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Jamaica

$98+ 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 9/20. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 August 14, 2025.

Round-trip from

$359
(FlightHub)

One-way from

$98
(Cheapflightsfares)

Popular in

June

Cheapest in

March

Average price

$623
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 ($65 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 14, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 8/12. 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 11/115:05 amORD - KIN
1 stop6h 08mSpirit Airlines
Wed 12/31:28 pmKIN - ORD
1 stop11h 14mSpirit Airlines
Deal found 8/12$358
This FlightHub deal was found by Cheapflights users on 8/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/95:05 amORD - KIN
1 stop5h 57mSpirit Airlines
Tue 9/1612:08 pmKIN - ORD
1 stop10h 40mSpirit Airlines
Deal found 8/12$359
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 10/212:25 pmMSP - MBJ
1 stop24h 20mFrontier
Sun 10/52:12 pmMBJ - MSP
1 stop18h 33mFrontier
Deal found 8/14$368
This Cheapflightsfares deal was found by Cheapflights users on 8/13. 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.
Mon 9/85:46 pmORD - KIN
2 stops17h 16mSpirit Airlines
Thu 9/1812:08 pmKIN - ORD
1 stop10h 40mSpirit Airlines
Deal found 8/13$369
This FlightHub deal was found by Cheapflights users on 8/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/125:05 amORD - KIN
1 stop6h 08mSpirit Airlines
Wed 12/31:28 pmKIN - ORD
1 stop11h 14mSpirit Airlines
Deal found 8/12$376
This Kiwi.com deal was found by Cheapflights users on 8/12. 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.
Sat 9/136:44 pmORD - KIN
1 stop16h 18mSpirit Airlines
Sat 9/2012:08 pmKIN - ORD
1 stop10h 40mSpirit Airlines
Deal found 8/12$379
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Sat 9/279:31 amMSP - MBJ
1 stop27h 10mMultiple Airlines
Sat 10/42:05 pmMBJ - MSP
1 stop18h 21mMultiple Airlines
Deal found 8/13$379
This FlightHub deal was found by Cheapflights users on 8/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/176:26 pmORD - KIN
2 stops16h 43mSpirit Airlines
Tue 10/2812:14 pmKIN - ORD
1 stop12h 49mSpirit Airlines
Deal found 8/13$380
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Sat 9/139:31 amMSP - MBJ
1 stop27h 10mMultiple Airlines
Sat 9/202:05 pmMBJ - MSP
1 stop21h 25mMultiple Airlines
Deal found 8/13$383
This Kiwi.com deal was found by Cheapflights users on 8/12. 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.
Mon 9/86:44 pmORD - KIN
1 stop16h 18mSpirit Airlines
Mon 9/1512:08 pmKIN - ORD
1 stop22h 44mSpirit Airlines
Deal found 8/12$385
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 9/129:31 amMSP - MBJ
1 stop27h 14mMultiple Airlines
Fri 9/192:12 pmMBJ - MSP
1 stop18h 14mMultiple Airlines
Deal found 8/13$385
This FlightHub deal was found by Cheapflights users on 8/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/46:44 pmORD - KIN
1 stop16h 18mSpirit Airlines
Sat 9/612:08 pmKIN - ORD
1 stop10h 40mSpirit Airlines
Deal found 8/12$387

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 August 14, 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

Wed 9/10

5:05 am-11:02 am

1 stop5h 57m

Kingston Norman Manley

Tue 9/16

12:08 pm-10:48 pm

1 stop10h 40m

$359

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 10/1

5:05 am-11:02 am

1 stop5h 57m

Kingston Norman Manley

Wed 10/8

12:14 pm-11:45 pm

1 stop11h 31m

$359

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Mon 9/8

5:05 am-11:02 am

1 stop5h 57m

Kingston Norman Manley

Thu 9/18

12:08 pm-10:48 pm

1 stop10h 40m

$359

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 9/10

5:05 am-11:02 am

1 stop5h 57m

Kingston Norman Manley

Thu 9/18

12:08 pm-10:48 pm

1 stop10h 40m

$359

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 9/11

5:05 am-11:02 am

1 stop5h 57m

Kingston Norman Manley

Tue 9/16

12:08 pm-10:48 pm

1 stop10h 40m

$359

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 9/11

5:05 am-11:02 am

1 stop5h 57m

Kingston Norman Manley

Thu 9/18

12:08 pm-10:48 pm

1 stop10h 40m

$359

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Tue 9/9

5:05 am-11:02 am

1 stop5h 57m

Kingston Norman Manley

Wed 9/17

12:08 pm-10:48 pm

1 stop10h 40m

$359

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Tue 9/9

5:05 am-11:02 am

1 stop5h 57m

Kingston Norman Manley

Tue 9/16

12:08 pm-10:48 pm

1 stop10h 40m

$359

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Tue 9/9

5:05 am-11:02 am

1 stop5h 57m

Kingston Norman Manley

Thu 9/18

12:08 pm-10:48 pm

1 stop10h 40m

$359

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 9/10

6:44 pm-11:02 am

1 stop16h 18m

Kingston Norman Manley

Wed 9/17

12:08 pm-10:48 pm

1 stop10h 40m

$359

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

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 August 14, 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.

  • 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 $98. American Airlines flights start at $244 while deals on Delta start at $271 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, 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

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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
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LaGuardia to Punta Cana flights
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Hobby to Luis Munoz Marin Intl flights
Atlanta to Montego Bay flights
LaGuardia to Santo Domingo flights
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Midway to Luis Munoz Marin Intl flights
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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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$328Average$385FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$443Average$681FlexibilityNo cancel feeOn-time69%
DeltaCheapest$469Average$661FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$490Average$647FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$502Average$694FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$519Average$540FlexibilityNo cancel feeOn-time83%

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