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Jamaica

$125+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
May 25 — Jun 11
Mon 5/25
Mon 6/1
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 April 25, 2026.

This Expedia deal was found by Cheapflights users on 4/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/44:28 pm
ORD
-
MBJ
1 stop19h 43m
Frontier
Thu 5/71:16 pm
MBJ
-
ORD
1 stop18h 39m
Frontier
Deal found 4/20$307
This FlightHub deal was found by Cheapflights users on 4/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:55 am
ORD
-
MBJ
1 stop29h 16m
Frontier
Mon 5/111:16 pm
MBJ
-
ORD
1 stop18h 39m
Frontier
Deal found 4/21$317
This American Airlines deal was found by Cheapflights users on 4/21. 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.
Tue 11/38:05 am
ORD
-
MBJ
Nonstop4h 09m
American Airlines
Tue 11/102:19 pm
MBJ
-
ORD
Nonstop4h 41m
American Airlines
Deal found 4/21$318
This Priceline deal was found by Cheapflights users on 4/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:55 am
ORD
-
MBJ
1 stop29h 16m
Frontier
Fri 5/151:16 pm
MBJ
-
ORD
2 stops29h 28m
Frontier
Deal found 4/21$320
This American Airlines deal was found by Cheapflights users on 4/20. 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.
Wed 10/288:05 am
ORD
-
MBJ
Nonstop4h 01m
American Airlines
Mon 11/22:19 pm
MBJ
-
ORD
Nonstop4h 41m
American Airlines
Deal found 4/20$323
This American Airlines deal was found by Cheapflights users on 4/20. 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.
Wed 4/225:00 am
ORD
-
MBJ
1 stop6h 24m
American Airlines
Thu 4/231:15 pm
MBJ
-
ORD
Nonstop4h 40m
American Airlines
Deal found 4/20$327
This American Airlines deal was found by Cheapflights users on 4/21. 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.
Sun 8/168:30 am
ORD
-
MBJ
Nonstop4h 01m
American Airlines
Thu 8/205:13 pm
MBJ
-
ORD
1 stop7h 18m
American Airlines
Deal found 4/21$328
This United Airlines deal was found by Cheapflights users on 4/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:00 am
ORD
-
MBJ
1 stop9h 10m
United Airlines
Wed 4/294:12 pm
MBJ
-
ORD
1 stop16h 35m
United Airlines
Deal found 4/20$332
This American Airlines deal was found by Cheapflights users on 4/21. 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.
Tue 12/158:10 am
ORD
-
MBJ
Nonstop4h 10m
American Airlines
Sun 12/2711:07 am
MBJ
-
ORD
1 stop14h 36m
American Airlines
Deal found 4/21$333
This American Airlines deal was found by Cheapflights users on 4/20. 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 7/136:00 pm
ORD
-
MBJ
1 stop19h 09m
American Airlines
Sat 7/182:25 pm
MBJ
-
ORD
Nonstop4h 53m
American Airlines
Deal found 4/20$336
This American Airlines deal was found by Cheapflights users on 4/23. 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 6/15:00 am
MKE
-
MBJ
1 stop8h 30m
American Airlines
Fri 6/52:30 pm
MBJ
-
MKE
1 stop17h 12m
American Airlines
Deal found 4/23$352
This United Airlines deal was found by Cheapflights users on 4/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/98:25 pm
MSN
-
MBJ
1 stop16h 21m
United Airlines
Sat 11/142:48 pm
MBJ
-
MSN
1 stop7h 06m
United Airlines
Deal found 4/21$352

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 April 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$307
(Expedia)

One-way from

$125
(Priceline)

Popular in

June

Cheapest in

January

Average price

$614
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 April 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 April 25, 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

