$88 Find Cheap Flights from Wisconsin to Caribbean

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Useful Info

Good to know

Low seasonSeptember
High seasonDecember
Cheapest flight$88
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 28% increase in price.
Flight from Chicago O'Hare Airport 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 from Wisconsin to 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 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 from Wisconsin to Caribbean 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 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 from Wisconsin to Caribbean 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 Caribbean?

    Based on KAYAK data, the cheapest day to fly to Caribbean is Tuesday where round-trip tickets can be as cheap as $389. On the other hand, the most expensive day to fly is Friday, where round-trip prices are $477 on average.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $360 on average. Morning departures are around 13% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $458.

  • What is the cheapest flight to Caribbean?

    The cheapest ticket to Caribbean from Wisconsin found in the last 72 hours was to Montego Bay, at $540 round-trip. The most popular route is Milwaukee (MKE) to Punta Cana (PUJ) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $574.

  • What is the cheapest month to fly from Wisconsin to Caribbean?

    The cheapest month for flights from Wisconsin to Caribbean is August, when tickets cost $623 (return) on average. On the other hand, the most expensive months are March and June, when the average cost of round-trip tickets is $825 and $791 respectively.

  • How far in advance should I book a flight from Wisconsin to Caribbean?

    To get a below average price on the flight from Wisconsin to Caribbean, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

  • How long is the flight to Caribbean?

    An average nonstop flight from Wisconsin to Caribbean takes 6h 23m, covering a distance of 2147 miles. The shortest route is Chicago O'Hare Intl Airport (ORD) to Nassau (NAS) with an average flight time of 3h 18m.

  • What are the most popular destinations in Caribbean?

    Based on KAYAK flight searches, the most popular destination is Punta Cana (18% of total searches to Caribbean). The next most popular destinations are Montego Bay (13%) and Saint Thomas Island (11%). Searches for flights to Oranjestad (10%), to Nassau (7%) and to Providenciales (6%) are also popular.

Book cheap flights from Wisconsin to Caribbean

Recent round-trip flight deals

9/16Tue
1 stopSouthwest
6h 45mMKE-SJU
9/23Tue
1 stopSouthwest
7h 45mSJU-MKE
$175
8/5Tue
1 stopSpirit Airlines
7h 59mORD-SJU
8/6Wed
1 stopSpirit Airlines
15h 21mSJU-ORD
$188
8/26Tue
1 stopDelta
7h 57mMKE-SJU
9/5Fri
1 stopDelta
6h 50mSJU-MKE
$215
8/30Sat
1 stopDelta
9h 20mMKE-SJU
9/5Fri
1 stopDelta
11h 46mSJU-MKE
$220
10/1Wed
nonstopUnited Airlines
4h 52mORD-SJU
10/5Sun
nonstopUnited Airlines
5h 07mSJU-ORD
$224
9/17Wed
nonstopUnited Airlines
4h 52mORD-SJU
9/24Wed
1 stopUnited Airlines
9h 31mSJU-ORD
$229
8/2Sat
1 stop
10h 21mORD-SJU
8/6Wed
1 stop
15h 21mSJU-ORD
$238
9/21Sun
1 stopAmerican Airlines
6h 53mMKE-SJU
9/24Wed
2 stopsAmerican Airlines
18h 21mSJU-MKE
$240
7/30Wed
1 stop
14h 11mORD-SJU
8/5Tue
1 stop
15h 21mSJU-ORD
$240
9/1Mon
1 stopAmerican Airlines
14h 46mMKE-SJU
9/6Sat
2 stopsAmerican Airlines
18h 47mSJU-MKE
$250

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Recent one-way flight deals

8/5Tue
1 stopSpirit Airlines
7h 59mORD-SJU
$88
9/16Tue
1 stopAmerican Airlines
6h 52mMKE-SJU
$88
8/1Fri
1 stopFrontier
12h 31mORD-SJU
$106
9/23Tue
1 stopDelta
9h 51mMKE-SJU
$108
8/8Fri
1 stopFrontier
7h 58mORD-SJU
$109
8/17Sun
nonstopUnited Airlines
4h 55mORD-SJU
$112
8/1Fri
1 stopSouthwest
12h 00mMKE-SJU
$113
9/18Thu
1 stopDelta
8h 20mORD-SJU
$117
9/14Sun
1 stopUnited Airlines
7h 44mMKE-SJU
$133
8/3Sun
1 stopSouthwest
11h 00mMKE-SJU
$158

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Last minute flights from Wisconsin to Caribbean

Last minute flight, train and bus deals

7/15Tue
multi-stopSpirit Airlines
7h 59mORD-SJU
8/2Sat
nonstopSpirit Airlines
5h 19mSJU-ORD
$236
7/15Tue
multi-stopSpirit Airlines
7h 59mORD-SJU
8/2Sat
multi-stopSpirit Airlines
15h 34mSJU-ORD
$245
7/11Fri
multi-stop
7h 58mORD-SJU
7/17Thu
multi-stop
11h 41mSJU-ORD
$262
7/15Tue
multi-stop
29h 34mORD-SJU
8/2Sat
nonstop
5h 16mSJU-ORD
$263
7/11Fri
multi-stopFrontier
7h 58mORD-SJU
7/18Fri
multi-stopFrontier
7h 42mSJU-ORD
$286
7/12Sat
multi-stopFrontier
10h 21mORD-SJU
7/15Tue
multi-stopFrontier
7h 34mSJU-ORD
$288
7/13Sun
multi-stopAmerican Airlines
15h 50mMKE-SJU
7/19Sat
multi-stopAmerican Airlines
9h 19mSJU-MKE
$379
7/11Fri
multi-stopAmerican Airlines
11h 05mMKE-SJU
7/13Sun
multi-stopAmerican Airlines
13h 53mSJU-MKE
$387
7/11Fri
multi-stopUnited Airlines
7h 09mMKE-SJU
7/12Sat
multi-stopUnited Airlines
9h 07mSJU-MKE
$397
7/11Fri
multi-stopUnited Airlines
10h 59mMKE-SJU
7/12Sat
multi-stopUnited Airlines
9h 07mSJU-MKE
$453

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Everything you need to know for your flight to Caribbean

Cabin class types available on flights to Wisconsin

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

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