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Jamaica

$377+ 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 11/26. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Find 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 October 29, 2025.

This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/275:45 amMKE - MBJ
1 stop7h 26mDelta
Thu 12/42:29 pmMBJ - MKE
1 stop6h 50mDelta
Deal found 10/28$564
This American Airlines deal was found by Cheapflights users on 10/27. 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 11/275:00 amMKE - MBJ
1 stop7h 14mAmerican Airlines
Thu 12/42:02 pmMBJ - MKE
2 stops10h 59mAmerican Airlines
Deal found 10/27$569
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Fri 12/53:45 pmMKE - MBJ
2 stops17h 28mAmerican Airlines
Mon 12/1511:13 amMBJ - MKE
2 stops12h 48mAmerican Airlines
Deal found 10/28$594
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/215:45 amMKE - MBJ
1 stop7h 26mDelta
Tue 11/255:59 pmMBJ - MKE
1 stop6h 56mDelta
Deal found 10/29$631
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Fri 11/216:05 amMKE - MBJ
1 stop6h 41mUnited Airlines
Tue 11/252:48 pmMBJ - MKE
1 stop8h 55mUnited Airlines
Deal found 10/28$654
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Mon 12/85:35 pmMKE - MBJ
2 stops19h 54mUnited Airlines
Sat 12/135:14 pmMBJ - MKE
2 stops18h 05mUnited Airlines
Deal found 10/28$659
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Sun 12/218:02 pmMKE - MBJ
1 stop18h 09mAmerican Airlines
Fri 12/2611:27 amMBJ - MKE
1 stop13h 31mAmerican Airlines
Deal found 10/29$661
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Fri 11/215:00 amMKE - MBJ
2 stops8h 50mAmerican Airlines
Tue 11/2511:17 amMBJ - MKE
2 stops13h 45mAmerican Airlines
Deal found 10/28$669
This American Airlines deal was found by Cheapflights users on 10/27. 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.
Fri 11/286:14 amMKE - KIN
2 stops14h 59mAmerican Airlines
Mon 12/17:30 amKIN - MKE
2 stops17h 32mAmerican Airlines
Deal found 10/27$676
This Delta deal was found by Cheapflights users on 10/27. 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.
Fri 11/285:45 amMKE - KIN
1 stop13h 15mDelta
Mon 12/19:00 amKIN - MKE
1 stop8h 17mDelta
Deal found 10/27$872
This American Airlines deal was found by Cheapflights users on 10/27. 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 10/278:16 pmMKE - KIN
2 stops23h 34mAmerican Airlines
Tue 11/47:30 amKIN - MKE
2 stops16h 26mAmerican Airlines
Deal found 10/27$916
This American Airlines deal was found by Cheapflights users on 10/27. 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 10/278:16 pmMKE - KIN
2 stops23h 34mAmerican Airlines
Sat 11/111:54 amKIN - MKE
2 stops9h 30mAmerican Airlines
Deal found 10/27$956

Cheap flight deals from Milwaukee to Jamaica

Keep the following information in mind while searching for Milwaukee to Jamaica flight deals. Data was last updated October 29, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$494
(Kiwi.com)

One-way from

$377
(Delta)

Popular in

June

Cheapest in

March

Average price

$560
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. 10% potential increase in price ($71 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 October 29, 2025.
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

Thu 11/27

5:45 am-2:11 pm

1 stop7h 26m

Montego Bay Sangster Intl

Thu 12/4

2:29 pm-8:19 pm

1 stop6h 50m

$564

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Thu 12/11

6:10 am-2:57 pm

1 stop7h 47m

Montego Bay Sangster Intl

Thu 12/18

1:22 pm-11:58 pm

1 stop11h 36m

$564

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Sat 12/13

6:34 pm-12:55 pm

1 stop17h 21m

Montego Bay Sangster Intl

Sat 12/20

1:22 pm-11:59 pm

1 stop11h 37m

$564

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Fri 1/23

5:20 am-8:36 pm

1 stop14h 16m

Montego Bay Sangster Intl

Tue 1/27

4:45 pm-11:46 pm

1 stop8h 01m

$564

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Fri 12/12

6:25 am-2:42 pm

1 stop7h 17m

Montego Bay Sangster Intl

Fri 12/19

1:22 pm-11:58 pm

1 stop11h 36m

$564

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Mon 12/8

5:45 am-4:33 pm

1 stop9h 48m

Montego Bay Sangster Intl

Sat 12/13

5:58 pm-11:40 pm

1 stop6h 42m

$564

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Mon 12/8

6:28 pm-1:00 pm

2 stops17h 32m

Montego Bay Sangster Intl

Sat 12/13

2:02 pm-10:29 pm

1 stop9h 27m

$569

MilwaukeeKingston

MKE - KIN

MKEKIN

Milwaukee-Mitchell

Fri 11/28

6:14 am-10:13 pm

2 stops14h 59m

Kingston Norman Manley

Mon 12/1

7:30 am-12:02 am

2 stops17h 32m

$676

MilwaukeeKingston

MKE - KIN

MKEKIN

Milwaukee-Mitchell

Tue 3/3

7:00 am-8:00 pm

1 stop12h 00m

Kingston Norman Manley

Fri 3/6

9:00 am-7:05 pm

1 stop11h 05m

$763

MilwaukeeKingston

MKE - KIN

MKEKIN

Milwaukee-Mitchell

Tue 3/3

4:58 pm-10:14 am

2 stops16h 16m

Kingston Norman Manley

Fri 3/6

11:09 am-10:07 pm

2 stops11h 58m

$798

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 14 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, February is the cheapest month in which you can book a flight from Milwaukee to Jamaica (average of $258). Flying from Milwaukee to Jamaica in March is currently the most expensive (average of $419). 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.

What is the cheapest time of day to fly from MKE to JM?

Find hourly flight availability from Milwaukee to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 29, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 29% on flights from Milwaukee to Jamaica by exploring options for tickets in the morning.

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 October 29, 2025.
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
4,241 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,993 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,032 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Sun Country Air
6.9
Okay
335 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,113 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 26m. 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, February is the cheapest month in which you can book a flight from Milwaukee to Jamaica (average of $258). Flying from Milwaukee to Jamaica in March is currently the most expensive (average of $419). 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.
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
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O'Hare Intl to Kingston flights
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Milwaukee to Providenciales flights

Top 5 airlines flying from Milwaukee to Jamaica

Discover the top 5 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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$328Average$403FlexibilityNo cancel feeOn-time65%
DeltaCheapest$499Average$644FlexibilityNo cancel feeOn-timeN/A
Sun Country AirCheapest$540Average$540FlexibilityNo cancel feeOn-time83%
American AirlinesCheapest$540Average$630FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$571Average$713FlexibilityNo cancel feeOn-time63%

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