What airlines fly to Caribbean Islands?

American Airlines, United Airlines and Spirit Airlines 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 37% 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?

Delta, American Airlines, and Frontier 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 May 2026, there are 7 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.

$163 Cheap Flights from Milwaukee to Caribbean Islands in 2026

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Find the cheapest flights from Milwaukee to Caribbean Islands

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:33 am - 2:51 pm

MKE

SJU

7h 18m

1 stop

1:38 pm - 10:59 pm

SJU

MKE

10h 21m

2 stops

$331American Airlines

Wed, Aug 12 - Tue, Aug 18

7:00 am - 9:59 pm

MKE

SJU

13h 59m

2 stops

6:51 am - 11:23 pm

SJU

MKE

17h 32m

1 stop

$336American Airlines

Tue, Aug 4 - Thu, Aug 13

5:56 pm - 1:30 pm

MKE

MBJ

19h 34m

1 stop

2:40 pm - 10:45 pm

MBJ

MKE

8h 05m

1 stop

$365United Airlines

Mon, Jun 29 - Sat, Jul 4

10:00 am - 9:05 pm

MKE

SJU

10h 05m

2 stops

6:00 am - 4:10 pm

SJU

MKE

11h 10m

1 stop

$365Southwest

Wed, Aug 12 - Mon, Aug 17

8:43 am - 5:34 pm

MKE

SJU

31h 51m

2 stops

6:31 pm - 7:58 am

SJU

MKE

14h 27m

1 stop

$375Frontier

Tue, Aug 4 - Wed, Aug 12

8:43 am - 2:11 am

MKE

SJU

16h 28m

1 stop

9:00 am - 7:58 am

SJU

MKE

23h 58m

2 stops

$378Frontier

Sun, Aug 2 - Wed, Aug 12

11:00 am - 11:05 pm

MKE

SJU

11h 05m

1 stop

10:00 am - 7:50 pm

SJU

MKE

10h 50m

2 stops

$387Southwest

Mon, Aug 10 - Mon, Aug 31

7:03 am - 3:34 pm

MKE

MBJ

8h 31m

1 stop

1:09 pm - 8:05 pm

MBJ

MKE

6h 56m

1 stop

$422Delta

Tue, Aug 11 - Sat, Aug 15

5:34 am - 1:53 pm

MKE

SXM

7h 19m

1 stop

3:18 pm - 11:53 pm

SXM

MKE

9h 35m

1 stop

$483Delta

Thu, Aug 13 - Thu, Aug 20

7:23 pm - 1:29 pm

MKE

NAS

17h 06m

2 stops

3:59 pm - 8:56 pm

NAS

MKE

5h 57m

1 stop

$586United Airlines

Mon, Aug 3 - Mon, Aug 10

American Airlines flights from Milwaukee to Caribbean Islands

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

American Airlines

Aug 12

MKE6:33 amMilwaukee-Mitchell

7h 18m

1 stop

SJU2:51 pmSan Juan Luis Munoz Marin Intl

Aug 18

SJU1:38 pmSan Juan Luis Munoz Marin Intl

10h 21m

2 stops

MKE10:59 pmMilwaukee-Mitchell

$331

American Airlines

Aug 4

MKE7:00 amMilwaukee-Mitchell

13h 59m

2 stops

SJU9:59 pmSan Juan Luis Munoz Marin Intl

Aug 13

SJU6:51 amSan Juan Luis Munoz Marin Intl

17h 32m

1 stop

MKE11:23 pmMilwaukee-Mitchell

$336

American Airlines

Aug 12

MKE6:33 amMilwaukee-Mitchell

13h 41m

2 stops

SJU9:14 pmSan Juan Luis Munoz Marin Intl

Aug 18

SJU1:38 pmSan Juan Luis Munoz Marin Intl

10h 45m

2 stops

MKE11:23 pmMilwaukee-Mitchell

$341

Frontier flights from Milwaukee to Caribbean Islands

Our best Frontier deals on Milwaukee to Caribbean Islands flight tickets

Frontier

Aug 4

MKE8:43 amMilwaukee-Mitchell

31h 51m

2 stops

SJU5:34 pmSan Juan Luis Munoz Marin Intl

Aug 12

SJU6:31 pmSan Juan Luis Munoz Marin Intl

14h 27m

1 stop

MKE7:58 amMilwaukee-Mitchell

$375

Frontier

Aug 2

MKE8:43 amMilwaukee-Mitchell

16h 28m

1 stop

SJU2:11 amSan Juan Luis Munoz Marin Intl

Aug 12

SJU9:00 amSan Juan Luis Munoz Marin Intl

23h 58m

2 stops

MKE7:58 amMilwaukee-Mitchell

$378

Frontier

Jul 9

MKE8:43 amMilwaukee-Mitchell

9h 49m

1 stop

