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

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

The number of flights available between Milwaukee and Caribbean Islands is 5 per week as of February 2026. The most frequent departure day is Mon, with 20% of weekly flights leaving on this day.

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.

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 February 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.

$101 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

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

12:36 pm - 1:58 am

MKE

SJU

12h 22m

1 stop

5:30 am - 3:00 pm

SJU

MKE

10h 30m

1 stop

$258Frontier

Mon, Mar 9 - Fri, Mar 13

7:42 pm - 12:59 pm

MKE

SJU

16h 17m

1 stop

7:15 am - 6:47 pm

SJU

MKE

12h 32m

1 stop

$259Frontier

Mon, May 11 - Mon, May 18

7:08 am - 11:02 pm

MKE

SJU

14h 54m

1 stop

6:00 am - 9:41 pm

SJU

MKE

16h 41m

1 stop

$266American Airlines

Tue, Apr 28 - Tue, May 5

2:55 pm - 10:17 pm

MKE

SJU

6h 22m

1 stop

12:50 pm - 9:02 pm

SJU

MKE

9h 12m

1 stop

$286Delta

Mon, May 18 - Thu, May 21

6:00 am - 2:15 pm

MKE

MBJ

8h 15m

1 stop

2:29 pm - 10:57 pm

MBJ

MKE

8h 28m

1 stop

$312American Airlines

Sun, Apr 12 - Thu, Apr 16

5:10 am - 4:05 pm

MKE

PLS

9h 55m

2 stops

5:15 pm - 10:00 am

PLS

MKE

17h 45m

2 stops

$394United Airlines

Wed, Apr 22 - Mon, Apr 27

7:00 am - 1:55 pm

MKE

PLS

5h 55m

1 stop

2:23 pm - 9:50 pm

PLS

MKE

8h 27m

1 stop

$395United Airlines

Tue, Mar 17 - Tue, Mar 24

5:45 am - 1:47 pm

MKE

STT

7h 02m

1 stop

3:05 pm - 11:57 pm

STT

MKE

9h 52m

1 stop

$400Delta

Tue, Apr 7 - Tue, Apr 14

5:30 am - 6:30 pm

MKE

NAS

12h 00m

1 stop

2:10 pm - 10:50 pm

NAS

MKE

9h 40m

1 stop

$467Southwest

Mon, Apr 20 - Mon, Apr 27

8:45 am - 6:30 pm

MKE

NAS

8h 45m

1 stop

8:45 am - 3:15 pm

NAS

MKE

7h 30m

1 stop

$528Southwest

Thu, Apr 2 - Tue, Apr 7

United Airlines flights from Milwaukee to Caribbean Islands

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

United Airlines

May 2

MKE8:15 amMilwaukee-Mitchell

11h 23m

1 stop

SJU8:38 pmSan Juan Luis Munoz Marin Intl

May 8

SJU1:00 amSan Juan Luis Munoz Marin Intl

9h 45m

2 stops

MKE9:45 amMilwaukee-Mitchell

$294

United Airlines

Apr 18

MKE10:45 amMilwaukee-Mitchell

9h 39m

2 stops

SJU9:24 pmSan Juan Luis Munoz Marin Intl

Apr 22

SJU1:00 amSan Juan Luis Munoz Marin Intl

10h 00m

2 stops

MKE10:00 amMilwaukee-Mitchell

$339

United Airlines

Apr 11

MKE6:50 amMilwaukee-Mitchell

12h 48m

2 stops

SJU8:38 pmSan Juan Luis Munoz Marin Intl

Apr 14

SJU1:00 amSan Juan Luis Munoz Marin Intl

11h 32m

2 stops

MKE11:32 amMilwaukee-Mitchell

$356

Frontier flights from Milwaukee to Caribbean Islands

Our best Frontier deals on Milwaukee to Caribbean Islands flight tickets

Frontier

Mar 9

MKE12:36 pmMilwaukee-Mitchell

12h 22m

1 stop

SJU1:58 amSan Juan Luis Munoz Marin Intl

Mar 13

SJU5:30 amSan Juan Luis Munoz Marin Intl

10h 30m

1 stop

MKE3:00 pmMilwaukee-Mitchell

$258

Frontier

May 11

MKE7:42 pmMilwaukee-Mitchell

16h 17m

1 stop

SJU12:59 pmSan Juan Luis Munoz Marin Intl

May 18

SJU7:15 amSan Juan Luis Munoz Marin Intl

12h 32m

1 stop

MKE6:47 pmMilwaukee-Mitchell

$259

Frontier

Mar 6

MKE12:36 pmMilwaukee-Mitchell

12h 22m

1 stop

SJU2:58 amSan Juan Luis Munoz Marin Intl

Mar 11

SJU6:30 amSan Juan Luis Munoz Marin Intl

12h 20m

1 stop

MKE5:50 pmMilwaukee-Mitchell

$269

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

