How many flights depart from Wisconsin to Caribbean on average per day?

17 flights are operational daily from Wisconsin to Caribbean as of March 2026. The most popular departure time for this route is 8:00AM, with 100% of flights per day taking off at noon.

How long is the flight from Wisconsin to Caribbean?

If you’re flying from a popular airport in Wisconsin, such as Milwaukee or Madison, and flying into Caribbean, then you can expect flight times to average 12h 04m and 19h 50m, respectively.

What is the cheapest airline that flies from Wisconsin to Caribbean?

Sun Country Air, Delta, and United Airlines are the most popular carriers operating from Wisconsin to Caribbean

What airlines fly to Caribbean?

American Airlines, Delta and United Airlines are the top three most popular airlines that fly to Caribbean from Wisconsin according to our data. American Airlines is the first choice among our users, with 50% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 7 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

How many flights depart from Wisconsin to Caribbean on average per week?

As of March 2026, 124 flights take off from Wisconsin and land in Caribbean each week. The most common flight departure day for this route is Mon, with 20% of weekly flights taking off on this day.

When did momondo last update prices for flights from Wisconsin to Caribbean?

Prices for flights from Wisconsin to Caribbean were last updated today.

How many operators does momondo search for flights from Wisconsin to Caribbean?

As of March 2026, there are 12 operators available to choose from for flights from Wisconsin to Caribbean.

How old do you have to be to fly from Wisconsin to Caribbean?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Wisconsin to Caribbean.

What documentation or ID do you need to fly to Caribbean?

The necessary travel and health documents for your Caribbean trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$95 Cheap Flights from Wisconsin to Caribbean in 2026

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Find the cheapest flights from Wisconsin to Caribbean

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:50 am - 2:06 am

ORD

SJU

17h 16m

1 stop

12:57 pm - 12:24 am

SJU

ORD

12h 27m

1 stop

$188Spirit Airlines

Mon, May 4 - Fri, May 8

5:05 am - 7:22 pm

ORD

SJU

13h 17m

1 stop

3:21 am - 1:05 pm

SJU

ORD

10h 44m

1 stop

$189Spirit Airlines

Mon, May 11 - Sun, May 17

12:59 am - 6:56 am

ORD

SJU

4h 57mnonstop

8:10 pm - 12:25 am

SJU

ORD

5h 15mnonstop

$190Frontier

Mon, Aug 10 - Tue, Aug 18

5:01 am - 2:01 am

ORD

SJU

20h 00m

2 stops

8:10 pm - 12:25 am

SJU

ORD

5h 15mnonstop

$195Frontier

Wed, May 20 - Thu, Jun 4

12:59 am - 6:56 am

ORD

SJU

4h 57mnonstop

4:54 pm - 9:04 pm

SJU

ORD

5h 10mnonstop

$196Multiple Airlines

Tue, Aug 11 - Wed, Aug 19

7:15 pm - 12:33 pm

ORD

SJU

16h 18m

1 stop

11:30 am - 11:59 pm

SJU

ORD

13h 29m

1 stop

$197Multiple Airlines

Sun, Apr 19 - Sat, Apr 25

3:35 pm - 11:40 pm

MKE

SJU

7h 05m

1 stop

2:00 pm - 10:35 pm

SJU

MKE

9h 35m

2 stops

$277Southwest

Sat, May 9 - Wed, May 13

3:35 pm - 11:40 pm

MKE

SJU

7h 05m

1 stop

6:25 am - 7:25 pm

SJU

MKE

14h 00m

1 stop

$283Southwest

Sat, May 2 - Sat, May 9

5:06 am - 3:35 pm

MKE

SJU

9h 29m

2 stops

7:25 am - 5:51 pm

SJU

MKE

11h 26m

1 stop

$286American Airlines

Sat, Apr 25 - Fri, May 1

8:05 am - 12:13 pm

ORD

MBJ

4h 08mnonstop

12:25 pm - 8:30 am

MBJ

ORD

20h 05m

1 stop

$294American Airlines

Wed, Apr 29 - Mon, May 4

Frontier flights from Wisconsin to Caribbean

Our best Frontier deals on Wisconsin to Caribbean flight tickets

Frontier

Aug 10

ORD12:59 amChicago O'Hare Intl

4h 57m

SJU6:56 amSan Juan Luis Munoz Marin Intl

Aug 18

SJU8:10 pmSan Juan Luis Munoz Marin Intl

5h 15m

ORD12:25 amChicago O'Hare Intl

$190

Frontier

May 20

ORD5:01 amChicago O'Hare Intl

20h 00m

2 stops

SJU2:01 amSan Juan Luis Munoz Marin Intl

Jun 4

SJU8:10 pmSan Juan Luis Munoz Marin Intl

5h 15m

ORD12:25 amChicago O'Hare Intl

$195

Frontier

Aug 24

ORD12:59 amChicago O'Hare Intl

4h 57m

SJU6:56 amSan Juan Luis Munoz Marin Intl

Sep 3

SJU8:10 pmSan Juan Luis Munoz Marin Intl

5h 15m

ORD12:25 amChicago O'Hare Intl

$197

Delta flights from Wisconsin to Caribbean

Our best Delta deals on Wisconsin to Caribbean flight tickets

Delta

Apr 11

MKE5:45 amMilwaukee-Mitchell

9h 33m

1 stop

SJU4:18 pmSan Juan Luis Munoz Marin Intl

Apr 22

SJU12:55 pmSan Juan Luis Munoz Marin Intl

12h 02m

1 stop

MKE11:57 pmMilwaukee-Mitchell

$302

Delta

Apr 1

MKE10:09 amMilwaukee-Mitchell

9h 09m

1 stop

SJU8:18 pmSan Juan Luis Munoz Marin Intl

May 1

SJU6:15 amSan Juan Luis Munoz Marin Intl

10h 03m

1 stop

MKE3:18 pmMilwaukee-Mitchell

$317

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 5/4

7:50 am-2:06 am

1 stop17h 16m

San Juan Luis Munoz Marin Intl

Fri 5/8

12:57 pm-12:24 am

1 stop12h 27m

$188

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 5/11

5:05 am-7:22 pm

1 stop13h 17m

San Juan Luis Munoz Marin Intl

Sun 5/17

3:21 am-1:05 pm

1 stop10h 44m

$189

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 8/10

12:59 am-6:56 am

Nonstop4h 57m

San Juan Luis Munoz Marin Intl

Tue 8/18

8:10 pm-12:25 am

Nonstop5h 15m

$190

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 5/20

5:01 am-2:01 am

2 stops20h 00m

San Juan Luis Munoz Marin Intl

Thu 6/4

8:10 pm-12:25 am

Nonstop5h 15m

$195

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/11

12:59 am-6:56 am

Nonstop4h 57m

San Juan Luis Munoz Marin Intl

Wed 8/19

4:54 pm-9:04 pm

Nonstop5h 10m

$196

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 4/19

7:15 pm-12:33 pm

1 stop16h 18m

San Juan Luis Munoz Marin Intl

Sat 4/25

11:30 am-11:59 pm

1 stop13h 29m

$197

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 5/9

3:35 pm-11:40 pm

1 stop7h 05m

San Juan Luis Munoz Marin Intl

Wed 5/13

2:00 pm-10:35 pm

2 stops9h 35m

$277

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 5/2

3:35 pm-11:40 pm

1 stop7h 05m

San Juan Luis Munoz Marin Intl

Sat 5/9

6:25 am-7:25 pm

1 stop14h 00m

$283

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 4/25

5:06 am-3:35 pm

2 stops9h 29m

San Juan Luis Munoz Marin Intl

Fri 5/1

7:25 am-5:51 pm

1 stop11h 26m

$286

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 4/29

8:05 am-12:13 pm

Nonstop4h 08m

Montego Bay Sangster Intl

Mon 5/4

12:25 pm-8:30 am

1 stop20h 05m

$294

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Wisconsin to Caribbean

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Caribbean?

In general, September is the cheapest month to fly from Wisconsin to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $315. If you don’t want to visit Caribbean in September, then you should wait until October to fly from Wisconsin, when ticket prices are also cheap, with an average price of $317.

What is the cheapest Wisconsin to Caribbean flight route?

Fly from Milwaukee-Mitchell to Punta Cana for the best Wisconsin - Caribbean flight prices

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

You are more likely to see cheaper flights to Caribbean from Wisconsin when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around $445 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from Wisconsin for as low as $383 on momondo.

What cabin class options are available on Wisconsin to Caribbean flights?

There is only 1 cabin class available to choose from on Wisconsin to Caribbean flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Wisconsin to Caribbean flights?

You could potentially save up to 63% on your flight if you consider stops on a Wisconsin to Caribbean flight.

Cheap Wisconsin to Caribbean flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Wisconsin to Caribbean

Best Price Found	$488
Fastest flight time	3h 25m
Direct flights	Every day
Airports in Caribbean	195 airports

The best flight deal from Wisconsin to Caribbean found on momondo in the last 72 hours is $488

The fastest flight from Wisconsin to Caribbean takes 3h 25m

Direct flights go from Wisconsin to Caribbean every day.

There are 195 airports in Caribbean. From Wisconsin there are direct flights to Nassau Intl (NAS).

Search flight deals

When did momondo last update prices for flights from Wisconsin to Caribbean?
Prices for flights from Wisconsin to Caribbean were last updated today.
How many operators does momondo search for flights from Wisconsin to Caribbean?
As of March 2026, there are 12 operators available to choose from for flights from Wisconsin to Caribbean.
How old do you have to be to fly from Wisconsin to Caribbean?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Wisconsin to Caribbean.
What documentation or ID do you need to fly to Caribbean?
The necessary travel and health documents for your Caribbean trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Wisconsin to Caribbean?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Wisconsin to Caribbean is Boeing 737-800 (73.77% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (6.56%), Boeing 737 MAX 9 (6.56%), and Boeing 737 (4.92%).

Best airlines flying from Wisconsin to Caribbean

Compare and see reviews for airlines that fly from Wisconsin to Caribbean with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $101	Free Cancellation	Rating 5.7 3,041 reviews	Search Frontier flights
Delta	PriceFrom $112	Free Cancellation	Rating 7.9 8,245 reviews	Search Delta flights
United Airlines	PriceFrom $158	Free Cancellation	Rating 7.4 9,382 reviews	Search United Airlines flights
Spirit Airlines	PriceFrom $208	Free Cancellation	Rating 6.3 8,490 reviews	Search Spirit Airlines flights
American Airlines	PriceFrom $215	Free Cancellation	Rating 7.1 11,378 reviews	Search American Airlines flights
Southwest	PriceFrom $315	Free Cancellation	Rating 8.0 4,304 reviews	Search Southwest flights
Sun Country Air	PriceFrom $497	Free Cancellation	Rating 6.8 339 reviews	Search Sun Country Air flights

Why use momondo?

Why should I use momondo to find a flight deal from Wisconsin to Caribbean?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Wisconsin to Caribbean for you.

Can I find flights from Wisconsin to Caribbean with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Wisconsin to Caribbean flights to just show those with flexible booking policies.

How can momondo help me find flights from Wisconsin to Caribbean?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Caribbean from Wisconsin.

I’m not ready to book a flight from Wisconsin to Caribbean right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Wisconsin to Caribbean flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Complete your trip

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Popular cities in Caribbean

Flights to San Juanfrom $89

Flights to Punta Canafrom $214

Flights to Santo Domingofrom $199

Flights to Montego Bayfrom $223

Flights to Oranjestadfrom $213

Flights to Nassaufrom $258

Flights to Santiago de los Caballerosfrom $240

Flights to Saint Thomas Islandfrom $132

Flights to Kingstonfrom $278

Flights to Simpson Bayfrom $245

Flights to Willemstadfrom $226

Flights to Port of Spainfrom $280

Cheap flights from Wisconsin to Caribbean from $95

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Wisconsin to Caribbean departing on 4/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Big names and deals

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Filter for what you want

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Frontier flights from Wisconsin to Caribbean

Our best Frontier deals on Wisconsin to Caribbean flight tickets

Delta flights from Wisconsin to Caribbean

Our best Delta deals on Wisconsin to Caribbean flight tickets

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Use the filters below to find and compare flights from Wisconsin to Caribbean that are best for you.

How to get the cheapest flight ticket from Wisconsin to Caribbean

What is the cheapest month to fly to Caribbean?

What is the cheapest Wisconsin to Caribbean flight route?

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

What cabin class options are available on Wisconsin to Caribbean flights?

Can stopping save me money on Wisconsin to Caribbean flights?

What is the cheapest airline that flies from Wisconsin to Caribbean?

What airlines fly to Caribbean?

How many flights depart from Wisconsin to Caribbean on average per day?

How many flights depart from Wisconsin to Caribbean on average per week?

How long is the flight from Wisconsin to Caribbean?

Cheap Wisconsin to Caribbean flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Wisconsin to Caribbean

Best Price Found

Fastest flight time

Direct flights

Airports in Caribbean

Best airlines flying from Wisconsin to Caribbean

Compare and see reviews for airlines that fly from Wisconsin to Caribbean with momondo

Why use momondo?

An easier way to manage your Caribbean trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Caribbean

Popular cities in Caribbean

Popular flights according to clicks in the last 7 days on momondo

Wisconsin flight routes

According to popular flight searches on momondo this year

Caribbean flight routes

According to popular flight searches on momondo this year

Fly your favorite airline to Caribbean

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Caribbean

List of cabin classes available on flights landing in Caribbean. Availability may vary depending on flight origin and airline.

Complete your trip to Caribbean

Explore popular destinations other users love

According to popular flight searches on momondo this year