$99 Find Cheap Flights from Caribbean to Wisconsin

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Low seasonMarch
High seasonDecember
Cheapest flight$99
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from San Juan Airport to Chicago O'Hare Airport

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.

  • What is the cheapest day to fly to Wisconsin?

    Based on KAYAK data, the cheapest day to fly to Wisconsin is Thursday where round-trip tickets can be as cheap as $331. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $624 on average.

  • What is the cheapest time of day to fly to Wisconsin?

    The cheapest time of day to fly to Wisconsin is generally at night, when round-trip flights cost $404 on average. Morning departures are around 2% cheaper than evening flights, on average. The most expensive time of day to fly to Wisconsin is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $429.

  • What is the cheapest flight to Wisconsin?

    The cheapest ticket to Wisconsin from Caribbean found in the last 72 hours was to Milwaukee, at $266 round-trip. The most popular route is Punta Cana (PUJ) to Milwaukee (MKE) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $266.

  • 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 $303 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $509 and $501 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. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

  • How long is the flight to Wisconsin?

    An average nonstop flight from Caribbean to Wisconsin takes 12h 42m, covering a distance of 2071 miles. The shortest route is Nassau (NAS) to Minneapolis (MSP) with an average flight time of 4h 25m.

  • What are the most popular destinations in Wisconsin?

    Based on KAYAK flight searches, the most popular destination is Chicago (87% of total searches to Wisconsin). The next most popular destinations are Minneapolis (6%) and Milwaukee (5%). Searches for flights to Madison (1%), to Appleton (1%) and to Green Bay (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 4266 reviews
8.0Comfort
7.6Entertainment
8.2Boarding
7.0Food
8.6Crew
Airline reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

4.0 OkayTraci, Jun 2025OAK - SEA
Read more Southwest reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Cluster mess boarding. Can't wait for SWA reserved seating. Internet didn't seem to work on the plane.

Flights delayed by 4-6 hours. Boarding was a mess and unclear. Bags were not at arrival airport and had never even been put on the plane. No idea when I’ll get them. Don’t fly into Denver!

My flight was canceled after being rescheduled for four days canceling my trip. Kayak and everyone affiliated with it I.e the airlines, and just fly have been excruciating to deal with. My trip to visit family had to be canceled as there was no way to make it. I am furious at all of you.

They delayed our flight because of bad weather in NY which was completely understandable. Then they cancelled our flight and a later flight that evening. The earliest we could fly was the next morning. We ended up buying last minute tickets on another airline and made it home slightly delayed but safely that evening. Delta kept saying it was weather related but if that was the case how did we make it back on another airline? The weather in NY was cloudy but not bad.

From Atlanta to Savannah - flight connection was way to short (we weren't even late landing ) and flight was already boarding when we landed - we were told we were the last on board and so we had to gate check our bags. Once we got on the plane, there were at least seven open bag spots so that was unnecessary delay. There should be better communication between the gate agent and the crew.

Crew was excellent. Comfort seats not as nice as other kinds of planes.

Not a "Delta" issue, but a JFK issue: We booked a connecting flight with 3 1/2 hours between to clearn immigration and customs. Our inbound flight (BCN to JFK) was on the taxiway 45 minutes which ate into our layover time. Immigtration was insanely quick with the CBP MPC app; however, clearing TSA (again, after we were ALREADY cleared in Spain on the inbound international flight) took over 95 minutes. This left us with 10 minutes before boarding the connecting flight (JFK to SAN) to walk to the far end of Terminal 4 and try to find food. We didn't find any food that could promise to serve us in under 10 minutes so we boarded the Delta flight after coming off a plance and an 8-hour flight knowing that we wouldn't be served any food on the next 5 1/2 hour flight. I feel like Delta needs to put pressure on the JFK TSA to open more screening stations (by our count, we saw only 5 scanners open and a line of - as we said - over 90 minutes. The insult is that we WERE ALREADY SCREENED through TSA, but as you come off one flight into the USA, you have to go through the whole process again. It seems like if you have a connecting flight, there should be a way to pass through immigration and customs without needing to return through TSA.

