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Wisconsin

$178+ 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 4/30. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — MKE
Apr 19 — Apr 261
Sun 4/19
Sun 4/26
1 adult, Economy
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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 March 20, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 3/15. 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.
Thu 5/71:21 pm
MBJ
-
ORD
1 stop11h 06m
Spirit Airlines
Tue 5/125:05 am
ORD
-
MBJ
1 stop7h 11m
Spirit Airlines
Deal found 3/15$270
This Cheapflightsfares deal was found by Cheapflights users on 3/17. 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 4/281:21 pm
MBJ
-
ORD
1 stop11h 03m
Spirit Airlines
Tue 5/125:05 am
ORD
-
MBJ
1 stop7h 11m
Spirit Airlines
Deal found 3/17$278
This American Airlines deal was found by Cheapflights users on 3/19. 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.
Fri 6/52:30 pm
MBJ
-
ORD
Nonstop4h 45m
American Airlines
Sun 8/238:30 am
ORD
-
MBJ
Nonstop4h 01m
American Airlines
Deal found 3/19$281
This United Airlines deal was found by Cheapflights users on 3/15. 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 5/161:52 pm
MBJ
-
ORD
Nonstop4h 23m
United Airlines
Tue 5/195:30 am
ORD
-
MBJ
1 stop8h 00m
United Airlines
Deal found 3/15$286
This United Airlines deal was found by Cheapflights users on 3/16. 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 5/162:40 pm
MBJ
-
ORD
1 stop18h 20m
United Airlines
Mon 5/189:56 pm
ORD
-
MBJ
1 stop15h 34m
United Airlines
Deal found 3/16$291
This United Airlines deal was found by Cheapflights users on 3/15. 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 5/94:12 pm
MBJ
-
ORD
1 stop7h 32m
United Airlines
Sat 5/168:40 am
ORD
-
MBJ
Nonstop4h 10m
United Airlines
Deal found 3/15$292
This FlightHub deal was found by Cheapflights users on 3/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/121:21 pm
MBJ
-
ORD
1 stop11h 06m
Spirit Airlines
Wed 5/137:45 pm
ORD
-
MBJ
1 stop16h 31m
Spirit Airlines
Deal found 3/20$294
This American Airlines deal was found by Cheapflights users on 3/15. 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 5/910:13 am
MBJ
-
ORD
1 stop9h 09m
American Airlines
Sat 5/166:41 pm
ORD
-
MBJ
1 stop14h 32m
American Airlines
Deal found 3/15$296
This American Airlines deal was found by Cheapflights users on 3/15. 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 5/173:20 pm
MBJ
-
ORD
1 stop8h 14m
American Airlines
Sat 9/126:35 pm
ORD
-
MBJ
1 stop14h 35m
American Airlines
Deal found 3/15$301
This United Airlines deal was found by Cheapflights users on 3/16. 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 5/12:40 pm
MBJ
-
MSN
2 stops18h 16m
United Airlines
Fri 5/88:55 pm
MSN
-
MBJ
2 stops16h 35m
United Airlines
Deal found 3/16$312
This United Airlines deal was found by Cheapflights users on 3/16. 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 5/12:40 pm
MBJ
-
MKE
2 stops17h 09m
United Airlines
Fri 5/86:56 pm
MKE
-
MBJ
2 stops18h 34m
United Airlines
Deal found 3/16$312
This United Airlines deal was found by Cheapflights users on 3/18. 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.
Thu 4/302:40 pm
MBJ
-
ORD
1 stop10h 05m
United Airlines
Thu 5/74:25 pm
ORD
-
MBJ
1 stop22h 45m
United Airlines
Deal found 3/18$312

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 March 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$270
(Cheapflightsfares)

One-way from

$178
(Super.com)
Provider with most accurate pricing for Montego Bay Sangster Intl-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for Montego Bay Sangster Intl-Milwaukee-Mitchell flights.
Search Deals
From Jamaica to Wisconsin
Search Deals
One-way flight from Jamaica to Wisconsin
Search Deals

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 March 20, 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

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 5/16

1:52 pm-6:15 pm

Nonstop4h 23m

Chicago O'Hare Intl

Tue 5/19

5:30 am-1:30 pm

1 stop8h 00m

$286

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 5/16

1:52 pm-6:15 pm

Nonstop4h 23m

Chicago O'Hare Intl

Mon 5/18

11:00 pm-1:30 pm

1 stop14h 30m

$286

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 4/16

1:52 pm-6:15 pm

Nonstop4h 23m

Chicago O'Hare Intl

Thu 4/30

9:35 pm-3:10 pm

1 stop17h 35m

$292

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 5/15

4:12 pm-4:30 pm

1 stop24h 18m

Chicago O'Hare Intl

Wed 5/27

5:30 am-1:30 pm

1 stop8h 00m

$292
Quickest round-trip

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 5/9

4:12 pm-11:44 pm

1 stop7h 32m

Chicago O'Hare Intl

Sat 5/16

8:40 am-12:50 pm

Nonstop4h 10m

$292

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Fri 5/1

2:40 pm-8:56 am

2 stops18h 16m

Madison Truax Field

Fri 5/8

8:55 pm-1:30 pm

2 stops16h 35m

$312

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Fri 5/15

2:40 pm-9:20 pm

2 stops30h 40m

Madison Truax Field

Mon 5/18

8:55 pm-1:30 pm

2 stops16h 35m

$312

Montego BayMilwaukee

MBJ - MKE

MBJMKE

Montego Bay Sangster Intl

Fri 5/1

2:40 pm-10:38 am

1 stop19h 58m

Milwaukee-Mitchell

Fri 5/8

8:45 pm-12:50 pm

1 stop16h 05m

$312

Montego BayMilwaukee

MBJ - MKE

MBJMKE

Montego Bay Sangster Intl

Thu 4/30

4:12 pm-1:11 pm

2 stops20h 59m

Milwaukee-Mitchell

Thu 5/7

5:55 am-3:10 pm

2 stops9h 15m

$312

Montego BayMilwaukee

MBJ - MKE

MBJMKE

Montego Bay Sangster Intl

Tue 5/12

12:25 pm-9:57 pm

1 stop9h 32m

Milwaukee-Mitchell

Tue 9/1

6:05 am-1:58 pm

1 stop7h 53m

$316

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/15

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 March 20, 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.
American Airlines
7.1
Good
11,480 reviews

Boarding

7.5

Comfort

7.2

Food

6.4

Entertainment

6.9

Crew

7.9

Overall

7.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes
American Airlines
7.1
Good
11,480 reviews
American Airlines
7.1
Good
11,480 reviews

Boarding

7.5

Comfort

7.2

Food

6.4

Entertainment

6.9

Crew

7.9

Overall

7.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes

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 23m. United Airlines provides one of the quickest options available for as low as $286. 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 ($192), Delta ($259), and United Airlines ($264).

  • 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

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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 March 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$436Average$488FlexibilityNo cancel feeOn-time71%

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