$90 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 2/14. 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 Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$404
Santo Domingo
Santo Domingo1 stop$379
Montego Bay
Montego Bay2 stops$453
Oranjestad
Oranjestad1 stop$572
Nassau
Nassau1 stop$393
Kingston
Kingston1 stop$683
Simpson Bay
Simpson Bay1 stop$501
Providenciales
Providenciales1 stop$354
George Town
George Town1 stop$379
Willemstad
Willemstad1 stop$561
St. John's
St. John's1 stop$599
Puerto Plata
Puerto Plata2 stops$582
Aguadilla
Aguadilla2 stops$235
Punta Cana
Punta Cana1 stop$404
Santo Domingo
Santo Domingo1 stop$379
Montego Bay
Montego Bay2 stops$453
Oranjestad
Oranjestad1 stop$572
Nassau
Nassau1 stop$393
Kingston
Kingston1 stop$683
Simpson Bay
Simpson Bay1 stop$501
Providenciales
Providenciales1 stop$354
George Town
George Town1 stop$379
Willemstad
Willemstad1 stop$561
St. John's
St. John's1 stop$599
Puerto Plata
Puerto Plata2 stops$582
Aguadilla
Aguadilla2 stops$235

Book Cheap Milwaukee to Caribbean 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 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, Feb 3 - Thu, Feb 5
Delta Logo
5:30 am - 2:31 pm
MKE
-
SJU
7h 01m1 stop
Delta Logo
6:27 pm - 11:44 pm
SJU
-
MKE
7h 17m1 stop
$235Delta
Fri, Jan 9 - Mon, Jan 12
Frontier Logo
10:53 am - 1:21 am
MKE
-
SJU
12h 28m1 stop
Frontier Logo
6:10 am - 6:45 pm
SJU
-
MKE
14h 35m1 stop
$236Frontier
Sun, Jan 25 - Tue, Feb 3
American Airlines Logo
6:00 am - 8:50 pm
MKE
-
SJU
12h 50m2 stops
American Airlines Logo
6:00 am - 3:57 pm
SJU
-
MKE
11h 57m2 stops
$241American Airlines
Sat, Jan 31 - Sat, Feb 7
Frontier Logo
7:48 pm - 9:54 am
MKE
-
SJU
12h 06m1 stop
Frontier Logo
8:00 am - 6:53 pm
SJU
-
MKE
12h 53m1 stop
$251Frontier
Sat, Jan 24 - Fri, Jan 30
United Airlines Logo
11:30 am - 12:36 am
MKE
-
SJU
11h 06m2 stops
United Airlines Logo
2:05 am - 10:15 am
SJU
-
MKE
10h 10m1 stop
$253United Airlines
Tue, Jan 13 - Wed, Jan 21
United Airlines Logo
8:33 am - 10:22 pm
MKE
-
SJU
11h 49m2 stops
United Airlines Logo
7:45 am - 2:55 pm
SJU
-
MKE
9h 10m1 stop
$270United Airlines
Sun, Feb 1 - Sun, Feb 8
American Airlines Logo
6:12 am - 2:32 pm
MKE
-
PLS
7h 20m1 stop
American Airlines Logo
3:21 pm - 11:17 am
PLS
-
MKE
20h 56m2 stops
$374American Airlines
Mon, Jan 5 - Fri, Jan 9
Multiple Airlines Logo
12:08 pm - 11:31 am
MKE
-
STT
21h 23m2 stops
Multiple Airlines Logo
3:57 pm - 7:14 pm
STT
-
MKE
29h 17m1 stop
$375Multiple Airlines
Mon, Jan 5 - Fri, Jan 9
Multiple Airlines Logo
12:08 pm - 2:28 pm
MKE
-
STT
24h 20m1 stop
Multiple Airlines Logo
3:57 pm - 7:14 pm
STT
-
MKE
29h 17m1 stop
$392Multiple Airlines
Tue, Jan 6 - Tue, Jan 13
Southwest Logo
5:40 pm - 2:25 pm
MKE
-
AUA
18h 45m2 stops
Southwest Logo
3:20 pm - 10:15 pm
AUA
-
MKE
8h 55m1 stop
$576Southwest
Booking Insights

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?

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

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 $576.

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 $315 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $558 and $540 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 18 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$90
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 5% 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.

