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 4/19. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Jan 26 — Feb 21
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Cheap flight deals from Wisconsin to Jamaica

Discover tips and strategies to find the most affordable flight options for your journey from Wisconsin (USWI) to Jamaica (JM0). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$277
(Mytrip)

One-way from

$108
(Cheapflightsfares)

Good round-trip deal

$540 or less
From Wisconsin to Jamaica
One-way flight from Wisconsin to Jamaica
Price to beat on a round-trip flight from Wisconsin to Jamaica.

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 January 21, 2025.

This Mytrip deal was found by Cheapflights users on 1/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/57:42 pmORD - KIN
1 stop16h 46mSpirit Airlines
Wed 3/121:36 pmKIN - ORD
1 stop10h 31mSpirit Airlines
Deal found 1/20$277
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/246:47 pmMKE - MBJ
1 stop17h 56mSpirit Airlines
Tue 3/42:48 pmMBJ - MKE
1 stop26h 57mSpirit Airlines
Deal found 1/19$313
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/252:14 pmMKE - MBJ
2 stops22h 29mMultiple Airlines
Tue 3/42:48 pmMBJ - MKE
1 stop26h 57mMultiple Airlines
Deal found 1/19$343
This American Airlines deal was found by Cheapflights users on 1/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/237:09 pmORD - KIN
1 stop16h 16mAmerican Airlines
Thu 2/276:00 amKIN - ORD
2 stops10h 41mAmerican Airlines
Deal found 1/19$366
This CheapOair deal was found by Cheapflights users on 1/21. 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 3/55:11 pmMSP - KIN
2 stops19h 17mSpirit Airlines
Wed 3/121:36 pmKIN - MSP
2 stops26h 03mSpirit Airlines
Deal found 1/21$389
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 2/2712:59 pmORD - KIN
2 stops22h 22mMultiple Airlines
Wed 3/52:36 pmKIN - ORD
1 stop10h 31mMultiple Airlines
Deal found 1/20$392
This FlightHub deal was found by Cheapflights users on 1/21. 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 2/257:13 pmORD - MBJ
2 stops17h 30mSpirit Airlines
Mon 3/32:48 pmMBJ - ORD
1 stop10h 10mSpirit Airlines
Deal found 1/21$397
This Frontier deal was found by Cheapflights users on 1/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/256:30 amORD - MBJ
1 stop6h 31mFrontier
Mon 4/282:21 pmMBJ - ORD
1 stop8h 50mFrontier
Deal found 1/21$407
This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
Tue 3/185:22 pmORD - MBJ
2 stops17h 40mMultiple Airlines
Tue 3/253:05 pmMBJ - ORD
1 stop9h 02mMultiple Airlines
Deal found 1/21$416
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 2/106:00 amMSP - KIN
2 stops30h 33mMultiple Airlines
Tue 2/181:26 pmKIN - MSP
1 stop22h 33mMultiple Airlines
Deal found 1/20$419
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 3/247:33 pmMKE - KIN
1 stop16h 55mSpirit Airlines
Tue 4/11:36 pmKIN - MKE
1 stop29h 02mSpirit Airlines
Deal found 1/21$437
This American Airlines deal was found by Cheapflights users on 1/21. 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 2/249:30 amORD - MBJ
Nonstop4h 05mAmerican Airlines
Thu 2/273:37 pmMBJ - ORD
Nonstop4h 40mAmerican Airlines
Deal found 1/21$456

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 3/5

7:42 pm-1:28 pm

1 stop16h 46m

Kingston Norman Manley

Wed 3/12

1:36 pm-12:07 am

1 stop10h 31m

$277

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sun 2/23

7:09 pm-12:25 pm

1 stop16h 16m

Kingston Norman Manley

Thu 2/27

6:00 am-3:41 pm

2 stops10h 41m

$366

MinneapolisKingston

MSP - KIN

MSPKIN

Minneapolis St Paul

Wed 3/5

5:11 pm-1:28 pm

2 stops19h 17m

Kingston Norman Manley

Wed 3/12

1:36 pm-3:39 pm

2 stops26h 03m

$389

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 2/27

12:59 pm-12:21 pm

2 stops22h 22m

Kingston Norman Manley

Wed 3/5

2:36 pm-12:07 am

1 stop10h 31m

$392

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 2/25

7:13 pm-1:43 pm

2 stops17h 30m

Montego Bay Sangster Intl

Mon 3/3

2:48 pm-11:58 pm

1 stop10h 10m

$397

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Sun 2/2

5:28 pm-12:10 pm

1 stop17h 42m

Montego Bay Sangster Intl

Tue 2/4

1:16 pm-9:54 am

2 stops21h 38m

$401

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 4/25

6:30 am-1:01 pm

1 stop6h 31m

Montego Bay Sangster Intl

Mon 4/28

2:21 pm-11:11 pm

1 stop8h 50m

$407

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 3/25

5:22 pm-11:02 am

2 stops17h 40m

Montego Bay Sangster Intl

Tue 4/1

3:05 pm-9:29 am

1 stop18h 24m

$409

MilwaukeeKingston

MKE - KIN

MKEKIN

Milwaukee-Mitchell

Wed 4/2

7:33 pm-12:28 pm

1 stop16h 55m

Kingston Norman Manley

Mon 4/7

1:36 pm-9:39 am

1 stop20h 03m

$415

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Tue 4/8

6:29 pm-11:41 am

1 stop17h 12m

Montego Bay Sangster Intl

Tue 4/15

12:46 pm-9:30 am

1 stop20h 44m

$418

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

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.

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 January 21, 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 January 21, 2025.
See what other customers who have flown with United Airlines, Delta and Sun Country Air from Wisconsin to Jamaica have to say. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.1
Very good
4,662 reviews
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
8,521 reviews
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.7
Good
1,662 reviews
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.4
Good
3,200 reviews
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.4
Good
8,984 reviews
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Sun Country Air, which is currently one of the cheapest options available, starting at $108. Spirit Airlines flights start at $117 while deals on Frontier start at $165 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.

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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$301Average$385FlexibilityNo cancel feeOn-time65%
DeltaCheapest$442Average$634FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$469Average$627FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$479Average$608FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$494Average$703FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$502Average$540FlexibilityNo cancel feeOn-time83%
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