$202 Find Cheap Flights from Milwaukee to Jamaica - Compare and Save

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Price, demand and travel trends for Milwaukee to Jamaica flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

Are flights from Milwaukee to Jamaica cheaper or more expensive than last year?

Fares from Milwaukee to Jamaica are running about the same as they were around this time last year, averaging $634 round-trip.

What are the cheapest fares from Milwaukee to Jamaica right now?

The cheapest fares from Milwaukee to Jamaica on KAYAK in the last week were to Montego Bay Sangster Intl (MBJ) from $453 round-trip, and to Kingston Norman Manley (KIN) from $888 round-trip.

What’s the cheapest month to fly from Milwaukee to Jamaica?

August is the cheapest time of year to fly, with average fares of $432. Prices are highest in March, when average flight costs increase to around $984.

Which airport in Jamaica is the cheapest to fly to from Milwaukee?

Based on KAYAK data from the past 12 months, the cheapest airports to fly into Jamaica are:

• Montego Bay Sangster Intl (MBJ) (avg. price $583)
• Kingston Norman Manley (KIN) (avg. price $988)

What’s the cheapest day to fly from Milwaukee to Jamaica?

Tuesday tends to be the cheapest day to fly from Milwaukee to Jamaica, while Friday is the most expensive. Fares run about 51% higher that day, based on the past 12 months of KAYAK data.

What's the cheapest time of day to fly from Milwaukee to Jamaica?

Data from the past 12 months shows it's cheapest to fly to Jamaica during the evening with average prices of $356. The afternoon is the most expensive time to fly, with average prices of $1,188.

Key details for Milwaukee to Jamaica flights

Low season

October

Cheapest flight

$202
Beat the crowds with an average 56% drop in travelers.
The most popular month to fly with an average 106% increase in travelers.
One-way flight from Milwaukee to Montego Bay

Your Milwaukee to Jamaica flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Milwaukee to Jamaica?

    Yes. Fares from Milwaukee to Jamaica are low right now. As a rule of thumb, a round-trip under $500 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Milwaukee to Jamaica?

    Over the past 12 months, round-trip fares from Milwaukee to Jamaica have ranged from $500 to $942.

  • What airlines fly nonstop from Milwaukee to Jamaica?

    Based on the flight schedule for the next 3 months, no airline regularly operates nonstop flights from Milwaukee to Jamaica. One-stop options include:

    • Delta
    • Southwest
    • American Airlines

  • Which cabin classes are available on flights from Milwaukee to Jamaica?

    On flights from Milwaukee to Jamaica you can only book Economy Class.

  • What are some popular landmarks in Jamaica?

    KAYAK travelers' favorite landmarks in Jamaica include:

    • Doctor's Cave Bathing Club
    • Cornwall Beach
    • Fort Montego Craft Market
    • AquaSol Theme Park

Your guide to booking Milwaukee to Jamaica flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your travel dates are flexible, book your trip for August when flights are typically cheapest and avoid March when prices are at their highest.
  • Flying on Tuesday is usually the cheapest. Flights on Friday cost about 51% more on average, so being flexible with your travel dates could help you save.
  • If you're looking to save, Montego Bay Sangster Intl (MBJ) is the cheapest airport to fly into from Milwaukee. If you have onward travel, don't forget to factor in the cost of your journey by train, bus or domestic flight.
  • Start your trip in Montego Bay, which is the most popular destination in Jamaica. From there, it's easy to continue on to other popular destinations such as Negril, Ocho Rios and Kingston.

Reviews of the top 4 airlines serving from Milwaukee to Jamaica

 
Need help choosing which airline to fly with from Milwaukee to Jamaica? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4215 reviews
8.6Crew
8.1Boarding
7.5Entertainment
7.0Food
8.0Comfort
Airline reviews

When I made my reservation it would have been nice if kayak would have included my luggage. Unaware that I had to pay $45 each way. Should have asked at reservation time if luggage was being checked

8.0 ExcellentJeremy, Nov 2026
Read more Southwest reviews

When I made my reservation it would have been nice if kayak would have included my luggage. Unaware that I had to pay $45 each way. Should have asked at reservation time if luggage was being checked

Crew was a little surly. But plane left on time and arrived early. All one can ask for. New 737 Max was nice.

Flight was delayed about 50 minutes and completely full. they did the usual demand for people to check carry-ons. they called all groups to board very fast only to stand in the gangway after having boarding passes scanned. Why don't airlines board from the back to front - since they now have assigned seats? our stewardess got drink orders confused, so she just called out "cranberry". etc.,.. I wish they wouldn't serve pretzels snacks with a powdered coating, as it sticks to your hands and they don't have wet wipes. don't want to lick my fingers after hanging out in the terminal for over an hour.

Delayed over 3 hours, extremely rough landing on all four flights. Would not recommend

Boarding, crew and inflight entertainment was great. Could have better food options for a long flight. Paid money and got a seat with extra leg space but was asked to keep my carry on under the seat in front of me which defeats the purpose of buying a extra space seat.

On time departure and arrival. Had to be the oldest plane in the SWA fleet but it got me where I needed to be.

Flight was delayed out of BWI unexpectedly / without a reason given but otherwise ok.

Flight time kept changing and so did the gate. It was very frustrating

It was a very good experience. No major issues at all.

We were headed for Florida and anxious to get there. Everything was absolutely the best. This is our first time with Southwest and it’s now our go to airline. Best ever.

The flights were on time; all went as expected which is a big positive! No delays! There was no food or drink service in any legs, which I understand due to the short flight time.

The Delta assistsed services were awesome for my aunt. So very helpful.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Pretty standard flight. Delta has a good selection of movies.

The flight was so late that I had to change connecting flights, turning a five-hour trip into a fourteen-hour nightmare.

It was terrible! Two hour delays, poor in flight service, made us check our carry on even though there was plenty of overhead storage

Despite being delayed, we would still give a high score for this flight experience. For the first time in quite some time we had excellent customer service throughout our entire round trip. The flight attendants were the most polite we have experienced in our last ten flights at least (non of which were Delta and include business class). The food offered was a better selection than most—we just didn’t have any of it. Overall, almost as good as flying used to be. Thank you to Delta.

1 person checking us as we boarded, left gate on time, 12.30 we are told we were held for 15 mins as other flights were waiting to take off, captain due to rain … they were having a longer gap between take offs , 3pm we took off , they went land route via New Orleans in to Florida landed at 5.45pm offered coffee and a biscuit

Service was slow Flight was very loud at back of plane

Good, our flight was delayed but that was totally out of their control due to weather and a presidential visit.

The flight was delayed by two de-icings. The seatbelt did not work correctly. It did not stay tight.

Why is it that United flights from Newark are constantly delayed? Newark is a United hub!!!!!

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

It was literally one of the worst travel experiences ever. My flight got delayed by over an hour and there was no communication of this from the gate staff. I realized it by checking the screen periodically. Once on board the flight attendants continued to serve alcohol to a man who was clearly already drunk and that was making a bunch of commotion. Never again will I fly United!

At least the delays were short. Business class, even in the new planes is very crowded now with crappy tray tables

All good except paid for wifi that did not work

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

My luggage was lost at some point during my layover between Chicago and LHR. I landed Tuesday morning, and did not get it until Thursday night. Ironically, the people at the ticket desk had added a “priority” sticker to my tracking tag.

The flight was delayed multiple times. Breakfast was not served and only an apology given and statement that we could find better pastries in Paris. Seats were extremely narrow and uncomfortable.

The flight could have actually taken place. Canceled flight and no option to rebook that day.

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

There were several different delays but we ended up being delayed a total of 40 mins or so. It was annoying we had a gate change which made it take longer to leave DFW, and we had to check our carry on. Ugh

The counter/baggage counter was busy and so many people missed flights. We got stuck sitting on the plane over 2 hours at the gate while they were doing an inspection is wrong. Many of us missed our connecting flights because of it.

Our flight was changed from Madison to DC to Madison to Charlotte.

We were told we had no flights before our flight was continually delayed then cancelled.

More options for your flight from Milwaukee to Jamaica

Complete your trip to Jamaica with a hotel stay or car rental