$287 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 6/7. 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.
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Best Jamaica Flight Deals from Milwaukee

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Montego Bay
Montego Bay1 stop$297

Good to know

Low season

May

High season

March

Cheapest flight

$287
Best time to beat the crowds with an average 8% 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 long is the flight to Jamaica from Milwaukee?

    Flights to Montego Bay0h 00m
  • What is the cheapest flight to Jamaica from Milwaukee?

    The cheapest ticket to Jamaica from Milwaukee found in the last 72 hours was $287 one-way, and $297 round-trip. The most popular route is from Milwaukee to Montego Bay, and the cheapest round-trip airline ticket found on this route in the last 72 hours was $287.

  • Which airlines fly to Jamaica?

    Sun Country Air flies most frequently to Montego Bay from Milwaukee.

  • 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.

See more FAQs

Top tips for finding cheap flights to Jamaica

  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be March, April and May. The cheapest month to fly from Milwaukee is September.
  • Morning departure is around 42% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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.
8.1
SouthwestOverall score based on 4411 reviews
7.6Entertainment
8.2Boarding
8.7Crew
8.1Comfort
7.1Food
Airline reviews

Gate agents were informative and friendly… flight attendants were as well. Had a fun time chatting about their legacy AirTran experiences as a former fan of the airline that Southwest acquired.

10.0 ExcellentAnonymous, Jan 2025ATL - LGA
Read more Southwest reviews

Gate agents were informative and friendly… flight attendants were as well. Had a fun time chatting about their legacy AirTran experiences as a former fan of the airline that Southwest acquired.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Wi Fi was horrible kept cutting out the whole time and too expensive

I really like open seating. I hate that I've heard this is going away. This is one of the unique things that makes Southwest my goto choice.

Boarding was a little late, but made up for it. It was quick to taxi to the runway, since it's a smallish airport.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

Multiple delays and gate changes. Arrived at final destination 6 hours late. All rental cars had been taken.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

It was 2 hours 45 minutes late, for no apparently clear reason.

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

I loved having a most black flight crew during Black History Month; rather by design or accident I appreciated the representation. ❤️

This was the second flight this week with flight attendant Marcus I’m not sure if his last name is Lane or Lang but this guy is awesome. He funny, attentive and his service is 5 stars. Marcus makes business travel more enjoyable !

Although the flight left late, we arrived early. It was one of the quickest boarding and off boarding experiences I’ve had. It was kind of annoying the only drinks they had were water, coffee, and tea. The flight was very smooth, temperature was just right, and flight attendants were friendly.

Rode in a smaller plane and short trip meant no snacks, no free wifi or tv. It was only 30min flight so honestly wasn’t a big deal to lack these items.

Lower number on this flight so spaced out passengers. Able to enjoy more room to relax during flight. It was lovely.

Kind staff. Snacks are small but that’s the new normal.

Overall, terrible. Flight from SFO was delayed due to “air traffic control issues”, and we were all mislead about connecting flights. Told “you have 20 minutes to catch your connection”. Reality was 5. We got to watch the plane sit at the bridge. Won’t fly Delta with a connection again.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.

I don’t understand the purpose of the orange “priority” tag on my bag. This tagged, my bag is last or near to the last bag to come down the carousel at IAH.

The tv monitor in front of my seat was not responding. The flight crew reset it and it still didn’t work.

The agents was very rude and they charged me $50 for a carry-on bag saying that it was too big and then I saw someone going on a plane with the same size bag as me

Liked nothing. As per previous segment it was delay delay delay.

Terrible. First of all we were delayed 4 3/4 hours departing Honolulu. As we had to leave our condo and the rental car had to be returned we had to go to the airport. Even though we had a business class boarding pass to Washington, since we did not have business class to Montreal we could not access the lounge without paying a $59 fee each. This does not make sense to us. Since we could not meet our original connection United booked us to Montreal via New York LaGuardia on Air Canada. In Washington a further delay got us into LaGuardia too late to make our connection to Montreal so we were booked on another Air Canada flight 3 hours later. We were originally scheduled to arrive in Montreal at 10:40 and arrived at 19:55. A totally exhausting day, United did not offer a meal voucher or any type of compensation. Air Canada did give us a digital meal voucher. The food in United business class is poor among all meals offered. The pods look nice but are not that confortable. Overall would not fly on United again.

