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Cheap flights from Milwaukee to Caribbean Islands from $118

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Milwaukee to Caribbean Islands departing on 10/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Milwaukee to Caribbean Islands

Cheap round-trip flights

American Airlines Logo
1:43 pm - 11:59 pmMKE-SJU
9h 16m1 stop
American Airlines Logo
5:30 am - 8:18 pmSJU-MKE
15h 48m1 stop
$235American Airlines
Find Deal
vie., oct. 24 - jue., oct. 30
American Airlines Logo
2:05 pm - 11:54 pmMKE-SJU
8h 49m1 stop
American Airlines Logo
5:30 am - 8:18 pmSJU-MKE
15h 48m1 stop
$236American Airlines
Find Deal
lun., oct. 6 - mié., oct. 15
United Airlines Logo
12:05 pm - 11:57 pmMKE-SJU
10h 52m2 stops
United Airlines Logo
1:05 am - 10:45 amSJU-MKE
10h 40m1 stop
$253United Airlines
Find Deal
sáb., oct. 4 - mar., oct. 7
United Airlines Logo
2:32 pm - 6:11 amMKE-SJU
13h 39m2 stops
United Airlines Logo
8:35 am - 1:53 pmSJU-MKE
7h 18m1 stop
$254United Airlines
Find Deal
dom., ene. 18 - vie., ene. 23
Southwest Logo
2:05 pm - 11:45 pmMKE-SJU
8h 40m1 stop
Southwest Logo
6:10 am - 4:15 pmSJU-MKE
11h 05m1 stop
$299Southwest
Find Deal
sáb., oct. 4 - mié., oct. 8
Delta Logo
12:20 pm - 11:49 pmMKE-SJU
9h 29m1 stop
Delta Logo
1:12 pm - 8:12 pmSJU-MKE
8h 00m1 stop
$305Delta
Find Deal
dom., mar. 1 - mar., mar. 10
Southwest Logo
12:10 pm - 1:25 amMKE-SJU
11h 15m1 stop
Southwest Logo
5:45 am - 10:45 amSJU-MKE
7h 00m1 stop
$350Southwest
Find Deal
vie., nov. 14 - lun., nov. 17
Delta Logo
6:00 am - 4:18 pmMKE-PUJ
8h 18m1 stop
Delta Logo
2:38 pm - 11:56 pmPUJ-MKE
11h 18m1 stop
$353Delta
Find Deal
dom., nov. 9 - vie., nov. 14
Spirit Airlines Logo
1:55 pm - 1:44 amMKE-SJU
10h 49m1 stop
Spirit Airlines Logo
2:49 am - 12:42 pmSJU-MKE
10h 53m1 stop
$358Spirit Airlines
Find Deal
jue., oct. 9 - mié., oct. 15
Spirit Airlines Logo
1:55 pm - 1:44 amMKE-SJU
10h 49m1 stop
Spirit Airlines Logo
2:49 am - 12:42 pmSJU-MKE
10h 53m1 stop
$382Spirit Airlines
Find Deal
jue., oct. 23 - sáb., oct. 25

American Airlines flights from Milwaukee to Caribbean Islands

Our best American Airlines deals on Milwaukee to Caribbean Islands flight tickets
American Airlines
Oct 24
MKE1:43 pmMilwaukee-Mitchell
9h 16m
1 stop
SJU11:59 pmSan Juan Luis Munoz Marin Intl
Oct 30
SJU5:30 amSan Juan Luis Munoz Marin Intl
15h 48m
1 stop
MKE8:18 pmMilwaukee-Mitchell
$235
Find similar
American Airlines
Oct 6
MKE2:05 pmMilwaukee-Mitchell
8h 49m
1 stop
SJU11:54 pmSan Juan Luis Munoz Marin Intl
Oct 15
SJU5:30 amSan Juan Luis Munoz Marin Intl
15h 48m
1 stop
MKE8:18 pmMilwaukee-Mitchell
$236
Find similar
American Airlines
Mar 10
MKE6:50 pmMilwaukee-Mitchell
16h 35m
1 stop
SJU12:25 pmSan Juan Luis Munoz Marin Intl
Mar 11
SJU3:15 pmSan Juan Luis Munoz Marin Intl
7h 01m
1 stop
MKE9:16 pmMilwaukee-Mitchell
$290
Find similar

