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 54% 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 July 2025, 83 flights take off from Wisconsin and land in Caribbean each week. The most common flight departure day for this route is Thu, with 16% of weekly flights taking off on this day.

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

Spirit Airlines, Arajet, and American Airlines are the most popular carriers operating from Wisconsin to Caribbean

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 16h 47m and 17h 46m, respectively.

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 July 2025, there are 11 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.

$91 Cheap Flights from Wisconsin to Caribbean in 2025

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Wisconsin to Caribbean

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

6:23 pm - 12:06 amORD-SJU

4h 43mnonstop

10:16 pm - 9:22 amSJU-ORD

12h 06m1 stop

$189Spirit Airlines

Find Deal

lun., août 11 - ven., août 15

12:55 pm - 6:34 pmORD-SJU

4h 39mnonstop

7:40 pm - 11:56 pmSJU-ORD

5h 16mnonstop

$190Spirit Airlines

Find Deal

jeu., sept. 18 - jeu., sept. 25

11:28 am - 2:39 amORD-SJU

14h 11m1 stop

10:16 pm - 9:22 amSJU-ORD

12h 06m1 stop

$214

Find Deal

mar., août 12 - ven., août 15

3:00 pm - 10:45 pmMKE-SJU

6h 45m1 stop

3:05 pm - 9:50 pmSJU-MKE

7h 45m1 stop

$215Southwest

Find Deal

mar., sept. 16 - mar., sept. 23

6:56 am - 11:57 pmORD-SJU

16h 01m1 stop

3:55 am - 6:41 pmSJU-ORD

15h 46m1 stop

$218

Find Deal

sam., août 16 - ven., août 22

6:23 pm - 12:47 pmMKE-SJU

17h 24m2 stops

4:45 pm - 10:04 amSJU-MKE

18h 19m2 stops

$220American Airlines

Find Deal

dim., sept. 21 - sam., sept. 27

7:00 am - 4:51 pmMKE-SJU

7h 51m1 stop

2:12 pm - 8:12 pmSJU-MKE

8h 00m1 stop

$225Delta

Find Deal

mer., janv. 21 - jeu., janv. 29

1:20 pm - 11:05 pmMKE-SJU

8h 45m1 stop

7:10 am - 12:11 amSJU-MKE

18h 01m1 stop

$240American Airlines

Find Deal

sam., oct. 11 - jeu., oct. 16

3:00 pm - 10:45 pmMKE-SJU

6h 45m1 stop

1:35 pm - 10:05 pmSJU-MKE

9h 30m2 stops

$265Southwest

Find Deal

mar., sept. 16 - mar., sept. 23

7:00 am - 5:10 pmMKE-SJU

8h 10m1 stop

2:26 pm - 8:07 pmSJU-MKE

7h 41m1 stop

$293Delta

Find Deal

mar., nov. 11 - jeu., nov. 27

Southwest flights from Wisconsin to Caribbean

Our best Southwest deals on Wisconsin to Caribbean flight tickets

Southwest

Sep 16

MKE3:00 pmMilwaukee-Mitchell

6h 45m

1 stop

SJU10:45 pmSan Juan Luis Munoz Marin Intl

Sep 23

SJU3:05 pmSan Juan Luis Munoz Marin Intl

7h 45m

1 stop

MKE9:50 pmMilwaukee-Mitchell

$215

Find similar

Southwest

Sep 16

MKE3:00 pmMilwaukee-Mitchell

6h 45m

1 stop

SJU10:45 pmSan Juan Luis Munoz Marin Intl

Sep 23

SJU1:35 pmSan Juan Luis Munoz Marin Intl

9h 30m

2 stops

MKE10:05 pmMilwaukee-Mitchell

$265

Find similar

Southwest

Nov 17

ORD6:05 amChicago O'Hare Intl

5h 10m

1 stop

NAS12:15 pmNassau Intl

Nov 21

NAS1:10 pmNassau Intl

9h 40m

1 stop

ORD9:50 pmChicago O'Hare Intl

$447

Find similar

Frontier flights from Wisconsin to Caribbean

Our best Frontier deals on Wisconsin to Caribbean flight tickets

Frontier

Aug 30

ORD7:46 pmChicago O'Hare Intl

12h 13m

1 stop

SJU8:59 amSan Juan Luis Munoz Marin Intl

Sep 5

SJU3:39 amSan Juan Luis Munoz Marin Intl

12h 38m

1 stop

ORD3:17 pmChicago O'Hare Intl

$238

Find similar

Frontier

Aug 30

ORD7:46 pmChicago O'Hare Intl

12h 13m

1 stop

SJU8:59 amSan Juan Luis Munoz Marin Intl

Sep 6

SJU4:42 pmSan Juan Luis Munoz Marin Intl

28h 02m

1 stop

ORD7:44 pmChicago O'Hare Intl

$239

Find similar

Frontier

Aug 9

ORD9:08 amChicago O'Hare Intl

22h 56m

1 stop

SJU9:04 amSan Juan Luis Munoz Marin Intl

Aug 16

SJU12:08 pmSan Juan Luis Munoz Marin Intl

28h 45m

1 stop

ORD3:53 pmChicago O'Hare Intl

$247

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

lun. 8/11

6:23 pm-12:06 am

Nonstop4h 43m

San Juan Luis Munoz Marin Intl

ven. 8/15

10:16 pm-9:22 am

1 stop12h 06m

$189

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

jeu. 9/18

12:55 pm-6:34 pm

Nonstop4h 39m

San Juan Luis Munoz Marin Intl

jeu. 9/25

7:40 pm-11:56 pm

Nonstop5h 16m

$190

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 8/12