The way BCN airport handled boarding was a huge improvement over our trip to Spain from JFK. Instead of gate-mosquitos edging in before their zone was called, in BCN they had clearly marked lines for Zones 1-8 and people just lined up correctly. The flight itself was uneventful. The meal (curried chicken and rice) was one of the better meals we've had on Delta. Entertainment options were plentiful, power chargers were available in Main Cabin, and seats were decent. Flight staff were very friendly and positive throughout the 8 hour flight.

It was a great flight and the stewards and stewardess were all kind and accommodating!! The seats were comfortable and entertainment screen excellent!

The checkpoint hornets are always looking fhrough Americans' luggage keeping what they deem impassible! Grrrrr!

There are 4 flights in consecutive gates with about the same departure time. Two flights were boarding at the same time. One was delayed or boarding would be happening at the same time. I am not sure what Delta and LAX need to do to have a better layout at the end of Terminal 2

Flight was an hour late, who knows why. It was OK, nothing outstanding.

Boarded plane and then delayed 1.5 hours while on the plane

It was all good flight was on time, service was good I enjoyed a few movies and everything was smooth

Survey sent before we actually left. Delay after delay. Now a crew problem.

I love flying with United. Unfortunately, I flew on an older plane with minimal upgraded technology (no Bluetooth functionality or handy charging ports). Otherwise, the flight was great and even arrived early.

They changed my seats after I checked in and I was stressed from the time I saw that information until just before boarding, when the gate attendant fixed it, but it shouldn't have happened. And if it couldn't be prevented, then the people on the phone I spoke with should have done something to help, which they did not, nor did they offer me compensation, just meaningless apologies.

Horrific. They missed my connecting flight to San Diego. I didn’t get there until Monday at 9am when I had a mandatory court settlement conference scheduled at 6am since we had parties on the east coast. This caused many issues. All because United apparently forgot to hold the doors open until my flight landed that only had a 10 minute delay. This was the last flight to Southern California. So I couldn’t even rent a car to finish the trip. United cannot be trusted when traveling on specific days and times since weather didn’t have anything to do with the delays.

My flight was delayed a very short period of time but they did not hold my connecting flight to San Diego, also through United. So they closed the doors before we got off our plane. They would only have to help the door open for another five to ten minutes. So I missed a court deadline for a manditory mediation settlement conference for my client. I had to get an associate to be there in person and be on the phone with him relaying what he needs to do the entire time. The court was very upset with me and so was my client. United cannot be trusted.

Very rough getting into denver. my kid threw up it was so rough.

We were given vouchers we couldn’t use with a 5.5 hour delay

We had a very long diversion and our food voucher didn’t work because the restaurants were closed

AA re-routed flight from HNL to LAX due to delay. My group of 3 with reserved seats in row 9 was broken up, with one assigned to a middle seat, another in the last row of the plane. Not happy. No explanation to the delay. No apologies. No compensation. Would have been nice to be offered an Admiral Club admission or a voucher for the extra 3 hours of layover in LAX. Could not hear the boarding gate announcements in LAX. Adjacent gate was boarding at the same time. Loud speakers were competing against each other. Barely made my boarding group.

Boarding gate in Honolulu was staffed with a great clerk with a soothing voice despite the flight delay of over an hour. Flight attendants in the plane were all grumpy, not pleasant looking bunch. Their sour attitude showed throughout the flight. Inly able to get a select few movies started. Most of the movie links in the “free entertainment” did not work.

Above and beyond effort from this crew in a tough situation. So helpful and understanding. Thank you!