  • How many flights are there between Milwaukee and Caribbean per day?

    There is a maximum of 1 nonstop flight a day that takes off from Milwaukee and lands in Caribbean, with an average flight time of 4h 27m. The most common departure time is 8:00 am and most flights take off in the morning. Each week, there are 3 flights.

Reviews of the 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 4252 reviews
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
8.0Comfort
Airline reviews

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

10.0 ExcellentDavid, Nov 2025
BUF - PHX
Read more Southwest reviews

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

Flight was delayed 8 times. We were sitting at the airport for 14 hours. We got 2 hours of sleep (if that) on what was not meant to be a red-eye.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very bad! They kept delaying my flight and wouldn’t do anything about it

They brought an empty plane to the gate. Then a flight delay was announced for maintenance and waiting on a part. I was then put on a flight to San Francisco instead with a connecting flight to my final destination. Arrived at my final destination 2 hours late.

The only downside was my cell phone charger wouldn’t work in the charging port but everyone else’s would work in them all. My cell phone cable works fine in my hotel room in Frankfurt.

Flight and crew were great. United didn't inform crew of immigration process which was disappointing!

Flight team stood out for perzonal attention, kindness at bright cheery attitudes at 8am. Very helpful.

Seats had less pitch than a regional jet. Food was OK. Have to buy alcohol on US based carriers flying international. Boarding was a mess. Did not have bags but overhead space was gone quick. Would like to see the airlines enforce the one bag over and one bag under policy

Ot was overall fine. Left on time and had basic snacks. Weather was finicky but that’s not the airlines fault.

Attendants were pleasant and the flight was smooth and relaxed.

A little late at the start but all worked out well.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

I liked the humor of the captain and crew on the flight from Flagstaff to Dallas. They were humorous.

AA delayed the flight for 3 hours and 50 minutes, but delayed the last 2 hours, 30 minutes at a time, so if we knew before, could have stayed at home and worked instead of being at the airport wasting time... The plane's crew was excellent, not their fault.

After arriving in Dallas, the aircraft taxied for an unusually long time and was unable to park at the gate, which caused a significant delay and made me miss my connecting flight. I then had to wait in a very long line to be rebooked, and I was told that no hotel or meal accommodations would be provided. What is even more unacceptable is that my luggage was mishandled and has still not been located. My suitcase contains important medications that I urgently need, and I have been unable to access them due to the airline’s mishandling. This situation has caused me considerable stress and inconvenience, and I need this issue to be resolved immediately.

RIC Staff was not enough. Elderly passengers had to wait 30 minutes to deplane, so we could board and still had to walk as no chairs were provided. And, passenger in front of my seat assignment rammed seat against my legs entire flight time. Was mildly bruised and left thigh still sore.

Liked that it was on time. Staff professional and friendly.

Things were delayed a little. But that didn’t affect my plans. It was fine. I was surprised it was so full thanksgiving day. The crew were friendly and professional.

I appreciated that it was on time, safe and professional. I didn’t like that I wasn’t in a place where I had a window at my window seat. It would have been nice to know that in advance. If it was mentioned in the ticketing, I didn’t notice it.

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

The Flight was fine, the staff treated me well, the flight got delayed over 5 1/2 hours for maintenance issues....but it worked out OK,, they were very apologetic about it, and it is better to not fly if there is any issue than endanger peoples lives, so in reality that was a good thing, It did cost me extra for parking because I went beyond the time I had purchased for parking at MSP. But all in all, Good flight

I did not take this flight because the reservation made by Kayak was wrong! Kayak owes me a trip from Minneapolis to Duluth.

When I got to the airport in Seattle, they told me the flight "did not exist". Kayak reserved me a seat on a flight that did not exist. This is inexcusable. I was able to change my reservation to a flight that actually did exist, but the flight was later and then I didn't make it in time for the next leg of my trip from Minneapolis to Duluth. Kayak owes me a trip from Minneapolis to Duluth, and a big apology for messing up my reservation.

The plane was freezing cold. Asked for a blanket and there were none. Was told twice that the pilots would warm the plane and it never happened Worst experience flying ever

Multiple delays because they screwed up on the crew schedule and had to wait for over an hour for more people to come.

The Wi-Fi was off, the arm rests are hard plastic.

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!!!!!

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports