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Wisconsin

$149+ 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 2/14. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — MKE
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This Orbitz deal was found by Cheapflights users on 1/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/251:00 pm
MBJ
-
ORD
1 stop9h 13m
Spirit Airlines
Wed 3/45:15 am
ORD
-
MBJ
1 stop5h 47m
Spirit Airlines
Deal found 1/28$230
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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 3/2412:00 pm
MBJ
-
ORD
1 stop7h 46m
Spirit Airlines
Tue 4/148:41 pm
ORD
-
MBJ
1 stop14h 21m
Spirit Airlines
Deal found 1/27$269
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Tue 3/241:14 pm
MBJ
-
ORD
Nonstop4h 41m
American Airlines
Tue 4/148:10 am
ORD
-
MBJ
Nonstop4h 05m
American Airlines
Deal found 1/27$320
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Tue 3/241:48 pm
MBJ
-
ORD
Nonstop4h 25m
United Airlines
Tue 4/148:45 am
ORD
-
MBJ
1 stop6h 25m
United Airlines
Deal found 1/27$325
This American Airlines deal was found by Cheapflights users on 1/27. 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 5/143:20 pm
MBJ
-
ORD
1 stop8h 33m
American Airlines
Mon 5/186:58 pm
ORD
-
MBJ
1 stop16h 53m
American Airlines
Deal found 1/27$335
This American Airlines deal was found by Cheapflights users on 1/27. 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 4/131:15 pm
MBJ
-
ORD
Nonstop4h 43m
American Airlines
Tue 4/218:10 am
ORD
-
MBJ
Nonstop4h 05m
American Airlines
Deal found 1/27$345
This Delta deal was found by Cheapflights users on 1/27. 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.
Tue 3/2411:15 am
MBJ
-
ORD
1 stop12h 39m
Delta
Tue 4/147:00 am
ORD
-
MBJ
2 stops8h 17m
Delta
Deal found 1/27$351
This United Airlines deal was found by Cheapflights users on 1/27. 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 4/134:12 pm
MBJ
-
ORD
1 stop7h 31m
United Airlines
Tue 4/218:45 am
ORD
-
MBJ
1 stop6h 25m
United Airlines
Deal found 1/27$365
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 5/1912:00 pm
KIN
-
ORD
1 stop9h 17m
Multiple Airlines
Mon 8/315:32 pm
ORD
-
KIN
1 stop17h 33m
Multiple Airlines
Deal found 1/28$372
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/2812:40 pm
MBJ
-
ORD
1 stop10h 59m
Multiple Airlines
Sat 3/146:01 pm
ORD
-
MBJ
2 stops16h 57m
Multiple Airlines
Deal found 1/28$373
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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.
Wed 5/1312:00 pm
KIN
-
ORD
1 stop7h 48m
Spirit Airlines
Wed 5/275:32 pm
ORD
-
KIN
1 stop17h 33m
Spirit Airlines
Deal found 1/27$389
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Wed 4/112:17 pm
KIN
-
ORD
2 stops34h 25m
Multiple Airlines
Fri 4/107:20 am
ORD
-
KIN
1 stop27h 40m
Multiple Airlines
Deal found 1/28$398

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$230
(Orbitz)

One-way from

$149
(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 January 29, 2026.
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

Tue 3/24

1:48 pm-6:13 pm

Nonstop4h 25m

Chicago O'Hare Intl

Tue 4/14

8:45 am-3:10 pm

1 stop6h 25m

$325

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 5/14

3:20 pm-11:53 pm

1 stop8h 33m

Chicago O'Hare Intl

Mon 5/18

6:58 pm-11:51 am

1 stop16h 53m

$335

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 4/13

1:15 pm-5:58 pm

Nonstop4h 43m

Chicago O'Hare Intl

Tue 4/21

5:00 am-11:24 am

1 stop6h 24m

$350

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 5/14

4:55 pm-7:26 am

2 stops14h 31m

Chicago O'Hare Intl

Mon 5/18

7:10 am-1:16 pm

1 stop6h 06m

$351

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 3/24

11:15 am-11:54 pm

1 stop12h 39m

Chicago O'Hare Intl

Tue 4/14

7:00 am-3:17 pm

2 stops8h 17m

$351

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 4/13

4:12 pm-11:43 pm

1 stop7h 31m

Chicago O'Hare Intl

Tue 4/21

8:45 am-3:10 pm

1 stop6h 25m

$365

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Tue 5/19

12:00 pm-9:17 pm

1 stop9h 17m

Chicago O'Hare Intl

Mon 8/31

5:32 pm-11:05 am

1 stop17h 33m

$372

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 2/28

12:40 pm-10:39 pm

1 stop10h 59m

Chicago O'Hare Intl

Sat 3/14

6:01 pm-10:58 am

2 stops16h 57m

$373

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 4/17

1:52 pm-6:15 pm

Nonstop4h 23m

Chicago O'Hare Intl

Fri 5/1

8:05 pm-1:30 pm

1 stop17h 25m

$380

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 3/30

3:04 pm-9:45 am

1 stop18h 41m

Chicago O'Hare Intl

Mon 4/6

8:05 am-12:11 pm

Nonstop4h 06m

$381

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 59 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 January 29, 2026.
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
8,128 reviews

Food

7.2

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.8

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,128 reviews
Delta
7.9
Good
8,128 reviews

Food

7.2

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.8

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,205 reviews
Delta
7.9
Good
8,128 reviews

Food

7.2

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.8

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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. United Airlines provides one of the quickest options available for as low as $325. 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 Spirit Airlines ($173), Delta ($259), and American Airlines ($263).

  • 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$449Average$458FlexibilityNo cancel feeOn-time71%
DeltaCheapest$457Average$493FlexibilityNo cancel feeOn-timeN/A

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