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Jamaica

$99+ 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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$342
(Cheapflightsfares)

One-way from

$99
(Cheapflightsfares)

Popular in

June

Cheapest in

March

Average price

$606
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. 9% potential increase in price ($66 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 17, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 11/115:59 pmORD - KIN
1 stop17h 14mSpirit Airlines
Wed 12/31:28 pmKIN - ORD
1 stop8h 32mSpirit Airlines
Deal found 9/15$342
This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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.
Sat 11/85:59 pmORD - KIN
1 stop17h 14mSpirit Airlines
Sat 11/151:28 pmKIN - ORD
1 stop8h 32mSpirit Airlines
Deal found 9/17$349
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Fri 10/245:43 pmMSP - MBJ
1 stop21h 03mFrontier
Thu 10/304:30 pmMBJ - MSP
1 stop18h 04mFrontier
Deal found 9/16$360
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
Thu 10/236:18 pmORD - KIN
2 stops16h 51mSpirit Airlines
Mon 10/2712:14 pmKIN - ORD
1 stop12h 49mSpirit Airlines
Deal found 9/15$369
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
Sat 10/116:00 pmORD - KIN
2 stops17h 09mSpirit Airlines
Sun 10/1912:14 pmKIN - ORD
1 stop11h 31mSpirit Airlines
Deal found 9/15$373
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Sat 11/88:42 amORD - MBJ
Nonstop4h 04mUnited Airlines
Sat 11/152:48 pmMBJ - ORD
Nonstop4h 25mUnited Airlines
Deal found 9/16$376
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 10/155:05 amORD - MBJ
1 stop5h 55mSpirit Airlines
Sat 10/1812:09 pmMBJ - ORD
1 stop11h 36mSpirit Airlines
Deal found 9/15$377
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
Thu 11/135:59 pmORD - MBJ
1 stop17h 06mSpirit Airlines
Sun 11/161:12 pmMBJ - ORD
1 stop11h 30mSpirit Airlines
Deal found 9/15$378
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 11/165:05 amORD - MBJ
1 stop6h 00mSpirit Airlines
Mon 11/171:12 pmMBJ - ORD
1 stop8h 48mSpirit Airlines
Deal found 9/15$379
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/148:44 amORD - MBJ
Nonstop4h 01mAmerican Airlines
Sat 10/182:05 pmMBJ - ORD
1 stop17h 20mAmerican Airlines
Deal found 9/15$380
This American Airlines deal was found by Cheapflights users on 9/15. 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 11/25:00 amORD - MBJ
1 stop6h 54mAmerican Airlines
Thu 11/63:13 pmMBJ - ORD
Nonstop4h 41mAmerican Airlines
Deal found 9/15$381
This Mytrip deal was found by Cheapflights users on 9/15. 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.
Thu 10/307:43 pmORD - KIN
1 stop15h 26mSpirit Airlines
Thu 11/61:28 pmKIN - ORD
1 stop8h 32mSpirit Airlines
Deal found 9/15$381

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 September 17, 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

Mon 11/10

10:15 am-3:28 pm

Nonstop4h 13m

Montego Bay Sangster Intl

Sat 11/15

2:14 pm-5:50 pm

Nonstop4h 36m

$376

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 11/8

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Sat 11/15

2:48 pm-6:13 pm

Nonstop4h 25m

$376

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 11/30

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Sat 12/6

2:48 pm-6:13 pm

Nonstop4h 25m

$376

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 11/28

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Wed 12/3

2:48 pm-6:13 pm

Nonstop4h 25m

$376

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 10/28

6:02 am-1:29 pm

1 stop7h 27m

Montego Bay Sangster Intl

Tue 11/4

2:48 pm-6:13 pm

Nonstop4h 25m

$378

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 10/14

8:44 am-12:45 pm

Nonstop4h 01m

Montego Bay Sangster Intl

Tue 10/21

4:05 pm-10:54 pm

1 stop6h 49m

$380

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 11/2

5:18 am-2:59 pm

1 stop8h 41m

Montego Bay Sangster Intl

Sat 11/8

2:14 pm-5:50 pm

Nonstop4h 36m

$381

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 12/6

6:00 am-2:29 pm

1 stop7h 29m

Montego Bay Sangster Intl

Sat 12/13

2:48 pm-6:13 pm

Nonstop4h 25m

$381

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 11/24

8:00 am-4:35 pm

1 stop7h 35m

Montego Bay Sangster Intl

Mon 12/1

5:45 pm-12:05 pm

1 stop19h 20m

$386

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 10/31

8:44 am-12:45 pm

Nonstop4h 01m

Montego Bay Sangster Intl

Fri 11/7

1:40 pm-7:36 pm

1 stop6h 56m

$386

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

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, January is the cheapest month in which you can book a flight from Wisconsin to Jamaica (average of $403). Flying from Wisconsin to Jamaica in July is currently the most expensive (average of $561). 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 September 17, 2025.

When flying from Wisconsin to Jamaica, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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?

    American Airlines, United Airlines, and Spirit Airlines can get you from Wisconsin to Jamaica in just under 4h 04m. Your travel time can differ by up to 13h 10m. 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.

  • 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, January is the cheapest month in which you can book a flight from Wisconsin to Jamaica (average of $403). Flying from Wisconsin to Jamaica in July is currently the most expensive (average of $561). 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.
John F Kennedy Intl to Luis Munoz Marin Intl flights
Newark to Luis Munoz Marin Intl flights
LaGuardia to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santo Domingo flights
John F Kennedy Intl to Santiago de los Caballeros flights
Dulles Intl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Punta Cana flights
Orlando to Luis Munoz Marin Intl flights
Newark to Oranjestad flights
Newark to Santiago de los Caballeros flights
Boston to Luis Munoz Marin Intl flights
Atlanta to Luis Munoz Marin Intl flights
John F Kennedy Intl to Montego Bay flights
Baltimore to Luis Munoz Marin Intl flights
Newark to Santo Domingo flights
Reagan-National to Luis Munoz Marin Intl flights
O'Hare Intl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Oranjestad flights
Dallas/Fort Worth to Luis Munoz Marin Intl flights
Newark to Punta Cana flights
Newark to Montego Bay flights
Boston to Oranjestad flights
Philadelphia to Luis Munoz Marin Intl flights
John F Kennedy Intl to Port of Spain flights
Fort Lauderdale to Luis Munoz Marin Intl flights
Tampa to Luis Munoz Marin Intl flights
LaGuardia to Punta Cana flights
Miami to Luis Munoz Marin Intl flights
Newark to Simpson Bay flights
Hartford to Luis Munoz Marin Intl flights
John F Kennedy Intl to Kingston flights
LaGuardia to Santo Domingo flights
Atlanta to Montego Bay flights
Hobby to Luis Munoz Marin Intl flights
LaGuardia to Montego Bay flights
LaGuardia to Oranjestad flights
Dulles Intl to Punta Cana flights
Boston to Punta Cana flights
John F Kennedy Intl to Simpson Bay flights
Raleigh to Luis Munoz Marin Intl flights
George Bush Intcntl to Luis Munoz Marin Intl flights
Newark to Saint Thomas Island flights
John F Kennedy Intl to Willemstad flights
Newark to Nassau flights
O'Hare Intl to Punta Cana flights
Midway to Luis Munoz Marin Intl flights
John F Kennedy Intl to Nassau flights
Detroit to Luis Munoz Marin Intl flights
LaGuardia to Santiago de los Caballeros flights
John F Kennedy Intl to Saint Thomas Island flights

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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$328Average$385FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$443Average$720FlexibilityNo cancel feeOn-time69%
DeltaCheapest$490Average$661FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$514Average$653FlexibilityNo cancel feeOn-time71%
Sun Country AirCheapest$540Average$540FlexibilityNo cancel feeOn-time83%
SouthwestCheapest$565Average$713FlexibilityNo cancel feeOn-time63%

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