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$107+ 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 5/10. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$286
(FlightHub)

One-way from

$107
(Cheapflightsfares)

Popular in

June

Cheapest in

October

Average price

$543

Good round-trip deal

$540 or less
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
Search Deals
Highest demand for flights based on searches. 9% 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 February 2025
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Price to beat on a round-trip flight from Wisconsin to Jamaica.
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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 February 20, 2025.

This FlightHub deal was found by Cheapflights users on 2/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/256:25 pmORD - KIN
2 stops18h 03mSpirit Airlines
Tue 4/11:36 pmKIN - ORD
2 stops19h 08mSpirit Airlines
Deal found 2/20$286
This FlightHub deal was found by Cheapflights users on 2/19. 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 4/86:29 pmMKE - MBJ
1 stop16h 26mSpirit Airlines
Wed 4/1612:00 pmMBJ - MKE
1 stop28h 05mSpirit Airlines
Deal found 2/19$302
This American Airlines deal was found by Cheapflights users on 2/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/82:50 pmORD - KIN
1 stop19h 34mAmerican Airlines
Wed 3/122:15 pmKIN - ORD
1 stop7h 15mAmerican Airlines
Deal found 2/20$369
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/34:41 pmMKE - MBJ
1 stop18h 21mMultiple Airlines
Wed 4/93:05 pmMBJ - MKE
1 stop25h 00mMultiple Airlines
Deal found 2/20$379
This FlightHub deal was found by Cheapflights users on 2/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/115:03 pmMSP - KIN
2 stops19h 25mSpirit Airlines
Tue 3/181:36 pmKIN - MSP
2 stops22h 06mSpirit Airlines
Deal found 2/20$382
This FlightHub deal was found by Cheapflights users on 2/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/244:27 pmMSP - MBJ
2 stops18h 35mSpirit Airlines
Mon 3/3112:07 pmMBJ - MSP
2 stops26h 11mSpirit Airlines
Deal found 2/20$431
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/38:47 amMSP - MBJ
1 stop27h 56mMultiple Airlines
Sun 3/912:07 pmMBJ - MSP
1 stop10h 43mMultiple Airlines
Deal found 2/20$432
This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/47:21 pmORD - MBJ
1 stop15h 41mSpirit Airlines
Fri 4/1112:00 pmMBJ - ORD
1 stop12h 41mSpirit Airlines
Deal found 2/20$441
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/306:00 amORD - MBJ
1 stop8h 13mMultiple Airlines
Sun 6/110:19 amMBJ - ORD
1 stop7h 18mMultiple Airlines
Deal found 2/20$442
This Mytrip deal was found by Cheapflights users on 2/19. 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.
Wed 4/25:30 amMSP - KIN
2 stops30h 58mMultiple Airlines
Sat 4/51:36 pmKIN - MSP
2 stops19h 51mMultiple Airlines
Deal found 2/19$446
This United Airlines deal was found by Cheapflights users on 2/19. 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.
Mon 3/108:41 amORD - MBJ
Nonstop4h 05mUnited Airlines
Tue 3/181:48 pmMBJ - ORD
Nonstop4h 22mUnited Airlines
Deal found 2/19$460
This American Airlines deal was found by Cheapflights users on 2/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/289:10 amORD - MBJ
Nonstop4h 00mAmerican Airlines
Fri 5/22:25 pmMBJ - ORD
Nonstop4h 35mAmerican Airlines
Deal found 2/20$476

Find flights from Wisconsin to Jamaica within your budget

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 February 20, 2025.

Fly from

Wisconsin

Fly to

Jamaica

Route

Depart

Return

Price

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Tue 3/25

6:25 pm-12:28 pm

2 stops18h 03m

Kingston Norman Manley

Tue 4/1

1:36 pm-8:44 am

2 stops19h 08m

$286

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Tue 4/8

6:29 pm-10:55 am

1 stop16h 26m

Montego Bay Sangster Intl

Wed 4/16

12:00 pm-4:05 pm

1 stop28h 05m

$302

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 3/8

2:50 pm-11:24 am

1 stop19h 34m

Kingston Norman Manley

Wed 3/12

2:15 pm-9:30 pm

1 stop7h 15m

$369

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Thu 4/3

4:41 pm-11:02 am

1 stop18h 21m

Montego Bay Sangster Intl

Wed 4/9

3:05 pm-4:05 pm

1 stop25h 00m

$379

MinneapolisKingston

MSP - KIN

MSPKIN

Minneapolis St Paul

Tue 3/11

5:03 pm-12:28 pm

2 stops19h 25m

Kingston Norman Manley

Tue 3/18

1:36 pm-11:42 am

2 stops22h 06m

$382

MinneapolisMontego Bay

MSP - MBJ

MSPMBJ

Minneapolis St Paul

Mon 3/24

4:27 pm-11:02 am

2 stops18h 35m

Montego Bay Sangster Intl

Mon 3/31

12:07 pm-2:18 pm

2 stops26h 11m

$431

MinneapolisMontego Bay

MSP - MBJ

MSPMBJ

Minneapolis St Paul

Mon 3/3

8:47 am-1:43 pm

1 stop27h 56m

Montego Bay Sangster Intl

Sun 3/9

12:07 pm-10:50 pm

1 stop10h 43m

$432

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 4/4

7:21 pm-11:02 am

1 stop15h 41m

Montego Bay Sangster Intl

Fri 4/11

12:00 pm-12:41 am

1 stop12h 41m

$441

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 5/30

6:00 am-2:13 pm

1 stop8h 13m

Montego Bay Sangster Intl

Sun 6/1

10:19 am-5:37 pm

1 stop7h 18m

$442

MinneapolisKingston

MSP - KIN

MSPKIN

Minneapolis St Paul

Wed 4/2

5:30 am-12:28 pm

2 stops30h 58m

Kingston Norman Manley

Sat 4/5

1:36 pm-9:27 am

2 stops19h 51m

$446

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

Showing 1-10 of 48 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.

Travel insights for flights from Wisconsin to Jamaica

Get recent, data-driven insights about flights from Wisconsin to Jamaica including ideal travel times, pricing trends, and more.

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 $569). 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 February 20, 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.

Rainfall in Jamaica by month

Plan your trip to Jamaica by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Jamaica ranges from 1.6 - 7.1 inches per month. October is typically the wettest month, when rainfall can reach 7.1 in. February is typically the driest time to visit Jamaica when rainfall is around 1.6 in.

Temperature in Jamaica by month

Plan your trip to Jamaica by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Jamaica, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Jamaica

Get insights into the airlines that provide service to Jamaica. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Jamaica. Reviews last updated February 20, 2025.
See what other customers who have flown with Southwest, Delta and SWISS from Wisconsin to Jamaica have to say. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

SWISS
7.5
Good
1,568 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $107. Sun Country Air flights start at $108 while deals on United Airlines start at $201 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 $569). 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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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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$301Average$399FlexibilityNo cancel feeOn-time65%
DeltaCheapest$458Average$658FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$469Average$628FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$479Average$622FlexibilityNo cancel feeOn-time69%
Sun Country AirCheapest$502Average$540FlexibilityNo cancel feeOn-time83%
SouthwestCheapest$502Average$707FlexibilityNo cancel feeOn-time63%
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