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Jamaica

$108+ 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 2/17. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Jan 29 — Feb 51
Thu 1/29
Thu 2/5
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 30, 2025.

This Delta deal was found by Cheapflights users on 12/29. 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.
Tue 12/306:45 amORD - MBJ
1 stop12h 56mDelta
Thu 1/18:00 amMBJ - ORD
1 stop9h 21mDelta
Deal found 12/29$551
This Delta deal was found by Cheapflights users on 12/29. 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.
Tue 12/306:45 amORD - MBJ
1 stop6h 28mDelta
Wed 12/313:38 pmMBJ - ORD
2 stops18h 23mDelta
Deal found 12/29$556
This American Airlines deal was found by Cheapflights users on 12/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2910:11 amORD - MBJ
Nonstop4h 13mAmerican Airlines
Wed 12/313:51 pmMBJ - ORD
Nonstop4h 38mAmerican Airlines
Deal found 12/28$561
This Kiwi.com deal was found by Cheapflights users on 12/28. 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.
Wed 12/315:00 amORD - MBJ
1 stop6h 05mSpirit Airlines
Wed 12/313:05 pmMBJ - ORD
2 stops28h 34mSpirit Airlines
Deal found 12/28$603
This FlightHub deal was found by Cheapflights users on 12/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:55 pmORD - MBJ
1 stop19h 35mAir Canada
Wed 1/71:30 pmMBJ - ORD
1 stop24h 31mAir Canada
Deal found 12/28$614
This Kiwi.com deal was found by Cheapflights users on 12/28. 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.
Wed 12/315:00 amORD - MBJ
1 stop6h 05mSpirit Airlines
Thu 1/11:05 pmMBJ - ORD
1 stop6h 34mSpirit Airlines
Deal found 12/28$622
This Delta deal was found by Cheapflights users on 12/29. 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.
Tue 12/308:07 pmORD - MBJ
1 stop17h 06mDelta
Fri 1/28:00 amMBJ - ORD
1 stop14h 14mDelta
Deal found 12/29$630
This Kiwi.com deal was found by Cheapflights users on 12/28. 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.
Wed 12/315:00 amORD - MBJ
1 stop6h 05mMultiple Airlines
Wed 12/313:05 pmMBJ - ORD
2 stops24h 57mMultiple Airlines
Deal found 12/28$642
This CheapOair deal was found by Cheapflights users on 12/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:30 pmORD - KIN
1 stop16h 15mMultiple Airlines
Fri 1/95:01 amKIN - ORD
2 stops13h 42mMultiple Airlines
Deal found 12/28$699
This Delta deal was found by Cheapflights users on 12/29. 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 12/299:08 amMSP - MBJ
Nonstop4h 42mDelta
Mon 1/54:05 pmMBJ - MSP
Nonstop5h 02mDelta
Deal found 12/29$725
This Delta deal was found by Cheapflights users on 12/29. 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.
Tue 12/309:08 amMSP - MBJ
Nonstop4h 42mDelta
Thu 1/12:23 pmMBJ - MSP
1 stop11h 10mDelta
Deal found 12/29$735
This Air Canada deal was found by Cheapflights users on 12/28. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/302:01 pmORD - KIN
2 stops22h 44mAir Canada
Wed 1/72:55 pmKIN - ORD
1 stop29h 50mAir Canada
Deal found 12/28$776

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 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$343
(Cheapflightsfares)

One-way from

$108
(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 ($60 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 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 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

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 1/24

5:32 pm-12:12 pm

1 stop17h 40m

Kingston Norman Manley

Fri 2/20

1:17 pm-9:13 pm

1 stop8h 56m

$343

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 2/21

12:06 pm-12:15 pm

1 stop23h 09m

Kingston Norman Manley

Mon 2/23

1:17 pm-9:13 pm

1 stop8h 56m

$356

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 1/29

2:52 pm-12:12 pm

1 stop20h 20m

Kingston Norman Manley

Mon 2/2

1:17 pm-11:22 am

1 stop23h 05m

$359

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 1/24

12:44 pm-12:12 pm

2 stops22h 28m

Kingston Norman Manley

Fri 2/20

1:17 pm-11:03 pm

1 stop10h 46m

$384

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 1/18

5:30 am-3:20 pm

1 stop8h 50m

Montego Bay Sangster Intl

Wed 1/21

12:38 pm-7:21 pm

1 stop7h 43m

$391

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 2/16

7:41 pm-3:19 pm

2 stops18h 38m

Montego Bay Sangster Intl

Thu 2/26

4:05 pm-8:40 am

1 stop17h 35m

$396

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 2/22

10:35 am-12:53 pm

2 stops25h 18m

Montego Bay Sangster Intl

Tue 2/24

2:19 pm-11:56 pm

1 stop10h 37m

$396

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 2/18

7:30 pm-1:56 pm

2 stops17h 26m

Montego Bay Sangster Intl

Wed 2/25

4:44 pm-8:38 am

1 stop16h 54m

$396

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 2/1

1:58 pm-12:32 pm

2 stops21h 34m

Montego Bay Sangster Intl

Thu 2/5

12:38 pm-6:49 pm

1 stop7h 11m

$396

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 2/16

7:41 pm-3:19 pm

2 stops18h 38m

Montego Bay Sangster Intl

Tue 2/24

2:00 pm-9:57 pm

1 stop8h 57m

$396

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/30

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 $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, Delta, and American Airlines can get you from Wisconsin to Jamaica in just under 7h 16m. Your travel time can differ by up to 10h 24m. Airlines will cover a distance of 1826 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

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
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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 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$473Average$635FlexibilityNo 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$565Average$678FlexibilityNo cancel feeOn-time63%

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