MSN
1 stop11h 28m
American Airlines
Deal found 5/2$352
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Tue 12/1510:15 am
ORD
-
MBJ
Nonstop4h 07m
American Airlines
Sun 12/2711:07 am
MBJ
-
ORD
1 stop14h 36m
American Airlines
Deal found 4/30$353
This American Airlines deal was found by Cheapflights users on 5/4. 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 6/209:05 pm
ORD
-
MBJ
1 stop19h 11m
American Airlines
Thu 6/252:31 pm
MBJ
-
ORD
Nonstop4h 39m
American Airlines
Deal found 5/4$355
This American Airlines deal was found by Cheapflights users on 5/4. 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 9/199:02 pm
ORD
-
MBJ
2 stops13h 48m
American Airlines
Wed 9/231:05 pm
MBJ
-
ORD
2 stops10h 29m
American Airlines
Deal found 5/4$357
This United Airlines deal was found by Cheapflights users on 5/4. 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.
Tue 10/276:10 pm
DLH
-
MBJ
2 stops16h 57m
United Airlines
Sat 10/312:36 pm
MBJ
-
DLH
2 stops21h 08m
United Airlines
Deal found 5/4$357
This American Airlines deal was found by Cheapflights users on 5/5. 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 6/16:00 am
MKE
-
MBJ
1 stop7h 55m
American Airlines
Fri 6/55:17 pm
MBJ
-
MKE
2 stops18h 47m
American Airlines
Deal found 5/5$357

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 May 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$338
(American Airlines)

One-way from

$147
(FlightHub)

Popular in

June

Cheapest in

January

Average price

$558
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. 1% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 5, 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

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 7/24

8:40 am-3:10 pm

1 stop6h 30m

Montego Bay Sangster Intl

Wed 7/29

4:12 pm-11:26 pm

1 stop7h 14m

$352

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Mon 6/1

6:00 am-1:55 pm

1 stop7h 55m

Montego Bay Sangster Intl

Fri 6/5

5:17 pm-12:04 pm

2 stops18h 47m

$357

DuluthMontego Bay

DLH - MBJ

DLHMBJ

Duluth Intl

Tue 10/27

6:10 pm-11:07 am

2 stops16h 57m

Montego Bay Sangster Intl

Sat 10/31

2:36 pm-11:44 am

2 stops21h 08m

$357

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Tue 7/14

6:00 am-2:02 pm

1 stop8h 02m

Montego Bay Sangster Intl

Tue 7/28

5:14 pm-12:34 pm

2 stops19h 20m

$357

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sat 9/5

4:10 pm-11:42 am

2 stops19h 32m

Montego Bay Sangster Intl

Sat 9/12

3:15 pm-12:22 pm

2 stops21h 07m

$357

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Thu 8/27

4:25 pm-1:28 pm

1 stop21h 03m

Montego Bay Sangster Intl

Mon 8/31

5:13 pm-11:37 am

2 stops18h 24m

$364

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 6/2

6:30 am-3:10 pm

1 stop8h 40m

Montego Bay Sangster Intl

Sat 6/6

4:12 pm-11:26 pm

1 stop7h 14m

$371

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 5/15

6:00 am-3:10 pm

1 stop9h 10m

Montego Bay Sangster Intl

Mon 5/18

4:12 pm-11:44 pm

1 stop7h 32m

$406

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 6/9

6:30 am-3:10 pm

1 stop8h 40m

Montego Bay Sangster Intl

Fri 6/12

4:12 pm-11:26 pm

1 stop7h 14m

$408

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 5/19

8:10 pm-1:30 pm

1 stop17h 20m

Montego Bay Sangster Intl

Tue 6/9

4:12 pm-11:26 pm

1 stop7h 14m

$412

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/2

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 $518). 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 Air Canada can get you from Wisconsin to Jamaica in just under 6h 30m. Your travel time can differ by up to 37h 03m. Airlines will cover a distance of 1724 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 $180. 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, 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 $518). 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

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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
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Newark to Montego Bay flights
LaGuardia to Punta Cana flights
Dulles Intl to Punta Cana flights
Atlanta to Montego Bay flights
Atlanta to Punta Cana flights
Boston to Oranjestad flights
Newark to Simpson Bay flights
LaGuardia to Santo Domingo flights
Raleigh to Luis Munoz Marin Intl flights
LaGuardia to Santiago de los Caballeros flights
John F Kennedy Intl to Kingston flights
Newark to Nassau flights
Orlando to Punta Cana flights
Miami to Punta Cana flights
Fort Lauderdale to Punta Cana flights
Midway to Luis Munoz Marin Intl flights
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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 May 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$336Average$698FlexibilityNo cancel feeOn-time71%
DeltaCheapest$362Average$579FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$571Average$716FlexibilityNo cancel feeOn-time63%

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