$113 Find Cheap Flights from Milwaukee to Caribbean Islands

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 Caribbean Islands departing on 9/18. 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

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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Milwaukee to Caribbean Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Milwaukee to Caribbean Islands.
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Cheap Flights from Milwaukee to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$565
Santo Domingo
Santo Domingo2 stops$590
Montego Bay
Montego Bay1 stop$372
Oranjestad
Oranjestad1 stop$564
Nassau
Nassau1 stop$552
Kingston
Kingston2 stops$780
Simpson Bay
Simpson Bay1 stop$503
Providenciales
Providenciales2 stops$480
George Town
George Town2 stops$464
Willemstad
Willemstad2 stops$703
Aguadilla
Aguadilla2 stops$336
Puerto Plata
Puerto Plata2 stops$889
St. John's
St. John's1 stop$830
Punta Cana
Punta Cana1 stop$565
Santo Domingo
Santo Domingo2 stops$590
Montego Bay
Montego Bay1 stop$372
Oranjestad
Oranjestad1 stop$564
Nassau
Nassau1 stop$552
Kingston
Kingston2 stops$780
Simpson Bay
Simpson Bay1 stop$503
Providenciales
Providenciales2 stops$480
George Town
George Town2 stops$464
Willemstad
Willemstad2 stops$703
Aguadilla
Aguadilla2 stops$336
Puerto Plata
Puerto Plata2 stops$889
St. John's
St. John's1 stop$830

Book Cheap Milwaukee to Caribbean Islands 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 Caribbean Islands 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 Caribbean Islands

Sun, Aug 23 - Thu, Aug 27
Southwest Logo
2:10 pm - 12:30 am
MKE
-
SJU
9h 20m
1 stop
Southwest Logo
6:00 am - 4:10 pm
SJU
-
MKE
11h 10m
1 stop
$226Southwest
Sat, Aug 22 - Tue, Aug 25
American Airlines Logo
2:49 pm - 11:43 pm
MKE
-
SJU
7h 54m
1 stop
American Airlines Logo
3:47 pm - 10:59 pm
SJU
-
MKE
8h 12m
1 stop
$276American Airlines
Wed, Sep 2 - Sun, Sep 6
American Airlines Logo
2:49 pm - 11:59 pm
MKE
-
SJU
8h 10m
1 stop
American Airlines Logo
2:33 pm - 9:06 pm
SJU
-
MKE
7h 33m
1 stop
$281American Airlines
Sun, Sep 6 - Tue, Sep 15
American Airlines Logo
4:25 pm - 12:15 am
MKE
-
SJU
6h 50m
1 stop
American Airlines Logo
6:27 am - 9:48 pm
SJU
-
MKE
16h 21m
2 stops
$284American Airlines
Mon, Aug 17 - Tue, Sep 1
Delta Logo
12:51 pm - 10:29 pm
MKE
-
SJU
8h 38m
1 stop
Delta Logo
5:49 pm - 11:53 pm
SJU
-
MKE
7h 04m
1 stop
$326Delta
Sat, Sep 19 - Sat, Sep 26
Delta Logo
5:30 am - 3:34 pm
MKE
-
MBJ
10h 04m
1 stop
Delta Logo
4:59 pm - 11:52 pm
MBJ
-
MKE
6h 53m
1 stop
$432Delta
Sat, Sep 19 - Sat, Sep 26
United Airlines Logo
6:00 am - 11:43 am
MKE
-
MBJ
29h 43m
1 stop
United Airlines Logo
2:40 pm - 10:45 pm
MBJ
-
MKE
8h 05m
1 stop
$440United Airlines
Thu, Jul 16 - Mon, Jul 20
United Airlines Logo
5:00 am - 4:05 pm
MKE
-
PLS
10h 05m
2 stops
United Airlines Logo
12:35 pm - 11:34 pm
PLS
-
MKE
11h 59m
1 stop
$528United Airlines
Sat, Aug 29 - Fri, Sep 4
JetBlue Logo
9:36 am - 10:06 am
MKE
-
PUJ
23h 30m
1 stop
JetBlue Logo
6:37 pm - 8:45 am
PUJ
-
MKE
15h 08m
1 stop
$565JetBlue
Sat, Aug 29 - Fri, Sep 4
JetBlue Logo
9:36 am - 10:06 am
MKE
-
PUJ
23h 30m
1 stop
JetBlue Logo
6:51 pm - 8:44 am
PUJ
-
MKE
14h 53m
1 stop
$581JetBlue
Booking Insights

KAYAK's insights & trends for Milwaukee to Caribbean Islands flights

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

What is the cheapest Milwaukee to Caribbean Islands flight route?

