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Jamaica

$114+ 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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
dic. 6 — dic. 131
sáb. 12/6
sáb. 12/13
1 adult, Economy
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Cheap flight deals from Wisconsin to Jamaica

Keep the following information in mind while searching for Wisconsin to Jamaica flight deals. Data was last updated noviembre 6, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$346
(Mytrip)

One-way from

$114
(Cheapflightsfares)

Popular in

June

Cheapest in

March

Average price

$589
Provider with most accurate pricing for Milwaukee-Mitchell-Montego Bay Sangster Intl flight deals.
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Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Montego Bay Sangster Intl flights.
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From Wisconsin to Jamaica
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One-way flight from Wisconsin to Jamaica
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Highest demand for flights based on searches. 10% potential increase in price ($71 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find 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 noviembre 6, 2025.

This Mytrip deal was found by Cheapflights users on 11/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/25:00 amORD - KIN
1 stop7h 21mSpirit Airlines
mar. 12/91:19 pmKIN - ORD
1 stop7h 42mSpirit Airlines
Deal found 11/4$346
This Mytrip deal was found by Cheapflights users on 11/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/165:10 amORD - MBJ
1 stop5h 52mSpirit Airlines
sáb. 11/221:07 pmMBJ - ORD
2 stops20h 54mSpirit Airlines
Deal found 11/6$355
This United Airlines deal was found by Cheapflights users on 11/6. 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.
sáb. 11/298:42 amORD - MBJ
Nonstop4h 04mUnited Airlines
mié. 12/32:48 pmMBJ - ORD
Nonstop4h 25mUnited Airlines
Deal found 11/6$356
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/73:20 pmORD - KIN
1 stop19h 54mMultiple Airlines
sáb. 12/131:19 pmKIN - ORD
1 stop7h 42mMultiple Airlines
Deal found 11/5$357
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/56:11 amORD - MBJ
1 stop8h 27mFrontier
lun. 12/83:31 pmMBJ - ORD
1 stop24h 41mFrontier
Deal found 11/4$360
This Mytrip deal was found by Cheapflights users on 11/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/25:00 amORD - KIN
1 stop7h 21mSpirit Airlines
vie. 12/51:19 pmKIN - ORD
1 stop7h 42mSpirit Airlines
Deal found 11/4$362
This Delta deal was found by Cheapflights users on 11/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/276:45 amORD - MBJ
2 stops8h 49mDelta
mié. 12/35:58 pmMBJ - ORD
2 stops15h 06mDelta
Deal found 11/6$363
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/93:26 pmORD - KIN
1 stop19h 48mSpirit Airlines
vie. 12/121:19 pmKIN - ORD
1 stop11h 50mSpirit Airlines
Deal found 11/6$364
This American Airlines deal was found by Cheapflights users on 11/6. 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.
dom. 11/3012:52 amORD - MBJ
1 stop12h 58mAmerican Airlines
dom. 12/72:30 pmMBJ - ORD
Nonstop4h 47mAmerican Airlines
Deal found 11/6$366
This American Airlines deal was found by Cheapflights users on 11/6. 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.
sáb. 11/298:15 amORD - MBJ
Nonstop3h 59mAmerican Airlines
mié. 12/34:51 pmMBJ - ORD
1 stop7h 48mAmerican Airlines
Deal found 11/6$367
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/165:00 amORD - MBJ
1 stop6h 10mSpirit Airlines
mar. 12/231:05 pmMBJ - ORD
1 stop6h 34mSpirit Airlines
Deal found 11/4$368
This Delta deal was found by Cheapflights users on 11/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/285:23 amORD - MBJ
1 stop10h 11mDelta
mié. 12/31:55 pmMBJ - ORD
1 stop8h 44mDelta
Deal found 11/6$371

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 noviembre 6, 2025.
Use the filters below to find and compare flights from Wisconsin to Jamaica that are best for you.

Fly from

Wisconsin

Fly to

Jamaica

Route

Depart

Return

Price

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

mar. 12/16

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

mar. 12/23

2:48 pm-6:13 pm

Nonstop4h 25m

$356

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

vie. 1/30

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

mar. 2/10

2:48 pm-6:13 pm

Nonstop4h 25m

$357

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

vie. 11/28

10:15 am-3:28 pm

Nonstop4h 13m

Montego Bay Sangster Intl

mié. 12/3

4:51 pm-9:08 am

1 stop17h 17m

$367

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

vie. 1/23

7:05 am-3:20 pm

1 stop7h 15m

Montego Bay Sangster Intl

mié. 1/28

12:38 pm-7:21 pm

1 stop7h 43m

$371

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

vie. 1/30

5:33 am-3:20 pm

1 stop8h 47m

Montego Bay Sangster Intl

mar. 2/10

12:38 pm-11:57 pm

1 stop12h 19m

$371

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

vie. 11/28

5:23 am-4:34 pm

1 stop10h 11m

Montego Bay Sangster Intl

mié. 12/3

1:55 pm-9:39 pm

1 stop8h 44m

$371

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

dom. 2/1

5:33 am-3:20 pm

1 stop8h 47m

Montego Bay Sangster Intl

vie. 2/6

12:38 pm-6:49 pm

1 stop7h 11m

$371

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

lun. 1/5

5:33 am-12:54 pm

1 stop6h 21m

Montego Bay Sangster Intl

vie. 1/9

12:38 pm-11:57 pm

1 stop12h 19m

$371

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

mar. 2/3

5:33 am-12:54 pm

1 stop6h 21m

Montego Bay Sangster Intl

dom. 2/8

12:38 pm-7:35 pm

1 stop7h 57m

$371

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

sáb. 12/6

6:00 am-2:39 pm

1 stop7h 39m

Montego Bay Sangster Intl

mié. 12/10

2:29 pm-10:46 pm

1 stop9h 17m

$371

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

Showing 1-10 of 60 results
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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, October is the cheapest month in which you can book a flight from Wisconsin to Jamaica (average of $312). Flying from Wisconsin to Jamaica in July is currently the most expensive (average of $595). 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.

What is the cheapest time of day to fly from WI to JM?

Find hourly flight availability from Wisconsin to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated noviembre 6, 2025.

One of the essential ways to save on airfare from Wisconsin to Jamaica is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight at noon could potentially save you up to 40% on airfare.

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 4h 04m. Your travel time can differ by up to 3h 11m. 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 Spirit Airlines, which is currently one of the cheapest options available, starting at $122. United Airlines flights start at $157 while deals on Delta start at $178 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, October is the cheapest month in which you can book a flight from Wisconsin to Jamaica (average of $312). Flying from Wisconsin to Jamaica in July is currently the most expensive (average of $595). 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.
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Top 6 airlines flying from Wisconsin to Jamaica

Discover the top 6 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 noviembre 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$328Average$403FlexibilityNo cancel feeOn-time65%
DeltaCheapest$499Average$637FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$514Average$654FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$529Average$745FlexibilityNo cancel feeOn-time69%
Sun Country AirCheapest$540Average$540FlexibilityNo cancel feeOn-time83%
SouthwestCheapest$571Average$720FlexibilityNo cancel feeOn-time63%

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