$91 Find Cheap Flights from Caribbean to Wisconsin

1 adult
1 adult, Economy, 0 bags

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Good to know

Low seasonMarch
Cheapest flight$91
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 19% 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 46% of all flights arriving there.

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

    The cheapest month for flights from Caribbean to Wisconsin is February, when tickets cost $268 (return) on average. On the other hand, the most expensive months are July and June, when the average cost of round-trip tickets is $495 and $490 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 3 weeks before departure, which saves you about 17% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 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 2 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 2 direct flights from within Caribbean to Wisconsin. The most common day for departures is Thursday, with 50% of flights taking off on this day.

  • How long is the flight to Wisconsin?

    An average nonstop flight from Caribbean to Wisconsin takes 14h 17m, covering a distance of 2067 miles. The shortest route is Nassau (NAS) to Chicago O'Hare Intl Airport (ORD) with an average flight time of 3h 56m.

  • 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 2 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 (91% of total searches to Wisconsin). The next most popular destinations are Minneapolis (4%) and Milwaukee (3%). Searches for flights to Madison (0%), to Appleton (0%) and to Eau Claire (0%) are also popular.

Reviews of the top 5 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 4256 reviews
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
7.5Entertainment
Airline reviews

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.

10.0 ExcellentDaniel, Jan 2026
BWI - MHT
Read more Southwest reviews

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

Never went on board this flight. Kayak uses Underpricer (which is a scam business) as it's "customer service provider". This customer service is a classic bait and switch "service". I Got caught in the UnderPricer Bait and switch scam. 14 hours on the phone with people from India with heavy accents and upselling me to useless products. The original sell was a flight on spirit. Then they contact me later, an say after they have my money that the flight is no good as is is only one seat for a party of two. I am still in dispute to get my money back. Went to Spirit direct and had a beautiful vacation. I should never have used Kayak and their rip off artists UnderPricer.

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.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Food is basically Sun Chips, cookies or Cheezits. I had an exit row seat so I had plenty of room. The crew was very nice and efficient. Pilot kept us informed. Pretty good flight.

Air travel sucks. It continues to be awful for all airlines. No shame on delta alone.

It was Delta, but the flight attendants were stressful and disrespectful. I am a diamond member a travel weekly. I have not had a negative thing to share in quite some time. But this was noticeable.

Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.

Flight was late from Newark to Atlanta, I asked flight attendant to please let my family of 3 out first when we landed to Atlanta because we were late for our connecting flight to Quito. She didn't and we were late for 5 minutes we couldn't board the plane and spend hours trying to get another flight with customer service for the next day.

I really liked the legroom. I am 6’4”.a at For some reason our seats were not together and using the app to fix it didn’t work. Passengers were nice enough to move for us but you should absolutely ensure a parent sits with their child.

Late delayed flight delays boarding and delays leaving and delays on arrival too. Cramped plane no room no food.

DTW line is too long. The flights from DTW to BWI are always delayed for unknown reasons.

Delta canceled our flight and we had to scramble to find another airline to get home. Phoenix is not a delta hub so they didn’t have another plane. It would have been a red eye though Salt Lake City. Getting in at 5am. No bueno.

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age 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.

Both flights delayed. 2nd flight over 3 hours late mechanical issues

l really enjoy very much the flight was very pleasant

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

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

Flight was delayed 45 minutes because originating flight was coming from Newark. No complimentary snacks were offered on this 5+ hour flight. No screens for the flight, but movies offered if you had already downloaded the United app (which I hadn't on my ipad). No USB ports, only a flimsy plug-in port near the bottom of the seat that was hard to see and kept coming unplugged.

It was good but only meal served is very less. Meantime good to add rice and chicken in one of meal

Teeny tiny bathrooms, crew was not realistic about when we'd arrive.

Check-in, boarding and the flight from Phoenix to Houston was quick and easy. The flight from Houston to Shreveport was delayed 5 hours. It was frustrating but I think United handled it the best they could.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

Tell the crew (when boarding) to yell at the imbeciles blocking us from walking up to scan. I promise everyone crowds around and half of us (most the time I’m group 4) have to push our way through. Your staff is awesome, the public - not so much-

Bags took over and hour to come out. Delays due to wind caused rebooking.

Services, food products, and crew friendliness on American Airlines international flights is mediocre compared to Emirates, Qatar, and Singapore Airways. American does not do much to differentiate its product on international routes. Its menu options are similar on international flights. American Airlines flight attendants do not call elite frequent travelers by their names; American Airlines flight attendants do not seem to be motivated to go above and beyond in the service they provide. American Airlines personnel do not seem to take pride in their work.

The flight was good. We had to spend almost an hour on the tarmac when we arrived in Dallas. Waiting for a gate. What’s the point of arriving early if you have no gate to park at?

Lower WiFi prices; allow us to see our flight on a map; more variety of drink choices.

I was originally scheduled on AA 1763. When I landed in Miami, I went to the counter for flight AA 2115 to try to move my flight to this one. I was in a first class seat on AA 1763. While they moved to me this flight, I was told that there were no other 1st class seats available and they assigned me into coach. However, when I was getting off the plane I noticed that one of the pilots who was also in line to go jump seat - somehow miraculously got a 1st class seat on this flight. It is actually infuriating that I had a paid 1st class seat yet somehow they would move an AA employee ahead of that. At a bare minimum, they should have compensated me for the fare difference and I really think paying customers should ALWAYs get the premiere seats.

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

UGH I HAD TO MISS MY FIRST FLIGHT TO TAMPA CAUSE OF THE 10 MINUTE DELAY OF THE ORLANDO TO MIAMI ONE SO THEY HAD ME GET ANOTHER TICKET. I AM NOT HAPPY AT ALL BECAUSE IT MADE ME MISS MY CONNECTING FLIGHT FROM TAMPA TO LONDON AND FORCED ME TO MISS A DAY AT MY ROOM IN THE UK.

Wish they didnt delay off-boarding for 10 minutes so i could connect to my flight from miami to tampa

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

It was delayed but the landing was the smoothest in a while that I’ve had.

Second time in 3 days I walked off the plane late. This time - almost an hour.

Our outgoing flight was cancelled two hours before boarding and Spirit was not able to get us onto another flight. Their customer service was slow and unhelpful.

Everything went well. The flight was slightly delayed however we landed on time.

I've flown two Spirit flights recently - boarding for one was somewhat chaotic, with the board listing the wrong flight and causing much confusion; boarding for the other was very smooth and easy. My seat (for which I did not pay extra) was a bit narrow and without great legroom, but it was fine for a NY-Florida trip and was more than worth the low price I paid. The crew was friendly and one flight landed early and the other was only very slightly delayed. All in all a very good experience.

Had to pay for water if wanted it. Seats are close unless you get upgraded. Flight was fine. Will travel again with spirit.

Spirit sucks. Horrible employees in Medellín. Never again. I hope this company goes out of business completely.

Your flight crew and boarding area crew need to have microphone use training. They all hold the microphone right up to their mouths, way to close making understanding them almost impossible. The microphone should be held about 3 to 4 inches away from their mouths. This would provide for much better clarity through the PA system. ‘Eating the mic’ DOES NOT work.

It was the first time I flew on that airline and had a very positive experience. Nearly identical to Jetblue which consider the standard of airlines excellence.

A bottled or canned drink, whether water or soda would have been appreciated upon settling in and flying, without being charged for it.

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.