I flew Business Class. Rory, one of the Cabin stewards, was attentive, explained the menu, provided appropriate drinks. was

The flight delay in Dallas created a domino effect that impacted all connecting flights, leading to an increase in the number of connections. As a result, I missed my flight from Casablanca to Marrakech due to the tight turnaround when landing in Casablanca. CMN Airport was understaffed; only one employee was available to assist passengers while others just stood by and watched. It was an extremely frustrating situation. Many passengers were crying and banging their hands on the counter while talking to customer service representative Allabough. Unfortunately, Allabough couldn’t change my flight in the system. At the same time, I was on the phone with an American Airlines customer service representative named Solomon, who said he couldn’t make the change either. So, I decided to take an ONYA Voyages train from Casablanca to Marrakech to reach my destination on Friday, June 26. It turned out to be an unpredictable trip.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

Almost a 6 hour flight and the only food option is a cheese plate… and chips. Also how is it there are no options for texting on American. I’ll be going back to delta and united.

This flight never occurred because AA couldn’t get their act together.

Terrible. Cancelled my original flight. It made getting a boarding pass difficult. The AA employee (in a loud voice, so everyone around could hear) griped at me for not getting a boarding pass 24 hours before. I asked how I was supposed to do that when I had no idea what flight I was going to be on. She said (loudly), “Talk to AA customer service, not me!” I could certainly tell serving customers was not important to her. Our new flight was set to a completely different city. We had to change our rental car, and the price went way up. It took 2-1/2 hours to get checked in. By then our new flight had left. We ended up on stand by and had to split up the family to get to our destination. It cost us the whole first day of the trip. AA needs to employ people who actually care about doing a good job. I suppose those people are getting harder to find, but atleast try.

A cookie and a soda, packed like sardines, will never be a positive experience. Also, boarded a 5:30 flight at 7:45pm

I didnt take the flight because your company booked it through a scam agency called airline assist. There was no flight. You guys suck.

Unfortunately, spirits crew had us boarding and parking the plane often, would wait long periods of time before allowing the people attending the flight on the plane to know what was going on this caused for my plane to not only get diverted but then canceled at an airport 2 hours away and basically stranded with charter buses MAYBE being hired. I was left with no choice but to stay overnight and use a comp room in Altantic City to then arrive home the next day. This trip was the first time seeing my partner since he joined the Air Force and this stressful ride caused unwarranted tears on what was supposed to be an east flight home. I understand weather is unpredictable but to have passengers deboard to then reboard an hour later to taxi on the runway for another hour to then basically leave an entire fight stranded. I waited almost 30 minutes at the airport and not one employee could tell me about a charter bus so I had to leave and make accommodations to stay overnight and get a ride home.

I wanted to upgrade my seat because I’m 6’2 and never have enough leg room for my comfort. They upgraded my seat for free putting me in an emergency exit seat. I was very comfortable

I have never flown Spirit it was much better than anticipated!

Staff was very friendly. They attended to people nicely and reprimanded, in a professional way, to those who wouldn’t listen. AC wasn’t working on the flight waiting to depart in Burbank, so it was uncomfortable for a while since the flight was delayed but then better before take off.

This was the first time I use Spirit Airlines and was pleasantly surprised. It was a last-minute booking and I was happy to see there was availability on your airline for a price that was affordable. The staff was friendly. The only things I thought were missing, were the ability to recline the seats, although I don’t use that very often, and it would’ve been nice to have power access at the seats to plug in my devices.

Flight was on time and was not crowded. Flight attendants were very understanding of my wife’s back problems.

Good on that leg. When I arrived in Detroit I had to wait over an hour for luggage.

Not very good because of an almost 3 hour delay for an hour long flight.

We had an almost 7 hour flight delay. We left the gate twice and taxi-ed and then returned the gate twice. Finally we got a new flight crew (our third one) and then left the gate to the final time before departing at 6:45pm (original flight time was 12pm). Out of Newark.

