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Jamaica

$123+ 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 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$329
(Cheapflightsfares)

One-way from

$123
(FlightHub)

Popular in

June

Cheapest in

January

Average price

$775
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. 11% potential increase in price ($78 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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 7/15:05 amORD - KIN
1 stop7h 27mSpirit Airlines
Tue 7/81:37 pmKIN - ORD
1 stop10h 08mSpirit Airlines
Deal found 6/10$329
This American Airlines deal was found by Cheapflights users on 6/11. 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 8/206:17 amMSP - MBJ
1 stop8h 17mAmerican Airlines
Wed 8/273:35 pmMBJ - MSP
1 stop7h 32mAmerican Airlines
Deal found 6/11$341
This FlightHub deal was found by Cheapflights users on 6/11. 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 9/32:22 pmMSP - MBJ
2 stops21h 19mSpirit Airlines
Mon 9/812:46 pmMBJ - MSP
2 stops24h 31mSpirit Airlines
Deal found 6/11$372
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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 7/115:40 pmORD - MBJ
1 stop17h 25mSpirit Airlines
Tue 7/1512:10 pmMBJ - ORD
2 stops11h 01mSpirit Airlines
Deal found 6/11$393
This Mytrip deal was found by Cheapflights users on 6/10. 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 7/85:05 amORD - KIN
1 stop7h 27mMultiple Airlines
Tue 7/157:05 amKIN - ORD
1 stop25h 50mMultiple Airlines
Deal found 6/10$393
This FlightHub deal was found by Cheapflights users on 6/12. 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.
Thu 9/116:16 pmORD - MBJ
1 stop13h 37mFrontier
Mon 9/159:13 amMBJ - ORD
1 stop28h 12mFrontier
Deal found 6/12$394
This Booking.com deal was found by Cheapflights users on 6/12. 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 6/286:16 pmORD - MBJ
1 stop13h 42mMultiple Airlines
Wed 7/212:07 pmMBJ - ORD
1 stop11h 38mMultiple Airlines
Deal found 6/12$397
This Delta deal was found by Cheapflights users on 6/11. 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 8/129:10 amORD - KIN
2 stops11h 15mDelta
Tue 8/269:25 amKIN - ORD
1 stop7h 03mDelta
Deal found 6/11$398
This American Airlines deal was found by Cheapflights users on 6/12. 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 7/310:05 pmORD - MBJ
1 stop16h 25mAmerican Airlines
Thu 7/102:26 pmMBJ - ORD
Nonstop4h 34mAmerican Airlines
Deal found 6/12$400
This FlightHub deal was found by Cheapflights users on 6/11. 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 9/162:22 pmMSP - KIN
2 stops20h 54mSpirit Airlines
Fri 9/2612:21 pmKIN - MSP
2 stops36h 10mSpirit Airlines
Deal found 6/11$403
This FlightHub deal was found by Cheapflights users on 6/12. 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.
Sat 7/124:37 pmMKE - MBJ
2 stops17h 16mSpirit Airlines
Thu 7/171:40 pmMBJ - MKE
2 stops26h 02mSpirit Airlines
Deal found 6/12$425
This Mytrip deal was found by Cheapflights users on 6/11. 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 9/162:22 pmMSP - MBJ
2 stops22h 23mMultiple Airlines
Fri 9/2612:46 pmMBJ - MSP
2 stops35h 45mMultiple Airlines
Deal found 6/11$431

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 June 12, 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 7/1

5:05 am-12:32 pm

1 stop7h 27m

Kingston Norman Manley

Tue 7/8

1:37 pm-11:45 pm

1 stop10h 08m

$329

MinneapolisMontego Bay

MSP - MBJ

MSPMBJ

Minneapolis St Paul

Wed 8/20

6:17 am-2:34 pm

1 stop8h 17m

Montego Bay Sangster Intl

Wed 8/27

3:35 pm-11:07 pm

1 stop7h 32m

$341

MinneapolisMontego Bay

MSP - MBJ

MSPMBJ

Minneapolis St Paul

Wed 9/3

2:22 pm-11:41 am

2 stops21h 19m

Montego Bay Sangster Intl

Mon 9/8

12:46 pm-1:17 pm

2 stops24h 31m

$372

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Tue 7/8

5:05 am-12:32 pm

1 stop7h 27m

Kingston Norman Manley

Tue 7/15

7:05 am-8:55 am

1 stop25h 50m

$393

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 7/11

5:40 pm-11:05 am

1 stop17h 25m

Montego Bay Sangster Intl

Tue 7/15

12:10 pm-11:11 pm

2 stops11h 01m

$393

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 9/11

6:16 pm-7:53 am

1 stop13h 37m

Montego Bay Sangster Intl

Mon 9/15

9:13 am-1:25 pm

1 stop28h 12m

$394

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 6/28

6:16 pm-7:58 am

1 stop13h 42m

Montego Bay Sangster Intl

Wed 7/2

12:07 pm-11:45 pm

1 stop11h 38m

$397

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Tue 8/12

9:10 am-8:25 pm

2 stops11h 15m

Kingston Norman Manley

Tue 8/26

9:25 am-4:28 pm

1 stop7h 03m

$398

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 7/3

10:05 pm-2:30 pm

1 stop16h 25m

Montego Bay Sangster Intl

Thu 7/10

2:26 pm-7:00 pm

Nonstop4h 34m

$400

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 7/14

8:52 am-3:10 pm

1 stop6h 18m

Montego Bay Sangster Intl

Sat 7/19

1:51 pm-6:20 pm

Nonstop4h 29m

$412

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

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 June 12, 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 June 12, 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
4,287 reviews

Food

7.1

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Copa Airlines
7.5
Good
1,451 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,925 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 $123. American Airlines flights start at $147 while deals on Delta start at $152 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$328Average$399FlexibilityNo cancel feeOn-time65%
DeltaCheapest$469Average$653FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$479Average$690FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$490Average$659FlexibilityNo cancel feeOn-time71%
Sun Country AirCheapest$502Average$540FlexibilityNo cancel feeOn-time83%
SouthwestCheapest$502Average$708FlexibilityNo cancel feeOn-time63%

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