Wisconsin

$204+ 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 12/16. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — MKE
Jul 23 — Jul 301
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Cheap 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 June 23, 2026.

This American Airlines deal was found by Cheapflights users on 6/19. 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.
Thu 6/252:31 pm
MBJ
-
ORD
Nonstop4h 39m
American Airlines
Sat 7/49:20 am
ORD
-
MBJ
Nonstop4h 16m
American Airlines
Deal found 6/19$320
This Delta deal was found by Cheapflights users on 6/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/214:59 pm
MBJ
-
MSN
2 stops15h 49m
Delta
Sun 9/276:00 am
MSN
-
MBJ
1 stop9h 34m
Delta
Deal found 6/19$327
This Delta deal was found by Cheapflights users on 6/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/244:59 pm
MBJ
-
ORD
1 stop7h 00m
Delta
Tue 6/306:35 am
ORD
-
MBJ
1 stop8h 59m
Delta
Deal found 6/21$327
This United Airlines deal was found by Cheapflights users on 6/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2112:52 pm
MBJ
-
MSN
2 stops32h 01m
United Airlines
Sun 9/276:49 am
MSN
-
MBJ
2 stops52h 54m
United Airlines
Deal found 6/19$331
This United Airlines deal was found by Cheapflights users on 6/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/252:40 pm
MBJ
-
ORD
1 stop17h 19m
United Airlines
Sat 7/48:43 am
ORD
-
MBJ
1 stop6h 27m
United Airlines
Deal found 6/21$331
This Delta deal was found by Cheapflights users on 6/18. 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.
Thu 9/171:25 pm
MBJ
-
MSN
1 stop9h 14m
Delta
Mon 9/286:00 am
MSN
-
MBJ
1 stop9h 34m
Delta
Deal found 6/18$332
This American Airlines deal was found by Cheapflights users on 6/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/43:02 pm
MBJ
-
ORD
1 stop8h 28m
American Airlines
Mon 8/319:00 am
ORD
-
MBJ
Nonstop4h 12m
American Airlines
Deal found 6/20$332
This American Airlines deal was found by Cheapflights users on 6/22. 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 9/232:09 pm
MBJ
-
ORD
1 stop9h 50m
American Airlines
Mon 9/285:20 am
ORD
-
MBJ
2 stops7h 33m
American Airlines
Deal found 6/22$341
This United Airlines deal was found by Cheapflights users on 6/18. 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.
Mon 9/1412:52 pm
MBJ
-
MSN
1 stop21h 22m
United Airlines
Sat 9/266:06 am
MSN
-
MBJ
1 stop29h 37m
United Airlines
Deal found 6/18$351
This United Airlines deal was found by Cheapflights users on 6/22. 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 8/222:40 pm
MBJ
-
MSN
2 stops23h 02m
United Airlines
Mon 8/242:44 pm
MSN
-
MBJ
2 stops44h 59m
United Airlines
Deal found 6/22$402
This United Airlines deal was found by Cheapflights users on 6/18. 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.
Mon 9/1412:52 pm
MBJ
-
MSN
1 stop21h 22m
United Airlines
Mon 9/286:06 am
MSN
-
MBJ
1 stop29h 37m
United Airlines
Deal found 6/18$403
This United Airlines deal was found by Cheapflights users on 6/18. 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.
Wed 9/1612:52 pm
MBJ
-
MSN
2 stops20h 48m
United Airlines
Tue 9/298:10 am
MSN
-
MBJ
2 stops27h 33m
United Airlines
Deal found 6/18$411

Find flight deals from Jamaica to Wisconsin

Keep the following information in mind while searching for Jamaica to Wisconsin flight deals. Data was last updated June 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$321
(American Airlines)

One-way from

$204
(United Airlines)
Provider with most accurate pricing for Montego Bay Sangster Intl-Milwaukee-Mitchell flight deals.
Provider most trusted by Cheapflights users for Montego Bay Sangster Intl-Milwaukee-Mitchell flights.
From Jamaica to Wisconsin
One-way flight from Jamaica to Wisconsin

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 June 23, 2026.
Use the filters below to find and compare flights from Jamaica to Wisconsin that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 11/23

2:48 pm-6:16 pm

Nonstop4h 28m

Chicago O'Hare Intl

Sun 11/29

8:42 am-1:46 pm

Nonstop4h 04m

$321

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 9/23

12:52 pm-9:00 am

1 stop20h 08m

Chicago O'Hare Intl

Mon 9/28

7:52 pm-11:43 am

1 stop15h 51m

$331

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Wed 9/16

1:25 pm-10:39 pm

1 stop9h 14m

Madison Truax Field

Mon 9/28

5:24 pm-11:25 am

2 stops18h 01m

$332

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 7/4

3:02 pm-11:30 pm

1 stop8h 28m

Chicago O'Hare Intl

Mon 8/31

9:00 am-1:12 pm

Nonstop4h 12m

$332

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Wed 9/16

1:25 pm-10:39 pm

1 stop9h 14m

Madison Truax Field

Fri 9/25

5:24 pm-11:25 am

2 stops18h 01m

$332

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 8/29

3:23 pm-7:30 am

1 stop16h 07m

Chicago O'Hare Intl

Sat 9/5

7:00 am-4:08 pm

1 stop9h 08m

$336

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Mon 9/14

12:52 pm-10:14 am

1 stop21h 22m

Madison Truax Field

Sat 9/26

6:06 am-11:43 am

1 stop29h 37m

$351

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Mon 9/14

12:52 pm-10:14 am

1 stop21h 22m

Madison Truax Field

Mon 9/28

6:06 am-11:43 am

1 stop29h 37m

$403

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sun 8/23

2:12 pm-6:55 pm

Nonstop4h 43m

Chicago O'Hare Intl

Mon 8/24

9:00 am-1:12 pm

Nonstop4h 12m

$434

Montego BayMilwaukee

MBJ - MKE

MBJMKE

Montego Bay Sangster Intl

Sat 10/17

4:55 pm-3:11 pm

2 stops22h 16m

Milwaukee-Mitchell

Sun 10/25

6:30 am-12:48 pm

1 stop6h 18m

$441

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/22

Showing 1-10 of 60 resultsSorted by cheapest first
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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 June 23, 2026.
See what other customers who have flown with 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.

Crew

7.9

Entertainment

6.8

Overall

7.1

Comfort

7.2

Boarding

7.5

Food

6.4

Reviews

1 / 20
10.0
Excellent

Beatriz,May 2026

HEL - DFW

Very modern and confortable plane. Dinner was delicious. Whole crew were polite and perfect.

Crew

7.9

Entertainment

6.8

Overall

7.1

Comfort

7.2

Boarding

7.5

Food

6.4

Reviews

1 / 20
10.0
Excellent

Beatriz,May 2026

HEL - DFW

Very modern and confortable plane. Dinner was delicious. Whole crew were polite and perfect.

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 28m. United Airlines provides one of the quickest options available for as low as $321. 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 American Airlines ($203), Delta ($204), and United Airlines ($228).

  • 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.

Top airline flying from Jamaica to Wisconsin

Discover the top airline 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 June 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$316Average$478FlexibilityNo cancel feeOn-time71%

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