Find flights
When to book
FAQs & Tips
Airlines
Deals

Find cheap flights from Caribbean to Wisconsin from $109

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 to Wisconsin departing on 5/29. 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
sön 6/9
sön 6/16

Search hundreds of travel sites at once for deals on flights to Wisconsin

In the last 7 days travelers have searched 43,895,468 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Good to know

Low season

April

High season

May

Cheapest flight

$109
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from San Juan to Milwaukee

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 to Wisconsin from Caribbean 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 to Wisconsin with an airline and back to Caribbean 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 to Wisconsin from Caribbean 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 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.
7.9
Caribbean AirlinesOverall score based on 186 reviews
7.6Comfort
8.2Boarding
8.3Crew
6.7Food
6.7Entertainment
Airline reviews

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

10.0 Excellentsusan, Apr 2024MIA - POS
Read more about Caribbean Airlines reviews

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

The captain was great he made jokes and make thebflight very comfortable. Alerted us about the islands we flew over and Yolandra and her team took great care of us, very personable.

Delayed departure. Delayed after landing pulling into gate. Delay due to sky bridge malfunction

Great. Loved that there was WiFi on flight to keep in touch and excellent service of beverages and snacks.

Flew business class. Everything was excellent. No issues at all. Not very many “good” movies to choose from. But lots of mediocre ones

Business class is great. New airplane, very comfortable, better than some of the major airlines I am used to

Terrible. Flight was cancelled due to the weather in the east and sout east(florida). Did not get any compesation of any kind. According to them, it was not under their control so I lost all the money paid for the 2 fairs from Raleigh, NC to Orlando, Fl.

great flight. Pilot was communicative, flight attendants were excellent. Really nice experience except my tv didn’t work.

The best experience that I have had traveling with JetBlue!

Overall, the flight was better than the flight I took to go to Florida, which had a bunch of problems. The crew is really nice and the plane was new so it had a small problem when we were on the runway, but the flight itself was great. They even made some time back up, which is always a good thing.

Crew was just ok. Flight was packed. On a 3/4 hour flight I would hope they would come around more than once to see if you needed anything further. Not very attentive.

There were multiple delays but JetBlue tried to make the boarding and departure process as quick and efficient as possible. The crew was as detached from reality as could be, meaning: not very friendly and just doing things by the numbers.

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

Book cheap flights from Caribbean to Wisconsin

Recent round-trip flight deals

6/7fre
2 stopsFrontier
17h 31mSJU-MKE
6/10mån
2 stopsFrontier
26h 32mMKE-SJU
$273
6/6tors
2 stopsFrontier
17h 22mSJU-MKE
6/11tis
1 stopFrontier
25h 40mMKE-SJU
$274
7/17ons
1 stopFrontier
10h 08mSJU-MKE
7/23tis
1 stopFrontier
12h 06mMKE-SJU
$290
7/18tors
1 stopSpirit Airlines
6h 56mSJU-MKE
7/23tis
1 stopSpirit Airlines
6h 51mMKE-SJU
$313
8/27tis
2 stopsAmerican Airlines
9h 42mSJU-MSN
9/7lör
2 stopsAmerican Airlines
17h 42mMSN-SJU
$333
8/27tis
2 stopsAmerican Airlines
11h 14mSJU-MSN
9/7lör
1 stopAmerican Airlines
9h 51mMSN-SJU
$334
6/7fre
1 stopUnited Airlines
7h 04mMBJ-MKE
6/14fre
2 stopsUnited Airlines
28h 25mMKE-MBJ
$436
6/7fre
1 stopUnited Airlines
8h 31mMBJ-MSN
6/14fre
2 stopsUnited Airlines
33h 06mMSN-MBJ
$464
6/9sön
1 stopJetBlue
8h 43mSJU-MKE
6/15lör
1 stopJetBlue
10h 07mMKE-SJU
$484
5/21tis
2 stopsAir Canada
27h 30mMBJ-MSN
9/1sön
2 stopsAir Canada
27h 25mMSN-MBJ
$1,475

Search by stops

Search by airline

Search by price

Recent one-way flight deals

5/29ons
1 stopFrontier
7h 27mSJU-MKE
$109
5/28tis
1 stopSpirit Airlines
17h 51mSJU-MKE
$115
5/29ons
2 stopsSpirit Airlines
28h 54mSJU-MKE
$122
5/21tis
1 stop
21h 51mSJU-MKE
$151
8/29tors
2 stopsAmerican Airlines
10h 55mSJU-MSN
$167
8/22tors
2 stopsAmerican Airlines
20h 16mSJU-MKE
$174
5/21tis
1 stop
8h 31mSJU-MSN
$190
5/21tis
2 stopsUnited Airlines
10h 12mSJU-MKE
$222
5/24fre
1 stopJetBlue
8h 33mSJU-MKE
$223
5/21tis
2 stopsUnited Airlines
11h 25mSJU-MSN
$277

Search by stops

Search by airline

Search by price

Last minute flights from Caribbean to Wisconsin

Last minute flight, train and bus deals

5/15ons
multi-stopAmerican Airlines
9h 07mMBJ-MKE
9/2mån
multi-stopAmerican Airlines
9h 40mMKE-MBJ
$409
5/15ons
multi-stopAmerican Airlines
9h 07mMBJ-MKE
9/2mån
multi-stopAmerican Airlines
18h 12mMKE-MBJ
$413
5/15ons
multi-stopAmerican Airlines
20h 26mMBJ-MKE
9/2mån
multi-stopAmerican Airlines
16h 58mMKE-MBJ
$440
5/13mån
multi-stopJetBlue
8h 16mSJU-MKE
5/15ons
multi-stopJetBlue
8h 35mMKE-SJU
$530
5/14tis
multi-stopUnited Airlines
10h 14mSJU-MKE
5/15ons
multi-stopUnited Airlines
8h 27mMKE-SJU
$579
5/13mån
multi-stopJetBlue
8h 16mSJU-MKE
5/15ons
multi-stopJetBlue
8h 35mMKE-SJU
$615
5/13mån
multi-stopAmerican Airlines
16h 52mSJU-MKE
5/15ons
multi-stopAmerican Airlines
11h 03mMKE-SJU
$618
5/14tis
multi-stopUnited Airlines
10h 44mSJU-MSN
5/18lör
multi-stopUnited Airlines
10h 55mMSN-SJU
$644
5/14tis
multi-stopDelta
11h 14mSJU-MSN
5/18lör
multi-stopDelta
14h 56mMSN-SJU
$684
5/15ons
multi-stop
32h 08mMBJ-MKE
9/2mån
multi-stop
25h 05mMKE-MBJ
$1,066

Search by stops

Search by airline

Search by price