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Find cheap flights from Wisconsin to Caribbean from $84

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Wisconsin to Caribbean departing on 5/19. 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
Sun 5/19
Sun 5/26

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Low season

September

High season

December

Cheapest flight

$84
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 29% increase in price.
Flight from Milwaukee to San Juan

FAQs for booking flights from Wisconsin to Caribbean

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

    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 Wisconsin to Caribbean.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Caribbean from 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 Wisconsin to Caribbean?

    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 Caribbean with an airline and back to Wisconsin with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Wisconsin to Caribbean?

    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 Caribbean from Wisconsin 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 Wisconsin to Caribbean

 
Need help choosing which airline to fly with from Wisconsin to Caribbean? 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.
9.1
Cape AirOverall score based on 58 reviews
9.1entertainment
9.5crew
8.9boarding
8.4comfort
8.8food
Airline reviews

It’s less complicated from Culebra to SJU airport. Next time I will prefer to leave from Isla Grande airport to Culebra !!

10.0 ExcellentSonia, Apr 2023CPX - SJU
Read more about Cape Air reviews

It’s less complicated from Culebra to SJU airport. Next time I will prefer to leave from Isla Grande airport to Culebra !!

10 seat Cesna. Equal parts transportation and adventure. 20 minute hop at 10000 feet and 160 mph, sitting 10 feet from the pilot. Panoramic views of the island. Very simple boarding, very low stress. VQS airport tiny, undeveloped. Highly recommended flight, Cape Air doing a great job here.

We traveled in a small Cesna so there was no food or entertainment. The pilot was excellent enjoy being able to see the places we were flying above. It was an OK flight.

Very smooth flight and landing. Pilot delivered his safety instruction in such a monotone that it wasn’t easily understandable. Words were said but he didn't communicate to us. If he was communicating to someone he cared about, he would have used inflection and other nuances of speaking. Virtually all emphasis was removed so it was just blah blah blah (really fast, like the end of a Pharma commercial)

My pilot on Cape Air was AMAZING!!!! I hoping that next time I fly I have him as my pilot. He made me feel safe and secure in his skills.

I so appreciate this service into and out of Glendive. Always a good experience with crew and support team.

It was not what I had expected but it was a great way to see the landscape.

Pros: "ground crew, pilot, flight was smooth and gate connections to Jet Blue in Boston were fantastic!"
Cons: "leg room"
Pros: "The pilot was kind and to the point."
Cons: "The guy who boarded us told me to wait as his computer could not check me in. 10min later he is rushing me to get on the runway. It was 30min before scheduled take off. I had ordered food and had to cancel my order before the café had finished, so he wasted food and did not get paid and I was hurried and boarded the plane hungry. I probably won't use Cape Air again unless it's an emergency situation"
Cons: "Boarded half hour late. No explanation. Pretty standard on Cape Air these days"

Delay flight more than 8hours waiting and poor customer service!

Plane was extremely small so mind the size of your carry on

Other than lack of snacks, everything else went very well.

They don’t keep you updated on the flight status very well. It was late but nothing said

Pros: "Nothing!!! Horrible airline with horrible staff members."
Cons: "Everything. The staff and crew of Intercaribbean airlines are very unprofessional and not helpful at all. On top of the flight delays all the luggage for that particular flight was left in Kingston. Everybody was rather nonchalant and unapologetic about the situation. I was told I would get the the following day. The next day only two of my three bags showed up. I was not compensated for the inconvenience and was told point blank that they will only deliver one of my bags to my address even though they were the reason I had NONE of my luggage in the first place. They are disgusting!!! I would never recommend this airline to anyone."
Pros: "Nice people"
Cons: "A long walk to the D3 gate, but there were no amenities there I.e. snacks (to be fair a new terminal is under construction)"
Cons: "There was no air. I understand when you are on the ground it can be limited but even after getting to altitude there was no air conditioning."
Cons: "The flight was delayed for over three hours, apparently it is a regular occurence."
Pros: "almost nothing"
Cons: "The plane had a problem that forced us to turn around right after take off and as of this writing we still don’t know what’s going on or how long we are stuck here. Planes are old and apparently maintenance could be better."
Cons: "Was a bit difficult understanding the flight attendant, she had a thick Spanish accent"

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.

Our pilot and flight attendant, Desiree, were great. I always fly this route and this crew was better than most.

The worst flight ever; 1st and last flying to this airlines

Easy boarding and deplaning. Short flight. Water was given but that was it.

Flight was delayed a bit since booking but otherwise everything was very good.

While this is a VERY SMALL plane; take-off to landing was fine. It's the constant departure time changes that wore me out and I'll try to never use this inconsistent airway again. Four delays in one day. Done!!!!!!

