What airlines fly to Caribbean Islands?

American Airlines, United Airlines and Frontier are the top three most popular airlines that fly to Caribbean Islands from Milwaukee according to our data. American Airlines is the first choice among our users, with 44% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 13 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Milwaukee-Mitchell to Caribbean Islands?

American Airlines, Delta, and Southwest are the most popular carriers operating from Milwaukee-Mitchell to Caribbean Islands

When did momondo last update prices for flights from Milwaukee-Mitchell Airport to Caribbean Islands?

Prices for flights from Milwaukee-Mitchell Airport to Caribbean Islands were last updated today.

How many operators does momondo search for flights from Milwaukee-Mitchell Airport to Caribbean Islands?

As of July 2026, there are 6 operators available to choose from for flights from Milwaukee-Mitchell Airport to Caribbean Islands.

How old do you have to be to fly from Milwaukee-Mitchell Airport to Caribbean Islands?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Milwaukee-Mitchell Airport to Caribbean Islands.

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

The required travel and health documents for your Caribbean Islands trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean Islands. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$162 Cheap Flights from Milwaukee to Caribbean Islands in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Milwaukee to Caribbean Islands

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:05 am - 4:49 pm

MKE

SJU

8h 44m

1 stop

12:56 pm - 8:55 pm

SJU

MKE

8h 59m

1 stop

$326Delta

Sat, Sep 19 - Mon, Oct 5

5:00 am - 6:33 pm

MKE

SJU

12h 33m

2 stops

7:03 am - 5:30 pm

SJU

MKE

11h 27m

1 stop

$331American Airlines

Wed, Sep 2 - Sun, Sep 6

6:27 pm - 11:31 am

MKE

SJU

16h 04m

2 stops

12:13 pm - 11:18 pm

SJU

MKE

12h 05m

2 stops

$332American Airlines

Mon, Oct 5 - Fri, Oct 30

6:27 pm - 11:31 am

MKE

SJU

16h 04m

2 stops

6:00 am - 9:49 pm

SJU

MKE

16h 49m

1 stop

$333American Airlines

Mon, Oct 5 - Fri, Oct 30

8:14 pm - 2:50 pm

MKE

SJU

17h 36m

2 stops

6:27 am - 8:29 pm

SJU

MKE

15h 02m

2 stops

$338American Airlines

Wed, Sep 16 - Sun, Sep 20

6:20 am - 6:30 pm

MKE

SJU

11h 10m

2 stops

12:55 am - 12:47 pm

SJU

MKE

12h 52m

1 stop

$351American Airlines

Mon, Aug 24 - Fri, Sep 4

10:30 am - 11:50 pm

MKE

SJU

12h 20m

2 stops

3:56 pm - 10:59 pm

SJU

MKE

8h 03m

1 stop

$354United Airlines

Sat, Sep 19 - Sun, Oct 4

6:15 am - 2:44 pm

MKE

SJU

7h 29m

1 stop

2:05 am - 11:43 am

SJU

MKE

10h 38m

1 stop

$357United Airlines

Sat, Oct 17 - Sat, Oct 31

5:30 am - 3:34 pm

MKE

MBJ

10h 04m

1 stop

1:32 pm - 11:53 pm

MBJ

MKE

10h 21m

1 stop

$442Delta

Sat, Oct 3 - Tue, Oct 6

6:20 pm - 1:50 pm

MKE

STT

18h 30m

2 stops

2:10 pm - 10:25 pm

STT

MKE

9h 15m

1 stop

$564Southwest

Thu, Sep 17 - Sun, Sep 20

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Frontier flights from Milwaukee to Caribbean Islands

Our best Frontier deals on Milwaukee to Caribbean Islands flight tickets

Frontier

Aug 18

MKE12:10 pmMilwaukee-Mitchell

13h 05m

1 stop

SJU2:15 amSan Juan Luis Munoz Marin Intl

Aug 29

SJU3:10 amSan Juan Luis Munoz Marin Intl

9h 03m

1 stop

MKE11:13 amMilwaukee-Mitchell

$396

Frontier

Aug 18

MKE12:10 pmMilwaukee-Mitchell

13h 05m

1 stop

SJU2:15 amSan Juan Luis Munoz Marin Intl

Aug 31

SJU8:57 pmSan Juan Luis Munoz Marin Intl

15h 16m

1 stop

MKE11:13 amMilwaukee-Mitchell

$399

Frontier

Aug 25

MKE12:10 pmMilwaukee-Mitchell

21h 56m

1 stop

SJU11:06 amSan Juan Luis Munoz Marin Intl

Sep 7

SJU11:24 amSan Juan Luis Munoz Marin Intl

24h 49m

2 stops

MKE11:13 amMilwaukee-Mitchell

$412

American Airlines flights from Milwaukee to Caribbean Islands

Our best American Airlines deals on Milwaukee to Caribbean Islands flight tickets

