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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 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Feb 6 — Feb 131
Fri 2/6
Fri 2/13
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 January 7, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$350
(Kiwi.com)

One-way from

$98
(Super.com)

Popular in

June

Cheapest in

October

Average price

$609
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. 8% potential increase in price ($61 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 January 2026
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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 January 7, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/7. 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 2/58:43 pmORD - KIN
1 stop14h 29mMultiple Airlines
Thu 2/121:17 pmKIN - ORD
1 stop11h 07mMultiple Airlines
Deal found 1/7$350
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 1/292:52 pmORD - KIN
1 stop20h 20mMultiple Airlines
Mon 2/21:17 pmKIN - ORD
1 stop23h 05mMultiple Airlines
Deal found 1/7$356
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 1/315:32 pmORD - KIN
1 stop17h 40mSpirit Airlines
Fri 2/61:17 pmKIN - ORD
1 stop7h 21mSpirit Airlines
Deal found 1/6$359
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 2/154:43 pmORD - KIN
1 stop18h 32mMultiple Airlines
Thu 2/191:17 pmKIN - ORD
1 stop11h 07mMultiple Airlines
Deal found 1/5$381
This Cheapflightsfares deal was found by Cheapflights users on 1/5. 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 1/285:32 pmORD - KIN
1 stop17h 40mSpirit Airlines
Mon 2/91:17 pmKIN - ORD
1 stop8h 46mSpirit Airlines
Deal found 1/5$383
This Air Canada deal was found by Cheapflights users on 1/6. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:20 pmORD - MBJ
1 stop15h 00mAir Canada
Wed 6/1012:15 pmMBJ - ORD
2 stops19h 50mAir Canada
Deal found 1/6$384
This Priceline deal was found by Cheapflights users on 1/5. 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.
Thu 2/55:15 amORD - MBJ
1 stop5h 47mSpirit Airlines
Mon 2/912:57 pmMBJ - ORD
1 stop11h 50mSpirit Airlines
Deal found 1/5$385
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 2/13:05 pmORD - KIN
1 stop20h 07mMultiple Airlines
Sun 2/81:17 pmKIN - ORD
2 stops26h 00mMultiple Airlines
Deal found 1/6$385
This Air Canada deal was found by Cheapflights users on 1/6. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1610:53 amORD - MBJ
2 stops24h 27mAir Canada
Sun 6/2112:30 pmMBJ - ORD
1 stop20h 30mAir Canada
Deal found 1/6$386
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 1/165:15 amORD - MBJ
1 stop5h 47mSpirit Airlines
Thu 1/2212:57 pmMBJ - ORD
1 stop7h 41mSpirit Airlines
Deal found 1/5$388
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 1/315:32 pmORD - KIN
1 stop17h 40mSpirit Airlines
Sun 2/81:17 pmKIN - ORD
2 stops26h 00mSpirit Airlines
Deal found 1/6$388
This FlightHub deal was found by Cheapflights users on 1/6. 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 9/156:20 pmORD - MBJ
2 stops41h 00mAir Canada
Sat 9/1912:30 pmMBJ - ORD
1 stop22h 23mAir Canada
Deal found 1/6$389

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 January 7, 2026.
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

Fri 1/23

5:15 am-12:12 pm

1 stop5h 57m

Kingston Norman Manley

Mon 2/23

1:17 pm-7:11 pm

1 stop6h 54m

$392

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sun 2/22

5:15 am-12:15 pm

1 stop6h 00m

Kingston Norman Manley

Mon 2/23

1:17 pm-9:13 pm

1 stop8h 56m

$398

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 1/31

5:32 pm-12:12 pm

1 stop17h 40m

Kingston Norman Manley

Sun 2/8

1:17 pm-9:03 pm

1 stop8h 46m

$406

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Fri 1/30

5:15 am-12:12 pm

1 stop5h 57m

Kingston Norman Manley

Mon 2/2

1:17 pm-11:47 pm

1 stop11h 30m

$407

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 3/2

2:22 pm-10:11 am

1 stop18h 49m

Montego Bay Sangster Intl

Wed 3/11

12:20 pm-1:04 am

1 stop12h 44m

$418

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 2/2

4:25 pm-1:00 pm

2 stops19h 35m

Montego Bay Sangster Intl

Thu 2/5

2:00 pm-9:50 pm

1 stop8h 50m

$421

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 2/19

5:25 am-3:19 pm

1 stop8h 54m

Montego Bay Sangster Intl

Fri 2/27

12:20 pm-8:44 pm

2 stops9h 24m

$426

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Tue 1/27

11:51 pm-1:53 pm

1 stop13h 02m

Kingston Norman Manley

Thu 2/5

3:00 pm-12:04 am

1 stop10h 04m

$434

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 1/19

5:35 pm-11:13 am

2 stops16h 38m

Montego Bay Sangster Intl

Wed 1/21

12:38 pm-11:56 pm

1 stop12h 18m

$441

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 2/20

8:40 pm-12:40 pm

1 stop15h 00m

Montego Bay Sangster Intl

Sun 3/1

7:05 pm-6:52 pm

2 stops24h 47m

$445

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

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.

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, Copa Airlines, and Southwest can get you from Wisconsin to Jamaica in just under 5h 57m. Your travel time can differ by up to 13h 38m. Airlines will cover a distance of 1785 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

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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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John F Kennedy Intl to Luis Munoz Marin Intl flights
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LaGuardia to Punta Cana 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 January 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$473Average$636FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$508Average$641FlexibilityNo cancel feeOn-time71%
Sun Country AirCheapest$540Average$541FlexibilityNo cancel feeOn-time83%
United AirlinesCheapest$563Average$759FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$565Average$678FlexibilityNo cancel feeOn-time63%

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