Sat 5/2

5:30 am-1:30 pm

1 stop8h 00m

Montego Bay Sangster Intl

Tue 5/5

2:40 pm-7:53 am

1 stop17h 13m

$332

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

3:00 pm-11:47 pm

1 stop8h 47m

$352

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Thu 8/27

7:37 pm-1:28 pm

2 stops17h 51m

Montego Bay Sangster Intl

Mon 8/31

5:13 pm-11:37 am

2 stops18h 24m

$357

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Mon 6/1

6:00 am-1:55 pm

1 stop7h 55m

Montego Bay Sangster Intl

Sat 6/6

5:17 pm-12:50 pm

2 stops19h 33m

$357

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Tue 7/14

6:30 am-1:23 pm

1 stop6h 53m

Montego Bay Sangster Intl

Tue 7/28

5:17 pm-12:34 pm

2 stops19h 17m

$357

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 6/10

6:30 am-3:10 pm

1 stop8h 40m

Montego Bay Sangster Intl

Fri 9/18

12:52 pm-11:16 pm

1 stop10h 24m

$405
Quickest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 7/15

6:30 am-3:10 pm

1 stop8h 40m

Montego Bay Sangster Intl

Sat 7/18

1:52 pm-6:15 pm

Nonstop4h 23m

$427

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 5/18

9:56 pm-1:30 pm

1 stop15h 34m

Montego Bay Sangster Intl

Sat 5/23

1:52 pm-6:15 pm

Nonstop4h 23m

$440

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 7/12

6:30 am-3:26 pm

1 stop8h 56m

Montego Bay Sangster Intl

Sat 7/18

1:52 pm-6:15 pm

Nonstop4h 23m

$442

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 6/27

8:40 am-12:50 pm

Nonstop4h 10m

Montego Bay Sangster Intl

Thu 7/9

2:40 pm-12:45 am

1 stop10h 05m

$448

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/24

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 7h 55m. Your travel time can differ by up to 14h 15m. 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 $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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
Newark to Santiago de los Caballeros flights
John F Kennedy Intl to Santiago de los Caballeros flights
John F Kennedy Intl to Santo Domingo flights
Orlando to Luis Munoz Marin Intl flights
LaGuardia to Luis Munoz Marin Intl flights
John F Kennedy Intl to Punta Cana flights
Philadelphia to Luis Munoz Marin Intl flights
Newark to Santo Domingo flights
Dallas/Fort Worth to Luis Munoz Marin Intl flights
Newark to Punta Cana flights
Boston to Luis Munoz Marin Intl flights
O'Hare Intl to Luis Munoz Marin Intl flights
Newark to Oranjestad flights
Dulles Intl to Luis Munoz Marin Intl flights
Baltimore to Luis Munoz Marin Intl flights
John F Kennedy Intl to Oranjestad flights
Atlanta to Luis Munoz Marin Intl flights
Newark to Montego Bay flights
John F Kennedy Intl to Montego Bay flights
Hobby to Luis Munoz Marin Intl flights
Tampa to Luis Munoz Marin Intl flights
Reagan-National to Luis Munoz Marin Intl flights
Hartford to Luis Munoz Marin Intl flights
Fort Lauderdale to Luis Munoz Marin Intl flights
George Bush Intcntl to Luis Munoz Marin Intl flights
LaGuardia to Punta Cana flights
Atlanta to Punta Cana flights
Dulles Intl to Punta Cana flights
LaGuardia to Santiago de los Caballeros flights
Newark to Nassau flights
Miami to Luis Munoz Marin Intl flights
Raleigh to Luis Munoz Marin Intl flights
LaGuardia to Santo Domingo flights
John F Kennedy Intl to Kingston flights
Boston to Oranjestad flights
Orlando to Punta Cana flights
LaGuardia to Montego Bay flights
Newark to Simpson Bay flights
Atlanta to Montego Bay flights
Baltimore to Punta Cana flights
Boston to Punta Cana flights
John F Kennedy Intl to Port of Spain flights
Midway to Luis Munoz Marin Intl flights
John F Kennedy Intl to Nassau flights
Dallas/Fort Worth to Punta Cana 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 April 25, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$277Average$640FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$336Average$702FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$571Average$716FlexibilityNo cancel feeOn-time63%

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