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

Spirit Airlines, Frontier, and JetBlue 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 18h 05m and 19h 05m, respectively.

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

As of December 2025, 179 flights take off from Wisconsin and land in Caribbean each week. The most common flight departure day for this route is Tue, with 16% of weekly flights taking off on this day.

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 51% 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.

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 December 2025, 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.

$72 Cheap Flights from Wisconsin to Caribbean in 2025/26

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Find the cheapest flights from Wisconsin to Caribbean

Round-trip

One-way

Last minute

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Cheap round-trip flights

Enter your travel dates to find the best prices.

9:18 am - 7:43 pm

ORD

SJU

8h 25m1 stop

5:25 pm - 11:15 pm

SJU

ORD

7h 50m1 stop

$195Multiple Airlines

Sat, Feb 21 - Mon, Mar 2

7:45 am - 6:05 pm

ORD

SJU

8h 20m1 stop

11:06 am - 7:36 pm

SJU

ORD

10h 30m1 stop

$196JetBlue

Tue, Jan 13 - Fri, Jan 23

12:17 pm - 6:49 pm

ORD

SJU

4h 32mnonstop

1:22 pm - 4:37 pm

SJU

ORD

5h 15mnonstop

$197Spirit Airlines

Sat, Jan 24 - Wed, Feb 4

9:25 am - 4:21 pm

ORD

SJU

28h 56m1 stop

5:25 pm - 3:52 pm

SJU

ORD

24h 27m1 stop

$198Frontier

Sat, Feb 7 - Tue, Feb 10

1:54 pm - 2:25 am

ORD

SJU

10h 31m1 stop

2:54 am - 9:11 am

SJU

ORD

8h 17m1 stop

$201Frontier

Thu, Feb 19 - Sun, Feb 22

5:15 am - 1:38 pm

ORD

GCM

7h 23m1 stop

2:34 pm - 11:46 pm

GCM

ORD

10h 12m1 stop

$240Spirit Airlines

Sat, Jan 10 - Sat, Jan 17

5:45 am - 12:30 pm

ORD

PUJ

4h 45mnonstop

6:00 pm - 9:10 pm

PUJ

ORD

5h 10mnonstop

$249Arajet

Wed, Feb 25 - Sun, Mar 1

10:27 am - 5:12 pm

ORD

PUJ

4h 45mnonstop

5:47 am - 8:57 am

PUJ

ORD

5h 10mnonstop

$251Arajet

Sat, Feb 21 - Sat, Feb 28

12:50 pm - 12:15 pm

ORD

NAS

22h 25m1 stop

11:15 am - 11:43 am

NAS

ORD

25h 28m1 stop

$356Air Canada

Sat, Mar 28 - Fri, Apr 3

6:04 pm - 12:15 pm

ORD

NAS

17h 11m2 stops

1:25 pm - 8:00 am

NAS

ORD

19h 35m2 stops

$359Air Canada

Sat, Mar 28 - Fri, Apr 3

Sun Country Air flights from Wisconsin to Caribbean

Our best Sun Country Air deals on Wisconsin to Caribbean flight tickets

Sun Country Air

May 23

MSP7:35 amMinneapolis St Paul

5h 07m

SJU1:42 pmSan Juan Luis Munoz Marin Intl

May 30

SJU4:10 pmSan Juan Luis Munoz Marin Intl

6h 00m

MSP9:10 pmMinneapolis St Paul

$296

Find similar

Sun Country Air

May 23

MSP7:35 amMinneapolis St Paul

5h 07m

SJU1:42 pmSan Juan Luis Munoz Marin Intl

May 30

SJU4:10 pmSan Juan Luis Munoz Marin Intl

6h 00m

MSP9:10 pmMinneapolis St Paul

$297

Find similar

Sun Country Air

Dec 21

MSP1:17 pmMinneapolis St Paul

8h 03m

1 stop

SJU11:20 pmSan Juan Luis Munoz Marin Intl

Dec 25

SJU5:14 pmSan Juan Luis Munoz Marin Intl

6h 04m

MSP9:18 pmMinneapolis St Paul

$471

Find similar

JetBlue flights from Wisconsin to Caribbean

Our best JetBlue deals on Wisconsin to Caribbean flight tickets

JetBlue

Jan 13

ORD7:45 amChicago O'Hare Intl

8h 20m

1 stop

SJU6:05 pmSan Juan Luis Munoz Marin Intl

Jan 23

SJU11:06 amSan Juan Luis Munoz Marin Intl

10h 30m

1 stop

ORD7:36 pmChicago O'Hare Intl

$196

Find similar

JetBlue

Feb 27

ORD12:41 pmChicago O'Hare Intl

9h 03m

