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Jamaica

$104+ 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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
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 December 23, 2025.

This Expedia deal was found by Cheapflights users on 12/20. 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.
Wed 12/246:05 amORD - MBJ
1 stop7h 24mFrontier
Wed 12/313:49 pmMBJ - ORD
1 stop7h 35mFrontier
Deal found 12/20$501
This Super.com deal was found by Cheapflights users on 12/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:00 amORD - MBJ
1 stop7h 29mFrontier
Wed 12/313:49 pmMBJ - ORD
1 stop7h 35mFrontier
Deal found 12/21$509
This Frontier deal was found by Cheapflights users on 12/22. 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 12/276:10 amORD - MBJ
1 stop7h 19mFrontier
Wed 12/313:49 pmMBJ - ORD
1 stop7h 35mFrontier
Deal found 12/22$542
This Frontier deal was found by Cheapflights users on 12/22. 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.
Thu 12/256:00 amORD - MBJ
1 stop7h 29mFrontier
Tue 12/303:47 pmMBJ - ORD
1 stop7h 37mFrontier
Deal found 12/22$546
This Delta deal was found by Cheapflights users on 12/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/227:59 pmORD - MBJ
1 stop14h 06mDelta
Thu 12/2512:30 pmMBJ - ORD
1 stop12h 32mDelta
Deal found 12/21$551
This Delta deal was found by Cheapflights users on 12/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:45 amORD - MBJ
1 stop12h 56mDelta
Wed 12/318:00 amMBJ - ORD
2 stops13h 36mDelta
Deal found 12/21$556
This American Airlines deal was found by Cheapflights users on 12/22. 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.
Thu 12/259:35 amORD - MBJ
Nonstop4h 16mAmerican Airlines
Tue 12/303:51 pmMBJ - ORD
Nonstop4h 38mAmerican Airlines
Deal found 12/22$561
This American Airlines deal was found by Cheapflights users on 12/21. 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 12/238:25 amORD - MBJ
1 stop7h 35mAmerican Airlines
Wed 12/313:51 pmMBJ - ORD
Nonstop4h 38mAmerican Airlines
Deal found 12/21$566
This Expedia deal was found by Cheapflights users on 12/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/226:00 amORD - MBJ
1 stop7h 29mMultiple Airlines
Thu 12/252:15 pmMBJ - ORD
1 stop28h 33mMultiple Airlines
Deal found 12/21$570
This KAYAK deal was found by Cheapflights users on 12/22. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:00 amORD - KIN
1 stop6h 14mSpirit Airlines
Fri 1/91:17 pmKIN - ORD
1 stop8h 46mSpirit Airlines
Deal found 12/22$592
This Delta deal was found by Cheapflights users on 12/22. 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 12/299:08 amMSP - MBJ
Nonstop4h 42mDelta
Mon 1/54:05 pmMBJ - MSP
Nonstop5h 02mDelta
Deal found 12/22$657
This Delta deal was found by Cheapflights users on 12/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/299:08 amMSP - MBJ
Nonstop4h 42mDelta
Fri 1/24:15 pmMBJ - MSP
Nonstop5h 00mDelta
Deal found 12/21$665

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 December 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$333
(Expedia)

One-way from

$104
(Cheapflightsfares)

Popular in

June

Cheapest in

October

Average price

$697
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. 8% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 23, 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

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Mon 1/26

5:15 am-12:12 pm

1 stop5h 57m

Kingston Norman Manley

Fri 1/30

1:17 pm-11:22 am

1 stop23h 05m

$333

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 2/10

10:07 am-12:02 pm

2 stops24h 55m

Montego Bay Sangster Intl

Sun 2/22

1:00 pm-11:47 pm

1 stop11h 47m

$378

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 2/18

6:02 pm-12:15 pm

2 stops17h 13m

Kingston Norman Manley

Sun 2/22

1:17 pm-11:22 am

1 stop23h 05m

$383

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 2/8

8:36 pm-12:02 pm

2 stops14h 26m

Montego Bay Sangster Intl

Sun 2/22

1:00 pm-11:47 pm

1 stop11h 47m

$394

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 2/6

8:36 pm-12:02 pm

2 stops14h 26m

Montego Bay Sangster Intl

Sun 2/22

1:00 pm-11:47 pm

1 stop11h 47m

$394

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 3/18

8:42 am-12:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Tue 3/24

1:48 pm-6:13 pm

Nonstop4h 25m

$399

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 2/10

10:07 am-12:02 pm

2 stops24h 55m

Montego Bay Sangster Intl

Wed 2/25

1:00 pm-9:22 am

2 stops21h 22m

$422

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 1/15

8:43 pm-12:12 pm

1 stop14h 29m

Kingston Norman Manley

Mon 1/19

1:17 pm-11:47 am

2 stops23h 30m

$422

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Mon 2/9

5:15 am-12:12 pm

1 stop5h 57m

Kingston Norman Manley

Thu 2/19

1:17 pm-7:54 am

2 stops19h 37m

$423

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 3/16

8:42 am-12:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Sun 3/22

1:48 pm-6:13 pm

Nonstop4h 25m

$429

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

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 December 23, 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 in the afternoon could potentially save you up to 36% 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 2h 18m. 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 Alaska Airlines, which is currently one of the cheapest options available, starting at $228. Delta flights start at $236 while deals on United Airlines start at $250 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.
John F Kennedy Intl to Luis Munoz Marin Intl flights
Newark to Luis Munoz Marin Intl flights
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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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$470Average$634FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$512Average$641FlexibilityNo cancel feeOn-time71%
Sun Country AirCheapest$540Average$541FlexibilityNo cancel feeOn-time83%
United AirlinesCheapest$563Average$759FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$571Average$727FlexibilityNo cancel feeOn-time63%

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