American Airlines

Sep 2

MKE5:00 amMilwaukee-Mitchell

12h 33m

2 stops

SJU6:33 pmSan Juan Luis Munoz Marin Intl

Sep 6

SJU7:03 amSan Juan Luis Munoz Marin Intl

11h 27m

1 stop

MKE5:30 pmMilwaukee-Mitchell

$331

American Airlines

Oct 5

MKE6:27 pmMilwaukee-Mitchell

16h 04m

2 stops

SJU11:31 amSan Juan Luis Munoz Marin Intl

Oct 30

SJU12:13 pmSan Juan Luis Munoz Marin Intl

12h 05m

2 stops

MKE11:18 pmMilwaukee-Mitchell

$332

American Airlines

Oct 5

MKE6:27 pmMilwaukee-Mitchell

16h 04m

2 stops

SJU11:31 amSan Juan Luis Munoz Marin Intl

Oct 30

SJU6:00 amSan Juan Luis Munoz Marin Intl

16h 49m

1 stop

MKE9:49 pmMilwaukee-Mitchell

$333

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 9/19

7:05 am-4:49 pm

1 stop8h 44m

San Juan Luis Munoz Marin Intl

Mon 10/5

12:56 pm-8:55 pm

1 stop8h 59m

$326

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 9/2

5:00 am-6:33 pm

2 stops12h 33m

San Juan Luis Munoz Marin Intl

Sun 9/6

7:03 am-5:30 pm

1 stop11h 27m

$331

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 10/5

6:27 pm-11:31 am

2 stops16h 04m

San Juan Luis Munoz Marin Intl

Fri 10/30

12:13 pm-11:18 pm

2 stops12h 05m

$332

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 10/5

6:27 pm-11:31 am

2 stops16h 04m

San Juan Luis Munoz Marin Intl

Fri 10/30

6:00 am-9:49 pm

1 stop16h 49m

$333

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 9/16

8:14 pm-2:50 pm

2 stops17h 36m

San Juan Luis Munoz Marin Intl

Sun 9/20

6:27 am-8:29 pm

2 stops15h 02m

$338

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 8/24

6:20 am-6:30 pm

2 stops11h 10m

San Juan Luis Munoz Marin Intl

Fri 9/4

12:55 am-12:47 pm

1 stop12h 52m

$351

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 9/19

10:30 am-11:50 pm

2 stops12h 20m

San Juan Luis Munoz Marin Intl

Sun 10/4

3:56 pm-10:59 pm

1 stop8h 03m

$354

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 10/17

6:15 am-2:44 pm

1 stop7h 29m

San Juan Luis Munoz Marin Intl

Sat 10/31

2:05 am-11:43 am

1 stop10h 38m

$357

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Sat 10/3

5:30 am-3:34 pm

1 stop10h 04m

Montego Bay Sangster Intl

Tue 10/6

1:32 pm-11:53 pm

1 stop10h 21m

$442

MilwaukeeSaint Thomas Island

MKE - STT

MKESTT

Milwaukee-Mitchell

Thu 9/17

6:20 pm-1:50 pm

2 stops18h 30m

Saint Thomas Island Cyril E King

Sun 9/20

2:10 pm-10:25 pm

1 stop9h 15m

$564

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 Milwaukee to Caribbean Islands

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

What is the cheapest month to fly to Caribbean Islands?

The month of January is, on average, the cheapest month to fly to Caribbean Islands from Milwaukee, with most prices found around $90. The month of July is another great option to travel to Caribbean Islands, with average flight prices from Milwaukee averaging around $124.

What is the cheapest Milwaukee-Mitchell to Caribbean Islands flight route?

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

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

You are more likely to see cheaper flights to Caribbean Islands from Milwaukee when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $465 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Milwaukee for as low as $391 on momondo.

What cabin class options are available on Milwaukee to Caribbean Islands flights?

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

No. A direct flight is the cheapest option for a flight between Milwaukee to Caribbean Islands.

Cheap Milwaukee to Caribbean Islands flight deals and tips

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

Fastest flight time	4h 32m
Direct flights	Mon and Fri
Airports in Caribbean Islands	99 airports

The fastest flight from Milwaukee to Caribbean Islands takes 4h 32m

Direct flights go from Milwaukee to Caribbean Islands on Monday and Friday. There are no airlines offering direct flights.

There are 99 airports in Caribbean Islands. From Milwaukee there are direct flights to Punta Cana (PUJ).

Search flight deals

Frequently asked questions about flying from Milwaukee to Caribbean Islands

When did momondo last update prices for flights from Milwaukee-Mitchell Airport to Caribbean Islands?
Prices for flights from Milwaukee-Mitchell Airport to Caribbean Islands were last updated today.
How many operators does momondo search for flights from Milwaukee-Mitchell Airport to Caribbean Islands?
As of July 2026, there are 6 operators available to choose from for flights from Milwaukee-Mitchell Airport to Caribbean Islands.
How old do you have to be to fly from Milwaukee-Mitchell Airport to Caribbean Islands?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Milwaukee-Mitchell Airport to Caribbean Islands.
What documentation or ID do you need to fly to Caribbean Islands?
The required travel and health documents for your Caribbean Islands trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean Islands. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Milwaukee to Caribbean Islands?
momondo data reveals that the most frequently booked plane model on the route from Milwaukee to Caribbean Islands is Boeing 737 MAX 8, representing 17.87% of all bookings. The subsequent popular models are Boeing 737-800 Passenger/BBJ2 (winglets) at 10.96%, Embraer 175 (Enhanced Winglets) at 8.07%, and Airbus A319 at 7.07%.

Best airlines flying from Milwaukee to Caribbean Islands

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

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $143	Free Cancellation	Rating 7.8 8,451 reviews	Search Delta flights
Frontier	PriceFrom $156	Free Cancellation	Rating 5.6 2,841 reviews	Search Frontier flights
United Airlines	PriceFrom $235	Free Cancellation	Rating 7.4 9,945 reviews	Search United Airlines flights
American Airlines	PriceFrom $256	Free Cancellation	Rating 7.1 11,783 reviews	Search American Airlines flights
Southwest	PriceFrom $316	Free Cancellation	Rating 7.9 4,250 reviews	Search Southwest flights
Sun Country Air	PriceFrom $547	Free Cancellation	Rating 6.8 327 reviews	Search Sun Country Air flights

Why use momondo?

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

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 Milwaukee to Caribbean Islands for you.

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

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

How can momondo help me find flights from Milwaukee to Caribbean Islands?

Once you have performed a search for Milwaukee to Caribbean Islands flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes momondo offers price alerts on flights to Caribbean Islands from Milwaukee. 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.