$64 Find Cheap Flights from Caribbean to Wisconsin

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Low seasonMarch
High seasonDecember
Cheapest flight$64
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 12% 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 $536 and $502 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 2 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 14h 10m, covering a distance of 2037 miles. The shortest route is Nassau (NAS) to Chicago O'Hare Intl Airport (ORD) with an average flight time of 3h 56m.

  • What are the most popular destinations in Wisconsin?

    Based on KAYAK flight searches, the most popular destination is Chicago (83% of total searches to Wisconsin). The next most popular destinations are Minneapolis (9%) and Milwaukee (4%). Searches for flights to Madison (2%), to Appleton (1%) and to La Crosse (0%) are also popular.

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 4294 reviews
8.0Comfort
8.2Boarding
7.6Entertainment
7.1Food
8.6Crew
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Fine except the person next to me took up her seat had raised the arm divide so she spilled into my seat. because of her size. Fortunately no one was in the seat on my right so I could use part of it.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

Delta is a cut above the others in customer service.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

Our flights got changed from United to Air Canada and our purchased seats did not get transferred so we had to pay for seats twice. I brought it up with Air Canada and they stated I had to go back and chase it with United. The united seats were $21 Canadian each and Air Canada were $56 each so we have paid $77 for each seat. Very unhappy

A bit rush for transit. Food and entertainment are not available

So far so good but food and entertainment are not available for this flight

Multiple delays and not straight answer from the United team

Stewardess spilled orange juice on my clothes/seat no help no apology just threw napkins at me to clean the mess up. Not Happy.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

The plane pushed back from the gate on time. However, it stopped on the ramp, and we waited for over 20 minutes before the aircraft pulled back to the gate. Apparently, something of importance had to be removed from the aircraft by the gate agent. I found this to be odd. The delay was not significant, but I felt that whatever was on the aircraft that had to be taken off, should’ve been done before we pushed back from the gate.

Electric plugs didn't work. Entertainment system wasn't working

The design of the light switch on the arm rest is ridiculous.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

Paid $35 and not able to access the internet at all.

Several delays. Next flight was worse. Did not arrive home until 2am PT

Very helpful ground crew after an earlier flight delay and being rebooked on a different flight.

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

First world problems, but still… We were seated in first class and asked for a cocktail on a very short, 50 minute flight. After our drink order was taken, a half hour went by, and we noticed that every other person in the small plane had been served except for us. We got up to ask about it, the drinks finally came, then were taken away three minutes later since the flight was so short. Really strange situation, on the other hand, we were in Utah.

We missed our flight. The boarding pass had the wrong gate and by the time we received the text from Kayak, our flight was already gone. I’ll never use Kayak again and will go direct to the airlines in the future.

Boarding took forever, the plane was cramped and cold, and the seatbelt song came on constantly throughout the red eye flight with a loud pre-recorded message playing each time

Cabin felt crammed Snacks are lame But crew was super efficient getting us out on time despite delay

Flight was delayed bc of mechanical issue. New plane had different configuration so some seats had to be switched. They called all passengers who needed new boarding cards. They did not call us so we thought our seats were the same and fine. When we boarded they informed us our receipts had changed and we are now all sitting separate and in the back row. Both my daughters had meltdowns and started to cry and once we got on the flight, we figured out how we could sit closer to each other, but this was very upsetting.

Took off on time and successfully avoided weather that looked to be a problem along the way

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

All was good expecting the seats need a bit of cushion. Besides that I can’t complain.

You get what you pay for, and the flights went smoothly. There’s no reclining chairs, no screens, And there isn’t always wifi, but the plane was clean and staff was friendly and the takeoff/landing were smooth.

The only positive is that the flight made it both ways. Getting charged for every little thing after the cost of the ticket itself is comical, considering how the plane and services are as bottom-tier as possible. The self check-in kiosks are useless. It’s nice to think that you can print your boarding pass, tag your checked bag, and then just drop it off. But no, they still make you go through the line once you finish- what’s the point of the self check-in then? Any questions for the staff seem like the biggest inconvenience and were met with condescending responses. This was my first and now last time ever flying with Spirit. After all the extra costs, subpar plane and staff, I see no value. I’d rather drive the 13 hours than give Spirit another dime.

The flight was fine however what started as a reasonable priced ticket could have become an overpriced ticket with additional charge for carry on as well as checked bag $79 per bag per person each way. Additional charge for choosing one’s seat, additional charge for beverage and snack, we were on what was described as a new plane yet there were no audio/visual on the jet. A bare bones service but not at a bare bones price. Will think twice before flying Spirit again. 😕

Flight was delayed a bit, but that was expected (and updated), so really not bad at all for the price. Could’ve used one less email asking me to upgrade my seat; otherwise no significant complaints

I love Spirit. New aircraft, great cabin service, the airfares are low cost which helps me visit my hospitalized daughter anytime I can without paying a fortune.