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 3/9

12:36 pm-1:58 am

1 stop12h 22m

San Juan Luis Munoz Marin Intl

Fri 3/13

5:30 am-3:00 pm

1 stop10h 30m

$258

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 5/11

7:42 pm-12:59 pm

1 stop16h 17m

San Juan Luis Munoz Marin Intl

Mon 5/18

7:15 am-6:47 pm

1 stop12h 32m

$259

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 4/28

7:08 am-11:02 pm

1 stop14h 54m

San Juan Luis Munoz Marin Intl

Tue 5/5

6:00 am-9:41 pm

1 stop16h 41m

$266

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 5/18

2:55 pm-10:17 pm

1 stop6h 22m

San Juan Luis Munoz Marin Intl

Thu 5/21

12:50 pm-9:02 pm

1 stop9h 12m

$286

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Sun 4/12

6:00 am-2:15 pm

1 stop8h 15m

Montego Bay Sangster Intl

Thu 4/16

2:29 pm-10:57 pm

1 stop8h 28m

$312

MilwaukeeProvidenciales

MKE - PLS

MKEPLS

Milwaukee-Mitchell

Wed 4/22

5:10 am-4:05 pm

2 stops9h 55m

Providenciales

Mon 4/27

5:15 pm-10:00 am

2 stops17h 45m

$394

MilwaukeeProvidenciales

MKE - PLS

MKEPLS

Milwaukee-Mitchell

Tue 3/17

7:00 am-1:55 pm

1 stop5h 55m

Providenciales

Tue 3/24

2:23 pm-9:50 pm

1 stop8h 27m

$395

MilwaukeeSaint Thomas Island

MKE - STT

MKESTT

Milwaukee-Mitchell

Tue 4/7

5:45 am-1:47 pm

1 stop7h 02m

Saint Thomas Island Cyril E King

Tue 4/14

3:05 pm-11:57 pm

1 stop9h 52m

$400

MilwaukeeNassau

MKE - NAS

MKENAS

Milwaukee-Mitchell

Mon 4/20

5:30 am-6:30 pm

1 stop12h 00m

Nassau Intl

Mon 4/27

2:10 pm-10:50 pm

1 stop9h 40m

$467

MilwaukeeNassau

MKE - NAS

MKENAS

Milwaukee-Mitchell

Thu 4/2

8:45 am-6:30 pm

1 stop8h 45m

Nassau Intl

Tue 4/7

8:45 am-3:15 pm

1 stop7h 30m

$528

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

Other information

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 $315. The month of October is another great option to travel to Caribbean Islands, with average flight prices from Milwaukee averaging around $317.

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 $445 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 $383 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	4h 35m
Direct flights	Mon, Tue, Fri, Sat and Sun
Airports in Caribbean Islands	99 airports

The fastest flight from Milwaukee to Caribbean Islands takes 4h 35m

Direct flights go from Milwaukee to Caribbean Islands on Monday, Tuesday, Friday, Saturday and Sunday. 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

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 February 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 22.29% of all bookings. The subsequent popular models are Boeing 737-800 Passenger/BBJ2 (winglets) at 17.81%, Airbus A320-100/200 at 7.60%, and Airbus A320neo at 7.55%.

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
Frontier	PriceFrom $85	Free Cancellation	Rating 5.7 3,045 reviews	Search Frontier flights
Delta	PriceFrom $118	Free Cancellation	Rating 7.9 8,221 reviews	Search Delta flights
United Airlines	PriceFrom $182	Free Cancellation	Rating 7.4 9,331 reviews	Search United Airlines flights
Spirit Airlines	PriceFrom $195	Free Cancellation	Rating 6.3 8,478 reviews	Search Spirit Airlines flights
American Airlines	PriceFrom $256	Free Cancellation	Rating 7.2 11,323 reviews	Search American Airlines flights
Southwest	PriceFrom $315	Free Cancellation	Rating 8.0 4,298 reviews	Search Southwest flights
Sun Country Air	PriceFrom $497	Free Cancellation	Rating 6.8 341 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.