SJU7:32 pmSan Juan Luis Munoz Marin Intl

Jul 13

SJU8:37 pmSan Juan Luis Munoz Marin Intl

12h 21m

1 stop

MKE7:58 amMilwaukee-Mitchell

$416

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

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 8/12

6:33 am-2:51 pm

1 stop7h 18m

San Juan Luis Munoz Marin Intl

Tue 8/18

1:38 pm-10:59 pm

2 stops10h 21m

$331

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 8/4

7:00 am-9:59 pm

2 stops13h 59m

San Juan Luis Munoz Marin Intl

Thu 8/13

6:51 am-11:23 pm

1 stop17h 32m

$336

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Mon 6/29

5:56 pm-1:30 pm

1 stop19h 34m

Montego Bay Sangster Intl

Sat 7/4

2:40 pm-10:45 pm

1 stop8h 05m

$365

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 8/12

10:00 am-9:05 pm

2 stops10h 05m

San Juan Luis Munoz Marin Intl

Mon 8/17

6:00 am-4:10 pm

1 stop11h 10m

$365

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 8/4

8:43 am-5:34 pm

2 stops31h 51m

San Juan Luis Munoz Marin Intl

Wed 8/12

6:31 pm-7:58 am

1 stop14h 27m

$375

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 8/2

8:43 am-2:11 am

1 stop16h 28m

San Juan Luis Munoz Marin Intl

Wed 8/12

9:00 am-7:58 am

2 stops23h 58m

$378

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 8/10

11:00 am-11:05 pm

1 stop11h 05m

San Juan Luis Munoz Marin Intl

Mon 8/31

10:00 am-7:50 pm

2 stops10h 50m

$387

Quickest round-trip

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Tue 8/11

7:03 am-3:34 pm

1 stop8h 31m

Montego Bay Sangster Intl

Sat 8/15

1:09 pm-8:05 pm

1 stop6h 56m

$422

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Thu 8/13

5:34 am-1:53 pm

1 stop7h 19m

Simpson Bay Princess Juliana

Thu 8/20

3:18 pm-11:53 pm

1 stop9h 35m

$483

MilwaukeeNassau

MKE - NAS

MKENAS

Milwaukee-Mitchell

Mon 8/3

7:23 pm-1:29 pm

2 stops17h 06m

Nassau Intl

Mon 8/10

3:59 pm-8:56 pm

1 stop5h 57m

$586

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 $449 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 $369 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	5h 06m
Direct flights	None

The fastest flight from Milwaukee to Caribbean Islands takes 5h 06m

There are no direct flights from Milwaukee to Caribbean Islands. There are no popular flight routes from Milwaukee to Caribbean Islands.

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 May 2026, there are 7 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 20.78% of all bookings. The subsequent popular models are Boeing 737-800 Passenger/BBJ2 (winglets) at 14.43%, Embraer 175 (Enhanced Winglets) at 6.38%, and Airbus A320-100/200 at 6.20%.

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 $112	Free Cancellation	Rating 7.9 8,445 reviews	Search Delta flights
Frontier	PriceFrom $156	Free Cancellation	Rating 5.6 2,944 reviews	Search Frontier flights
United Airlines	PriceFrom $202	Free Cancellation	Rating 7.4 9,752 reviews	Search United Airlines flights
Spirit Airlines	PriceFrom $219	Free Cancellation	Rating 6.2	Search Spirit Airlines flights
American Airlines	PriceFrom $256	Free Cancellation	Rating 7.1 11,643 reviews	Search American Airlines flights
Southwest	PriceFrom $315	Free Cancellation	Rating 7.9 4,277 reviews	Search Southwest flights
Sun Country Air	PriceFrom $547	Free Cancellation	Rating 6.8 334 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.