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Wisconsin

$166+ Cheap flights from Jamaica to Wisconsin

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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — MKE
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
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Cheap flight deals from Jamaica to Wisconsin

Keep the following information in mind while searching for Jamaica to Wisconsin flight deals. Data was last updated November 2, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$320
(United Airlines)

One-way from

$166
(Mytrip)
Provider with most accurate pricing for Montego Bay Sangster Intl-Milwaukee-Mitchell flight deals.
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Provider most trusted by Cheapflights users for Montego Bay Sangster Intl-Milwaukee-Mitchell flights.
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From Jamaica to Wisconsin
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One-way flight from Jamaica to Wisconsin
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Find flight deals from Jamaica to Wisconsin

Cheapest flights from Jamaica to Wisconsin
Explore the most affordable flight options available from Jamaica to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 2, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/81:07 pmMBJ - ORD
1 stop12h 20mSpirit Airlines
Tue 11/115:10 amORD - MBJ
1 stop5h 52mSpirit Airlines
Deal found 11/1$304
This United Airlines deal was found by Cheapflights users on 10/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/122:48 pmMBJ - ORD
Nonstop4h 25mUnited Airlines
Fri 1/28:42 amORD - MBJ
Nonstop4h 04mUnited Airlines
Deal found 10/31$320
This Cheapflightsfares deal was found by Cheapflights users on 10/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/231:07 pmMBJ - ORD
1 stop11h 06mSpirit Airlines
Sun 11/305:00 amORD - MBJ
1 stop6h 02mSpirit Airlines
Deal found 10/31$321
This Delta deal was found by Cheapflights users on 10/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/33:38 pmMBJ - ORD
1 stop8h 05mDelta
Fri 12/55:30 amORD - MBJ
1 stop10h 03mDelta
Deal found 10/31$326
This American Airlines deal was found by Cheapflights users on 10/31. 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.
Sun 11/232:14 pmMBJ - ORD
Nonstop4h 36mAmerican Airlines
Sun 11/305:00 amORD - MBJ
1 stop8h 12mAmerican Airlines
Deal found 10/31$330
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/161:19 pmKIN - ORD
1 stop7h 42mSpirit Airlines
Wed 12/313:26 pmORD - KIN
1 stop19h 48mSpirit Airlines
Deal found 11/1$343
This United Airlines deal was found by Cheapflights users on 11/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/82:48 pmMBJ - ORD
Nonstop4h 25mUnited Airlines
Sat 11/158:42 amORD - MBJ
Nonstop4h 04mUnited Airlines
Deal found 11/1$350
This Delta deal was found by Cheapflights users on 11/1. 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 11/82:32 pmMBJ - ORD
2 stops18h 34mDelta
Sat 11/156:45 amORD - MBJ
1 stop8h 46mDelta
Deal found 11/1$361
This Air Canada deal was found by Cheapflights users on 11/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/77:05 pmMBJ - ORD
1 stop25h 55mAir Canada
Sun 11/97:05 amORD - MBJ
1 stop10h 00mAir Canada
Deal found 11/1$376
This United Airlines deal was found by Cheapflights users on 11/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/82:48 pmMBJ - ORD
Nonstop4h 25mUnited Airlines
Thu 11/138:42 amORD - MBJ
Nonstop4h 04mUnited Airlines
Deal found 11/1$380
This oojo deal was found by Cheapflights users on 10/31. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/271:19 pmKIN - ORD
1 stop12h 11mSpirit Airlines
Sat 1/35:00 amORD - KIN
1 stop6h 14mSpirit Airlines
Deal found 10/31$389
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/161:19 pmKIN - ORD
1 stop7h 42mMultiple Airlines
Wed 12/319:34 pmORD - KIN
2 stops37h 40mMultiple Airlines
Deal found 11/1$398

Cheapflights Fare Finder

 
Customize your flight search to find flights from Jamaica to Wisconsin 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 November 2, 2025.
Use the filters below to find and compare flights from Jamaica to Wisconsin that are best for you.

