$82 Find Cheap Flights from Wisconsin to Caribbean

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Useful Info
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Good to know

Low seasonSeptember
High seasonDecember
Cheapest flight$82
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 29% 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 $604.

  • 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 $610 (return) on average. On the other hand, the most expensive months are June and March, when the average cost of round-trip tickets is $792 and $786 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 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

  • How long is the flight to Caribbean?

    An average nonstop flight from Wisconsin to Caribbean takes 7h 22m, covering a distance of 2116 miles. The shortest route is Chicago O'Hare Intl Airport (ORD) to Nassau (NAS) with an average flight time of 3h 26m.

  • What are the most popular destinations in Caribbean?

    Based on KAYAK flight searches, the most popular destination is Punta Cana (26% of total searches to Caribbean). The next most popular destinations are Montego Bay (17%) and Oranjestad (10%). Searches for flights to Saint Thomas Island (6%), to Castries (6%) and to Nassau (5%) are also popular.

Book cheap flights from Wisconsin to Caribbean

Recent round-trip flight deals

5/25Sun
nonstopSpirit Airlines
4h 46mORD-SJU
5/29Thu
1 stopSpirit Airlines
13h 38mSJU-ORD
$184
6/1Sun
1 stopSpirit Airlines
10h 45mORD-SJU
6/6Fri
1 stopSpirit Airlines
13h 38mSJU-ORD
$186
5/17Sat
nonstopFrontier
4h 50mORD-PUJ
5/23Fri
nonstopFrontier
5h 03mPUJ-ORD
$223
5/10Sat
nonstopFrontier
4h 50mORD-PUJ
5/15Thu
nonstopFrontier
5h 06mPUJ-ORD
$224
9/16Tue
1 stopDelta
6h 23mMKE-SJU
9/23Tue
1 stopDelta
7h 06mSJU-MKE
$225
5/17Sat
1 stop
7h 19mORD-SJU
5/21Wed
1 stop
15h 22mSJU-ORD
$248
9/17Wed
1 stopUnited Airlines
6h 44mMKE-SJU
9/20Sat
2 stopsUnited Airlines
10h 08mSJU-MKE
$254
5/25Sun
1 stopDelta
8h 44mMKE-SJU
5/31Sat
1 stopDelta
7h 24mSJU-MKE
$266
5/17Sat
nonstop
4h 50mORD-PUJ
5/24Sat
1 stop
8h 21mPUJ-ORD
$271
5/24Sat
1 stopUnited Airlines
7h 24mMSP-SJU
5/31Sat
1 stopUnited Airlines
9h 45mSJU-MSP
$281

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Recent one-way flight deals

5/17Sat
1 stopSpirit Airlines
7h 19mORD-SJU
$82
6/3Tue
nonstopSpirit Airlines
4h 46mORD-SJU
$92
8/4Mon
nonstopFrontier
4h 40mORD-PUJ
$103
5/12Mon
nonstopFrontier
4h 41mORD-PUJ
$104
9/16Tue
1 stopDelta
6h 23mMKE-SJU
$113
8/9Sat
2 stopsAmerican Airlines
11h 45mMKE-SJU
$115
8/6Wed
nonstopUnited Airlines
4h 42mORD-PUJ
$116
8/5Tue
nonstopUnited Airlines
4h 42mORD-PUJ
$122
7/30Wed
1 stopAmerican Airlines
9h 35mORD-PUJ
$126
5/20Tue
1 stopDelta
8h 44mMKE-SJU
$154

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Last minute flights from Wisconsin to Caribbean

Last minute flight, train and bus deals

5/5Mon
nonstopFrontier
4h 41mORD-PUJ
5/8Thu
nonstopFrontier
5h 06mPUJ-ORD
$238
5/5Mon
nonstopFrontier
4h 41mORD-PUJ
5/16Fri
nonstopFrontier
5h 03mPUJ-ORD
$241
5/3Sat
nonstopSun Country Air
5h 11mMSP-SJU
5/10Sat
nonstopSun Country Air
6h 11mSJU-MSP
$291
5/4Sun
nonstop
4h 41mORD-PUJ
5/8Thu
multi-stop
11h 47mPUJ-ORD
$293
5/3Sat
nonstopSun Country Air
5h 11mMSP-SJU
5/10Sat
nonstopSun Country Air
6h 11mSJU-MSP
$296
5/5Mon
nonstop
4h 41mORD-PUJ
5/15Thu
multi-stop
9h 43mPUJ-ORD
$297
5/3Sat
multi-stopSpirit Airlines
8h 10mORD-SJU
5/10Sat
multi-stopSpirit Airlines
11h 49mSJU-ORD
$299
5/3Sat
nonstopSpirit Airlines
4h 41mORD-SJU
5/10Sat
multi-stopSpirit Airlines
11h 49mSJU-ORD
$304
5/3Sat
multi-stopAmerican Airlines
7h 00mORD-PUJ
5/30Fri
multi-stopAmerican Airlines
8h 31mPUJ-ORD
$315
5/3Sat
multi-stopAmerican Airlines
16h 47mORD-PUJ
5/7Wed
nonstopAmerican Airlines
5h 20mPUJ-ORD
$320

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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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