$473 Find Cheap Flights from Milwaukee to Jamaica

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Milwaukee to Jamaica departing on 2/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Milwaukee to Jamaica

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Montego Bay
Montego Bay1 stop$473
Kingston
Kingston1 stop$683
Montego Bay
Montego Bay1 stop$473
Kingston
Kingston1 stop$683

Book Cheap Milwaukee to Jamaica Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Milwaukee to Jamaica that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Milwaukee to Jamaica

Tue, Feb 10 - Wed, Feb 18
Delta Logo
5:48 pm - 12:32 pm
MKE
-
MBJ
17h 44m1 stop
Delta Logo
2:19 pm - 8:13 pm
MBJ
-
MKE
6h 54m1 stop
$473Delta
Tue, Feb 10 - Thu, Feb 19
Delta Logo
11:03 am - 12:32 pm
MKE
-
MBJ
24h 29m2 stops
Delta Logo
2:19 pm - 8:13 pm
MBJ
-
MKE
6h 54m1 stop
$478Delta
Sat, Feb 7 - Wed, Feb 18
Delta Logo
6:21 pm - 11:13 am
MKE
-
MBJ
15h 52m1 stop
Delta Logo
2:19 pm - 11:48 pm
MBJ
-
MKE
10h 29m1 stop
$503Delta
Sat, Feb 7 - Wed, Feb 18
Delta Logo
6:21 pm - 12:32 pm
MKE
-
MBJ
17h 11m2 stops
Delta Logo
2:00 pm - 11:13 am
MBJ
-
MKE
22h 13m2 stops
$508Delta
Sat, Feb 7 - Sat, Feb 14
American Airlines Logo
1:04 pm - 3:22 pm
MKE
-
MBJ
25h 18m1 stop
American Airlines Logo
2:30 pm - 11:54 pm
MBJ
-
MKE
10h 24m1 stop
$509American Airlines
Wed, Feb 18 - Wed, Feb 25
American Airlines Logo
6:00 am - 3:37 pm
MKE
-
MBJ
8h 37m2 stops
American Airlines Logo
4:29 pm - 11:54 pm
MBJ
-
MKE
8h 25m1 stop
$511American Airlines
Sat, Jan 31 - Sat, Feb 7
American Airlines Logo
12:07 pm - 3:16 pm
MKE
-
MBJ
26h 09m1 stop
American Airlines Logo
12:18 pm - 11:35 pm
MBJ
-
MKE
12h 17m1 stop
$512American Airlines
Sat, Feb 21 - Sat, Feb 28
American Airlines Logo
9:43 am - 3:28 pm
MKE
-
MBJ
28h 45m1 stop
American Airlines Logo
4:29 pm - 10:05 am
MBJ
-
MKE
18h 36m2 stops
$513American Airlines
Sat, Feb 21 - Sat, Feb 28
American Airlines Logo
4:46 pm - 3:28 pm
MKE
-
MBJ
21h 42m1 stop
American Airlines Logo
4:00 pm - 10:59 am
MBJ
-
MKE
19h 59m1 stop
$518American Airlines
Sat, Feb 21 - Tue, Feb 24
United Airlines Logo
8:28 am - 1:53 pm
MKE
-
KIN
52h 25m3 stops
United Airlines Logo
3:00 pm - 12:35 pm
KIN
-
MKE
22h 35m2 stops
$1,044United Airlines
Booking Insights

KAYAK's insights & trends for Milwaukee to Jamaica flights

Get data-powered insights and trends into flights from Milwaukee to Jamaica to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Milwaukee to Jamaica flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Jamaica from Milwaukee found in the last 72 hours was to Montego Bay, at $540 round-trip. The most popular route is from Milwaukee (MKE) to Montego Bay (MBJ), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $540.

What is the cheapest month to fly from Milwaukee to Jamaica?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Milwaukee to Jamaica, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Milwaukee to Jamaica is October, when tickets cost $560 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $805 and $697 respectively.

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

The average price of all round-trip flights from Milwaukee to Jamaica clicked on KAYAK for each day over the last 12 months.

For Milwaukee to Jamaica, Tuesday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Jamaica back to Milwaukee, the best deals are generally found on Tuesday, with Monday being the most expensive.

How far in advance should I book a flight from Milwaukee to Jamaica?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Milwaukee to Jamaica, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Milwaukee to Jamaica, you should book around 3 weeks before departure, which saves you about 10% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonMay
Cheapest flight$473
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from Milwaukee to Montego Bay

FAQs - booking Jamaica flights

  • How does KAYAK find such low prices on flights from Milwaukee to Jamaica?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Milwaukee to Jamaica.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Milwaukee to Jamaica?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Milwaukee to Jamaica is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Milwaukee to Jamaica?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Milwaukee to Jamaica with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Milwaukee to Jamaica?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Milwaukee to Jamaica up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Jamaica?

    The cheapest time of day to fly to Jamaica is generally in the afternoon, when round-trip flights cost $534 on average. Morning departures are around 4% cheaper than evening flights, on average. The most expensive time of day to fly to Jamaica is generally in the evening, which is peak travel time and where the average cost of a ticket is $566.

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 4257 reviews
7.0Food
8.6Crew
7.5Entertainment
8.0Comfort
8.1Boarding
Airline reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

2.0 MediocreRobert, Dec 2025
LAS - TPA
Read more Southwest reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

Great. I had to modify a flight. That was easy and free. Thank You

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

None of the airplane features were available during the flight.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

delayed due to weather. Could not communicate with family since the wifi was broken

Experience was good, however I had a delay due to weather happening and had to re purchase a seat on a new plane for a higher price (could be my own issue and misunderstanding) but other than that situation. First time flyer (by myself) was terrific!! The last from ORD to ALO didn't have wifi, but it was only 45 minutes so I'm sure that was part of the reason. Overall my experience was great! Next time I will remember to buy tickets with longer layovers. The delays really saved my overall anxiety. :)

Flight was delayed 17 hours due to aircraft issues. American did provide hotel, transportation and meals, 3 hours past boarding time, but it took us another hour to get the vouchers.

Flight was on time is the only good thing. Person loading the plane called 1-6 to board at the same time, made it chaotic. Plane was too small for even putting backpacks in overhead. Seat for normal sized people were too small. The WIFI didn't work. When we landed had to wait because not enough ground crew.

Did not understand a single word the attendant said on the pa system. I was glad it was not an emergency.

Flight was late and boarding was confusing because gate changed and I didn’t get a notification

Gate was overcrowded. Gate agents performed very well. Flight crew was top notch! Efficient & professional & courteous. Both meals not thermalized well. Dinner main dish was actually cold in the center. Almost inedible. Breakfast sandwich was lukewarm.

The boarding was as always, the crew tried their best but not enough. The food was a disaster I had dietary restrictions that were half met because the company did not loaded the food for the flight. The entertainment screen was fine but content was not and also they removed the free messaging option from the flight and they charged 30 dollars for that crappy bandwidth. This flight is not worth the cost and the company is going down on quality.

Not comparable to Qatar Airways services on flights to Doha. Flight attendants provided basic services; I was never recognized by name or as an Executive Platinum member. Restrooms were not kept clean during the flight.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

It was a good experience. I do wish the seats were roomier. Also, I did not like being charged for my carry on bag

Exceptional take off and landing in snow and wind…thank you to the well skilled pilots!

I liked entertainment system being downloaded on my iPad. The selections were limited but I appreciated being able to use my own screen. The flight was just fine. My only issue was both terminals being far from the main airport. Especially stoning at LAX near midnight and having to wait for a bus to take us to baggage pickup. Very inconvenient.

Just fine but comfort is always an issue since the seats are so close

The Flight was fine, the staff treated me well, the flight got delayed over 5 1/2 hours for maintenance issues....but it worked out OK,, they were very apologetic about it, and it is better to not fly if there is any issue than endanger peoples lives, so in reality that was a good thing, It did cost me extra for parking because I went beyond the time I had purchased for parking at MSP. But all in all, Good flight

I did not take this flight because the reservation made by Kayak was wrong! Kayak owes me a trip from Minneapolis to Duluth.

When I got to the airport in Seattle, they told me the flight "did not exist". Kayak reserved me a seat on a flight that did not exist. This is inexcusable. I was able to change my reservation to a flight that actually did exist, but the flight was later and then I didn't make it in time for the next leg of my trip from Minneapolis to Duluth. Kayak owes me a trip from Minneapolis to Duluth, and a big apology for messing up my reservation.

The plane was freezing cold. Asked for a blanket and there were none. Was told twice that the pilots would warm the plane and it never happened Worst experience flying ever

Multiple delays because they screwed up on the crew schedule and had to wait for over an hour for more people to come.

The Wi-Fi was off, the arm rests are hard plastic.

Everything you need to know for your flight from Milwaukee to Jamaica

Information on your arrival and departure airports