$113 Find Cheap Flights from Milwaukee to Caribbean

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 departing on 9/16. 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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Best Caribbean Flight Deals from Milwaukee

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$351
Santo Domingo
Santo Domingo1 stop$401
Montego Bay
Montego Bay2 stops$436
Oranjestad
Oranjestad2 stops$510
Nassau
Nassau1 stop$449
Kingston
Kingston2 stops$555
Simpson Bay
Simpson Bay3 stops$607
Providenciales
Providenciales1 stop$436
George Town
George Town1 stop$538
Willemstad
Willemstad1 stop$595
St. John's
St. John's2 stops$648
Puerto Plata
Puerto Plata2 stops$579
Aguadilla
Aguadilla1 stop$565
Punta Cana
Punta Cana1 stop$351
Santo Domingo
Santo Domingo1 stop$401
Montego Bay
Montego Bay2 stops$436
Oranjestad
Oranjestad2 stops$510
Nassau
Nassau1 stop$449
Kingston
Kingston2 stops$555
Simpson Bay
Simpson Bay3 stops$607
Providenciales
Providenciales1 stop$436
George Town
George Town1 stop$538
Willemstad
Willemstad1 stop$595
St. John's
St. John's2 stops$648
Puerto Plata
Puerto Plata2 stops$579
Aguadilla
Aguadilla1 stop$565

Cheap Flights from Milwaukee to Caribbean

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Milwaukee to Caribbean 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

Tue, Sep 16 - Tue, Sep 23
Delta Logo
6:00 am - 4:08 pmMKE-SJU
9h 08m1 stop
Delta Logo
5:19 pm - 11:25 pmSJU-MKE
7h 06m1 stop
$225Delta
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Sun, Sep 7 - Sat, Sep 13
American Airlines Logo
7:04 am - 6:15 pmMKE-SJU
10h 11m2 stops
American Airlines Logo
4:45 pm - 10:32 amSJU-MKE
18h 47m2 stops
$275American Airlines
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Tue, Jul 1 - Tue, Jul 8
Spirit Airlines Logo
7:03 pm - 12:29 pmMKE-STT
16h 26m1 stop
Spirit Airlines Logo
3:03 pm - 3:42 pmSTT-MKE
25h 39m1 stop
$293Spirit Airlines
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Wed, Nov 12 - Mon, Nov 17
United Airlines Logo
12:04 pm - 9:00 pmMKE-SJU
6h 56m1 stop
United Airlines Logo
2:05 am - 10:19 amSJU-MKE
10h 14m1 stop
$294United Airlines
Find Deal
Fri, Aug 22 - Thu, Aug 28
Spirit Airlines Logo
7:45 am - 4:46 pmMKE-SJU
8h 01m1 stop
Spirit Airlines Logo
5:41 pm - 6:40 amSJU-MKE
13h 59m1 stop
$298Spirit Airlines
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Sun, Aug 31 - Fri, Sep 5
Delta Logo
11:47 am - 10:07 pmMKE-SJU
9h 20m1 stop
Delta Logo
5:46 pm - 11:36 pmSJU-MKE
6h 50m1 stop
$302Delta
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Sun, Aug 17 - Fri, Aug 29
United Airlines Logo
3:45 pm - 11:54 pmMKE-SJU
7h 09m1 stop
United Airlines Logo
3:56 pm - 9:56 pmSJU-MKE
7h 00m1 stop
$312United Airlines
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Sat, Aug 30 - Fri, Sep 5
American Airlines Logo
11:24 am - 11:59 pmMKE-SJU
11h 35m2 stops
American Airlines Logo
4:42 pm - 10:04 amSJU-MKE
18h 22m2 stops
$322American Airlines
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Sun, Aug 17 - Fri, Aug 29
Southwest Logo
5:30 am - 4:20 pmMKE-SJU
9h 50m2 stops
Southwest Logo
11:10 am - 9:25 pmSJU-MKE
11h 15m1 stop
$345Southwest
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Tue, Jul 8 - Tue, Jul 15
Southwest Logo
6:30 am - 5:25 pmMKE-SJU
9h 55m1 stop
Southwest Logo
6:30 am - 5:20 pmSJU-MKE
11h 50m1 stop
$347Southwest
Find Deal
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KAYAK's insights & trends for Milwaukee to Caribbean flights

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

What is the cheapest Milwaukee to Caribbean 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 Caribbean.

