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Jamaica

$116+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Dec 30 — Jan 61
Tue 12/30
Tue 1/6
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 November 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$339
(Kiwi.com)

One-way from

$116
(Priceline)

Popular in

June

Cheapest in

March

Average price

$588
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 ($70 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 November 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1812:39 pmORD - MBJ
1 stop19h 20mMultiple Airlines
Mon 12/221:05 pmMBJ - ORD
1 stop12h 25mMultiple Airlines
Deal found 11/28$351
This Frontier deal was found by Cheapflights users on 11/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:11 amORD - MBJ
1 stop8h 40mFrontier
Thu 12/253:47 pmMBJ - ORD
1 stop7h 37mFrontier
Deal found 11/27$357
This Frontier deal was found by Cheapflights users on 11/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:00 amORD - MBJ
1 stop7h 29mFrontier
Fri 12/263:47 pmMBJ - ORD
1 stop7h 37mFrontier
Deal found 11/27$358
This Frontier deal was found by Cheapflights users on 11/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:00 amORD - MBJ
1 stop7h 29mFrontier
Sat 12/273:34 pmMBJ - ORD
1 stop8h 12mFrontier
Deal found 11/28$359
This Kiwi.com deal was found by Cheapflights users on 11/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/174:01 pmORD - MBJ
1 stop21h 28mMultiple Airlines
Tue 12/231:05 pmMBJ - ORD
1 stop12h 25mMultiple Airlines
Deal found 11/28$360
This Kiwi.com deal was found by Cheapflights users on 11/29. 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.
Thu 12/1812:39 pmORD - MBJ
1 stop19h 20mFrontier
Sun 12/214:16 pmMBJ - ORD
1 stop27h 17mFrontier
Deal found 11/29$361
This Kiwi.com deal was found by Cheapflights users on 11/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/174:01 pmORD - MBJ
1 stop21h 28mMultiple Airlines
Mon 12/221:05 pmMBJ - ORD
1 stop12h 25mMultiple Airlines
Deal found 11/28$362
This Frontier deal was found by Cheapflights users on 11/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:11 amORD - MBJ
1 stop8h 40mFrontier
Sun 12/214:16 pmMBJ - ORD
2 stops17h 31mFrontier
Deal found 11/27$364
This Kiwi.com deal was found by Cheapflights users on 11/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/25:00 amORD - MBJ
1 stop6h 02mSpirit Airlines
Thu 12/41:05 pmMBJ - ORD
1 stop7h 56mSpirit Airlines
Deal found 11/28$365
This Frontier deal was found by Cheapflights users on 11/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:11 amORD - MBJ
1 stop8h 40mFrontier
Thu 12/183:47 pmMBJ - ORD
1 stop7h 37mFrontier
Deal found 11/28$366
This Kiwi.com deal was found by Cheapflights users on 11/29. 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.
Wed 12/247:34 pmMSP - MBJ
2 stops17h 55mFrontier
Wed 12/313:49 pmMBJ - MSP
1 stop19h 40mFrontier
Deal found 11/29$458
This Mytrip deal was found by Cheapflights users on 11/29. 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.
Wed 12/247:34 pmMSP - MBJ
2 stops17h 55mFrontier
Sun 12/284:16 pmMBJ - MSP
2 stops29h 58mFrontier
Deal found 11/29$463

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 November 30, 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

Sun 1/25

8:36 pm-12:02 pm

2 stops14h 26m

Montego Bay Sangster Intl

Thu 1/29

12:57 pm-7:38 pm

1 stop7h 41m

$357

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 1/29

2:52 pm-12:12 pm

1 stop20h 20m

Kingston Norman Manley

Fri 2/6

1:17 pm-9:03 pm

1 stop8h 46m

$377

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 2/17

10:22 am-3:28 pm

Nonstop4h 06m

Montego Bay Sangster Intl

Tue 2/24

4:38 pm-8:15 pm

Nonstop4h 37m

$393

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 2/3

5:30 am-12:54 pm

1 stop6h 24m

Montego Bay Sangster Intl

Tue 2/17

4:44 pm-1:22 pm

2 stops21h 38m

$412

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 1/6

1:55 pm-12:54 pm

2 stops21h 59m

Montego Bay Sangster Intl

Wed 1/14

12:38 pm-11:59 pm

1 stop12h 21m

$412

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 1/5

1:55 pm-11:13 am

2 stops20h 18m

Montego Bay Sangster Intl

Wed 1/14

2:19 pm-1:08 pm

2 stops23h 49m

$412

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 2/17

5:15 am-12:02 pm

1 stop5h 47m

Montego Bay Sangster Intl

Tue 2/24

1:00 pm-2:28 pm

3 stops26h 28m

$423

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Tue 1/13

5:00 am-2:03 pm

1 stop8h 03m

Kingston Norman Manley

Tue 1/20

1:39 pm-11:08 pm

1 stop10h 29m

$437

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 1/23

5:30 am-12:54 pm

1 stop6h 24m

Montego Bay Sangster Intl

Wed 1/28

12:38 pm-7:21 pm

1 stop7h 43m

$437

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 12/8

5:30 am-1:04 pm

1 stop6h 34m

Montego Bay Sangster Intl

Sat 12/13

1:55 pm-9:39 pm

1 stop8h 44m

$437

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/30

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 $637). 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 November 30, 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?

    Spirit Airlines, American Airlines, and Delta can get you from Wisconsin to Jamaica in just under 4h 06m. Your travel time can differ by up to 10h 23m. 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. Arajet flights start at $128 while deals on Frontier start at $210 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 $637). 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.
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Top 5 airlines flying from Wisconsin to Jamaica

Discover the top 5 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 November 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$490Average$636FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$514Average$656FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$529Average$747FlexibilityNo cancel feeOn-time69%
Sun Country AirCheapest$540Average$540FlexibilityNo cancel feeOn-time83%
SouthwestCheapest$571Average$723FlexibilityNo cancel feeOn-time63%

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