United Airlines flights from Milwaukee to Caribbean Islands

Our best United Airlines deals on Milwaukee to Caribbean Islands flight tickets
United Airlines
Oct 4
MKE12:05 pmMilwaukee-Mitchell
10h 52m
2 stops
SJU11:57 pmSan Juan Luis Munoz Marin Intl
Oct 7
SJU1:05 amSan Juan Luis Munoz Marin Intl
10h 40m
1 stop
MKE10:45 amMilwaukee-Mitchell
$253
Find similar
United Airlines
Jan 18
MKE2:32 pmMilwaukee-Mitchell
13h 39m
2 stops
SJU6:11 amSan Juan Luis Munoz Marin Intl
Jan 23
SJU8:35 amSan Juan Luis Munoz Marin Intl
7h 18m
1 stop
MKE1:53 pmMilwaukee-Mitchell
$254
Find similar
United Airlines
Jan 18
MKE11:30 amMilwaukee-Mitchell
7h 30m
1 stop
SJU9:00 pmSan Juan Luis Munoz Marin Intl
Jan 22
SJU2:05 amSan Juan Luis Munoz Marin Intl
12h 04m
2 stops
MKE12:09 pmMilwaukee-Mitchell
$260
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Milwaukee to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated septiembre 11, 2025.
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

vie. 10/24

1:43 pm-11:59 pm

1 stop9h 16m

San Juan Luis Munoz Marin Intl

jue. 10/30

5:30 am-8:18 pm

1 stop15h 48m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

lun. 10/6

2:05 pm-11:54 pm

1 stop8h 49m

San Juan Luis Munoz Marin Intl

mié. 10/15

5:30 am-8:18 pm

1 stop15h 48m

$236

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

sáb. 10/4

12:05 pm-11:57 pm

2 stops10h 52m

San Juan Luis Munoz Marin Intl

mar. 10/7

1:05 am-10:45 am

1 stop10h 40m

$253

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

dom. 1/18

2:32 pm-6:11 am

2 stops13h 39m

San Juan Luis Munoz Marin Intl

vie. 1/23

8:35 am-1:53 pm

1 stop7h 18m

$254

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

sáb. 10/4

2:05 pm-11:45 pm

1 stop8h 40m

San Juan Luis Munoz Marin Intl

mié. 10/8

6:10 am-4:15 pm

1 stop11h 05m

$299

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

dom. 3/1

12:20 pm-11:49 pm

1 stop9h 29m

San Juan Luis Munoz Marin Intl

mar. 3/10

1:12 pm-8:12 pm

1 stop8h 00m

$305

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

vie. 11/14

12:10 pm-1:25 am

1 stop11h 15m

San Juan Luis Munoz Marin Intl

lun. 11/17

5:45 am-10:45 am

1 stop7h 00m

$350

MilwaukeePunta Cana

MKE - PUJ

MKEPUJ

Milwaukee-Mitchell

dom. 11/9

6:00 am-4:18 pm

1 stop8h 18m

Punta Cana

vie. 11/14

2:38 pm-11:56 pm

1 stop11h 18m

$353

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

jue. 10/9

1:55 pm-1:44 am

1 stop10h 49m

San Juan Luis Munoz Marin Intl

mié. 10/15

2:49 am-12:42 pm

1 stop10h 53m

$358

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

jue. 10/23

1:55 pm-1:44 am

1 stop10h 49m

San Juan Luis Munoz Marin Intl

sáb. 10/25

2:49 am-12:42 pm

1 stop10h 53m

$382

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Caribbean Islands from

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

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 $324. The month of October is another great option to travel to Caribbean Islands, with average flight prices from Milwaukee averaging around $345.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Milwaukee to Caribbean Islands is on a Tuesday. Travelers who choose to depart for Caribbean Islands on a Tuesday will often find tickets for as low as $389. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $477. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is in the evening. momondo users have found flights departing from Milwaukee to Caribbean Islands in the evening for as low as $360. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets at noon because they tend to be around $458. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

Fly from Milwaukee-Mitchell to Montego Bay Sangster Intl 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 $438 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 $374 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 19m

Direct flights

Mon, Tue, Fri, Sat and Sun

Airports in Caribbean Islands

1 airport
The fastest flight from Milwaukee to Caribbean Islands takes 4h 19m
Direct flights go from Milwaukee to Caribbean Islands on Monday, Tuesday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There is 1 airport near Caribbean Islands: 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?

  • 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?

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
FrontierPriceFrom $129Free CancellationRating
5.8
3,177 reviews
Search Frontier flights
United AirlinesPriceFrom $202Free CancellationRating
7.4
8,937 reviews
Search United Airlines flights
Spirit AirlinesPriceFrom $208Free CancellationRating
6.3
8,023 reviews
Search Spirit Airlines flights
DeltaPriceFrom $215Free CancellationRating
7.9
7,960 reviews
Search Delta flights
American AirlinesPriceFrom $275Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $315Free CancellationRating
8.0
4,248 reviews
Search Southwest flights
Sun Country AirPriceFrom $540Free CancellationRating
6.9
330 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.

An easier way to manage your Caribbean Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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