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Find cheap flights from Caribbean Islands to Wisconsin from $69

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Caribbean Islands to Wisconsin departing on 6/14. 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
0 bags
Tue 7/9
Tue 7/16

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Good to know

Low season

February

High season

July

Cheapest flight

$69
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 16% increase in price.
Flight from San Juan to Minneapolis

FAQs for booking flights from Caribbean Islands to Wisconsin

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Wisconsin from Caribbean Islands 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 Islands 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 to Wisconsin with an airline and back to Caribbean Islands with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean Islands 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 to Wisconsin from Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 4 airlines serving from Caribbean Islands to Wisconsin

Need help choosing which airline to fly with from Caribbean Islands 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.
7.9
Caribbean AirlinesOverall score based on 182 reviews
8.3Crew
6.6Entertainment
7.6Comfort
8.1Boarding
6.7Food
Airline reviews

I was treated well in first class. I have no complaints. I will definitely fly with my favourite airline again this year.

10.0 Excellentroderick, May 2024MIA - POS
Read more about Caribbean Airlines reviews

I was treated well in first class. I have no complaints. I will definitely fly with my favourite airline again this year.

There was no music on the flights unless you came with your headset.

Their bar selection could be greatly improved; they only had one spirit option

Music would have been great and information about the flight. Meaning how high and the weather conditions.

It was good but the food was small for the duration of the flight.

I wrote to the entertainment and food OK because it was non-applicable All excellent

Checking in online still requires going on the physical check in line

I enjoyed the smooth flow and well coordinated boarding and the very courteous attitude from the cabin crew We look forward to flying with ya’ll again

Pleasant experience checking in. Seating is way too tight, especially for persons who are not petite. I thought the pilot was excellent in terms of his commentary and information. Wrong gate information on boarding passes. If I was not alert I could have lined up to board the wrong plane.

The crew was excellent, check in was easy ,the food wasn't good, movies should be recent and more selections

They put me on a chair in between two men, one overweight who was almost falling on top of me, and the other was even uncomfortable because I was half falling because of what the other was pushing me. I stayed with. my feet were swollen from fluid retention and from being unable to accommodate myself. it was very uncomfortable. I asked for help but they told me that the flight was full and they couldn't help me. I got off the plane almost unable to walk due to the inflammation. and then at FLL airport I asked for help because I couldn't go to my next flight, which was a connection.

The walk from baggage claim to the taxi is very difficult for older people I will never fly into JFK again. It is physically challenging

Overall fine but both ways for this trip was delayed.

Flight was delayed by almost 5 hours. Suitcase was not loaded despite the flight being near empty (my colleagues’ suitcases did reach JFK, unlike mine). Had to argue on phone to get JetBlue to deliver the case to my hotel. Never again

The flight was excellent. The crew was welcoming and attentive.

Great! I love Jet Blue. My favorite airline! Very efficient, clean and timely.

Run out of snack choices. Why are the seats not padded for your butt? Are we sitting on blocks of wood or metal for $250-300 a pop? This ain’t spirit. Let’s get it together people

We were told that our flight would be delayed for 90+ minutes because of weather, so we went to get something to eat only to have them randomly start boarding 15 minutes after the announcement, with no warning.

Entertainment... No earphones passed out. Many including me couldn't use the TV. Legroom was good. Crew was indifferent and a bit surly. Free wifi was a nice convenience. Check in desk location was unknown. Gate number on the boarding passes was wrong.

Going through JFK’s security is a mess. The TSA security said no shoes on the bins. So, we place our shoes in the belt and they came out all over the belt. Boarding was delayed and Flight as well.

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

My flight was cancelled from Gainesville. I was able to get on another flight on Friday. Will see if this one cancels also?

the hospitality was excellent to me and I will return flying with them

I am very disappointed. I booked with kiwi when I got to the airport there was no reservation I had to purchase another ticket after my card was already charged for almost double the cost I payed through kiwi eight days after I went to their office in Tortola and they refuse to give me a receipt so that I can cancel the original payment. They said “ there is no record that you used silver to travel “ I know I did not swim to Puerto Rico . If someone can help me please so that I can cancel the payment the credit card company said I need it, I have less than 14 days or I will loose my money. This is terrible and there is no local number for them.

I booked because of time of the flights. I needed to be at my destination at a specific time, and missed my appointment because of your delays.Get rid of these junk planes. The ATR planes are dated old scary planes. And maybe you could actually be on time. This airlines on time record is horrible. The communications between the gate agents and this company dont exist.. They couldn't give any answers,. When trying to find out when the flight would leave, they get no response when they asked for details on flights, they receivedconflicting information. I felt bad for the gate agents having to deal with Silver's inability to communicate simple information. This is my last choice in air travel. On time flights are everywhere, and both flights I took were delayed. It's a sad company.

The flight itself was good and the flight attendant was very good.

It was awesome until we ran into some bad weather but the pilots did an amazing job getting us to safety and landed

If you take this airline, they WILL change the flight time, and make you miss your connection. It has happened every time I used it. It's so unreliable that I think it shouldn't be offered on Kayak. You will regret it!

