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Jamaica

$109+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
May 5 — May 121
Mon 5/5
Mon 5/12
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 April 30, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$331
(Cheapflightsfares)

One-way from

$109
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$612
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 ($51 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 April 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 April 30, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/27. 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 5/275:05 amORD - KIN
1 stop7h 24mSpirit Airlines
Tue 6/31:34 pmKIN - ORD
1 stop9h 30mSpirit Airlines
Deal found 4/27$331
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Tue 6/108:05 amORD - KIN
2 stops11h 50mAmerican Airlines
Wed 7/26:00 amKIN - ORD
1 stop13h 45mAmerican Airlines
Deal found 4/28$446
This FlightHub deal was found by Cheapflights users on 4/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/148:51 pmMKE - MBJ
2 stops14h 50mSpirit Airlines
Sat 10/2512:11 pmMBJ - MKE
1 stop7h 45mSpirit Airlines
Deal found 4/29$446
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/114:35 pmORD - MBJ
2 stops18h 27mSpirit Airlines
Fri 5/1612:07 pmMBJ - ORD
2 stops11h 22mSpirit Airlines
Deal found 4/29$448
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/115:00 amORD - MBJ
1 stop8h 35mAmerican Airlines
Fri 5/162:41 pmMBJ - ORD
1 stop8h 07mAmerican Airlines
Deal found 4/29$449
This Booking.com deal was found by Cheapflights users on 4/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/145:05 amORD - MBJ
1 stop5h 57mMultiple Airlines
Mon 5/192:08 pmMBJ - ORD
1 stop9h 03mMultiple Airlines
Deal found 4/29$450
This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/187:05 amORD - KIN
2 stops12h 55mDelta
Mon 6/239:00 amKIN - ORD
1 stop7h 59mDelta
Deal found 4/28$456
This Booking.com deal was found by Cheapflights users on 4/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/95:31 pmORD - MBJ
1 stop20h 22mFrontier
Mon 5/122:08 pmMBJ - ORD
1 stop9h 03mFrontier
Deal found 4/29$458
This United Airlines deal was found by Cheapflights users on 4/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/118:50 amORD - MBJ
1 stop6h 20mUnited Airlines
Sat 5/171:51 pmMBJ - ORD
Nonstop4h 29mUnited Airlines
Deal found 4/29$460
This CheapOair deal was found by Cheapflights users on 4/27. 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.
Sun 9/79:12 pmORD - KIN
1 stop15h 23mMultiple Airlines
Sat 9/1312:21 pmKIN - ORD
1 stop8h 19mMultiple Airlines
Deal found 4/27$463
This Delta deal was found by Cheapflights users on 4/29. 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 6/37:10 amORD - MBJ
2 stops8h 20mDelta
Tue 6/104:50 pmMBJ - ORD
1 stop7h 07mDelta
Deal found 4/29$467
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/186:08 amMKE - MBJ
1 stop8h 27mAmerican Airlines
Thu 5/2212:35 pmMBJ - MKE
1 stop11h 23mAmerican Airlines
Deal found 4/29$491

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 April 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

Tue 5/27

5:05 am-12:29 pm

1 stop7h 24m

Kingston Norman Manley

Tue 6/3

1:34 pm-11:04 pm

1 stop9h 30m

$331

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Tue 6/10

8:05 am-7:55 pm

2 stops11h 50m

Kingston Norman Manley

Wed 7/2

6:00 am-7:45 pm

1 stop13h 45m

$446

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Tue 10/14

8:51 pm-11:41 am

2 stops14h 50m

Montego Bay Sangster Intl

Sat 10/25

12:11 pm-7:56 pm

1 stop7h 45m

$446

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 6/2

2:19 pm-11:02 am

3 stops20h 43m

Montego Bay Sangster Intl

Tue 6/10

12:07 pm-10:39 pm

3 stops34h 32m

$448

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 7/5

9:13 pm-12:20 pm

1 stop15h 07m

Montego Bay Sangster Intl

Wed 7/9

2:26 pm-7:00 pm

Nonstop4h 34m

$452

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 6/18

7:05 am-8:00 pm

2 stops12h 55m

Kingston Norman Manley

Mon 6/23

9:00 am-4:59 pm

1 stop7h 59m

$456

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 5/9

5:31 pm-1:53 pm

1 stop20h 22m

Montego Bay Sangster Intl

Mon 5/12

2:08 pm-11:11 pm

1 stop9h 03m

$458

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 6/4

5:03 pm-11:02 am

2 stops17h 59m

Montego Bay Sangster Intl

Fri 6/13

12:07 pm-6:44 pm

1 stop6h 37m

$459

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 5/10

6:19 pm-12:35 pm

2 stops42h 16m

Kingston Norman Manley

Mon 6/2

1:34 pm-11:29 pm

2 stops9h 55m

$471

MinneapolisMontego Bay

MSP - MBJ

MSPMBJ

Minneapolis St Paul

Tue 6/10

9:36 am-11:02 am

2 stops25h 26m

Montego Bay Sangster Intl

Wed 6/25

12:07 pm-7:02 am

2 stops18h 55m

$493

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 49 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 April 30, 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 April 30, 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
4,295 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,936 reviews
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Copa Airlines
7.5
Good
1,411 reviews
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,922 reviews
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 $109. American Airlines flights start at $196 while deals on United Airlines start at $202 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.
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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 April 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$347Average$403FlexibilityNo cancel feeOn-time65%
DeltaCheapest$459Average$632FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$471Average$631FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$479Average$669FlexibilityNo cancel feeOn-time69%
Sun Country AirCheapest$502Average$540FlexibilityNo cancel feeOn-time83%
SouthwestCheapest$502Average$705FlexibilityNo cancel feeOn-time63%

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