$88 Find Cheap Flights from Caribbean to Wisconsin

1 adult
1 adult, Economy, 0 bags

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

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Useful Info

Good to know

Low seasonJanuary
Cheapest flight$88
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly with an average 7% increase in price.
Flight from San Juan to Milwaukee

FAQs for booking flights from Caribbean to Wisconsin

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

    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 Caribbean to Wisconsin.

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

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

    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 Caribbean to Wisconsin 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 Caribbean to Wisconsin?

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

  • How many airports are there in Wisconsin?

    There are 8 airports in Wisconsin. The busiest airport is Milwaukee-Mitchell Airport (MKE), with 45% of all flights arriving there.

  • Which is the cheapest airport to fly into in Wisconsin?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Wisconsin is Milwaukee-Mitchell Airport (MKE), with an average flight price of $560.

  • What is the cheapest month to fly from Caribbean to Wisconsin?

    The cheapest month for flights from Caribbean to Wisconsin is January, when tickets cost $253 (return) on average. On the other hand, the most expensive months are March and June, when the average cost of round-trip tickets is $486 and $470 respectively.

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

    To get a below average price on the flight from Caribbean to Wisconsin, you should book around 4 weeks before departure, which saves you about 28% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

  • How many cities have direct flights to Wisconsin?

    From Caribbean, there are direct flights to Wisconsin from 1 city. This city is Punta Cana and there are 4 direct flights each week.

  • How many direct flights to Wisconsin are there each day?

    There are around 1 direct flights from within Caribbean to Wisconsin every day. All flights depart in the afternoon.

  • How many direct flights to Wisconsin are there each week?

    Each week there are around 4 direct flights from within Caribbean to Wisconsin. The most common day for departures is Monday, with 25% of flights taking off on this day.

  • How long is the flight to Wisconsin?

    An average nonstop flight from Caribbean to Wisconsin takes 12h 49m, covering a distance of 2092 miles. The shortest route is Nassau (NAS) to Chicago O'Hare Intl Airport (ORD) with an average flight time of 3h 43m.

  • How many long-haul flights are there to Wisconsin each week?

    There are not any long-haul (6-12 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Wisconsin. Instead, there are 4 medium-haul flights (3-6 hour flight duration), with the most arriving from Punta Cana.

  • What are the most popular destinations in Wisconsin?

    Based on KAYAK flight searches, the most popular destination is Chicago (81% of total searches to Wisconsin). The next most popular destinations are Minneapolis (9%) and Milwaukee (4%). Searches for flights to Madison (4%), to Appleton (1%) and to Green Bay (0%) are also popular.

Reviews of the top 4 airlines serving from Caribbean to Wisconsin

 
Need help choosing which airline to fly with from Caribbean to Wisconsin? 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 4335 reviews
8.1Boarding
7.5Entertainment
7.0Food
8.6Crew
8.0Comfort
Airline reviews

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

2.0 MediocreAnonymous, Apr 2026
BWI - MKE
Read more Southwest reviews

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Had a great flight. Delayed takeoff, but comfortable. Snacks were good.

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

The flight was smooth, the crew was great but the plane was quite old

Everything was great until I lost my water bottle and they can’t seem to locate it. I know I left it on the plane though.

WiFi didn’t work most of the time. The usb chargers would work only occasionally for 5 mins and wouldn’t charge after that. Had to keep trying repeatedly at each of the seats in the row.

The crew bent over backwards to thank us for flying and make us comfortable. The food service was quick and efficient. The Captain communicated and said goodbye and thank you as we departed. They really stood out!

Okay considering we had weather delays which the Pilot notified us of immediately!

Generally on time departures and arrivals, clean planes, sky miles membership provides great benefits (complimentary upgrades, etc).

Flight from Fort Wayne to Atlanta was the smallest in terms of cabin space that I've ever seen. A carry on I've used for 20 years BARELY fit in overhead compartment. I'm 5'10" and felt very cramped. Not the best experience.

