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

As of April 2026, there are 113 flights per week flying from Caribbean to Wisconsin. The most common day of the week flights depart is Mon, with 16% of flights taking off on this day.

What airlines fly to Wisconsin?

American Airlines, Delta and Southwest are the top three most popular airlines that fly to Wisconsin from Caribbean according to our data. American Airlines is the first choice among our users, with 45% of people opting to fly with this airline when traveling to Wisconsin. Keep in mind that there are 4 different airlines that fly to Wisconsin on a routine basis, so you have a few additional options to choose from.

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

Delta, United Airlines, and Southwest are the most popular carriers operating from Caribbean to Wisconsin

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

Prices for flights from Caribbean to Wisconsin are refreshed on a daily basis.

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

There are 11 operators available for flights from Caribbean to Wisconsin as of April 2026.

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

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Caribbean to Wisconsin.

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

The travel and health documents required for your trip to Wisconsin can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Wisconsin. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$94 Cheap Flights from Caribbean to Wisconsin in 2026

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Caribbean to Wisconsin

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

4:34 pm - 8:49 pm

SJU

ORD

5h 15mnonstop

4:44 pm - 10:21 pm

ORD

SJU

4h 37mnonstop

$151Spirit Airlines

Fri, May 1 - Mon, May 4

4:34 pm - 8:49 pm

SJU

ORD

5h 15mnonstop

4:44 pm - 10:21 pm

ORD

SJU

4h 37mnonstop

$152Spirit Airlines

Fri, May 1 - Mon, May 4

1:15 pm - 5:55 pm

MBJ

ORD

4h 40mnonstop

9:13 am - 1:23 pm

ORD

MBJ

4h 10mnonstop

$281American Airlines

Thu, May 7 - Tue, Jul 7

1:52 pm - 6:15 pm

MBJ

ORD

4h 23mnonstop

9:56 pm - 1:30 pm

ORD

MBJ

15h 34m

1 stop

$286United Airlines

Sat, May 16 - Mon, May 18

5:56 pm - 11:56 pm

SJU

MKE

7h 00m

1 stop

12:20 pm - 10:23 pm

MKE

SJU

9h 03m

1 stop

$289Delta

Tue, Aug 4 - Fri, Sep 4

2:40 pm - 12:45 am

MBJ

ORD

10h 05m

1 stop

6:30 am - 3:10 pm

ORD

MBJ

8h 40m

1 stop

$291United Airlines

Thu, May 7 - Tue, Jul 7

10:17 am - 7:22 pm

MBJ

ORD

9h 05m

1 stop

8:46 pm - 9:13 am

ORD

MBJ

12h 27m

1 stop

$296American Airlines

Fri, May 8 - Fri, May 15

5:45 pm - 11:25 pm

SJU

MKE

6h 40m

1 stop

5:55 am - 4:35 pm

MKE

SJU

9h 40m

1 stop

$326Delta

Thu, Aug 27 - Mon, Aug 31

6:50 am - 7:10 pm

SJU

MKE

13h 20m

1 stop

1:35 pm - 12:25 am

MKE

SJU

9h 50m

1 stop

$365Southwest

Mon, Jun 1 - Sun, Jun 7

7:00 am - 6:50 pm

SJU

MKE

12h 50m

1 stop

8:15 pm - 9:00 am

MKE

SJU

11h 45m

1 stop

$387Southwest

Thu, Jun 11 - Mon, Jun 22

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Frontier flights from Caribbean to Wisconsin

