$97 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$360
Santo Domingo
Santo Domingo2 stops$405
Montego Bay
Montego Bay1 stop$488
Oranjestad
Oranjestad2 stops$530
Nassau
Nassau2 stops$414
Kingston
Kingston1 stop$704
Simpson Bay
Simpson Bay1 stop$597
Providenciales
Providenciales1 stop$363
George Town
George Town1 stop$359
Willemstad
Willemstad1 stop$589
St. John's
St. John's2 stops$650
Puerto Plata
Puerto Plata2 stops$603
Aguadilla
Aguadilla1 stop$243
Punta Cana
Punta Cana1 stop$360
Santo Domingo
Santo Domingo2 stops$405
Montego Bay
Montego Bay1 stop$488
Oranjestad
Oranjestad2 stops$530
Nassau
Nassau2 stops$414
Kingston
Kingston1 stop$704
Simpson Bay
Simpson Bay1 stop$597
Providenciales
Providenciales1 stop$363
George Town
George Town1 stop$359
Willemstad
Willemstad1 stop$589
St. John's
St. John's2 stops$650
Puerto Plata
Puerto Plata2 stops$603
Aguadilla
Aguadilla1 stop$243

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

Sun, Mar 1 - Thu, Mar 5
Frontier Logo
6:39 pm - 10:09 am
MKE
-
SJU
13h 30m
1 stop
Frontier Logo
7:09 pm - 5:02 pm
SJU
-
MKE
23h 53m
1 stop
$236Frontier
Fri, Jan 30 - Tue, Feb 3
Frontier Logo
7:28 pm - 11:59 pm
MKE
-
SJU
26h 31m
1 stop
Frontier Logo
8:00 am - 5:58 pm
SJU
-
MKE
11h 58m
1 stop
$237Frontier
Sun, Feb 22 - Wed, Feb 25
Delta Logo
12:20 pm - 9:12 pm
MKE
-
SJU
6h 52m
1 stop
Delta Logo
6:37 pm - 11:47 pm
SJU
-
MKE
7h 10m
1 stop
$256Delta
Tue, Mar 3 - Tue, Mar 10
Delta Logo
5:25 am - 12:29 pm
MKE
-
GCM
6h 04m
1 stop
Delta Logo
1:12 pm - 8:55 pm
GCM
-
MKE
7h 43m
1 stop
$359Delta
Sat, Feb 28 - Fri, Mar 6
American Airlines Logo
4:47 pm - 1:24 pm
MKE
-
PLS
19h 37m
1 stop
American Airlines Logo
11:14 am - 11:55 pm
PLS
-
MKE
13h 41m
1 stop
$369American Airlines
Sat, Mar 7 - Sat, Mar 14
American Airlines Logo
8:00 am - 12:21 pm
MKE
-
PLS
27h 21m
1 stop
American Airlines Logo
2:24 pm - 11:12 pm
PLS
-
MKE
9h 48m
1 stop
$380American Airlines
Tue, Feb 17 - Sat, Feb 21
United Airlines Logo
7:00 am - 4:00 pm
MKE
-
PLS
8h 00m
2 stops
United Airlines Logo
2:23 pm - 9:44 pm
PLS
-
MKE
8h 21m
1 stop
$385United Airlines
Sun, Feb 1 - Thu, Feb 5
United Airlines Logo
5:00 am - 2:32 pm
MKE
-
NAS
8h 32m
2 stops
United Airlines Logo
3:35 pm - 10:56 pm
NAS
-
MKE
8h 21m
1 stop
$414United Airlines
Mon, May 11 - Wed, May 20
Southwest Logo
6:30 pm - 1:25 pm
MKE
-
MBJ
18h 55m
2 stops
Southwest Logo
12:15 pm - 10:15 pm
MBJ
-
MKE
10h 00m
2 stops
$543Southwest
Mon, May 4 - Sat, May 9
Southwest Logo
5:30 am - 1:25 pm
MKE
-
MBJ
7h 55m
1 stop
Southwest Logo
11:35 am - 10:50 pm
MBJ
-
MKE
11h 15m
2 stops
$554Southwest
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 $547.

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 December and November, when the average cost of round-trip tickets is $657 and $519 respectively.

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$97
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 2% 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.

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 4267 reviews
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
7.5Entertainment
Airline reviews

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

6.0 Goodha, Jan 2026
LAS - HOU
Read more Southwest reviews

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

We got exit row seats both flights. Everything was running on time

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Pretty seamless, just a tad bit late in taking off and landing.

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

Easiest airport experience ever in my life at MSP with Delta check-in and flight attendant gave us a bottle of champagne in celebration of our 10-year wedding anniversary, so overall amazing!

No in flight service, no explanation - FC got service, C+ did not, unsure about Economy. No turbulence to speak of, so I guess another way to cut cost, or promote health and well being of Delta employees? Also, boarding in MEM combined zones, and with overhead space already full on both flights after Zone 2/ Diamond, presents a huge challenge to find a space for a bag. Delta, other than point A to B, is no longer reasonable to fly - very poor experiences, not even taking into account the chastising at the gate and rude crews, across the board.

It would have been better if the flight wasn't delayed by 2.5 hours

Delta’s staff is unmatched. From the gate agents, to the pilots, to the flight attendants… all top of the industry.

Delta flight Delay for ,more that two hours i.e original flight was 6.30 PM and it starts at 8.45 PM, When we connect Delta team for meal vouchers as it is late arrival in designation,But we did not get it as per delta policy , which is not good for mid night arrival,

Inexperienced boarding crew allowed too many bags on to a full flight and delayed takeoff causing a missed connection and unplanned overnight stay. There was a hotel at the airport but Delta would not pay for it offering only to shuttle me to an area hotel. Never even offerred so much as an apology by anyone working for Delta.

Staff was great! Kind and cordial! Middle seat row 28 seat B has a hump in it. Trays were getting stuck when putting down and up. Good flight

Departure was delayed resulting in me missing my connection. Delta did not autimatically find me another flight.

The seats weren’t reclining even though it wasn’t as exit seat

I wish there were outlets to charge my iPhone. The crew was great; we had a female pilot who was great with explaining what was happening and delays,

The flight crew where really good. Better then the crew from BNE to SFO

Food should be changed in menu Many muslims travels in this airlime they need to add one Halal meal

Delayed, toilets did not flush, pilot parked to far away from Gate

Was happy we finally got upgraded in 1st class. The seat getting old. The cushiness need some improvement.

Yet another flight in which beverage and snack service was skipped. Other that that, firmly mediocre. Landed early, to gate late due to congestion at the gates. Airline's fault or airports fault: unknown.

Ineffective communication with United resulted in lost baggage. Their Baggage Tracing counter at MUC was shut down from 11:00-14:15 on my arrival. Undertrained, underinformed staff had me Running all over MUC to find someone to help me to no avail. Staff was rude, unhelpful, and unable to effectively use the systems they did have operational. They refused to contact United in any way or provide any accommodation or other resources while I waited for my luggage. This has destroyed my downstream itinerary. If they had even the slightest visibility I may have been able to reschedule/plan, but again, their staff provided nothing, and did nothing more than their website, which doesn’t even work on a standard phone browser. Miserable failure at all levels that weren’t associated with the operation of the aircraft.

Miserable. They moved my seat, but canceled the next leg of my flight. I resolved the issue at my transfer, but that resulted in lost luggage that has taken days off my schedule with no resolution. Worse, they fail to interface effectively with Lufthansa, forcing me to bounce between two equally useless help desks. The apps are unable to handle the situation, the bag dropped off the tracker, and while the call centers are polite, they do not provide written information to assist with cross-airline communication.

left on time, reasonable boarding process arrived early luggage came out quickly

I like flying first class, and United has a nice one

It was a good trip. Flight Attendants were friendly and responsive.

Qatar airways ,boarding arrangements at Hamid international airport could been better

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

My seat tv didn’t work the whole trip. And the seat space is too small despite being seated at the front.

The seat cushions were very worn so they were extremely uncomfortable.

Delayed, no updates, had a rewards number but was not working

The seats from lax to DFW was so tight that I could not move my legs . No WiFi and had to pay . Not a good selection of entertainment

AA should improve their in air internet & entertainment options. Seems unreasonable to charge $20/hr and should have some form of free connections. The entertainment options are also pretty limited, movies are outdated and the series only show 3-5 episodes.

The professionals have excellent customer service, the seats don´t have enough space.

We were upgraded to First Class and it was a great flight

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

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

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports