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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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$353
(Kiwi.com)

One-way from

$114
(Kiwi.com)

Popular in

June

Cheapest in

March

Average price

$560
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 October 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 October 30, 2025.

This Priceline deal was found by Cheapflights users on 10/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/145:00 amORD - MBJ
1 stop6h 10mSpirit Airlines
Sun 12/211:05 pmMBJ - ORD
1 stop12h 25mSpirit Airlines
Deal found 10/30$354
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 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
Fri 12/191:05 pmMBJ - ORD
1 stop6h 34mSpirit Airlines
Deal found 10/30$355
This United Airlines deal was found by Cheapflights users on 10/30. 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.
Tue 12/28:42 amORD - MBJ
Nonstop4h 04mUnited Airlines
Fri 12/192:48 pmMBJ - ORD
Nonstop4h 25mUnited Airlines
Deal found 10/30$356
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/205:00 amORD - MBJ
1 stop6h 02mSpirit Airlines
Sun 11/231:07 pmMBJ - ORD
1 stop11h 06mSpirit Airlines
Deal found 10/29$360
This American Airlines deal was found by Cheapflights users on 10/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/17:17 pmORD - MBJ
1 stop14h 00mAmerican Airlines
Fri 12/53:12 pmMBJ - ORD
Nonstop4h 47mAmerican Airlines
Deal found 10/29$361
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/15:23 amORD - MBJ
1 stop10h 11mDelta
Thu 12/111:55 pmMBJ - ORD
2 stops23h 15mDelta
Deal found 10/29$362
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Tue 12/25:00 amORD - MBJ
1 stop6h 02mMultiple Airlines
Sun 12/712:13 pmMBJ - ORD
1 stop25h 39mMultiple Airlines
Deal found 10/29$363
This Cheapflightsfares deal was found by Cheapflights users on 10/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/45:10 amORD - MBJ
1 stop5h 52mSpirit Airlines
Sun 11/91:07 pmMBJ - ORD
1 stop12h 20mSpirit Airlines
Deal found 10/29$365
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/193:26 pmORD - MBJ
1 stop19h 36mSpirit Airlines
Thu 11/271:07 pmMBJ - ORD
1 stop8h 20mSpirit Airlines
Deal found 10/29$366
This American Airlines deal was found by Cheapflights users on 10/30. 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.
Sat 12/1310:15 amORD - MBJ
Nonstop4h 07mAmerican Airlines
Thu 12/183:45 pmMBJ - ORD
1 stop8h 30mAmerican Airlines
Deal found 10/30$367
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Sun 12/143:20 pmORD - KIN
1 stop19h 54mMultiple Airlines
Wed 12/241:19 pmKIN - ORD
1 stop26h 43mMultiple Airlines
Deal found 10/28$368
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/125:10 amORD - KIN
1 stop5h 51mSpirit Airlines
Wed 11/191:06 pmKIN - ORD
1 stop12h 21mSpirit Airlines
Deal found 10/28$369

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 October 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 1/11

5:05 am-12:05 pm

1 stop6h 00m

Montego Bay Sangster Intl

Sun 1/25

1:12 pm-11:42 pm

1 stop11h 30m

$353

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 11/13

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Sun 11/16

2:48 pm-6:13 pm

Nonstop4h 25m

$356

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 12/2

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Sat 12/6

2:48 pm-6:13 pm

Nonstop4h 25m

$356

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 1/11

6:05 am-2:37 pm

1 stop7h 32m

Montego Bay Sangster Intl

Sun 1/25

2:48 pm-6:13 pm

Nonstop4h 25m

$361

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 1/7

6:05 am-2:37 pm

1 stop7h 32m

Montego Bay Sangster Intl

Wed 1/14

2:48 pm-6:13 pm

Nonstop4h 25m

$361

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 12/2

5:30 am-4:33 pm

1 stop10h 03m

Montego Bay Sangster Intl

Wed 12/10

1:55 pm-9:39 pm

1 stop8h 44m

$362

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 1/11

10:09 am-3:22 pm

Nonstop4h 13m

Montego Bay Sangster Intl

Sun 1/25

3:12 pm-6:51 pm

Nonstop4h 39m

$362

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 12/1

5:23 am-4:34 pm

1 stop10h 11m

Montego Bay Sangster Intl

Thu 12/11

1:55 pm-12:10 pm

2 stops23h 15m

$362

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 1/13

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Sat 1/17

3:55 pm-10:59 pm

1 stop8h 04m

$367

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 11/12

5:10 am-12:01 pm

1 stop5h 51m

Kingston Norman Manley

Wed 11/19

1:06 pm-12:27 am

1 stop12h 21m

$369

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

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 $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 October 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, United Airlines, and American Airlines can get you from Wisconsin to Jamaica in just under 4h 04m. Your travel time can differ by up to 11h 59m. 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 Frontier, which is currently one of the cheapest options available, starting at $153. Spirit Airlines flights start at $153 while deals on American Airlines start at $157 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$328Average$403FlexibilityNo cancel feeOn-time65%
DeltaCheapest$499Average$628FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$514Average$653FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$529Average$728FlexibilityNo cancel feeOn-time69%
Sun Country AirCheapest$540Average$540FlexibilityNo cancel feeOn-time83%
SouthwestCheapest$571Average$713FlexibilityNo cancel feeOn-time63%

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