$64 Find Cheap Flights from Caribbean Islands 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 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 from Caribbean Islands 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 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 from Caribbean Islands 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 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 from Caribbean Islands 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 Islands 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 Islands to Wisconsin?

    The cheapest month for flights from Caribbean Islands 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 Islands to Wisconsin?

    To get a below average price on the flight from Caribbean Islands 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 Islands to Wisconsin takes 13h 16m, covering a distance of 2093 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 airlines flying 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.
8.0
DeltaOverall score based on 7934 reviews
7.9Entertainment
7.3Food
8.5Crew
7.9Comfort
8.2Boarding
Airline reviews

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.

10.0 ExcellentAnonymous, Apr 2025AMS - ATL
Read more Delta reviews

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.

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

Book cheap flights from Caribbean Islands 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
7/16Wed
nonstopFrontier
5h 08mPUJ-ORD
8/13Wed
nonstopFrontier
4h 40mORD-PUJ
$234
5/11Sun
1 stop
20h 36mSJU-ORD
6/3Tue
nonstop
4h 46mORD-SJU
$253
5/21Wed
1 stop
15h 22mSJU-ORD
5/27Tue
nonstop
4h 46mORD-SJU
$258
9/4Thu
1 stopDelta
7h 28mSJU-MKE
9/18Thu
1 stopDelta
9h 08mMKE-SJU
$266
5/10Sat
1 stopFrontier
11h 45mSJU-ORD
5/11Sun
1 stopFrontier
6h 50mORD-SJU
$298
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
8/20Wed
1 stopAmerican Airlines
8h 09mSJU-MKE
8/27Wed
2 stopsAmerican Airlines
10h 50mMKE-SJU
$310

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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
5/7Wed
nonstopFrontier
5h 06mPUJ-ORD
$125
8/7Thu
nonstopFrontier
5h 08mPUJ-ORD
$126
5/10Sat
nonstopSun Country Air
6h 11mSJU-MSP
$132
6/7Sat
nonstopSun Country Air
5h 37mSJU-MSP
$146
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

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Last minute flights from Caribbean Islands 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
5/2Fri
nonstopSpirit Airlines
5h 23mSJU-ORD
6/3Tue
nonstopSpirit Airlines
4h 46mORD-SJU
$285
5/1Thu
multi-stopSpirit Airlines
11h 55mSJU-ORD
5/6Tue
nonstopSpirit Airlines
4h 41mORD-SJU
$301
5/4Sun
multi-stopFrontier
20h 36mSJU-ORD
5/12Mon
multi-stopFrontier
6h 50mORD-SJU
$309
5/1Thu
multi-stopFrontier
20h 36mSJU-ORD
5/5Mon
multi-stopFrontier
22h 55mORD-SJU
$324
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-stopDelta
7h 48mSJU-ORD
5/14Wed
multi-stopDelta
8h 17mORD-SJU
$450

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Everything you need to know for your flight to Wisconsin

Cabin class types available on flights to Caribbean Islands

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

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