$246 Find Cheap Flights from Milwaukee to Jamaica

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Milwaukee to Jamaica departing on 3/7. 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

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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$539
Kingston
Kingston2 stops$698
Montego Bay
Montego Bay1 stop$539
Kingston
Kingston2 stops$698

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

Wed, Feb 18 - Wed, Feb 25
Delta Logo
1:20 pm - 8:25 pmMKE-MBJ
6h 05m1 stop
Delta Logo
12:35 pm - 7:05 pmMBJ-MKE
7h 30m1 stop
$539Delta
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Tue, Mar 3 - Wed, Mar 11
American Airlines Logo
6:50 pm - 12:00 pmMKE-MBJ
16h 10m2 stops
American Airlines Logo
5:00 pm - 10:27 amMBJ-MKE
17h 27m2 stops
$544American Airlines
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Wed, Mar 25 - Wed, Apr 1
American Airlines Logo
7:18 am - 3:05 pmMKE-MBJ
7h 47m1 stop
American Airlines Logo
1:15 pm - 1:52 pmMBJ-MKE
24h 37m1 stop
$545American Airlines
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Wed, Mar 25 - Tue, Mar 31
American Airlines Logo
7:18 am - 3:05 pmMKE-MBJ
7h 47m1 stop
American Airlines Logo
10:55 am - 10:30 amMBJ-MKE
23h 35m1 stop
$549American Airlines
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Mon, Dec 8 - Sat, Dec 13
Delta Logo
5:45 am - 1:04 pmMKE-MBJ
6h 19m1 stop
Delta Logo
5:58 pm - 11:40 pmMBJ-MKE
6h 42m1 stop
$564Delta
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Mon, Dec 8 - Sat, Dec 13
American Airlines Logo
3:45 pm - 10:13 amMKE-MBJ
17h 28m2 stops
American Airlines Logo
5:22 pm - 12:01 amMBJ-MKE
7h 39m1 stop
$569American Airlines
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Sun, Nov 16 - Sun, Nov 23
American Airlines Logo
6:48 pm - 10:12 amMKE-MBJ
14h 24m2 stops
American Airlines Logo
1:55 pm - 12:03 amMBJ-MKE
11h 08m2 stops
$574American Airlines
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Mon, Oct 27 - Sat, Nov 1
Spirit Airlines Logo
7:38 pm - 11:00 amMKE-MBJ
15h 22m2 stops
Spirit Airlines Logo
12:09 pm - 7:08 pmMBJ-MKE
30h 59m3 stops
$580Spirit Airlines
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Tue, Mar 10 - Wed, Mar 11
United Airlines Logo
5:00 am - 12:46 pmMKE-MBJ
7h 46m1 stop
United Airlines Logo
2:20 pm - 10:30 amMBJ-MKE
20h 10m2 stops
$634United Airlines
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Wed, Feb 18 - Wed, Feb 25
United Airlines Logo
1:25 pm - 2:37 pmMKE-MBJ
24h 12m2 stops
United Airlines Logo
1:25 pm - 10:30 amMBJ-MKE
22h 05m2 stops
$649United Airlines
Find Deal
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 March, when tickets cost $542 (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 $675 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

Good to know

Low seasonMay
Cheapest flight$246
Best time to beat the crowds with an average 0% drop in price.
Most popular time to fly and prices are also 14% 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 5% 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 5 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 4235 reviews
7.5Entertainment
7.0Food
8.0Comfort
8.6Crew
8.1Boarding
Airline reviews

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

4.0 OkayAnnette, Oct 2025LGA - MCI
Read more Southwest reviews

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

mandatory demand customer to check their carry on because not enough people check bags.

Connecting flight is on time and boarding was a breeze!

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

As always, the entire Southwest experience was perfect. Purchasing the tickets on the Southwest web site was effortless, departure and arrival gates were spotless and comfortable, plane was clean and comfortable, crew was excellent and flight was on time. Wheelchair service in Las Vegas at departure was somewhat chaotic and disjointed, but I am not sure if that was Southwest problem, airport problem or combination.

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

The boarding process needs to be refined. Sometimes the gate crew calls out the zones and then flip to showing the.zones boarding on the gate monitor display. So, unless you are huddled around the gate lanes watching the monitor, you could miss your boarding zone. Suggest the zones be announced each time a new zone is allowed to board.

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

On time flight. Seat comfort could be better in the Comfort section.

