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Jamaica

$111+ 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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Apr 5 — Apr 121
Sat 4/5
Sat 4/12
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 March 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$346
(Booking.com)

One-way from

$111
(Cheapflightsfares)

Popular in

June

Cheapest in

October

Average price

$542
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. 7% potential increase in price ($48 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 March 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 March 31, 2025.

This Booking.com deal was found by Cheapflights users on 3/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/145:05 amORD - KIN
1 stop7h 24mSpirit Airlines
Wed 5/211:34 pmKIN - ORD
1 stop9h 30mSpirit Airlines
Deal found 3/30$346
This Mytrip deal was found by Cheapflights users on 3/30. 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.
Sat 4/127:34 amMSP - MBJ
1 stop27h 21mMultiple Airlines
Sat 4/1912:00 pmMBJ - MSP
1 stop23h 30mMultiple Airlines
Deal found 3/30$376
This Cheapflightsfares deal was found by Cheapflights users on 3/30. 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 4/129:07 amMSP - MBJ
Nonstop4h 40mSun Country Air
Sat 4/192:50 pmMBJ - MSP
Nonstop5h 11mSun Country Air
Deal found 3/30$392
This Mytrip deal was found by Cheapflights users on 3/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/125:06 pmMKE - MBJ
2 stops17h 49mSpirit Airlines
Sat 4/1912:00 pmMBJ - MKE
2 stops25h 40mSpirit Airlines
Deal found 3/29$415
This American Airlines deal was found by Cheapflights users on 3/30. 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.
Wed 5/147:00 amORD - KIN
2 stops12h 40mAmerican Airlines
Wed 5/216:30 amKIN - ORD
2 stops10h 59mAmerican Airlines
Deal found 3/30$437
This Delta deal was found by Cheapflights users on 3/30. 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.
Wed 5/149:39 amORD - KIN
1 stop10h 21mDelta
Wed 5/219:00 amKIN - ORD
1 stop8h 11mDelta
Deal found 3/30$443
This Mytrip deal was found by Cheapflights users on 3/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/277:27 amMSP - KIN
2 stops29h 04mMultiple Airlines
Sun 5/41:39 pmKIN - MSP
2 stops24h 01mMultiple Airlines
Deal found 3/29$461
This Booking.com deal was found by Cheapflights users on 3/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/246:15 pmORD - KIN
2 stops42h 20mMultiple Airlines
Sat 5/311:34 pmKIN - ORD
1 stop10h 31mMultiple Airlines
Deal found 3/30$461
This Mytrip deal was found by Cheapflights users on 3/30. 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.
Tue 5/277:47 amORD - MBJ
2 stops27h 15mMultiple Airlines
Sat 5/313:05 pmMBJ - ORD
1 stop9h 00mMultiple Airlines
Deal found 3/30$462
This Delta deal was found by Cheapflights users on 3/30. 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.
Sun 9/217:10 amORD - MBJ
1 stop8h 23mDelta
Wed 10/11:12 pmMBJ - ORD
1 stop8h 00mDelta
Deal found 3/30$463
This American Airlines deal was found by Cheapflights users on 3/31. 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.
Thu 5/154:50 pmORD - MBJ
1 stop19h 04mAmerican Airlines
Thu 5/222:25 pmMBJ - ORD
Nonstop4h 35mAmerican Airlines
Deal found 3/31$464
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 4/31:24 pmMKE - MBJ
2 stops21h 38mMultiple Airlines
Wed 4/93:05 pmMBJ - MKE
1 stop25h 00mMultiple Airlines
Deal found 3/30$464

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 March 31, 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 5/14

5:05 am-12:29 pm

1 stop7h 24m

Kingston Norman Manley

Wed 5/21

1:34 pm-11:04 pm

1 stop9h 30m

$346

MinneapolisMontego Bay

MSP - MBJ

MSPMBJ

Minneapolis St Paul

Sat 4/12

7:34 am-10:55 am

1 stop27h 21m

Montego Bay Sangster Intl

Sat 4/19

12:00 pm-11:30 am

1 stop23h 30m

$376

MinneapolisMontego Bay

MSP - MBJ

MSPMBJ

Minneapolis St Paul

Sat 4/12

9:07 am-1:47 pm

Nonstop4h 40m

Montego Bay Sangster Intl

Sat 4/19

2:50 pm-8:01 pm

Nonstop5h 11m

$392

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Sat 4/12

5:06 pm-10:55 am

2 stops17h 49m

Montego Bay Sangster Intl

Sat 4/19

12:00 pm-1:40 pm

2 stops25h 40m

$415

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 5/14

7:00 am-7:40 pm

2 stops12h 40m

Kingston Norman Manley

Wed 5/21

6:30 am-5:29 pm

2 stops10h 59m

$437

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 5/14

9:39 am-8:00 pm

1 stop10h 21m

Kingston Norman Manley

Wed 5/21

9:00 am-5:11 pm

1 stop8h 11m

$443

MinneapolisKingston

MSP - KIN

MSPKIN

Minneapolis St Paul

Sun 4/27

7:27 am-12:31 pm

2 stops29h 04m

Kingston Norman Manley

Sun 5/4

1:39 pm-1:40 pm

2 stops24h 01m

$461

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 5/24

6:15 pm-12:35 pm

2 stops42h 20m

Kingston Norman Manley

Sat 5/31

1:34 pm-12:05 am

1 stop10h 31m

$461

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 5/27

7:47 am-11:02 am

2 stops27h 15m

Montego Bay Sangster Intl

Sat 5/31

3:05 pm-12:05 am

1 stop9h 00m

$462

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 9/21

6:00 am-12:58 pm

1 stop6h 58m

Montego Bay Sangster Intl

Fri 9/26

4:58 pm-11:53 pm

1 stop6h 55m

$463

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

Showing 1-10 of 53 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 $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 March 31, 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 March 31, 2025.
See what other customers who have flown with Southwest, Delta and Copa Airlines 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
8.0
Very good
4,275 reviews

Overall

8.0

Comfort

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,275 reviews
Southwest
8.0
Very good
4,275 reviews

Overall

8.0

Comfort

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,899 reviews
Southwest
8.0
Very good
4,275 reviews

Overall

8.0

Comfort

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Copa Airlines
7.6
Good
1,400 reviews
Southwest
8.0
Very good
4,275 reviews

Overall

8.0

Comfort

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
SWISS
7.5
Good
1,570 reviews
Southwest
8.0
Very good
4,275 reviews

Overall

8.0

Comfort

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,614 reviews
Southwest
8.0
Very good
4,275 reviews

Overall

8.0

Comfort

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $111. Delta flights start at $183 while deals on Frontier start at $195 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

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.
Newark to Luis Munoz Marin Intl flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
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Newark to Punta Cana flights
Boston to Luis Munoz Marin Intl flights
Newark to Santiago de los Caballeros 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 March 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$311Average$403FlexibilityNo cancel feeOn-time65%
DeltaCheapest$458Average$648FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$471Average$628FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$479Average$632FlexibilityNo cancel feeOn-time69%
Sun Country AirCheapest$502Average$540FlexibilityNo cancel feeOn-time83%
SouthwestCheapest$502Average$705FlexibilityNo cancel feeOn-time63%
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