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 38% 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?

Frontier, American Airlines, and Delta 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 April 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.

$88 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.

2:47 pm - 11:29 pm

MKE

SJU

7h 42m

1 stop

7:15 am - 1:52 pm

SJU

MKE

7h 37m

1 stop

$291Frontier

Fri, Apr 17 - Mon, Apr 20

9:56 am - 1:15 pm

MKE

SJU

26h 19m

1 stop

3:03 am - 8:01 am

SJU

MKE

29h 58m

1 stop

$295Frontier

Tue, May 12 - Tue, May 19

5:29 pm - 9:13 am

MKE

MBJ

15h 44m

1 stop

2:19 pm - 9:57 pm

MBJ

MKE

7h 38m

1 stop

$352American Airlines

Tue, May 5 - Tue, May 12

5:55 am - 3:10 pm

MKE

MBJ

9h 15m

2 stops

1:52 pm - 10:03 pm

MBJ

MKE

8h 11m

1 stop

$353United Airlines

Sat, May 2 - Sat, May 9

6:34 pm - 11:45 am

MKE

MBJ

17h 11m

2 stops

2:55 pm - 11:47 pm

MBJ

MKE

8h 52m

1 stop

$357American Airlines

Mon, Jun 1 - Fri, Jun 5

5:40 am - 3:34 pm

MKE

MBJ

9h 54m

1 stop

1:21 pm - 11:59 pm

MBJ

MKE

10h 38m

1 stop

$362Delta

Mon, Jun 29 - Thu, Jul 2

5:00 pm - 11:34 am

MKE

MBJ

18h 34m

2 stops

12:59 pm - 11:50 am

MBJ

MKE

22h 51m

2 stops

$367Delta

Sat, Jun 6 - Thu, Jun 11

8:55 pm - 3:10 pm

MKE

MBJ

18h 15m

2 stops

2:40 pm - 10:45 pm

MBJ

MKE

8h 05m

1 stop

$380United Airlines

Mon, Jun 29 - Sat, Jul 4

5:00 am - 2:25 pm

MKE

SXM

8h 25m

1 stop

2:35 pm - 10:55 pm

SXM

MKE

9h 20m

1 stop

$519Southwest

Sun, May 17 - Sat, May 23

9:15 am - 6:30 pm

MKE

NAS

8h 15m

2 stops

2:10 pm - 9:45 pm

NAS

MKE

8h 35m

2 stops

$557Southwest

Wed, May 20 - Wed, May 27

Delta flights from Milwaukee to Caribbean Islands

Our best Delta deals on Milwaukee to Caribbean Islands flight tickets

Delta

Apr 25

MKE7:05 amMilwaukee-Mitchell

8h 18m

1 stop

SJU4:23 pmSan Juan Luis Munoz Marin Intl

May 1

SJU5:34 pmSan Juan Luis Munoz Marin Intl

7h 23m

1 stop

MKE11:57 pmMilwaukee-Mitchell

$326

Delta

Jun 29

MKE5:40 amMilwaukee-Mitchell

9h 54m

1 stop

MBJ3:34 pmMontego Bay Sangster Intl

Jul 2

MBJ1:21 pmMontego Bay Sangster Intl

10h 38m

1 stop

MKE11:59 pmMilwaukee-Mitchell

$362

Delta

Jun 6

MKE5:00 pmMilwaukee-Mitchell

18h 34m

2 stops

MBJ11:34 amMontego Bay Sangster Intl

Jun 11

MBJ12:59 pmMontego Bay Sangster Intl

22h 51m

2 stops

MKE11:50 amMilwaukee-Mitchell

$367

Frontier flights from Milwaukee to Caribbean Islands

Our best Frontier deals on Milwaukee to Caribbean Islands flight tickets

Frontier

Apr 11

MKE4:15 pmMilwaukee-Mitchell

7h 36m

1 stop

SJU12:51 amSan Juan Luis Munoz Marin Intl

Apr 15

SJU10:54 amSan Juan Luis Munoz Marin Intl

25h 32m

1 stop

MKE11:26 amMilwaukee-Mitchell

$285

Frontier

Apr 9

MKE7:02 pmMilwaukee-Mitchell

27h 38m

1 stop

SJU11:40 pmSan Juan Luis Munoz Marin Intl

Apr 18

SJU8:00 amSan Juan Luis Munoz Marin Intl

25h 38m

1 stop

MKE8:38 amMilwaukee-Mitchell

$290

Frontier

Apr 17

MKE2:47 pmMilwaukee-Mitchell

7h 42m

1 stop

SJU11:29 pmSan Juan Luis Munoz Marin Intl

Apr 20

SJU7:15 amSan Juan Luis Munoz Marin Intl

7h 37m

1 stop

MKE1:52 pmMilwaukee-Mitchell

$291

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

Fri 4/17

2:47 pm-11:29 pm

1 stop7h 42m

San Juan Luis Munoz Marin Intl

Mon 4/20

7:15 am-1:52 pm