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

The cheapest ticket to Caribbean Islands from Milwaukee found in the last 5 days was to Punta Cana, at $628 round-trip. The most popular route is from Milwaukee (MKE) to Punta Cana (PUJ), and the cheapest round-trip airline ticket found on this route in the last 5 days was $628.

Can I save money by flying with a layover from Milwaukee to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $419, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Milwaukee to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Milwaukee to Caribbean Islands, 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 Caribbean Islands is January, when tickets cost $90 (return) on average. On the other hand, the most expensive months are November and October, when the average cost of round-trip tickets is $357 and $348 respectively.

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

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 Caribbean Islands, 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 Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$113
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 8% increase in price.
Flight from Milwaukee to San Juan

FAQs - booking Caribbean Islands flights

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

    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 Caribbean Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Milwaukee to Caribbean Islands 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 Caribbean Islands?

    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 Caribbean Islands 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 Caribbean Islands?

    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 Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from Milwaukee to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Milwaukee to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Milwaukee to Caribbean Islands? 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 4243 reviews
8.0Comfort
8.6Crew
7.5Entertainment
8.1Boarding
7.0Food
Airline reviews

It was just okay, no frills, basic transportation with no luxury. No screens on the seats, no water or drinks on a short flight. Full flight but at least it was on time.

6.0 GoodSteven, Jun 2026
LAS - ONT
Read more Southwest reviews

It was just okay, no frills, basic transportation with no luxury. No screens on the seats, no water or drinks on a short flight. Full flight but at least it was on time.

Flight was constantly delayed with significant changes in time, it was supposed to get to Colorado Springs at 8:30 PM but it got there after midnight.

Over a 3 hour flight. The turbulence was almost imperceptible except for 2 short periods which were not bad and over quickly. The attendants claimed "Safety first" and sat looking at their phones for 3 hours with no drink or snack service. This isn't the first time with Southwest. I thinkit may be there new plan of operation. Oh, and it was June 18, Southwest's Birthday which offered free drinks. NOT.

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

The flights are constantly late anymore, and they won't even give you a glass of water on the plane. For years, they were able to do a service on this flight from Atlanta to Knoxville and Knoxville Atlanta now they say it's too short of a flight. You can't even get a quick drink of water.

Flight got canceled 4 times, missed my connecting flight due to delays, have to wait to go home tomorrow

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Great experience nice pilot very soft and easy landing and take off

We sat on the runway for over an hour before departure. That was unwelcome.

Horrible. Faucet in sink not working, wifi not working. Didn’t bring food or snacks

Flight was delayed before take off and at landing. Baggage took 20 minutes. Flight crew would not serve full soft drink and had to ask multiple times before receiving water.

From checking to boarding, it was a seamless experience. The service agents were so helpful. The flight crew was so pleasant.

Gate agent showed up 20 minutes before boarding and was not at all friendly. Had to take this flight due to the one on the day before being cancelled and any later options were already full with long standby lists. Despite having paid for Delta Comfort seats, Delta did not allow me (or anyone) to choose their seat. The agent assigned them for everyone just prior to boarding. Self seat selection was allowed on the original flight. Flight staff was great - very friendly.

Flight attendants were great. Cheerful, upbeat and friendly. Jet, in particular, was fantastic.

Lost one piece of luggage even though I checked in 2.5 hours before the flight

It was Swiss. Our kosher meals were literally frozen solid and therefore inedible, and the crew didnt care.

For the expense of first class, the seats could have been nicer and higher tier snacks would have been nice.

The boarding process on the departure from LA was rather slow even though I was in Group 1. For first class, I was not expecting to have to pay for Wi-fi but I did and then the wi-fi was spotty. The entree was surprisingly good and so that was a pleasant surprise. However, once I got to Houston, it was terrible. Unfortunately there was bad weather but the constant gate changes for my connecting flight was difficult to manage due to having to navigate back and forth between different terminals.

We used Kayak to reserve our tickets and specifically checked the luggage option which was a more expensive option. When we arrived at the terminal we had to pay an extra $90 per suitcase for the three passengers. This has been a pattern for the past 3 years. Why charge for a more expensive luggage option, and the ticket price not include luggage?