This has been, by far, my worst experience with an airline company. I had a reservation for a Tuesday at 8:30 pm departure from Gainesville, FL (1.5 hours - direct flight) I received an email on Monday that my flight had been changed to Monday at night to depart from Jacksonville, FL (and it was an 11 .5 hours flight ). There was no way I would have had the time to gather my things, drive 1.5 hours to the Jacksonville airport, and make it on time to board the plane. Besides, I had a full day of work on Tuesday. The only good thing I xan say about Silver airlines is that they did give me a refund, but I had to wait about 4 hours for a call back

No comments, the complete handling and flying was excellent,keep up the good works.

Book cheap flights from Wisconsin to Caribbean

Recent round-trip flight deals

5/18Sat
1 stop
7h 28mMKE-SJU
5/22Wed
1 stop
7h 27mSJU-MKE
$173
5/18Sat
1 stop
7h 28mMKE-SJU
5/22Wed
1 stop
28h 57mSJU-MKE
$179
5/9Thu
1 stopFrontier
21h 09mMKE-SJU
5/15Wed
1 stopFrontier
29h 45mSJU-MKE
$186
5/11Sat
2 stopsAmerican Airlines
20h 37mMKE-STT
5/13Mon
2 stopsAmerican Airlines
21h 04mSTT-MKE
$223
5/9Thu
1 stopFrontier
15h 06mMKE-SJU
5/15Wed
1 stopFrontier
7h 27mSJU-MKE
$223
5/12Sun
2 stopsAmerican Airlines
10h 03mMKE-STT
5/14Tue
2 stopsAmerican Airlines
21h 04mSTT-MKE
$224
5/8Wed
1 stopJetBlue
8h 35mMKE-SJU
5/14Tue
1 stopJetBlue
8h 16mSJU-MKE
$333
5/4Sat
1 stopJetBlue
11h 13mMKE-SJU
5/7Tue
1 stopJetBlue
8h 16mSJU-MKE
$342
5/11Sat
2 stopsUnited Airlines
12h 25mMKE-SJU
5/14Tue
2 stopsUnited Airlines
11h 22mSJU-MKE
$465
5/4Sat
2 stopsUnited Airlines
11h 57mMKE-SJU
5/7Tue
1 stopUnited Airlines
8h 53mSJU-MKE
$469

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Recent one-way flight deals

5/19Sun
1 stopFrontier
16h 13mMKE-SJU
$84
5/18Sat
1 stopSpirit Airlines
7h 28mMKE-SJU
$99
5/11Sat
1 stopAmerican Airlines
9h 05mMKE-SJU
$125
5/11Sat
2 stopsAmerican Airlines
11h 03mMKE-SJU
$126
5/11Sat
2 stops
21h 55mMSN-SJU
$129
4/25Thu
1 stop
11h 15mMKE-SJU
$143
6/1Sat
1 stopJetBlue
10h 55mMKE-SJU
$167
6/18Tue
1 stopJetBlue
8h 56mMKE-SJU
$199
10/10Thu
2 stopsUnited Airlines
14h 20mMKE-SJU
$269
10/10Thu
3 stopsUnited Airlines
20h 44mMKE-SJU
$275

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Last minute flights from Wisconsin to Caribbean

Last minute flight, train and bus deals

4/21Sun
multi-stopSpirit Airlines
6h 35mMKE-STT
4/23Tue
multi-stopSpirit Airlines
11h 23mSTT-MKE
$440
4/22Mon
multi-stopSpirit Airlines
6h 46mMKE-STT
4/23Tue
multi-stopSpirit Airlines
11h 23mSTT-MKE
$448
4/22Mon
multi-stop
6h 46mMKE-STT
4/24Wed
multi-stop
20h 50mSTT-MKE
$479
4/22Mon
multi-stop
23h 19mMKE-PUJ
4/29Mon
multi-stop
11h 33mPUJ-MKE
$500
4/23Tue
multi-stopAmerican Airlines
10h 35mATW-SJU
4/30Tue
multi-stopAmerican Airlines
20h 30mSJU-ATW
$533
4/23Tue
multi-stopAmerican Airlines
23h 13mMKE-PUJ
4/29Mon
multi-stopAmerican Airlines
25h 43mPUJ-MKE
$567
4/23Tue
multi-stopUnited Airlines
7h 12mATW-SJU
4/29Mon
multi-stopUnited Airlines
11h 49mSJU-ATW
$669
4/23Tue
multi-stopDelta
6h 23mMKE-STT
4/28Sun
multi-stopDelta
11h 13mSTT-MKE
$688
4/20Sat
multi-stopDelta
7h 50mMKE-STT
4/26Fri
multi-stopDelta
11h 13mSTT-MKE
$768
4/23Tue
multi-stopUnited Airlines
9h 01mMKE-STT
4/24Wed
multi-stopUnited Airlines
10h 13mSTT-MKE
$791

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