Fly from

Jamaica

Fly to

Wisconsin

Route

Depart

Return

Price

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 1/9

1:12 pm-11:42 pm

1 stop11h 30m

Chicago O'Hare Intl

Tue 1/13

5:05 am-12:05 pm

1 stop6h 00m

$316

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 12/12

2:48 pm-6:13 pm

Nonstop4h 25m

Chicago O'Hare Intl

Fri 1/2

8:42 am-1:46 pm

Nonstop4h 04m

$320

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sun 11/23

2:48 pm-6:13 pm

Nonstop4h 25m

Chicago O'Hare Intl

Sun 11/30

8:42 am-1:46 pm

Nonstop4h 04m

$320

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 1/8

2:48 pm-6:13 pm

Nonstop4h 25m

Chicago O'Hare Intl

Sun 1/18

6:05 am-2:37 pm

1 stop7h 32m

$325

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 12/3

2:48 pm-6:13 pm

Nonstop4h 25m

Chicago O'Hare Intl

Fri 12/5

7:45 pm-2:05 pm

1 stop17h 20m

$325

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 12/3

3:38 pm-10:43 pm

1 stop8h 05m

Chicago O'Hare Intl

Fri 12/5

5:30 am-4:33 pm

1 stop10h 03m

$326

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 1/8

2:16 pm-9:04 pm

1 stop7h 48m

Chicago O'Hare Intl

Sun 1/18

5:33 am-8:36 pm

1 stop14h 03m

$326

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Tue 12/16

1:19 pm-8:01 pm

1 stop7h 42m

Chicago O'Hare Intl

Wed 12/31

3:26 pm-12:14 pm

1 stop19h 48m

$343

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Sat 12/27

1:19 pm-12:30 am

1 stop12h 11m

Chicago O'Hare Intl

Sat 1/3

5:00 am-12:14 pm

1 stop6h 14m

$389

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Tue 12/16

1:42 pm-11:35 pm

2 stops10h 53m

Chicago O'Hare Intl

Wed 12/31

5:00 am-5:05 pm

2 stops11h 05m

$402

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 60 results
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Best time to book a flight from Jamaica to Wisconsin

Have a flexible travel schedule? Discover the best time to fly to Wisconsin from Jamaica 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 Jamaica to Wisconsin
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Wisconsin

Get insights into the airlines that provide service to Wisconsin. 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 Wisconsin. Reviews last updated November 2, 2025.
See what other customers who have flown with Delta and American Airlines from Jamaica to Wisconsin have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,001 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Boarding

8.2

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Lane,Nov 2025

MEM - ATL

The crew was very friendly, but they only came around and offered the better Delta Comfort snacks one time. I thought they would come around more frequently on a 5 hour flight. They did do two beverage services though, which was nice.
Delta
7.9
Good
8,001 reviews
Delta
7.9
Good
8,001 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Boarding

8.2

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Lane,Nov 2025

MEM - ATL

The crew was very friendly, but they only came around and offered the better Delta Comfort snacks one time. I thought they would come around more frequently on a 5 hour flight. They did do two beverage services though, which was nice.
American Airlines
7.2
Good
11,034 reviews
Delta
7.9
Good
8,001 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Boarding

8.2

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Lane,Nov 2025

MEM - ATL

The crew was very friendly, but they only came around and offered the better Delta Comfort snacks one time. I thought they would come around more frequently on a 5 hour flight. They did do two beverage services though, which was nice.

Related info for your journey

Find useful and relevant information for your journey from Jamaica to Wisconsin. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Jamaica to Wisconsin?

    A quick flight from Jamaica to Wisconsin can take about 4h 25m. Spirit Airlines provides one of the quickest options available for as low as $320. The distance from Jamaica to Wisconsin is about 1724 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Jamaica to Wisconsin one-way?

    The cheapest airlines for a one-way flight from Jamaica to Wisconsin are United Airlines ($203), Spirit Airlines ($223), and Sun Country Air ($245).

  • Can I find deals for flights from Jamaica to Wisconsin that include hotel bookings?

    Yes. In addition to deals on Jamaica to Wisconsin flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Jamaica to Wisconsin?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Jamaica to Wisconsin.

  • Can I find deals for business class flights from Jamaica to Wisconsin?

    Yes. Cheapflights offers flight deals from Jamaica to Wisconsin by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Alternative routes for Jamaica to Wisconsin

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Jamaica to Wisconsin

Discover the top 2 airlines that operate flights from Jamaica to Wisconsin. 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 November 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$436Average$488FlexibilityNo cancel feeOn-time71%
DeltaCheapest$484Average$493FlexibilityNo cancel feeOn-timeN/A

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