They delayed the flight 3 hours because it wasn't full they moved us to 5 different gates probably the worst airline ever not even spirit is this bad.

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Checking bag at terminal was horrible. No agents to check us in and only 1 kiosk working. Boarding went ok. Crew onboard was very scattered rained. Missed our row while serving and then didn’t see them hardly again.

Crew was amazing, takeoff wonderful. The bathroom was disgusting from before takeoff the odor made the flight uncomfortable as you could smell the bathroom from the center of the plane where we were sitting. Smelled like raw sewage. My daughter was throwing up as we landed due to the smell and horrible turbulence as we approached Newark.

Airline tickets are not cheap. You expect reliable competent service. Thanks to canceled flights and botched transfers we arrived at our destination two days late. This is not acceptable

Hydraulic leak caused the flight to be cancelled. Auto system scheduled us on a 3 am flight. Wevhsedvrebook on the app and hit schedules later in the afternoon. Our luggage per gate and ticket agent would be rescanned and put in our new flight. Did not happen. Our luggage stayed in hsv. Baggage claim in wash dc unable to help. We filed a claim. Several emails about our luggage were in conflict with one another. Called as baggage and was on hold 30 minutes. Oscar said one of 2 was out fir delivery then cancelled. About 45 minutes later both pieces were delivered. Their system is suspect

I was not clear if food was offered or not.

Because I bought my ticket from Underpricer, I could not check in online. I could only check in at the airport and that was deeply frustrating because I had to arrive very early. The flight also departed 45 min late and passengers were given no explanations about why we were delayed. I was worried I would miss my connecting flight. Once on board, however, the flight was fine.

Absolutely terrible. They boarded the plane, supposedly realized they didn't refuel the plane or load the luggage so we sat as the gate inside the plane for over 2 hours while they supposedly did things that should have been done before having passengers board the planem

Flight cancelled. Twice. And no communication. No gate agent. Went past boarding time and had to go and see email from AA. Airport communication was bad

I love the e fact that the staff communicated swiftly when my flight was delayed and gate number changed

It was awful. The communication between corporate and the crew on the ground left more to be desired. The crew even said that Corporate was waiting on answers because they themselves didn't know. Every hour, there was a new excuse. I also understood that passengers were angry, but the crew should have done a better job at crowd control. There was a racial exchange between passengers that could've been avoided has the crew acted sooner.

Delayed and horrible communication and sat on flight for an hour before taking off

Flight was delayed three times and we had an international connecting flight which we would’ve missed but AA manage to find us a flight that allowed us to catch and we made our international flight. However, due to the flight change, I’m in Amman, Jordan missing all 4 bags. It’s been a nightmare. Been waiting since June 17 and today is June 20th. Still without luggage. Customer service wait times are two hours and I get disconnected while waiting. I’ll update when/if my luggage arrives. Every day is costing money in a hotel in Amman. I can’t continue my trip to Palestine until the luggage arrives. Then, I will be updating my review.

They did not offer coffee on a 7am flight…awful!!

Boarding and crew were great, but seats are terribly uncomfortable. No food or entertainment options.

Everything went very smoothly! Thanks for a great first experience flying with small children!

Crew members great. Everything else a 0! Got on plane at 530am. Got de boarded for mechanical issue. Supposed to leave by 830 am. Zero communication from gate agents. Then supposed to leave by 230pm. Then delayed till 330pm. Still zero communication with gate agents. All they would say is if you have an issue call the 1800 number. You call and sit on hold minimum 45 minutes for zero answer. Finally board at 345pm didn’t take off till after 4pm! Sat in airport for 11 hours with 4 adults and 3 kids. Finally offered a $100 (we are sorry) voucher for next trip. Missed whole day in Florida had to change reservations in Florida! Absolute joke of an airline! And I usually really like sun country.

Booked through Kayak for $236. They canceled the flight unknown to me; retaining $100 for canceling it. Found out when I went to check in. Rebooked the same flight for $400. Incredibly disappointed. The Sun Country part was as to be expected. Crowded, no food, no arm room but got me where I wanted to go.

3 seperate extremely rude unhelpful staff. Delayed flight. Lost my bag

Sat between 2 big men. I was uncomfortable. Flight was delayed twice. About 2 hours altogether.

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

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports