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Jamaica

$113+ 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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Apr 5 — Apr 121
Sun 4/5
Sun 4/12
1 adult, Economy
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Cheap 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 March 6, 2026.

This American Airlines deal was found by Cheapflights users on 3/2. 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.
Wed 4/298:05 am
ORD
-
MBJ
Nonstop4h 08m
American Airlines
Mon 5/412:25 pm
MBJ
-
ORD
1 stop20h 05m
American Airlines
Deal found 3/2$294
This American Airlines deal was found by Cheapflights users on 3/2. 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.
Sat 4/188:05 am
ORD
-
MBJ
Nonstop4h 08m
American Airlines
Mon 4/274:37 pm
MBJ
-
ORD
1 stop19h 34m
American Airlines
Deal found 3/2$295
This American Airlines deal was found by Cheapflights users on 3/1. 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.
Thu 5/77:15 am
ORD
-
MBJ
1 stop6h 10m
American Airlines
Sun 5/103:20 pm
MBJ
-
ORD
1 stop8h 14m
American Airlines
Deal found 3/1$297
This American Airlines deal was found by Cheapflights users on 3/3. 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 11/38:05 am
ORD
-
MBJ
Nonstop4h 09m
American Airlines
Tue 11/102:19 pm
MBJ
-
ORD
Nonstop4h 41m
American Airlines
Deal found 3/3$298
This Kiwi.com deal was found by Cheapflights users on 3/3. 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.
Sun 4/125:05 am
ORD
-
MBJ
1 stop6h 00m
Spirit Airlines
Thu 4/231:21 pm
MBJ
-
ORD
1 stop11h 03m
Spirit Airlines
Deal found 3/3$301
This Cheapflightsfares deal was found by Cheapflights users on 3/4. 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 5/35:05 am
ORD
-
MBJ
1 stop7h 11m
Spirit Airlines
Thu 5/71:21 pm
MBJ
-
ORD
1 stop11h 03m
Spirit Airlines
Deal found 3/4$306
This United Airlines deal was found by Cheapflights users on 3/4. 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 4/188:40 am
ORD
-
MBJ
Nonstop4h 10m
United Airlines
Sat 4/251:52 pm
MBJ
-
ORD
Nonstop4h 23m
United Airlines
Deal found 3/4$308
This American Airlines deal was found by Cheapflights users on 3/1. 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.
Sat 9/58:26 pm
MSN
-
MBJ
1 stop16h 05m
American Airlines
Sat 9/1212:43 pm
MBJ
-
MSN
1 stop10h 40m
American Airlines
Deal found 3/1$312
This American Airlines deal was found by Cheapflights users on 3/2. 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.
Thu 4/166:41 pm
MKE
-
MBJ
2 stops17h 10m
American Airlines
Thu 4/2312:56 pm
MBJ
-
MKE
2 stops18h 45m
American Airlines
Deal found 3/2$317
This American Airlines deal was found by Cheapflights users on 3/1. 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.
Wed 5/66:40 pm
MKE
-
MBJ
1 stop17h 33m
American Airlines
Mon 5/111:15 pm
MBJ
-
MKE
1 stop24h 15m
American Airlines
Deal found 3/1$318
This American Airlines deal was found by Cheapflights users on 3/2. 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.
Tue 4/148:24 pm
MSN
-
MBJ
1 stop15h 49m
American Airlines
Sat 4/181:15 pm
MBJ
-
MSN
1 stop19h 30m
American Airlines
Deal found 3/2$318
This American Airlines deal was found by Cheapflights users on 3/1. 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.
Thu 5/148:24 pm
MSN
-
MBJ
1 stop15h 49m
American Airlines
Thu 5/2112:47 pm
MBJ
-
MSN
1 stop21h 51m
American Airlines
Deal found 3/1$319

Find flight deals from Wisconsin to Jamaica

Keep the following information in mind while searching for Wisconsin to Jamaica flight deals. Data was last updated March 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$294
(American Airlines)

One-way from

$113
(FlightHub)

Popular in

June

Cheapest in

May

Average price

$671
Provider with most accurate pricing for Milwaukee-Mitchell-Montego Bay Sangster Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Montego Bay Sangster Intl flights.
Search Deals
From Wisconsin to Jamaica
Search Deals
One-way flight from Wisconsin to Jamaica
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($44 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

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 March 6, 2026.
Use the filters below to find and compare flights from Wisconsin to Jamaica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 4/19

8:40 am-12:50 pm

Nonstop4h 10m

Montego Bay Sangster Intl

Thu 4/23

1:52 pm-6:15 pm

Nonstop4h 23m

$298

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 4/18

8:40 am-12:50 pm

Nonstop4h 10m

Montego Bay Sangster Intl

Thu 4/23

1:52 pm-6:15 pm

Nonstop4h 23m

$303

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Wed 5/6

6:42 pm-9:13 am

1 stop14h 31m

Montego Bay Sangster Intl

Mon 5/11

4:37 pm-10:09 am

2 stops17h 32m

$317

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Wed 4/29

5:06 am-12:13 pm

1 stop7h 07m

Montego Bay Sangster Intl

Mon 5/4

4:37 pm-10:09 am

2 stops17h 32m

$317

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Thu 5/14

8:24 pm-12:13 pm

1 stop15h 49m

Montego Bay Sangster Intl

Thu 5/21

2:30 pm-7:49 am

1 stop17h 19m

$332

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Sat 4/25

4:26 pm-9:13 am

2 stops16h 47m

Montego Bay Sangster Intl

Sat 5/2

10:13 am-10:00 pm

2 stops11h 47m

$337

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Tue 8/18

6:46 am-2:20 pm

1 stop7h 34m

Montego Bay Sangster Intl

Tue 9/1

2:30 pm-8:15 am

2 stops17h 45m

$337

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Tue 4/14

5:30 am-1:19 pm

2 stops7h 49m

Montego Bay Sangster Intl

Tue 4/28

4:37 pm-10:55 am

2 stops18h 18m

$337

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Thu 5/14

8:55 pm-1:30 pm

2 stops16h 35m

Montego Bay Sangster Intl

Thu 5/21

2:40 pm-8:55 am

2 stops18h 15m

$347

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Wed 5/6

5:10 am-3:10 pm

2 stops10h 00m

Montego Bay Sangster Intl

Sun 5/10

4:12 pm-7:49 am

2 stops15h 37m

$367

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/2

Showing 1-10 of 60 resultsSorted by cheapest first
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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, October is the cheapest month in which you can book a flight from Wisconsin to Jamaica (average of $312). Flying from Wisconsin to Jamaica in July is currently the most expensive (average of $637). 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.

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.

  • How long is the flight from Wisconsin to Jamaica?

    United Airlines, American Airlines, and Delta can get you from Wisconsin to Jamaica in just under 4h 10m. Your travel time can differ by up to 11h 11m. Airlines will cover a distance of 1724 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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, October is the cheapest month in which you can book a flight from Wisconsin to Jamaica (average of $312). Flying from Wisconsin to Jamaica in July is currently the most expensive (average of $637). 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

Browse thousands of different options on Cheapflights for your next trip

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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.
Newark to Luis Munoz Marin Intl flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santiago de los Caballeros flights
LaGuardia to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santo Domingo flights
Newark to Santiago de los Caballeros flights
Dulles Intl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Punta Cana flights
O'Hare Intl to Luis Munoz Marin Intl flights
Philadelphia to Luis Munoz Marin Intl flights
Orlando to Luis Munoz Marin Intl flights
Newark to Oranjestad flights
John F Kennedy Intl to Oranjestad flights
Dallas/Fort Worth to Luis Munoz Marin Intl flights
Newark to Punta Cana flights
Boston to Luis Munoz Marin Intl flights
Newark to Santo Domingo flights
Reagan-National to Luis Munoz Marin Intl flights
John F Kennedy Intl to Montego Bay flights
Atlanta to Luis Munoz Marin Intl flights
Hartford to Luis Munoz Marin Intl flights
Baltimore to Luis Munoz Marin Intl flights
LaGuardia to Punta Cana flights
Newark to Montego Bay flights
John F Kennedy Intl to Kingston flights
Newark to Nassau flights
John F Kennedy Intl to Nassau flights
Dulles Intl to Punta Cana flights
Boston to Oranjestad flights
Tampa to Luis Munoz Marin Intl flights
Hobby to Luis Munoz Marin Intl flights
Atlanta to Punta Cana flights
Raleigh to Luis Munoz Marin Intl flights
LaGuardia to Santiago de los Caballeros flights
Fort Lauderdale to Luis Munoz Marin Intl flights
Newark to Simpson Bay flights
Miami to Luis Munoz Marin Intl flights
Midway to Luis Munoz Marin Intl flights
LaGuardia to Nassau flights
John F Kennedy Intl to Providenciales flights
George Bush Intcntl to Luis Munoz Marin Intl flights
Boston to Punta Cana flights
LaGuardia to Santo Domingo flights
Atlanta to Montego Bay flights
O'Hare Intl to Punta Cana flights
Newark to Saint Thomas Island flights
John F Kennedy Intl to Port of Spain flights
Fort Lauderdale to Punta Cana flights

Top 4 airlines flying from Wisconsin to Jamaica

Discover the top 4 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 March 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$277Average$624FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$490Average$707FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$563Average$687FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$571Average$678FlexibilityNo cancel feeOn-time63%

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