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 50% 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 American Airlines are the most popular carriers operating from Caribbean to Wisconsin

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

As of June 2026, there are 98 flights per week flying from Caribbean to Wisconsin. The most common day of the week flights depart is Sat, with 19% of flights taking off on this day.

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 8 operators available for flights from Caribbean to Wisconsin as of June 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.

$113 Cheap Flights from Caribbean to Wisconsin in 2026

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.

2:59 pm - 8:53 pm

SJU

MKE

6h 54m

1 stop

7:03 am - 4:38 pm

MKE

SJU

8h 35m

1 stop

$226Delta

Thu, Aug 27 - Mon, Aug 31

7:14 pm - 11:27 pm

SJU

ORD

5h 13mnonstop

12:44 am - 6:44 am

ORD

SJU

5h 00mnonstop

$235Frontier

Fri, Aug 28 - Sun, Aug 30

2:20 pm - 11:26 pm

SJU

ORD

10h 06m

1 stop

8:55 am - 2:44 pm

ORD

SJU

4h 49mnonstop

$242United Airlines

Wed, Aug 26 - Sun, Aug 30

5:37 pm - 12:50 pm

SJU

ORD

44h 13m

2 stops

12:44 am - 6:44 am

ORD

SJU

5h 00mnonstop

$243Multiple Airlines

Tue, Aug 18 - Tue, Aug 25

4:55 pm - 11:40 pm

SJU

ORD

7h 45m

1 stop

5:30 am - 3:42 pm

ORD

SJU

9h 12m

1 stop

$246United Airlines

Wed, Aug 26 - Sun, Aug 30

7:24 pm - 7:34 am

SJU

ORD

13h 10m

1 stop

5:20 pm - 11:15 pm

ORD

SJU

4h 55mnonstop

$247American Airlines

Wed, Aug 26 - Wed, Sep 2

3:44 pm - 11:30 pm

SJU

ORD

8h 46m

1 stop

6:45 am - 10:24 pm

ORD

SJU

14h 39m

1 stop

$251American Airlines

Fri, Aug 28 - Sun, Aug 30

5:15 am - 10:55 am

SJU

MKE

6h 40m

1 stop

1:55 pm - 11:50 pm

MKE

SJU

8h 55m

1 stop

$316Southwest

Tue, Aug 11 - Mon, Aug 17

11:39 am - 11:27 pm

PUJ

ORD

12h 48m

1 stop

6:45 am - 12:30 pm

ORD

PUJ

4h 45mnonstop

$354Multiple Airlines

Fri, Sep 4 - Fri, Sep 11

5:20 pm - 12:05 am

SJU

MSP

7h 45m

1 stop

10:35 am - 10:40 pm

MSP

SJU

11h 05m

1 stop

$376Southwest

Mon, Oct 12 - Wed, Oct 14

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Arajet flights from Caribbean to Wisconsin

Our best Arajet deals on Caribbean to Wisconsin flight tickets

Arajet

Sep 12

PUJ7:02 amPunta Cana

5h 10m

ORD11:12 amChicago O'Hare Intl

Sep 19

ORD12:12 pmChicago O'Hare Intl

4h 45m

PUJ5:57 pmPunta Cana

$289

Arajet

Nov 7

PUJ5:47 amPunta Cana

5h 10m

ORD8:57 amChicago O'Hare Intl

Nov 14

ORD10:27 amChicago O'Hare Intl

4h 45m

PUJ5:12 pmPunta Cana

$290

Arajet

Nov 7

PUJ5:47 amPunta Cana

5h 10m

ORD8:57 amChicago O'Hare Intl

Nov 14

ORD10:27 amChicago O'Hare Intl

4h 45m

PUJ5:12 pmPunta Cana

$302

American Airlines flights from Caribbean to Wisconsin

Our best American Airlines deals on Caribbean to Wisconsin flight tickets

American Airlines

Aug 26

SJU7:24 pmSan Juan Luis Munoz Marin Intl

13h 10m

1 stop

ORD7:34 amChicago O'Hare Intl

Sep 2

ORD5:20 pmChicago O'Hare Intl

4h 55m

SJU11:15 pmSan Juan Luis Munoz Marin Intl

$247

American Airlines

Aug 28

SJU3:44 pmSan Juan Luis Munoz Marin Intl

8h 46m

1 stop

ORD11:30 pmChicago O'Hare Intl

Aug 30

ORD6:45 amChicago O'Hare Intl

14h 39m

1 stop

SJU10:24 pmSan Juan Luis Munoz Marin Intl

$251

American Airlines

Aug 26

SJU7:24 pmSan Juan Luis Munoz Marin Intl

13h 10m

1 stop

ORD7:34 amChicago O'Hare Intl

Aug 29

ORD4:59 pmChicago O'Hare Intl

4h 55m

SJU10:54 pmSan Juan Luis Munoz Marin Intl

$252

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 8/27

2:59 pm-8:53 pm

1 stop6h 54m

Milwaukee-Mitchell

Mon 8/31

7:03 am-4:38 pm

1 stop8h 35m

$226

Quickest round-trip

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 8/28

7:14 pm-11:27 pm

Nonstop5h 13m

Chicago O'Hare Intl

Sun 8/30

12:44 am-6:44 am

Nonstop5h 00m

$235

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 8/26

2:20 pm-11:26 pm

1 stop10h 06m

Chicago O'Hare Intl

Sun 8/30

8:55 am-2:44 pm

Nonstop4h 49m

$242

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 8/18

5:37 pm-12:50 pm

2 stops44h 13m

Chicago O'Hare Intl

Tue 8/25

12:44 am-6:44 am

Nonstop5h 00m

$243

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 8/26

4:55 pm-11:40 pm

1 stop7h 45m

Chicago O'Hare Intl

Sun 8/30

5:30 am-3:42 pm

1 stop9h 12m

$246

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 8/26

7:24 pm-7:34 am

1 stop13h 10m

Chicago O'Hare Intl

Wed 9/2

5:20 pm-11:15 pm

Nonstop4h 55m

$247

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 8/28

3:44 pm-11:30 pm

1 stop8h 46m

Chicago O'Hare Intl

Sun 8/30

6:45 am-10:24 pm

1 stop14h 39m

$251

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Tue 8/11

5:15 am-10:55 am

1 stop6h 40m

Milwaukee-Mitchell

Mon 8/17

1:55 pm-11:50 pm

1 stop8h 55m

$316

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 9/4

11:39 am-11:27 pm

1 stop12h 48m

Chicago O'Hare Intl

Fri 9/11

6:45 am-12:30 pm

Nonstop4h 45m

$354

San JuanMinneapolis

SJU - MSP

SJUMSP

San Juan Luis Munoz Marin Intl

Mon 10/12

5:20 pm-12:05 am

1 stop7h 45m

Minneapolis St Paul

Wed 10/14

10:35 am-10:40 pm

1 stop11h 05m

$376

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 May, then book flights to Wisconsin from Caribbean during October instead. Flights to Wisconsin in October, while not as cheap as those in May, still average around $108.

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 from Caribbean 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 $383 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 66% 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 56m
Direct flights	Every day
Airports in Wisconsin	80 airports

The fastest flight from Caribbean to Wisconsin takes 3h 56m

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 8 operators available for flights from Caribbean to Wisconsin as of June 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 7.8 8,451 reviews	Search Delta flights
United Airlines	PriceFrom $235	Free Cancellation	Rating 7.4 9,896 reviews	Search United Airlines flights
American Airlines	PriceFrom $235	Free Cancellation	Rating 7.1 11,779 reviews	Search American Airlines flights
Southwest	PriceFrom $256	Free Cancellation	Rating 7.9 4,246 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.