11:28 am-2:39 am

1 stop14h 11m

San Juan Luis Munoz Marin Intl

ven. 8/15

10:16 pm-9:22 am

1 stop12h 06m

$214

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

mar. 9/16

3:00 pm-10:45 pm

1 stop6h 45m

San Juan Luis Munoz Marin Intl

mar. 9/23

3:05 pm-9:50 pm

1 stop7h 45m

$215

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sam. 8/16

6:56 am-11:57 pm

1 stop16h 01m

San Juan Luis Munoz Marin Intl

ven. 8/22

3:55 am-6:41 pm

1 stop15h 46m

$218

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

dim. 9/21

6:23 pm-12:47 pm

2 stops17h 24m

San Juan Luis Munoz Marin Intl

sam. 9/27

4:45 pm-10:04 am

2 stops18h 19m

$220

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

mer. 1/21

7:00 am-4:51 pm

1 stop7h 51m

San Juan Luis Munoz Marin Intl

jeu. 1/29

2:12 pm-8:12 pm

1 stop8h 00m

$225

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

sam. 10/11

1:20 pm-11:05 pm

1 stop8h 45m

San Juan Luis Munoz Marin Intl

jeu. 10/16

7:10 am-12:11 am

1 stop18h 01m

$240

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

mar. 9/16

3:00 pm-10:45 pm

1 stop6h 45m

San Juan Luis Munoz Marin Intl

mar. 9/23

1:35 pm-10:05 pm

2 stops9h 30m

$265

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

mar. 11/11

7:00 am-5:10 pm

1 stop8h 10m

San Juan Luis Munoz Marin Intl

jeu. 11/27

2:26 pm-8:07 pm

1 stop7h 41m

$293

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 $325. 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 $356.

What is the cheapest day to depart on your flight to Caribbean?

The cheapest day to depart from Wisconsin to Caribbean is on a Tuesday when prices can be found for as low as $389. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $477. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean.

What is the cheapest time of day to depart on your flight to Caribbean?

In the evening is the cheapest time of day to fly from Wisconsin to Caribbean when you can find flight prices for as low as $360. Flying to Caribbean in the evening is an ideal time because this is during off-peak travel hours. Flights at noon are often more expensive with an average ticket price of $458.

What is the cheapest Wisconsin to Caribbean flight route?

Fly from Milwaukee-Mitchell to Montego Bay Sangster Intl 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 $435 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 $351 on momondo.

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

There are 1 cabin classes 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 64% 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	$91
Fastest flight time	3h 18m
Direct flights	Every day
Airports in Caribbean	6 airports

The best one-way flight to Caribbean from Wisconsin in the past 72 hours is $91. The best round-trip flight deal from Wisconsin to Caribbean found on momondo in the last 72 hours is $189.

The fastest flight from Wisconsin to Caribbean takes 3h 18m

Direct flights go from Wisconsin to Caribbean every day.

There are 6 airports near Caribbean: Nassau Intl (NAS), Saint Thomas Island Cyril E King (STT), Punta Cana (PUJ), Montego Bay Sangster Intl (MBJ), Providenciales (PLS), San Juan Luis Munoz Marin Intl (SJU)

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 July 2025, there are 11 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 (47.83% of total bookings). The next most popular plane models are Boeing 737 MAX 9 (17.39%), Boeing 737 MAX 8 (8.70%), and Airbus A321-100/200 (8.70%).

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 $129	Free Cancellation	Rating 5.9 3,239 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $208	Free Cancellation	Rating 6.3 8,049 reviews	Search Spirit Airlines flights
United Airlines	PriceFrom $215	Free Cancellation	Rating 7.4 8,900 reviews	Search United Airlines flights
Delta	PriceFrom $225	Free Cancellation	Rating 8.0 7,981 reviews	Search Delta flights
American Airlines	PriceFrom $269	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Southwest	PriceFrom $325	Free Cancellation	Rating 8.0 4,246 reviews	Search Southwest flights
Sun Country Air	PriceFrom $519	Free Cancellation	Rating 6.9 334 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.