Plenty of room for me and the cat in Premium Economy. Seat was comfortable. Boarding was a breeze. The lady at the special check-in desk was great, super helpful and professional.

For the most part united was a good experience, how ever when they came by with the snacks and water, they completely passed by my wife and I. As we were in separate rows. On a 5 hr flight we were not offered water

Fantastic crew. Flight was delayed at last minute but we were given updates every 20 minutes and the crew was so friendly and considerate. I miss the touch screens on the back of the seats, wish they would bring that back though.

Our seats were all the way in back of the plane,

Food choices were very limited. Taste of the dishes was average.

The boarding experience was good; $20 for wifi per flight is uncompetitive compared to Delta, Southwest, and others, and puts American lower on my list given similar pricing.

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Delays on all NY flights. There was no communication on why but they didn’t say it was weather. Other carriers were not delayed.

The flights were terribly delayed and then cancelled which forced us booking another night at the hotel. Very poor management from American Airlines

Extraordinary service in business class, and very good breakfast and snacks. A really lovely flight.

Same as before being upgraded to business class made it perfect

I flew out of Reagan National. My flight was delayed, delayed, delayed, and then canceled ...THREE TIMES over TWO DAYS. Staff were seemingly not empowered to provide information on why the flights were screwed up. A real nightmare.

They cancelled our flight without warning OR a refund. Never doing business with American Airlines again! This is the second AA booked trip in a row that we've had challenges with.

Crew was late. Baggage was late. 2hs inside the plane waiting fro de-icing and traffic. A 3:30hs flight ended up being almost 6hs inside the airplane.

Flight delayed on both ends - have a gate ready at DCA, don't make us sit for 30min after being late to take off as well.

Flight was delayed in phoenix by 1 hour. When Kenny got to minneapolis st paul, Kenny missed his connecting flight to Duluth on Sun country air. Sun country customer service did nothing to help Kenny get home to Duluth. We will not fly with sun country ever again.

When we landed in Minneapolis from Providence, the ground crew was unable to move the jet bridge to meet our plane because the wheels were frozen. We waited patiently on the plane for about 45 minutes while they tried to solve this problem. It was mind boggling that this would not be more quickly resolved, or anticipated, in a place where sever winter weather is the norm. We stressed about meeting our connecting flight to Portland, which we assumed would be our only option for that day. Fortunately, when we finally raced from our gate to the next one, that Sun Country flight had been delayed so we didn't miss it. We decided not to take anything but direct flights from now on, no matter how much cheaper.

No line to check my bag. Reasonable overweight fee. When the connection was late due to weather, the gate agent opened the door and let me on the second flight. The plane waited for my luggage transfer. My bag arrived on time at my final destination:)

I had paid for a seat assignment at the time of reservation but when I checked in the night before it wasn’t there. Had to purchase another seat.

So unprofessional. They changed my connecting flight to a time that made it literally impossible to make the flight with no way to contact them or reject the changes. When I missed the flight as expected, there was no one to be found at their ticketing counter and the phone support put me on hold for an indefinite time. Since they didn't have another flight that day, all sun country air personell had left the airport (this was at 7pm) and my only options were to get a hotel for the night and come back the next afternoon to hopefully get rescheduled or buy a flight with another airline.

I purchased an aisle seat but was put in the middle seat surrounded by families with small sick children (3). That can happen anytime and I was prepared. The ticket agent questioned why I hadn’t paid for my luggage and had to explain that 2 pieces were included with my ticket. I hate that nickel and diming attitude. Please inform your staff better.

I know the airline has been open for 40 years and the flight crew looked just as old. The flight attendants were not friendly and rude. They should think of retiring this crew.