Our best Frontier deals on Caribbean to Wisconsin flight tickets

Frontier

May 8

SJU11:00 amSan Juan Luis Munoz Marin Intl

13h 59m

1 stop

ORD11:59 pmChicago O'Hare Intl

May 12

ORD3:55 pmChicago O'Hare Intl

9h 13m

1 stop

SJU2:08 amSan Juan Luis Munoz Marin Intl

$159

Frontier

May 23

SJU7:04 pmSan Juan Luis Munoz Marin Intl

5h 22m

ORD11:26 pmChicago O'Hare Intl

May 24

ORD12:33 amChicago O'Hare Intl

4h 51m

SJU6:24 amSan Juan Luis Munoz Marin Intl

$172

Frontier

May 21

SJU6:24 pmSan Juan Luis Munoz Marin Intl

5h 22m

ORD10:46 pmChicago O'Hare Intl

May 23

ORD12:33 amChicago O'Hare Intl

4h 51m

SJU6:24 amSan Juan Luis Munoz Marin Intl

$185

American Airlines flights from Caribbean to Wisconsin

Our best American Airlines deals on Caribbean to Wisconsin flight tickets

American Airlines

May 7

MBJ1:15 pmMontego Bay Sangster Intl

4h 40m

ORD5:55 pmChicago O'Hare Intl

Jul 7

ORD9:13 amChicago O'Hare Intl

4h 10m

MBJ1:23 pmMontego Bay Sangster Intl

$281

American Airlines

May 8

MBJ10:17 amMontego Bay Sangster Intl

9h 05m

1 stop

ORD7:22 pmChicago O'Hare Intl

May 15

ORD8:46 pmChicago O'Hare Intl

12h 27m

1 stop

MBJ9:13 amMontego Bay Sangster Intl

$296

American Airlines

May 14

MBJ2:29 pmMontego Bay Sangster Intl

9h 25m

1 stop

ORD11:54 pmChicago O'Hare Intl

Sep 12

ORD9:02 pmChicago O'Hare Intl

12h 08m

2 stops

MBJ9:10 amMontego Bay Sangster Intl

$301

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/1

4:34 pm-8:49 pm

Nonstop5h 15m

Chicago O'Hare Intl

Mon 5/4

4:44 pm-10:21 pm

Nonstop4h 37m

$151

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/1

4:34 pm-8:49 pm

Nonstop5h 15m

Chicago O'Hare Intl

Mon 5/4

4:44 pm-10:21 pm

Nonstop4h 37m

$152

Quickest round-trip

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 5/7

1:15 pm-5:55 pm

Nonstop4h 40m

Chicago O'Hare Intl

Tue 7/7

9:13 am-1:23 pm

Nonstop4h 10m

$281

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 5/16

1:52 pm-6:15 pm

Nonstop4h 23m

Chicago O'Hare Intl

Mon 5/18

9:56 pm-1:30 pm

1 stop15h 34m

$286

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Tue 8/4

5:56 pm-11:56 pm

1 stop7h 00m

Milwaukee-Mitchell

Fri 9/4

12:20 pm-10:23 pm

1 stop9h 03m

$289

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 5/7

2:40 pm-12:45 am

1 stop10h 05m

Chicago O'Hare Intl

Tue 7/7

6:30 am-3:10 pm

1 stop8h 40m

$291

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 5/8

10:17 am-7:22 pm

1 stop9h 05m

Chicago O'Hare Intl

Fri 5/15

8:46 pm-9:13 am

1 stop12h 27m

$296

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 8/27

5:45 pm-11:25 pm

1 stop6h 40m

Milwaukee-Mitchell

Mon 8/31

5:55 am-4:35 pm

1 stop9h 40m

$326

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Mon 6/1

6:50 am-7:10 pm

1 stop13h 20m

Milwaukee-Mitchell

Sun 6/7

1:35 pm-12:25 am

1 stop9h 50m

$365

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 6/11

7:00 am-6:50 pm

1 stop12h 50m

Milwaukee-Mitchell

Mon 6/22

8:15 pm-9:00 am

1 stop11h 45m

$387

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 Caribbean to Wisconsin

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 Wisconsin?

If you aren’t able to travel during the month of January, then book flights to Wisconsin from Caribbean during February instead. Flights to Wisconsin in February, while not as cheap as those in January, still average around $294.

What is the cheapest Caribbean to Wisconsin flight route?

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

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

You are more likely to see cheaper flights to Wisconsin from Caribbean when booking weeks ahead of your departure date. In general, you can expect to find flights to Wisconsin for around $371 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Wisconsin from Caribbean for as low as $215 on momondo.

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

There is only 1 cabin class available to choose from on Caribbean to Wisconsin 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 Caribbean to Wisconsin flights?

You could potentially save up to 74% on your flight if you consider stops on a Caribbean to Wisconsin flight.

Cheap Caribbean to Wisconsin flight deals and tips

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

Fastest flight time	3h 53m
Direct flights	Every day
Airports in Wisconsin	80 airports

The fastest flight from Caribbean to Wisconsin takes 3h 53m

Direct flights go from Caribbean to Wisconsin every day.

There are 80 airports in Wisconsin. From Caribbean there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

Frequently asked questions about flying from Caribbean to Wisconsin

When did momondo last update prices for flights from Caribbean to Wisconsin?
Prices for flights from Caribbean to Wisconsin are refreshed on a daily basis.
How many operators does momondo search for flights from Caribbean to Wisconsin?
There are 11 operators available for flights from Caribbean to Wisconsin as of April 2026.
How old do you have to be to fly from Caribbean to Wisconsin?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Caribbean to Wisconsin.
What documentation or ID do you need to fly to Wisconsin?
The travel and health documents required for your trip to Wisconsin can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Wisconsin. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Caribbean to Wisconsin

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

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $112	Free Cancellation	Rating 7.9 8,434 reviews	Search Delta flights
United Airlines	PriceFrom $235	Free Cancellation	Rating 7.4 9,613 reviews	Search United Airlines flights
American Airlines	PriceFrom $235	Free Cancellation	Rating 7.1 11,645 reviews	Search American Airlines flights
Southwest	PriceFrom $256	Free Cancellation	Rating 8.0 4,331 reviews	Search Southwest flights

Why use momondo?

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

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 Caribbean to Wisconsin for you.

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

momondo does allow users to show only those flights to Wisconsin from Caribbean which offer a flexible booking policy as well as other useful filters and features.

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

momondo helps you find the best flight between Caribbean and Wisconsin by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Yes momondo offers price alerts on flights to Wisconsin from Caribbean. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.