I am writing to express my dissatisfaction with the poor service and unprofessional staff we encountered when traveling with an infant. Our flight was delayed, and the gate staff failed to manage the boarding process appropriately. Due to incorrect, unavailable, or missing 'pink tag' stroller and car seat check-in procedures at the gate, we were forced to board last. Furthermore, the gate staff was rude and dismissive, causing significant distress to our infant. To make matters worse, one of our checked items—an infant sleeper/lounger—was returned to us broken. Given the unsafe handling of essential equipment and unprofessional treatment, I expect a prompt resolution regarding compensation for the damaged items.

We departed and landed early which was a nice surprise. The boarding process was slow.

Checking in united could not figure out my star alliance gold. Baggage did not get marked priority and didn't receive boarding passes. When got to SFO lounge personal fixed everything Immediately

Meals were poor and service rendered on return flight was mediocre as compared to the flight we took to Germany earlier where the attendants were more attentive, energetic, and mindful of passengers' needs. Thumbs up to crew of UA 58. Thumbs down to UA 59..

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

This was the first flight in the morning. We boarded fine. The cabin door was closed and we were ready to go. We were notified by the Captain that ATC issued and ground stop for 40 minutes. So, without even pushing back from the gate, we were already 40 minutes late. We actually were released to push-back and taxi at 30 minutes. But, some passengers had tight connections and were not going to make their connections. Some passengers asked about the delay and the effect on the connections and were told by the cabin attendant that all flights will be delayed and so they should be OK. However, that was not true. My connecting flight was on time and I arrived at IAH with 21 minutes to make my connection. I did and I'm happy about that, but the flight crew should not have given assurances to the passengers who might have missed their connections.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

The crew was generally professional. Though one of the crew members seemed to be easily annoyed, the others were fine and helpful. The green olives and almonds snack was really good. A great idea, and nice balance of tastes.

It as confusing with the connections and I almost missed my next flight because of the first delay with the first flight. United could have helped passengers go through immigration quicker rather than waiting with everyone else. The flight attendants were super friendly and lovely. The vegetarian food was awful- I did not finish. I would suggest they just do pasta next time

The plane was very creaky and lots of ringing. Plane was dirty and dingy. I couldn't hear the captain's announcements from the flight deck. Not sure if it was the captain or the audio equipment, but good thing there wasn't an emergency where we needed clear instructions. The overhead compartments were clearly full, but the flight crew allowed people to stand in the back with their carry on luggage. Then after everyone boarded, they had to go to the front to gate check their luggage because there was no room for their bags and then they returned to their seats...such a waste of time when clearly the overhead compartments were full when they originally boarded.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I have been flying American Airlines—almost exclusively—for years. The airline is consistent with fares, timely departures/arrivals, and customer service, whether on the phone or in the air.

Cleared standby and gave up my seat. Terrible policy and boarding experience

Flight was delayed and they gave up my seat on my connection, even when I could still make the flight

Checked bag was severely damaged. Whole corner was riped off including 1 of 4 wheels gone. Insulation exposed. This made it not possible to fly with on my next-day American Airlines flight.

The WiFi would not connect enough for me to do my actual work. It permaspooled, disconnected, said it was connected, then wouldn't open an email... it was frustrating. I am not a tall person, 5'4" - and I felt cramped with little room to reach into my bag under the seat in front of me. I feel sorry for anyone taller than me having to fly. the one positive thing I will add, is the overhead bins are roomy enough to manage more bags than other carriers.

Air condition was not working for long both after boarding and also after landing ; unbearably hot and suffocating

On time flight, good communication about boarding, lines didn't form unnecessarily for boarding before their group was announced (kept aisles clear), friendly flight attendants and service

Flight was extremely hot and they made us check our bags when the space was nowhere near full

Everything you need to know for your flight to Wisconsin

Cabin class types available on flights to Caribbean

Cabin classes available on flights to Caribbean. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.