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Jamaica

$171+ Cheap flights from Milwaukee (MKE) 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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
fev 27 — mar 61
sex 2/27
sex 3/6
1 adult, Economy
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Cheap flight deals from Milwaukee to Jamaica

Cheapest flights from Milwaukee to Jamaica
Explore the most affordable flight options available from Milwaukee to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on janeiro 28, 2026.

This Delta deal was found by Cheapflights users on 1/26. 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.
qua 2/186:15 am
MKE
-
MBJ
1 stop7h 25m
Delta
qua 2/252:19 pm
MBJ
-
MKE
1 stop10h 28m
Delta
Deal found 1/26$490
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 3/36:00 am
MKE
-
MBJ
1 stop6h 26m
American Airlines
qua 3/111:14 pm
MBJ
-
MKE
1 stop7h 11m
American Airlines
Deal found 1/28$507
This Southwest deal was found by Cheapflights users on 1/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 2/156:45 am
MKE
-
MBJ
1 stop6h 25m
Southwest
sex 2/271:30 pm
MBJ
-
MKE
2 stops11h 20m
Southwest
Deal found 1/26$514
This Delta deal was found by Cheapflights users on 1/26. 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.
qua 5/65:21 am
MKE
-
MBJ
1 stop7h 33m
Delta
seg 5/1112:55 pm
MBJ
-
MKE
1 stop10h 32m
Delta
Deal found 1/26$524
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.
qua 5/66:00 am
MKE
-
MBJ
1 stop8h 15m
American Airlines
seg 5/114:44 pm
MBJ
-
MKE
2 stops17h 25m
American Airlines
Deal found 1/27$526
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.
qua 2/186:01 am
MKE
-
MBJ
1 stop6h 32m
American Airlines
qua 2/252:33 pm
MBJ
-
MKE
2 stops9h 51m
American Airlines
Deal found 1/27$530
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.
sáb 4/116:32 pm
MKE
-
MBJ
1 stop16h 52m
American Airlines
sáb 4/182:29 pm
MBJ
-
MKE
1 stop8h 18m
American Airlines
Deal found 1/27$532
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.
seg 2/93:53 pm
MKE
-
MBJ
2 stops18h 40m
American Airlines
qui 2/122:33 pm
MBJ
-
MKE
2 stops10h 22m
American Airlines
Deal found 1/27$535
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.
sex 3/135:00 am
MKE
-
KIN
2 stops14h 12m
American Airlines
sex 3/202:34 pm
KIN
-
MKE
1 stop9h 25m
American Airlines
Deal found 1/27$709
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.
sex 3/137:00 am
MKE
-
KIN
1 stop13h 00m
Delta
sex 3/209:00 am
KIN
-
MKE
1 stop14h 58m
Delta
Deal found 1/27$744
This American Airlines deal was found by Cheapflights users on 1/26. 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.
qui 2/193:05 pm
MKE
-
KIN
2 stops18h 17m
American Airlines
qui 2/2611:12 am
KIN
-
MKE
2 stops12h 45m
American Airlines
Deal found 1/26$749
This Delta deal was found by Cheapflights users on 1/26. 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.
qui 2/195:23 am
MKE
-
KIN
1 stop13h 37m
Delta
qui 2/269:00 am
KIN
-
MKE
1 stop12h 38m
Delta
Deal found 1/26$784

Find flight deals from Milwaukee to Jamaica

Keep the following information in mind while searching for Milwaukee to Jamaica flight deals. Data was last updated janeiro 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$490
(Delta)

One-way from

$171
(Kiwi.com)

Popular in

June

Cheapest in

October

Average price

$588
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 Milwaukee-Mitchell to Jamaica
Search Deals
One-way flight from Milwaukee-Mitchell to Jamaica
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($62 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 January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Milwaukee 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 janeiro 28, 2026.
Use the filters below to find and compare flights from Milwaukee to Jamaica that are best for you.