The cheapest ticket to Caribbean 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 Punta Cana (PUJ), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $764.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Milwaukee to Caribbean, 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 is September, when tickets cost $328 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $571 and $564 respectively.

What’s the cheapest day of the week to fly from Milwaukee to Caribbean?

The average price of all round-trip flights from Milwaukee to Caribbean clicked on KAYAK for each day over the last 12 months.

When flying from Milwaukee to Caribbean, you should consider leaving on a Tuesday and avoid Thursdays if you are looking for the best rates. For your return to Milwaukee, you’ll find the best rates on Thursdays and the most expensive ones on Sundays.

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

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, 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, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.


Good to know

Low seasonSeptember
High seasonMarch
Cheapest flight$113
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from Milwaukee to San Juan

FAQs - booking Caribbean flights

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

    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.

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

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

    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 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?

    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 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 Caribbean?

    The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $360 on average. Morning departures are around 13% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $458.

Top 5 airlines serving from Milwaukee to Caribbean

 
Need help choosing which airline to fly with from Milwaukee to Caribbean? 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
8.2Boarding
8.0Comfort
7.6Entertainment
8.6Crew
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

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

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Great flight! Only complaint I had was that I didn’t get breakfast that morning because I don’t eat eggs for breakfast.. I ate an energy bar I bought in the airport which I had never done before. Otherwise, another great Delta flight!

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

it was so bad. I tried to board my flight from vancouver to saskatoon. And to my surprise they did not board me cause the flight was changed and no email was send to me. and on my boarding pass which i got from seattle says different flight. I did not knew anyone from Vancouver, air canada crew was rude, i asked for today flight but they were rude and i had early morning dental appointment in saskatoon. I was so much in pain and my whole day is wasted today. and i suffered alot. They did provide me hotel but they did not provide me any food. I am really really disappointed first time had so bad experience with air canada. I may think twice to book it again. If i can get any reply or any composition that would be great. Thanks

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

Terrible. Out flight was delayed for 21 (twenty one) hours. United is a joke.

Boarding was mayhem. Late boarding by 15 minutes because of lack of staff (missing 1 flight attendant. We had to wait for an arrival of another plane before we could board). Flight was a little rough, but cannot blame on airlines.

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

Very comfortable (upgraded to business class). The audio on my screen didn’t work, but I managed to play the audio through my phone while watching the screen.

The food was the worst I’ve had on any flight I’ve ever been on.

Great experience…left a bit behind schedule but made up fir that in the air and landed 10 minutes early 😁

I was supposed to be on business class at first class from Denver back to Miami due to weather changes. I missed my connection and it’s put on a flight to Fort Lauderdale. Instead of honoring my business class/1st class ticket, they put me in coach, but there were two first class seats open. I think it’s absolutely disgusting that I paid for first class $1300 ticket and they put me in economy and they had to open seats available and I have still not been refunded the difference. I ended up having to eat a snack box instead of the meal I was supposed to get and did not get home till 2 AM so I think that’s a little pathetic that I had to live off crackers for dinner And my poor dog ate some cheese and salami. Oh yes, apparently when they switched me to the new flight they forgot to mention I had a service dog

Excellent service despite turbulence during the flight. Flight attendants were remarkable!

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

Honestly, I haven’t flown American in years, probably due to the pandemic and my being unable to travel for certain periods in the last two years, but it was a good experience to dig out or obtain a new American Airlines account after many years of traveling for business with American in the past.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious.

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious. this return flight not as tasty, but filling.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Weather delay for 2.5 hours followed by half hour crew delay, did not have ginger ale, uncomfortable seats

Flight was full, and would have preferred an aisle seat, but due to getting a late ticket ,the seat I had was adequate. The flight crew were very help full and hard working. Food and drink were excellent for the 11hr flight. Overall I was pleased with flight, and would recommend British Airways again.

So awful Unreliable Unfriendly Bad Mad Mean Smelly Hot Late Overbooked Understaffed Expensive Cramped Narcs If they were a fruit they’d be rotten durian

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!!!!!

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.

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