My issue was with TSA agents for delta airlines. My luggage got flagged. The agent was going thru another persons first. He took 20 min to go thru hers. I asked them to bring mine closer so I could sit down . They said you can go sit it will be fine. I said I am supposed to keep my eyes on my bags at all times. The agent was meticulously unwrapping 2 gifts that the lady had and then tried to re warp it. He was trying to be kind i get it but 20 min for me to stand watching him do that was ridiculous. It was 6 am and there were a ton of travelers. Mine was flagged for some air packed tea that I bought in Turkey. My previous delta flight and 2 others before didn’t flag it. Consistency would be nice. Also on the flight the window shades were down for take off and landing - I thought that was very odd I thought they had to remain open for take off and landing.

The flight was an hour and a half late departing which was inconvenient

Delay in SLC jammed us up in Chicago. Got caught up in rush hour traffic

The crew took good care of us. The flight from ATL to SFO is a longer one, and there were multiple beverage offerings. I like the 757's that Delta uses. Good airplane that is comfortable. I do wish Delta would separate Priority boarding from the better seats. I would gladly take a smaller seat in an open row than be jammed into Comfort just to get priority boarding, just to make sure I don't have to check a bag.

The flight was great. The gate location was way to far away!!!

The flight attendant in first class was beyond rude and didn't care at all about her job. AND the gate agent was even worse than the flight attendant for rudeness. She was awful.

Gate agent rushed to fill hot jetway with crowd so it took over 12 minutes to go from gate to plane. Just like a discount airline Pooly prepared cabin and third time that claim of rough air prevented any cabin service. Friends on a Southwest flight at similar time had service.

Mostly good. Flight was crowded but Airline personnel were very friendly & accommodating. It would be good to have savory snacks rather than just sweet Biscoff cookies.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

Flight attendants on this flight were very attentive and friendly

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Food should be better quality. Video screens have poor resolution and the library of movies is poor. The other airlines are much better.

the trip to madrid was uncomfortable with my legs touching the seat in front of me

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My flight was delayed for 17hs because the pilot forgot his passport!!! What a joke. AA used to be a great airline, now I have to think twice before flying with them again.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

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.

The assistance with the wheel chairs was fabulous. All the people were so very friendly and helpful. I want to thank them all.

We almost missed our return flight. We got to the gate one minute from closing the cabin door, and the agent got us aboard the plane! We are so very grateful!!!!!

I already filled out a survey for this flight. We booked through KAYAK with airfare assist, and airfare assist did not confirm or honor our flight. Therefore, we had to go to a different place with a different travel agency. I tried very hard with airfare assist, They also promoted this on cheapair.com, but it was a bait and switch in both instances.

Boarded flight, issues with the place and had to get off the plane, wait, and then board a different plane at a different gate. This impacted my short trip negatively. A worker died outside of the plane window and we sat there the entire time while they tried to revive him, unsuccessfully, which was traumatic.

Vegas is such a quick flight that amenities aren’t the important part, in my opinion. Just get me there efficiently and safely, and that’s exactly what they did!

The flight was severely delayed due to the missing flight attendants.

Absolutely horrible. Usually pay $40-$50 to check luggage in. I tried to check my suitcase in and the price is raised to $70. That's ridiculously greedy c'mon. I had to leave my suitcase with all my clothes and hygiene products and repurchase once i landed in Atlanta. You guys make it really stressful to travel. Don't even want to travel anymore.

They cancelled the flight 3 hours prior departure. Had to spend $400 for a ne way flight with Delta Airlines! Spirit Airlines are not serios!

My luggage didn’t arrive at LAX, so that wasn’t a good experience.

Terrible seat, no in flight entertainment. No complimentary food or drinks. Seats really hurt my back after flying spirit for the day.

Plastic seat really hurt my back. Cannot even recline on the flight. Very hard to sleep on the plane due to terrible seats . Food and drinks were expensive and not very good. There were like 2 open exit rows behind me. My isle was full so I asked flight attendants if I could sit there. They told me it was a safety issue??? I think it more unsafe to have no one sitting there. In case of emergency, you’d want someone there to help.

The delays and the lack of communication and organization within the airport itself for Staffing this flight and coordinating the paper log necessary to depart was ridiculous and deplorable

It was a no show, so we got put in hotels for a nite. The A320 plane was very modern and flite and crew (if a pilot shows up were fine). Price was very good.

The entire staff from check in agents to flight attendants were pleasant and professional. Would suggest a complimentary water.

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