$93 Find Cheap Flights from Wisconsin to Caribbean Islands

1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 20% or moreCompare multiple travel sites with one search.

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

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

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

Useful Info
Useful Info

Good to know

Low seasonSeptember
High seasonDecember
Cheapest flight$93
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 $764.

  • 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 $626 (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 $797 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 30m, covering a distance of 2153 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 (22% of total searches to Caribbean Islands). The next most popular destinations are Montego Bay (15%) and Oranjestad (11%). Searches for flights to Castries (10%), to Saint Thomas Island (7%) and to Nassau (5%) are also popular.

Book cheap flights from Wisconsin to Caribbean Islands

Recent round-trip flight deals

8/30Sat
1 stopFrontier
12h 13mORD-SJU
9/5Fri
1 stopFrontier
12h 13mSJU-ORD
$185
9/13Sat
1 stopFrontier
14h 54mORD-SJU
9/18Thu
1 stopFrontier
11h 41mSJU-ORD
$194
7/8Tue
1 stopSpirit Airlines
12h 22mORD-SJU
7/15Tue
1 stopSpirit Airlines
15h 21mSJU-ORD
$207
7/8Tue
1 stopSpirit Airlines
12h 22mORD-SJU
7/15Tue
1 stopSpirit Airlines
15h 21mSJU-ORD
$214
7/12Sat
1 stop
11h 07mORD-SJU
7/22Tue
1 stop
15h 21mSJU-ORD
$220
9/16Tue
1 stopDelta
9h 08mMKE-SJU
9/23Tue
1 stopDelta
7h 06mSJU-MKE
$225
9/13Sat
1 stop
14h 54mORD-SJU
9/21Sun
nonstop
4h 58mSJU-ORD
$232
12/2Tue
nonstopArajet
4h 45mORD-PUJ
12/7Sun
nonstopArajet
5h 10mPUJ-ORD
$238
12/2Tue
nonstopArajet
4h 45mORD-PUJ
12/7Sun
nonstopArajet
5h 10mPUJ-ORD
$239
8/31Sun
1 stopDelta
9h 20mMKE-SJU
9/5Fri
1 stopDelta
6h 50mSJU-MKE
$302

Search by stops

Search by airline

Search by price

Recent one-way flight deals

8/23Sat
1 stopFrontier
12h 13mORD-SJU
$93
8/12Tue
1 stopSpirit Airlines
9h 25mORD-SJU
$96
9/16Tue
1 stopDelta
8h 08mMKE-SJU
$113
9/23Tue
2 stopsAmerican Airlines
18h 00mMKE-SJU
$115
9/23Tue
2 stopsAmerican Airlines
19h 08mMKE-SJU
$116
7/15Tue
nonstopUnited Airlines
4h 42mORD-PUJ
$126
10/19Sun
1 stopUnited Airlines
7h 44mMKE-SJU
$134
7/4Fri
1 stop
27h 03mMSP-SJU
$145
6/28Sat
1 stop
25h 49mMSP-SJU
$149
9/15Mon
1 stopDelta
5h 48mORD-MBJ
$152

Search by stops

Search by airline

Search by price

Last minute flights from Wisconsin to Caribbean Islands

Last minute flight, train and bus deals

6/17Tue
multi-stopFrontier
14h 07mORD-SJU
6/24Tue
multi-stopFrontier
28h 29mSJU-ORD
$226
6/17Tue
multi-stopFrontier
14h 07mORD-SJU
6/30Mon
multi-stopFrontier
29h 37mSJU-ORD
$229
6/13Fri
multi-stop
12h 08mORD-SJU
6/27Fri
multi-stop
13h 26mSJU-ORD
$231
6/17Tue
multi-stop
14h 07mORD-SJU
7/1Tue
multi-stop
13h 26mSJU-ORD
$254
6/17Tue
nonstopSpirit Airlines
4h 44mORD-SJU
6/26Thu
multi-stopSpirit Airlines
13h 26mSJU-ORD
$300
6/17Tue
multi-stopSpirit Airlines
16h 35mORD-SJU
6/24Tue
multi-stopSpirit Airlines
13h 26mSJU-ORD
$317
6/14Sat
nonstopAmerican Airlines
4h 35mORD-PUJ
6/16Mon
multi-stopAmerican Airlines
10h 15mPUJ-ORD
$350
6/14Sat
multi-stopAmerican Airlines
7h 55mORD-PUJ
6/16Mon
multi-stopAmerican Airlines
12h 47mPUJ-ORD
$355
6/14Sat
multi-stopUnited Airlines
7h 09mMKE-SJU
6/15Sun
multi-stopUnited Airlines
7h 53mSJU-MKE
$379
6/14Sat
multi-stopUnited Airlines
7h 09mMKE-SJU
7/8Tue
multi-stopUnited Airlines
11h 25mSJU-MKE
$392

Search by stops

Search by airline

Search by price

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

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.