Book cheap flights from Caribbean to Wisconsin

Recent round-trip flight deals

8/14Thu
1 stopFrontier
10h 14mSJU-ORD
8/17Sun
1 stopFrontier
15h 11mORD-SJU
$148
9/24Wed
1 stopFrontier
23h 47mSJU-ORD
9/29Mon
1 stopFrontier
8h 01mORD-SJU
$153
9/24Wed
1 stopAmerican Airlines
7h 27mSJU-MSN
9/29Mon
2 stopsAmerican Airlines
17h 03mMSN-SJU
$225
9/4Thu
1 stopDelta
6h 50mSJU-MKE
9/18Thu
1 stopDelta
8h 00mMKE-SJU
$225
9/10Wed
2 stopsAmerican Airlines
18h 20mSJU-MKE
9/24Wed
2 stopsAmerican Airlines
19h 59mMKE-SJU
$231
9/4Thu
1 stopDelta
6h 50mSJU-MKE
9/18Thu
1 stopDelta
6h 36mMKE-SJU
$265
7/24Thu
1 stopSouthwest
13h 35mSJU-MKE
7/27Sun
1 stopSouthwest
10h 20mMKE-SJU
$270
9/23Tue
2 stopsUnited Airlines
9h 43mSJU-MSN
9/29Mon
1 stopUnited Airlines
7h 14mMSN-SJU
$280
9/10Wed
1 stopUnited Airlines
7h 34mSJU-MKE
9/24Wed
1 stopUnited Airlines
8h 44mMKE-SJU
$315
9/10Wed
1 stopSouthwest
6h 45mSJU-MKE
9/14Sun
1 stopSouthwest
6h 30mMKE-SJU
$345

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Recent one-way flight deals

7/31Thu
1 stopSpirit Airlines
11h 41mSJU-ORD
$99
8/2Sat
1 stopSpirit Airlines
15h 34mSJU-ORD
$103
7/20Sun
2 stopsSpirit Airlines
24h 16mSJU-ORD
$104
9/4Thu
1 stopDelta
6h 50mSJU-MKE
$113
12/9Tue
1 stopDelta
7h 19mSJU-MSN
$113
9/24Wed
2 stopsAmerican Airlines
18h 16mSJU-MSN
$119
9/19Fri
2 stopsAmerican Airlines
18h 21mSJU-MKE
$121
11/26Wed
1 stopUnited Airlines
7h 51mSJU-MKE
$158
9/23Tue
2 stopsUnited Airlines
11h 39mSJU-MSN
$158
8/3Sun
1 stopSouthwest
13h 45mSJU-MKE
$203

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Last minute flights from Caribbean to Wisconsin

Last minute flight, train and bus deals

7/8Tue
multi-stop
25h 44mSJU-ORD
7/22Tue
multi-stop
7h 59mORD-SJU
$262
7/8Tue
multi-stopSpirit Airlines
13h 31mSJU-ORD
7/22Tue
multi-stopSpirit Airlines
19h 43mORD-SJU
$264
7/8Tue
nonstopSpirit Airlines
5h 16mSJU-ORD
7/22Tue
multi-stopSpirit Airlines
19h 43mORD-SJU
$280
7/7Mon
multi-stopFrontier
7h 40mSJU-ORD
7/11Fri
multi-stopFrontier
7h 06mORD-SJU
$282
7/4Fri
multi-stopFrontier
11h 37mSJU-ORD
7/8Tue
multi-stopFrontier
13h 40mORD-SJU
$286
7/3Thu
multi-stopAmerican Airlines
16h 59mSJU-MKE
7/17Thu
multi-stopAmerican Airlines
16h 46mMKE-SJU
$379
7/8Tue
multi-stopAmerican Airlines
10h 05mSJU-MSP
7/16Wed
multi-stopAmerican Airlines
9h 56mMSP-SJU
$430
7/7Mon
multi-stopSouthwest
12h 00mSJU-MSP
7/12Sat
multi-stopSouthwest
11h 50mMSP-SJU
$505
7/3Thu
multi-stopUnited Airlines
7h 49mSJU-MKE
7/6Sun
multi-stopUnited Airlines
6h 44mMKE-SJU
$559
7/8Tue
multi-stopUnited Airlines
14h 18mSJU-MSP
7/16Wed
multi-stopUnited Airlines
15h 17mMSP-SJU
$828

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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.

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