The crew was friendly, but I only got a drink, no food.

Flight was late, boarding was a mess, families separated so they could make extra profit.

Great! A delay in taking off but that’s it

Book cheap flights from Milwaukee to Jamaica

Recent round-trip flight deals

4/1Tue
1 stopSpirit Airlines
16h 33mMKE-MBJ
4/9Wed
1 stopSpirit Airlines
28h 05mMBJ-MKE
$297
4/8Tue
1 stopSpirit Airlines
16h 26mMKE-MBJ
4/16Wed
1 stopSpirit Airlines
28h 05mMBJ-MKE
$302
3/31Mon
1 stopAmerican Airlines
8h 15mMKE-MBJ
4/8Tue
1 stopAmerican Airlines
7h 46mMBJ-MKE
$521
3/5Wed
1 stopDelta
7h 14mMKE-MBJ
3/10Mon
1 stopDelta
7h 44mMBJ-MKE
$541
4/14Mon
1 stopDelta
9h 38mMKE-MBJ
4/23Wed
1 stopDelta
7h 06mMBJ-MKE
$551
4/1Tue
2 stopsAmerican Airlines
17h 33mMKE-MBJ
4/9Wed
2 stopsAmerican Airlines
9h 00mMBJ-MKE
$555
3/6Thu
2 stopsSouthwest
17h 25mMKE-MBJ
3/12Wed
1 stopSouthwest
8h 55mMBJ-MKE
$605
5/4Sun
2 stopsUnited Airlines
8h 20mMKE-MBJ
5/6Tue
2 stopsUnited Airlines
21h 17mMBJ-MKE
$615
3/5Wed
2 stopsUnited Airlines
23h 51mMKE-MBJ
3/11Tue
2 stopsUnited Airlines
22h 41mMBJ-MKE
$620
6/13Fri
2 stopsSouthwest
8h 45mMKE-MBJ
6/14Sat
1 stopSouthwest
10h 10mMBJ-MKE
$791

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Recent one-way flight deals

6/7Sat
1 stopAmerican Airlines
14h 29mMKE-MBJ
$287
6/7Sat
3 stops
36h 45mMKE-MBJ
$521

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Last minute flights from Milwaukee to Jamaica

Last minute flight, train and bus deals

2/22Sat
nonstopSun Country Air
4h 06mMKE-MBJ
3/1Sat
nonstopSun Country Air
4h 31mMBJ-MKE
$540
2/22Sat
multi-stopDelta
8h 40mMKE-MBJ
3/1Sat
multi-stopDelta
8h 08mMBJ-MKE
$596
2/21Fri
multi-stop
17h 56mMKE-MBJ
2/28Fri
multi-stop
23h 26mMBJ-MKE
$606
2/21Fri
multi-stopSouthwest
9h 00mMKE-MBJ
2/28Fri
multi-stopSouthwest
8h 10mMBJ-MKE
$631
2/21Fri
multi-stopSouthwest
18h 25mMKE-MBJ
2/28Fri
multi-stopSouthwest
8h 40mMBJ-MKE
$680
2/25Tue
multi-stopUnited Airlines
20h 16mMKE-MBJ
3/1Sat
multi-stopUnited Airlines
26h 25mMBJ-MKE
$687
2/25Tue
multi-stopUnited Airlines
23h 16mMKE-MBJ
3/1Sat
multi-stopUnited Airlines
26h 25mMBJ-MKE
$693
2/22Sat
multi-stopUnited Airlines
20h 16mMKE-MBJ
3/1Sat
multi-stopUnited Airlines
24h 27mMBJ-MKE
$715
2/22Sat
multi-stopUnited Airlines
21h 21mMKE-MBJ
3/1Sat
multi-stopUnited Airlines
24h 27mMBJ-MKE
$721
2/22Sat
nonstop
4h 06mMKE-MBJ
3/1Sat
multi-stop
28h 04mMBJ-MKE
$736

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

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