1 stop7h 37m

$291

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 5/12

9:56 am-1:15 pm

1 stop26h 19m

San Juan Luis Munoz Marin Intl

Tue 5/19

3:03 am-8:01 am

1 stop29h 58m

$295

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Tue 5/5

5:29 pm-9:13 am

1 stop15h 44m

Montego Bay Sangster Intl

Tue 5/12

2:19 pm-9:57 pm

1 stop7h 38m

$352

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Sat 5/2

5:55 am-3:10 pm

2 stops9h 15m

Montego Bay Sangster Intl

Sat 5/9

1:52 pm-10:03 pm

1 stop8h 11m

$353

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Mon 6/1

6:34 pm-11:45 am

2 stops17h 11m

Montego Bay Sangster Intl

Fri 6/5

2:55 pm-11:47 pm

1 stop8h 52m

$357

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Mon 6/29

5:40 am-3:34 pm

1 stop9h 54m

Montego Bay Sangster Intl

Thu 7/2

1:21 pm-11:59 pm

1 stop10h 38m

$362

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Sat 6/6

5:00 pm-11:34 am

2 stops18h 34m

Montego Bay Sangster Intl

Thu 6/11

12:59 pm-11:50 am

2 stops22h 51m

$367

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Mon 6/29

8:55 pm-3:10 pm

2 stops18h 15m

Montego Bay Sangster Intl

Sat 7/4

2:40 pm-10:45 pm

1 stop8h 05m

$380

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 5/17

5:00 am-2:25 pm

1 stop8h 25m

Simpson Bay Princess Juliana

Sat 5/23

2:35 pm-10:55 pm

1 stop9h 20m

$519

MilwaukeeNassau

MKE - NAS

MKENAS

Milwaukee-Mitchell

Wed 5/20

9:15 am-6:30 pm

2 stops8h 15m

Nassau Intl

Wed 5/27

2:10 pm-9:45 pm

2 stops8h 35m

$557

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 September is, on average, the cheapest month to fly to Caribbean Islands from Milwaukee, with most prices found around $305. The month of October is another great option to travel to Caribbean Islands, with average flight prices from Milwaukee averaging around $315.

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 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 $443 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 $337 on momondo.

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

There is only 1 cabin class available to choose from on Milwaukee-Mitchell 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 28m
Direct flights	None

The fastest flight from Milwaukee to Caribbean Islands takes 5h 28m

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 April 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 22.32% of all bookings. The subsequent popular models are Boeing 737-800 Passenger/BBJ2 (winglets) at 16.74%, Airbus A320neo at 8.20%, and Airbus A320-100/200 at 7.15%.

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 8,383 reviews	Search Delta flights
Frontier	PriceFrom $156	Free Cancellation	Rating 5.7 3,000 reviews	Search Frontier flights
United Airlines	PriceFrom $202	Free Cancellation	Rating 7.4 9,548 reviews	Search United Airlines flights
Spirit Airlines	PriceFrom $219	Free Cancellation	Rating 6.3 8,597 reviews	Search Spirit Airlines flights
American Airlines	PriceFrom $256	Free Cancellation	Rating 7.1 11,546 reviews	Search American Airlines flights
Southwest	PriceFrom $315	Free Cancellation	Rating 8.0 4,338 reviews	Search Southwest flights
Sun Country Air	PriceFrom $547	Free Cancellation	Rating 6.8 336 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.