1 stop

SJU11:44 pmSan Juan Luis Munoz Marin Intl

Mar 7

SJU5:10 amSan Juan Luis Munoz Marin Intl

8h 48m

1 stop

ORD11:58 amChicago O'Hare Intl

$202

Find similar

JetBlue

Jan 31

ORD9:40 amChicago O'Hare Intl

7h 46m

1 stop

SJU7:26 pmSan Juan Luis Munoz Marin Intl

Feb 7

SJU1:30 pmSan Juan Luis Munoz Marin Intl

8h 15m

1 stop

ORD7:45 pmChicago O'Hare Intl

$205

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/21

9:18 am-7:43 pm

1 stop8h 25m

San Juan Luis Munoz Marin Intl

Mon 3/2

5:25 pm-11:15 pm

1 stop7h 50m

$195

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 1/13

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Fri 1/23

11:06 am-7:36 pm

1 stop10h 30m

$196

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/24

12:17 pm-6:49 pm

Nonstop4h 32m

San Juan Luis Munoz Marin Intl

Wed 2/4

1:22 pm-4:37 pm

Nonstop5h 15m

$197

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/7

9:25 am-4:21 pm

1 stop28h 56m

San Juan Luis Munoz Marin Intl

Tue 2/10

5:25 pm-3:52 pm

1 stop24h 27m

$198

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 2/19

1:54 pm-2:25 am

1 stop10h 31m

San Juan Luis Munoz Marin Intl

Sun 2/22

2:54 am-9:11 am

1 stop8h 17m

$201

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/10

5:15 am-1:38 pm

1 stop7h 23m

George Town Owen Roberts Intl

Sat 1/17

2:34 pm-11:46 pm

1 stop10h 12m

$240

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 2/25

5:45 am-12:30 pm

Nonstop4h 45m

Punta Cana

Sun 3/1

6:00 pm-9:10 pm

Nonstop5h 10m

$249

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 2/21

10:27 am-5:12 pm

Nonstop4h 45m

Punta Cana

Sat 2/28

5:47 am-8:57 am

Nonstop5h 10m

$251

ChicagoNassau

ORD - NAS

ORDNAS

Chicago O'Hare Intl

Sat 3/28

12:50 pm-12:15 pm

1 stop22h 25m

Nassau Intl

Fri 4/3

11:15 am-11:43 am

1 stop25h 28m

$356

ChicagoNassau

ORD - NAS

ORDNAS

Chicago O'Hare Intl

Sat 3/28

6:04 pm-12:15 pm

2 stops17h 11m

Nassau Intl

Fri 4/3

1:25 pm-8:00 am

2 stops19h 35m

$359

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 $350.

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 $434 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 $343 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 52% 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	$716
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 $716

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 George Town Owen Roberts Intl (GCM), Nassau Intl (NAS), Montego Bay Sangster Intl (MBJ).

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 December 2025, 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 (69.05% of total bookings). The next most popular plane models are Boeing 737 MAX 9 (9.52%), Boeing 737 MAX 8 (7.14%), and Airbus A321-100/200 (4.76%).

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 5.8 3,081 reviews	Search Frontier flights
Delta	PriceFrom $191	Free Cancellation	Rating 7.9 8,007 reviews	Search Delta flights
United Airlines	PriceFrom $215	Free Cancellation	Rating 7.4 9,091 reviews	Search United Airlines flights
Spirit Airlines	PriceFrom $226	Free Cancellation	Rating 6.3 8,190 reviews	Search Spirit Airlines flights
American Airlines	PriceFrom $268	Free Cancellation	Rating 7.2 11,054 reviews	Search American Airlines flights
Southwest	PriceFrom $315	Free Cancellation	Rating 7.9 4,249 reviews	Search Southwest flights
Sun Country Air	PriceFrom $497	Free Cancellation	Rating 6.9 333 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.