Fly from

Milwaukee

Fly to

Jamaica

Route

Depart

Return

Price

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

qua 2/18

6:15 am-2:40 pm

1 stop7h 25m

Montego Bay Sangster Intl

qua 2/25

2:19 pm-11:47 pm

1 stop10h 28m

$490

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

dom 2/15

6:15 am-2:40 pm

1 stop7h 25m

Montego Bay Sangster Intl

sex 2/27

12:20 pm-11:47 pm

1 stop12h 27m

$490

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

ter 3/3

5:00 am-1:26 pm

1 stop7h 26m

Montego Bay Sangster Intl

qua 3/11

12:28 pm-11:45 pm

1 stop11h 17m

$507

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

dom 2/15

6:45 am-2:10 pm

1 stop6h 25m

Montego Bay Sangster Intl

sex 2/27

1:30 pm-11:50 pm

2 stops11h 20m

$514

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

qua 5/6

5:21 am-12:54 pm

1 stop7h 33m

Montego Bay Sangster Intl

seg 5/11

12:55 pm-11:27 pm

1 stop10h 32m

$524

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

qua 5/6

6:10 am-12:15 pm

1 stop6h 05m

Montego Bay Sangster Intl

seg 5/11

4:44 pm-10:09 am

2 stops17h 25m

$526

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

qua 4/15

5:21 am-3:17 pm

1 stop9h 56m

Montego Bay Sangster Intl

qua 4/22

4:32 pm-11:57 pm

1 stop7h 25m

$526

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

ter 3/3

5:25 am-12:53 pm

1 stop6h 28m

Montego Bay Sangster Intl

qua 3/11

11:15 am-8:55 pm

1 stop9h 40m

$526

MilwaukeeKingston

MKE - KIN

MKEKIN

Milwaukee-Mitchell

sex 3/13

5:00 am-7:12 pm

2 stops14h 12m

Kingston Norman Manley

sex 3/20

2:34 pm-11:59 pm

1 stop9h 25m

$709

MilwaukeeKingston

MKE - KIN

MKEKIN

Milwaukee-Mitchell

sex 3/13

7:00 am-8:00 pm

1 stop13h 00m

Kingston Norman Manley

sex 3/20

9:00 am-11:58 pm

1 stop14h 58m

$744

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 17 results
1
2

Best time to book a flight from Milwaukee to Jamaica

Have a flexible travel schedule? Discover the best time to fly to Jamaica from Milwaukee 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 Milwaukee to Jamaica

What is the cheapest month to book a flight from Milwaukee to Jamaica?

Currently, January is the cheapest month in which you can book a flight from Milwaukee to Jamaica (average of $96). Flying from Milwaukee to Jamaica in March is currently the most expensive (average of $405). 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.

Reviews of airlines servicing Jamaica

Get insights into the airlines that provide service to Jamaica. 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 Jamaica. Reviews last updated janeiro 28, 2026.
Get a feel of what it's like to fly with Southwest, Delta, and American Airlines from Milwaukee to Jamaica by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,267 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,124 reviews
Southwest
8.0
Very good
4,267 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,201 reviews
Southwest
8.0
Very good
4,267 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Sun Country Air
6.9
Okay
343 reviews
Southwest
8.0
Very good
4,267 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

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

  • What airport do you fly from for flights from Milwaukee to Jamaica?

    Most people fly from Milwaukee-Mitchell (MKE) if they book a flight from Milwaukee to Jamaica. Milwaukee-Mitchell is conveniently located just 6.4 mi from Milwaukee’s city center.

  • How long is the flight from Milwaukee to Jamaica?

    Departing from Milwaukee to Jamaica will take you 7h 25m. The distance from Milwaukee to Jamaica is about 1786 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 Milwaukee to Jamaica that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Milwaukee 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 Milwaukee to Jamaica?

    Currently, January is the cheapest month in which you can book a flight from Milwaukee to Jamaica (average of $96). Flying from Milwaukee to Jamaica in March is currently the most expensive (average of $405). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Milwaukee to Jamaica

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Milwaukee to Jamaica

Discover the top 4 airlines that operate flights from Milwaukee 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 janeiro 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$473Average$644FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$538Average$626FlexibilityNo cancel feeOn-time71%
Sun Country AirCheapest$540Average$540FlexibilityNo cancel feeOn-time83%
SouthwestCheapest$571Average$698FlexibilityNo cancel feeOn-time63%

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