$158 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 7/25. 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$357
Kingston
Kingston2 stops$811
Montego Bay
Montego Bay1 stop$357
Kingston
Kingston2 stops$811

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

Mon, Jun 1 - Fri, Jun 5
American Airlines Logo
6:00 am - 1:55 pm
MKE
-
MBJ
7h 55m
1 stop
American Airlines Logo
5:17 pm - 12:04 pm
MBJ
-
MKE
18h 47m
2 stops
$357American Airlines
Sat, Jul 11 - Thu, Jul 16
American Airlines Logo
6:40 pm - 4:14 pm
MKE
-
MBJ
21h 34m
1 stop
American Airlines Logo
3:02 pm - 11:44 pm
MBJ
-
MKE
8h 42m
1 stop
$359American Airlines
Thu, Oct 1 - Fri, Oct 9
American Airlines Logo
4:33 pm - 10:50 am
MKE
-
MBJ
18h 17m
2 stops
American Airlines Logo
2:27 pm - 3:42 pm
MBJ
-
MKE
25h 15m
1 stop
$362American Airlines
Thu, Aug 27 - Mon, Aug 31
American Airlines Logo
4:25 pm - 1:28 pm
MKE
-
MBJ
21h 03m
1 stop
American Airlines Logo
5:13 pm - 11:37 am
MBJ
-
MKE
18h 24m
2 stops
$364American Airlines
Sat, Jun 6 - Wed, Jun 10
Delta Logo
5:48 pm - 11:34 am
MKE
-
MBJ
17h 46m
2 stops
Delta Logo
12:59 pm - 8:51 am
MBJ
-
MKE
19h 52m
2 stops
$367Delta
Mon, Jun 1 - Fri, Jun 5
American Airlines Logo
6:00 am - 1:55 pm
MKE
-
MBJ
7h 55m
1 stop
American Airlines Logo
3:00 pm - 11:47 pm
MBJ
-
MKE
8h 47m
1 stop
$434American Airlines
Mon, Sep 21 - Wed, Sep 23
United Airlines Logo
6:00 am - 1:54 pm
MKE
-
KIN
31h 54m
2 stops
United Airlines Logo
2:57 pm - 11:36 pm
KIN
-
MKE
32h 39m
2 stops
$901United Airlines
Sat, Jul 25 - Mon, Aug 17
Delta Logo
5:45 am - 8:03 pm
MKE
-
KIN
14h 18m
1 stop
Delta Logo
9:13 am - 11:53 pm
KIN
-
MKE
14h 40m
1 stop
$926Delta
Mon, Sep 21 - Wed, Sep 23
Air Canada Logo
5:05 am - 1:55 pm
MKE
-
KIN
32h 50m
2 stops
Air Canada Logo
3:05 pm - 8:45 pm
KIN
-
MKE
29h 40m
2 stops
$1,391Air Canada
Sat, Jul 25 - Mon, Aug 17
United Airlines Logo
5:29 pm - 1:54 pm
MKE
-
KIN
20h 25m
3 stops
United Airlines Logo
2:56 pm - 10:00 am
KIN
-
MKE
19h 04m
2 stops
$1,413United 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 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 January, when tickets cost $352 (return) on average. On the other hand, the most expensive months are August and July, when the average cost of round-trip tickets is $540 and $518 respectively.

Good to know

Low seasonMay
Cheapest flight$158
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 11% 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.

Reviews of the top 3 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.
7.9
SouthwestOverall score based on 4305 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
Airline reviews

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

2.0 MediocreJoshua, May 2026
TPA - LAS
Read more Southwest reviews

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Terrible, horrible, disappointing- without telling us they changed planes and moved and separated our seats to opposite sides - said they changed seats putting us together - got to airport to find no, they did not - we sat opposing sides of plane - food overly salty to inedible, never saw stewardess but once - it was terrible

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

The crew was very attentive through out the flight. Seats were comfortable, nice flight bag with pillow and blanket. Food was okay, since it was a overnight flight seemed to go by fast.

The flight attendant on my side of business class seemed like a novice and did not provide good service. Otherwise the flight was good and the entertainment system was very good. No free WiFi.

Cancelled BOYH legs of our flight home 30 min before initial boarding

Cancelled the flight half hour before boarding. Then cancelled the connecting flight too.

Left early arrived early..right amount of talking from pilots..of course had to love the biscuit and water!

I would like a refund for the extra cost the seat I paid for. An oversized person sat next to me and I couldn’t fit on my seat and had to move to another seat.

Boarding gate at LAX was too crowded—two gates next to one another

The flight was delayed about an hour for a maintenance specialist to approve the maintenance repair

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

Information on your arrival and departure airports