$212 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 6/19. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Jamaica

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Best Jamaica Flight Deals from Milwaukee

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

Montego Bay
Montego Bay2 stops$400

Cheap Flights from Milwaukee to Jamaica

 
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.

Recent round-trip flight deals from Milwaukee to Jamaica

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Milwaukee to Jamaica.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
 Logo
2:50 pm - 11:02 amMKE-MBJ
20h 12m2 stops
 Logo
12:07 pm - 11:27 amMBJ-MKE
23h 20m2 stops
Thu, May 8 - Thu, May 15
Spirit Airlines Logo
12:22 pm - 11:02 amMKE-MBJ
22h 40m2 stops
Spirit Airlines Logo
12:07 pm - 7:43 amMBJ-MKE
19h 36m2 stops
$407Spirit Airlines
Find Deal
Mon, Jun 2 - Thu, Jun 5
Delta Logo
7:00 am - 12:57 pmMKE-MBJ
5h 57m1 stop
Delta Logo
1:15 pm - 11:25 pmMBJ-MKE
10h 10m1 stop
$486Delta
Find Deal
Mon, Aug 25 - Sun, Aug 31
United Airlines Logo
5:47 pm - 1:30 pmMKE-MBJ
19h 43m2 stops
United Airlines Logo
2:48 pm - 8:45 pmMBJ-MKE
6h 57m1 stop
$541United Airlines
Find Deal
Tue, May 6 - Sat, Jan 17
American Airlines Logo
5:43 pm - 12:05 pmMKE-MBJ
18h 22m2 stops
American Airlines Logo
5:05 pm - 9:34 amMBJ-MKE
16h 29m2 stops
$545American Airlines
Find Deal
Sun, Aug 3 - Thu, Aug 7
American Airlines Logo
6:20 am - 2:48 pmMKE-MBJ
8h 28m1 stop
American Airlines Logo
2:26 pm - 9:34 amMBJ-MKE
19h 08m1 stop
$546American Airlines
Find Deal
Sun, Aug 3 - Thu, Aug 7
United Airlines Logo
5:50 pm - 1:30 pmMKE-MBJ
19h 40m2 stops
United Airlines Logo
4:12 pm - 10:22 amMBJ-MKE
18h 10m2 stops
$570United Airlines
Find Deal
Fri, Jun 6 - Fri, Jun 13
Delta Logo
7:05 am - 3:25 pmMKE-MBJ
8h 20m1 stop
Delta Logo
1:09 pm - 11:57 pmMBJ-MKE
10h 48m1 stop
$611Delta
Find Deal
Mon, Jun 16 - Thu, Jun 19
Southwest Logo
5:55 am - 1:30 pmMKE-MBJ
7h 35m1 stop
Southwest Logo
11:20 am - 11:15 pmMBJ-MKE
11h 55m2 stops
$620Southwest
Find Deal
Sun, Jun 15 - Wed, Jun 18
Southwest Logo
5:55 am - 1:30 pmMKE-MBJ
7h 35m1 stop
Southwest Logo
11:20 am - 10:25 pmMBJ-MKE
11h 05m1 stop
$671Southwest
Find Deal
Sun, Jun 15 - Wed, Jun 18

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Milwaukee to Jamaica.
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 time of day to fly to Jamaica?

The average price for all round-trip flights from Milwaukee to Jamaica depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
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.

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 May, when tickets cost $528 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $775 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 Saturday 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 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Good to know

Low season

August

High season

March

Cheapest flight

$212
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 10% 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.

See more FAQs

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 4287 reviews
7.1Food
8.6Crew
8.0Comfort
8.2Boarding
7.6Entertainment
Airline reviews

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

8.0 ExcellentJonathan, Apr 2025AUS - MSY
Read more Southwest reviews

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

1.5 hour delay, poor service, no compassion from the crew. Terrible experience

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

It was an overnight flight and I desperately needed coffee before we landed, but Delta does only one beverage service, and that is shortly after takeoff, not before landing at 5 am.

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

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

After a 5 hour delay waiting at the gate (3 delays adding up) with no clear reason provided, we finally boarded flew 3/4 of the way to Toronto then were turned back to New York. As we neared New York, the pilot declared that it was his fault, something to do with timing and him not being allowed into the country???? How could the airline let his happen? They had hours to prepare and make sure they had a crew available for the flight! We ended up in Toronto a day late with no sleep.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Terrible and im avoiding them in the future. My initial flight was delayed causing me to rebook my flight and when speaking with the representative to rebook I explained this is the second time my flights were delayed and they did nothing to help me. I wasn't booked to comfort plus or given a voucher or anything. I was almost late for my meeting that I needed to attend on Monday because of the games delta played delaying my flights even more and putting me in the very back of the plane next to an extremely intoxicated passenger

Multiple delays and not straight answer from the United team

For economy, it was very good. Staff was great, they even let some of us change seats for more leg room... Put an empty seat between us which was fantastic for a 12hr flight. Onboard entertainment was excellent, I think over 200 choices of movies/tv/etc The bad was the barely/nonfunctional wifi that cost either $16.99 or 1700 miles (full flight). It was atrocious... Definitely the worst of the last 3 long haul major airlines I was on the last few months.

Stewardess spilled orange juice on my clothes/seat no help no apology just threw napkins at me to clean the mess up. Not Happy.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

The plane pushed back from the gate on time. However, it stopped on the ramp, and we waited for over 20 minutes before the aircraft pulled back to the gate. Apparently, something of importance had to be removed from the aircraft by the gate agent. I found this to be odd. The delay was not significant, but I felt that whatever was on the aircraft that had to be taken off, should’ve been done before we pushed back from the gate.

I didn’t get on plane. Passport being processed by consulate with visa application. Tried to cancel through underpricer after purchasing cacelling for any reason. No dice, they are thieves.

Electric plugs didn't work. Entertainment system wasn't working

The design of the light switch on the arm rest is ridiculous.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

leg space better than expected. two washrooms for one plane isn't enough.

We missed our flight. The boarding pass had the wrong gate and by the time we received the text from Kayak, our flight was already gone. I’ll never use Kayak again and will go direct to the airlines in the future.

Boarding took forever, the plane was cramped and cold, and the seatbelt song came on constantly throughout the red eye flight with a loud pre-recorded message playing each time

Cabin felt crammed Snacks are lame But crew was super efficient getting us out on time despite delay

Took off on time and successfully avoided weather that looked to be a problem along the way

There were five broken seats on the plane. The crew was very rude in telling people they had to get off the plane and get a flight the next day. No call for volunteers, but telling people they had to get off. One woman was flying with her elderly mother and daughter and was told she had to leave or all three had to leave. Fortunately, a volunteer offered to stay. The situation was handled poorly.

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

British Airways staff are very polite and willing to help.

Any sort of gluten free snack option would be nice

They lost my luggage and it didn’t get delivered until the next day.

Would have thought that they would gas up plane before everyone got on board

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.

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.

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.