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Jamaica

$230+ 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 6/15. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
May 30 — Jun 61
Sat 5/30
Sat 6/6
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 April 30, 2026.

This American Airlines deal was found by Cheapflights users on 4/30. 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 6/16:08 am
MKE
-
MBJ
1 stop7h 22m
American Airlines
Fri 6/53:00 pm
MBJ
-
MKE
1 stop8h 47m
American Airlines
Deal found 4/30$352
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Sat 7/187:00 pm
MKE
-
MBJ
1 stop18h 31m
American Airlines
Thu 7/232:31 pm
MBJ
-
MKE
1 stop17h 31m
American Airlines
Deal found 4/28$358
This American Airlines deal was found by Cheapflights users on 4/27. 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 5/146:42 pm
MKE
-
MBJ
2 stops17h 09m
American Airlines
Tue 5/194:37 pm
MBJ
-
MKE
2 stops18h 22m
American Airlines
Deal found 4/27$359
This American Airlines deal was found by Cheapflights users on 4/27. 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 9/104:33 pm
MKE
-
MBJ
1 stop16h 37m
American Airlines
Sun 9/133:15 pm
MBJ
-
MKE
2 stops18h 46m
American Airlines
Deal found 4/27$362
This American Airlines deal was found by Cheapflights users on 4/30. 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 8/274:25 pm
MKE
-
MBJ
1 stop21h 03m
American Airlines
Mon 8/315:13 pm
MBJ
-
MKE
2 stops18h 24m
American Airlines
Deal found 4/30$364
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Wed 9/166:26 pm
MKE
-
MBJ
2 stops16h 24m
American Airlines
Sun 9/203:15 pm
MBJ
-
MKE
2 stops18h 46m
American Airlines
Deal found 4/28$367
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Tue 12/86:01 am
MKE
-
MBJ
2 stops8h 52m
American Airlines
Sun 12/133:39 pm
MBJ
-
MKE
1 stop19h 06m
American Airlines
Deal found 4/28$369
This American Airlines deal was found by Cheapflights users on 4/25. 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 5/66:00 am
MKE
-
MBJ
1 stop8h 15m
American Airlines
Mon 5/114:37 pm
MBJ
-
MKE
2 stops17h 32m
American Airlines
Deal found 4/25$393
This American Airlines deal was found by Cheapflights users on 4/29. 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 5/87:00 am
MKE
-
MBJ
1 stop6h 25m
American Airlines
Wed 5/1312:25 pm
MBJ
-
MKE
1 stop10h 22m
American Airlines
Deal found 4/29$405
This American Airlines deal was found by Cheapflights users on 4/27. 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 12/146:50 pm
MKE
-
MBJ
2 stops17h 10m
American Airlines
Mon 12/286:00 pm
MBJ
-
MKE
1 stop18h 03m
American Airlines
Deal found 4/27$407
This United Airlines deal was found by Cheapflights users on 4/27. 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 5/195:56 pm
MKE
-
KIN
3 stops19h 58m
United Airlines
Sun 5/242:59 pm
KIN
-
MKE
2 stops24h 47m
United Airlines
Deal found 4/27$712
This United Airlines deal was found by Cheapflights users on 4/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:40 pm
MKE
-
KIN
2 stops19h 12m
United Airlines
Tue 5/52:59 pm
KIN
-
MKE
2 stops18h 46m
United Airlines
Deal found 4/28$777

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 April 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$352
(American Airlines)

One-way from

$230
(United Airlines)

Popular in

June

Cheapest in

January

Average price

$614
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. 1% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 30, 2026.
Use the filters below to find and compare flights from Milwaukee to Jamaica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Sat 9/26

5:21 pm-11:43 am

2 stops18h 22m

Montego Bay Sangster Intl

Sat 10/3

2:40 pm-10:41 pm

1 stop8h 01m

$352

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Mon 6/1

6:08 am-1:30 pm

1 stop7h 22m

Montego Bay Sangster Intl

Fri 6/5

3:00 pm-11:47 pm

1 stop8h 47m

$352

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Thu 8/27

4:25 pm-11:42 am

2 stops19h 17m

Montego Bay Sangster Intl

Mon 8/31

5:13 pm-11:37 am

2 stops18h 24m

$357

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Wed 9/16

5:51 pm-10:50 am

2 stops16h 59m

Montego Bay Sangster Intl

Sun 9/20

3:15 pm-10:01 am

2 stops18h 46m

$367

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Mon 8/10

6:05 am-3:10 pm

2 stops9h 05m

Montego Bay Sangster Intl

Sat 8/15

4:12 pm-10:00 am

2 stops17h 48m

$410

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Tue 6/9

6:05 am-3:10 pm

2 stops9h 05m

Montego Bay Sangster Intl

Fri 6/12

4:12 pm-11:08 am

2 stops18h 56m

$410

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Thu 5/28

1:30 pm-3:10 pm

2 stops25h 40m

Montego Bay Sangster Intl

Thu 6/11

2:40 pm-12:48 pm

2 stops22h 08m

$467

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Mon 6/1

5:00 am-1:30 pm

1 stop8h 30m

Montego Bay Sangster Intl

Sat 6/6

3:00 pm-11:47 pm

1 stop8h 47m

$480

MilwaukeeKingston

MKE - KIN

MKEKIN

Milwaukee-Mitchell

Tue 5/19

12:06 pm-1:54 pm

2 stops25h 48m

Kingston Norman Manley

Sun 5/24

2:59 pm-11:19 am

2 stops20h 20m

$854

MilwaukeeKingston

MKE - KIN

MKEKIN

Milwaukee-Mitchell

Tue 6/23

9:36 am-11:37 pm

2 stops14h 01m

Kingston Norman Manley

Wed 7/1

8:25 am-8:46 am

2 stops24h 21m

$861

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/25

Showing 1-10 of 18 resultsSorted by cheapest first
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 $352). Flying from Milwaukee to Jamaica in August is currently the most expensive (average of $540). 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 April 30, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andAmerican 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
4,314 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,314 reviews
Southwest
8.0
Very good
4,314 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,463 reviews
Southwest
8.0
Very good
4,314 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,681 reviews
Southwest
8.0
Very good
4,314 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 8h 30m. 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 $352). Flying from Milwaukee to Jamaica in August is currently the most expensive (average of $540). 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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Top 3 airlines flying from Milwaukee to Jamaica

Discover the top 3 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 April 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$357Average$795FlexibilityNo cancel feeOn-time71%
DeltaCheapest$473Average$539FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$571Average$716FlexibilityNo cancel feeOn-time63%

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