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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 8/1. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Jul 7 — Jul 141
Mon 7/7
Mon 7/14
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 July 2, 2025.

Round-trip from

$324
(Priceline)

One-way from

$109
(Priceline)

Popular in

June

Cheapest in

January

Average price

$690
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. 10% potential increase in price ($76 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 2, 2025.

This Priceline deal was found by Cheapflights users on 7/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/85:47 pmMSP - MBJ
2 stops17h 18mSpirit Airlines
Fri 8/1512:19 pmMBJ - MSP
2 stops19h 58mSpirit Airlines
Deal found 7/1$324
This FlightHub deal was found by Cheapflights users on 7/1. 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.
Sun 7/275:05 amORD - KIN
1 stop5h 55mSpirit Airlines
Sat 8/28:47 amKIN - ORD
1 stop15h 06mSpirit Airlines
Deal found 7/1$341
This Booking.com deal was found by Cheapflights users on 7/2. 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 8/166:00 amMKE - MBJ
1 stop7h 01mSpirit Airlines
Sat 8/232:06 pmMBJ - MKE
1 stop9h 00mSpirit Airlines
Deal found 7/2$382
This Priceline deal was found by Cheapflights users on 6/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/199:22 amMSP - KIN
2 stops26h 05mSpirit Airlines
Sun 8/249:47 amKIN - MSP
2 stops22h 30mSpirit Airlines
Deal found 6/30$388
This American Airlines deal was found by Cheapflights users on 7/2. 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.
Fri 10/37:15 pmORD - KIN
1 stop16h 37mAmerican Airlines
Fri 10/317:00 amKIN - ORD
1 stop16h 47mAmerican Airlines
Deal found 7/2$391
This Mytrip deal was found by Cheapflights users on 7/1. 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.
Fri 8/1511:21 amORD - KIN
2 stops24h 06mMultiple Airlines
Fri 8/226:25 pmKIN - ORD
2 stops15h 27mMultiple Airlines
Deal found 7/1$399
This American Airlines deal was found by Cheapflights users on 7/1. 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.
Fri 10/35:00 amORD - MBJ
1 stop9h 54mAmerican Airlines
Thu 10/92:00 pmMBJ - ORD
Nonstop4h 33mAmerican Airlines
Deal found 7/1$400
This CheapOair deal was found by Cheapflights users on 7/2. 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.
Mon 8/115:05 amORD - MBJ
1 stop6h 00mMultiple Airlines
Mon 8/189:05 amMBJ - ORD
1 stop15h 17mMultiple Airlines
Deal found 7/2$401
This FlightHub deal was found by Cheapflights users on 7/2. 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 9/175:05 amORD - MBJ
1 stop6h 05mSpirit Airlines
Sun 9/2112:15 pmMBJ - ORD
1 stop10h 33mSpirit Airlines
Deal found 7/2$402
This Delta deal was found by Cheapflights users on 7/1. 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.
Sat 8/237:05 amORD - KIN
1 stop13h 20mDelta
Sat 8/309:25 amKIN - ORD
1 stop9h 54mDelta
Deal found 7/1$403
This Delta deal was found by Cheapflights users on 6/29. 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.
Sat 10/186:10 pmORD - MBJ
1 stop17h 28mDelta
Wed 10/222:19 pmMBJ - ORD
1 stop9h 34mDelta
Deal found 6/29$410
This FlightHub deal was found by Cheapflights users on 7/2. 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.
Sun 11/26:16 pmORD - MBJ
1 stop13h 37mFrontier
Sat 11/810:13 amMBJ - ORD
1 stop14h 08mFrontier
Deal found 7/2$418

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 July 2, 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

MinneapolisMontego Bay

MSP - MBJ

MSPMBJ

Minneapolis St Paul

Fri 8/8

5:47 pm-11:05 am

2 stops17h 18m

Montego Bay Sangster Intl

Fri 8/15

12:19 pm-8:17 am

2 stops19h 58m

$324

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sun 7/27

5:05 am-11:00 am

1 stop5h 55m

Kingston Norman Manley

Sat 8/2

8:47 am-11:53 pm

1 stop15h 06m

$341

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Sat 8/16

6:00 am-1:01 pm

1 stop7h 01m

Montego Bay Sangster Intl

Sat 8/23

2:06 pm-11:06 pm

1 stop9h 00m

$382

MinneapolisKingston

MSP - KIN

MSPKIN

Minneapolis St Paul

Tue 8/19

9:22 am-11:27 am

2 stops26h 05m

Kingston Norman Manley

Sun 8/24

9:47 am-8:17 am

2 stops22h 30m

$388

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Fri 10/3

7:15 pm-11:52 am

1 stop16h 37m

Kingston Norman Manley

Fri 10/31

7:00 am-11:47 pm

1 stop16h 47m

$391

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Fri 8/15

11:21 am-11:27 am

2 stops24h 06m

Kingston Norman Manley

Fri 8/22

6:25 pm-9:52 am

2 stops15h 27m

$399

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 7/15

7:05 am-3:25 pm

1 stop8h 20m

Montego Bay Sangster Intl

Sat 7/26

2:26 pm-7:00 pm

Nonstop4h 34m

$400

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 8/11

5:05 am-11:05 am

1 stop6h 00m

Montego Bay Sangster Intl

Mon 8/18

9:05 am-12:22 am

1 stop15h 17m

$401

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 9/17

5:05 am-11:10 am

1 stop6h 05m

Montego Bay Sangster Intl

Sun 9/21

12:15 pm-10:48 pm

1 stop10h 33m

$402

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 8/23

7:05 am-8:25 pm

1 stop13h 20m

Kingston Norman Manley

Sat 8/30

9:25 am-7:19 pm

1 stop9h 54m

$403

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 51 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 July 2, 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.

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 July 2, 2025.
Read through reviews of airlines operating flights from Wisconsin to Jamaica, such as Delta, Copa Airlines, and United Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,983 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,983 reviews
Delta
8.0
Very good
7,983 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Copa Airlines
7.5
Good
1,465 reviews
Delta
8.0
Very good
7,983 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,861 reviews
Delta
8.0
Very good
7,983 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
JetBlue
7.3
Good
2,918 reviews
Delta
8.0
Very good
7,983 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,983 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 Frontier, which is currently one of the cheapest options available, starting at $109. Spirit Airlines flights start at $113 while deals on American Airlines start at $164 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 July 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$328Average$399FlexibilityNo cancel feeOn-time65%
DeltaCheapest$458Average$655FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$479Average$698FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$490Average$656FlexibilityNo cancel feeOn-time71%
Sun Country AirCheapest$502Average$540FlexibilityNo cancel feeOn-time83%
SouthwestCheapest$502Average$710FlexibilityNo cancel feeOn-time63%

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