Flight was 2hours late they had no crew or the pilot.

I paid for streaming wifi and the connection was poor.

Book cheap flights from Caribbean to Wisconsin

Recent round-trip flight deals

5/29Thu
1 stopSpirit Airlines
13h 38mSJU-ORD
6/5Thu
nonstopSpirit Airlines
4h 46mORD-SJU
$188
5/29Thu
1 stopSpirit Airlines
13h 38mSJU-ORD
6/2Mon
nonstopSpirit Airlines
4h 46mORD-SJU
$192
9/4Thu
1 stopDelta
7h 28mSJU-MKE
9/18Thu
1 stopDelta
9h 08mMKE-SJU
$266
5/20Tue
1 stopUnited Airlines
8h 12mSJU-MKE
5/25Sun
1 stopUnited Airlines
8h 29mMKE-SJU
$300
5/21Wed
1 stopDelta
7h 11mSJU-MKE
5/25Sun
1 stopDelta
8h 44mMKE-SJU
$302
8/20Wed
1 stopAmerican Airlines
8h 09mSJU-MKE
8/27Wed
2 stopsAmerican Airlines
11h 45mMKE-SJU
$308
5/20Tue
2 stopsUnited Airlines
11h 52mSJU-MKE
5/25Sun
1 stopUnited Airlines
8h 29mMKE-SJU
$309
8/20Wed
1 stopAmerican Airlines
8h 09mSJU-MKE
8/27Wed
2 stopsAmerican Airlines
10h 50mMKE-SJU
$310
9/5Fri
2 stopsSouthwest
11h 20mSJU-MSP
9/8Mon
2 stopsSouthwest
10h 55mMSP-SJU
$420
6/25Wed
1 stopSouthwest
7h 10mSJU-MKE
6/30Mon
1 stopSouthwest
11h 25mMKE-SJU
$470

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Recent one-way flight deals

5/29Thu
1 stopSpirit Airlines
13h 38mSJU-ORD
$64
5/29Thu
1 stopSpirit Airlines
13h 38mSJU-ORD
$69
9/4Thu
1 stopDelta
7h 28mSJU-MKE
$113
7/3Thu
nonstopUnited Airlines
5h 05mPUJ-ORD
$141
6/11Wed
nonstopUnited Airlines
5h 05mPUJ-ORD
$149
5/31Sat
1 stopDelta
8h 39mSJU-MKE
$154
8/7Thu
1 stopAmerican Airlines
11h 41mPUJ-ORD
$157
5/7Wed
nonstopAmerican Airlines
5h 20mPUJ-ORD
$164
5/10Sat
1 stopSouthwest
11h 20mSJU-MSP
$179
10/2Thu
2 stopsSouthwest
12h 10mSJU-MSP
$187

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Last minute flights from Caribbean to Wisconsin

Last minute flight, train and bus deals

5/5Mon
multi-stop
13h 25mSJU-ORD
5/12Mon
nonstop
4h 46mORD-SJU
$260
5/3Sat
nonstopSun Country Air
6h 11mSJU-MSP
5/10Sat
nonstopSun Country Air
5h 11mMSP-SJU
$264
5/1Thu
multi-stopDelta
7h 43mSJU-MKE
5/17Sat
multi-stopDelta
9h 53mMKE-SJU
$379
5/1Thu
multi-stopAmerican Airlines
10h 31mSJU-MKE
5/17Sat
multi-stopAmerican Airlines
15h 32mMKE-SJU
$389
5/3Sat
multi-stopAmerican Airlines
10h 30mSJU-MSN
5/10Sat
multi-stopAmerican Airlines
13h 09mMSN-SJU
$389
5/5Mon
multi-stopUnited Airlines
15h 49mSJU-MSP
5/13Tue
multi-stopUnited Airlines
7h 32mMSP-SJU
$448
5/5Mon
multi-stopDelta
7h 48mSJU-ORD
5/14Wed
multi-stopDelta
8h 17mORD-SJU
$450
5/2Fri
multi-stopUnited Airlines
10h 50mSJU-MSP
5/3Sat
multi-stopUnited Airlines
11h 37mMSP-SJU
$505
5/2Fri
multi-stopSouthwest
14h 50mSJU-ORD
5/4Sun
multi-stopSouthwest
10h 10mORD-SJU
$573
5/5Mon
multi-stopSouthwest
11h 15mSJU-ORD
6/2Mon
multi-stopSouthwest
9h 05mORD-SJU
$633

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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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