$65 Find Cheap Flights from Wisconsin to Caribbean Islands

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Useful Info

Good to know

Low seasonSeptember
High seasonDecember
Cheapest flight$65
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 Islands

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

    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 Islands.

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

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

    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 Islands 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 Islands?

    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 Islands 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 Islands?

    Based on KAYAK data, the cheapest day to fly to Caribbean Islands 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 Islands?

    The cheapest time of day to fly to Caribbean Islands 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 Islands 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 Islands?

    The cheapest ticket to Caribbean Islands 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 Islands?

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

    To get a below average price on the flight from Wisconsin to Caribbean Islands, 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 Islands?

    An average nonstop flight from Wisconsin to Caribbean Islands takes 6h 51m, covering a distance of 2135 miles. The shortest route is Chicago O'Hare Intl Airport (ORD) to Nassau (NAS) with an average flight time of 3h 25m.

  • What are the most popular destinations in Caribbean Islands?

    Based on KAYAK flight searches, the most popular destination is Punta Cana (23% of total searches to Caribbean Islands). The next most popular destinations are Montego Bay (17%) and Oranjestad (10%). Searches for flights to Saint Thomas Island (8%), to Providenciales (6%) and to Nassau (6%) are also popular.

Book cheap flights from Wisconsin to Caribbean Islands

Recent round-trip flight deals

8/11Mon
1 stopFrontier
8h 17mORD-SJU
8/14Thu
1 stopFrontier
10h 14mSJU-ORD
$143
8/12Tue
1 stopFrontier
29h 34mORD-SJU
8/15Fri
1 stopFrontier
7h 42mSJU-ORD
$148
10/2Thu
1 stopFrontier
8h 01mORD-SJU
10/5Sun
1 stopFrontier
9h 54mSJU-ORD
$153
8/1Fri
1 stop
8h 17mORD-SJU
8/6Wed
1 stop
15h 21mSJU-ORD
$176
8/1Fri
1 stop
8h 17mORD-SJU
8/6Wed
1 stop
8h 23mSJU-ORD
$179
7/12Sat
1 stopSpirit Airlines
14h 35mORD-SJU
7/18Fri
1 stopSpirit Airlines
16h 14mSJU-ORD
$228
8/1Fri
nonstopSpirit Airlines
4h 43mORD-SJU
8/5Tue
1 stopSpirit Airlines
15h 21mSJU-ORD
$232
12/7Sun
nonstopArajet
4h 45mORD-PUJ
12/16Tue
nonstopArajet
5h 10mPUJ-ORD
$244
8/7Thu
1 stopAmerican Airlines
15h 31mORD-PUJ
8/14Thu
nonstopAmerican Airlines
5h 00mPUJ-ORD
$275
8/7Thu
1 stopAmerican Airlines
15h 31mORD-PUJ
8/14Thu
1 stopAmerican Airlines
12h 43mPUJ-ORD
$285

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Recent one-way flight deals

8/11Mon
1 stopFrontier
8h 17mORD-SJU
$65
8/13Wed
1 stopFrontier
14h 11mORD-SJU
$70
7/12Sat
1 stopSpirit Airlines
14h 35mORD-SJU
$97
7/29Tue
1 stopSpirit Airlines
6h 00mORD-MBJ
$104
8/12Tue
1 stop
8h 44mORD-SJU
$114
11/16Sun
nonstopArajet
4h 45mORD-PUJ
$116
7/15Tue
1 stop
9h 22mORD-SJU
$120
8/9Sat
nonstopUnited Airlines
4h 42mORD-PUJ
$126
11/15Sat
nonstopArajet
4h 45mORD-PUJ
$137
8/4Mon
nonstopUnited Airlines
4h 42mORD-PUJ
$147

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Last minute flights from Wisconsin to Caribbean Islands

Last minute flight, train and bus deals

7/5Sat
multi-stopFrontier
11h 07mORD-SJU
7/25Fri
multi-stopFrontier
10h 14mSJU-ORD
$256
7/4Fri
multi-stopFrontier
13h 30mORD-SJU
7/12Sat
multi-stopFrontier
22h 16mSJU-ORD
$259
7/5Sat
multi-stop
11h 07mORD-SJU
7/10Thu
multi-stop
11h 41mSJU-ORD
$266
7/4Fri
multi-stop
15h 37mORD-SJU
7/10Thu
multi-stop
11h 41mSJU-ORD
$269
7/5Sat
nonstopSpirit Airlines
4h 44mORD-SJU
7/12Sat
nonstopSpirit Airlines
5h 16mSJU-ORD
$284
7/5Sat
nonstopSun Country Air
5h 16mMSP-SJU
7/26Sat
nonstopSun Country Air
5h 37mSJU-MSP
$344
7/1Tue
multi-stopAmerican Airlines
6h 25mORD-PUJ
7/15Tue
nonstopAmerican Airlines
5h 05mPUJ-ORD
$349
7/4Fri
multi-stopAmerican Airlines
20h 19mORD-PUJ
7/9Wed
multi-stopAmerican Airlines
8h 07mPUJ-ORD
$357
7/3Thu
multi-stopSpirit Airlines
25h 37mMSP-SJU
7/24Thu
multi-stopSpirit Airlines
11h 39mSJU-MSP
$374
7/5Sat
nonstopSun Country Air
5h 16mMSP-SJU
7/19Sat
nonstopSun Country Air
5h 37mSJU-MSP
$380

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Everything you need to know for your flight to Caribbean Islands

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.
First Class flights to Caribbean Islandsfrom $244
Business Class flights to Caribbean Islandsfrom $287
Prem Econ Class flights to Caribbean Islandsfrom $218
Economy Class flights to Caribbean Islandsfrom $30

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