In addition to the fact that Silver changed the flight time several days before the trip without offering any choices , I was sick with Covid and unable to go on the trip. I tried to ask Silver for a credit for a flight when I’d recooperated but they don’t do credits, even for illness. I will Never fly on Silver again

I canceled due to a 7 hour delay. Was forced to book another airline last minute , very expensive. Silver Aorways sucks

I spent hours with orbitz to get my tsa # on my ticket. They didn’t have a place to enter. I will never use orbitz again. No customer service. A number in which u press offered options and the message replays instead of getting customer to that area. Silver did not make the promised call back. Finally someone responded to my email and took care of it after I lost hours of my vacation arranging this. Staff on flight barked orders.

Book cheap flights from Caribbean Islands to Wisconsin

Recent round-trip flight deals

7/10Wed
1 stopSpirit Airlines
13h 59mSJU-ORD
7/16Tue
1 stopSpirit Airlines
14h 16mORD-SJU
$176
8/22Thu
1 stopSpirit Airlines
15h 01mSJU-ORD
8/25Sun
1 stopSpirit Airlines
17h 30mORD-SJU
$179
6/14Fri
1 stopFrontier
19h 24mSJU-ORD
6/18Tue
1 stopFrontier
9h 49mORD-SJU
$191
8/8Thu
1 stopFrontier
9h 27mSJU-ORD
8/10Sat
1 stopFrontier
12h 58mORD-SJU
$199
8/6Tue
1 stopAmerican Airlines
7h 30mSJU-MKE
9/3Tue
1 stopAmerican Airlines
7h 45mMKE-SJU
$246
8/6Tue
1 stopAmerican Airlines
11h 33mSJU-MKE
9/3Tue
2 stopsAmerican Airlines
15h 23mMKE-SJU
$268
7/22Mon
1 stopJetBlue
9h 11mSDQ-ORD
8/20Tue
1 stopJetBlue
7h 15mORD-SDQ
$457
6/30Sun
1 stopJetBlue
8h 55mSJU-MKE
7/5Fri
1 stopJetBlue
9h 10mMKE-SJU
$468
6/17Mon
1 stopCopa Airlines
13h 15mSDQ-ORD
6/26Wed
1 stopCopa Airlines
26h 19mORD-SDQ
$634
7/13Sat
1 stopCopa Airlines
10h 33mSDQ-ORD
7/20Sat
1 stopCopa Airlines
9h 35mORD-SDQ
$668

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Recent one-way flight deals

6/14Fri
1 stopFrontier
9h 01mSJU-MSP
$69
8/9Fri
2 stopsFrontier
19h 11mSJU-MKE
$98
8/18Sun
1 stopJetBlue
10h 19mSJU-ORD
$128
7/4Thu
1 stopJetBlue
9h 01mSJU-MSP
$136
6/12Wed
1 stopAmerican Airlines
13h 35mSJU-ORD
$157
7/4Thu
nonstopAmerican Airlines
5h 05mPUJ-ORD
$159
7/4Thu
1 stopCopa Airlines
13h 15mPUJ-ORD
$264
6/25Tue
1 stopCopa Airlines
13h 15mSDQ-ORD
$280
6/18Tue
2 stopsAir Canada
18h 48mMBJ-ORD
$314
6/20Thu
2 stopsAir Canada
19h 30mKIN-ORD
$379

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Last minute flights from Caribbean Islands to Wisconsin

Last minute flight, train and bus deals

6/14Fri
multi-stopFrontier
19h 24mSJU-ORD
6/18Tue
multi-stopFrontier
9h 49mORD-SJU
$191
6/13Thu
nonstopSpirit Airlines
5h 09mSJU-ORD
7/13Sat
multi-stopSpirit Airlines
15h 12mORD-SJU
$216
6/11Tue
multi-stopSpirit Airlines
9h 29mSJU-ORD
6/30Sun
multi-stopSpirit Airlines
16h 13mORD-SJU
$227
6/14Fri
multi-stop
19h 24mSJU-ORD
6/21Fri
multi-stop
17h 15mORD-SJU
$230
6/14Fri
multi-stop
19h 24mSJU-ORD
6/16Sun
multi-stop
10h 01mORD-SJU
$283
6/11Tue
multi-stopUnited Airlines
9h 30mSJU-ORD
6/30Sun
multi-stopUnited Airlines
11h 39mORD-SJU
$404
6/10Mon
multi-stopAmerican Airlines
16h 50mSJU-ORD
6/13Thu
multi-stopAmerican Airlines
15h 04mORD-SJU
$425
6/11Tue
multi-stopUnited Airlines
8h 30mSJU-ORD
6/30Sun
nonstopUnited Airlines
4h 50mORD-SJU
$444
6/13Thu
multi-stopAmerican Airlines
10h 50mSJU-ORD
7/13Sat
multi-stopAmerican Airlines
17h 15mORD-SJU
$486
6/12Wed
multi-stopJetBlue
9h 18mSDQ-ORD
6/18Tue
multi-stopJetBlue
7h 15mORD-SDQ
$575

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