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Cheap flights from Milwaukee to Caribbean Islands from $90

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 2/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Milwaukee to Caribbean Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
1:35 pm - 11:58 pm
MKE
-
SJU
8h 23m1 stop
Delta Logo
5:10 pm - 11:51 pm
SJU
-
MKE
7h 41m1 stop
$235Delta
Wed, Mar 4 - Tue, Mar 10
Frontier Logo
7:42 pm - 9:25 am
MKE
-
SJU
11h 43m1 stop
Frontier Logo
8:00 am - 6:01 pm
SJU
-
MKE
12h 01m1 stop
$236Frontier
Sun, Jan 18 - Wed, Jan 21
Frontier Logo
7:48 pm - 9:54 am
MKE
-
SJU
12h 06m1 stop
Frontier Logo
8:00 am - 6:53 pm
SJU
-
MKE
12h 53m1 stop
$247Frontier
Sat, Jan 31 - Sat, Feb 7
Frontier Logo
7:30 pm - 8:54 am
MKE
-
SJU
11h 24m1 stop
Frontier Logo
8:57 am - 6:47 pm
SJU
-
MKE
11h 50m1 stop
$249Frontier
Thu, Jan 8 - Sat, Jan 17
United Airlines Logo
8:33 am - 9:26 pm
MKE
-
SJU
10h 53m2 stops
United Airlines Logo
2:05 am - 10:46 am
SJU
-
MKE
10h 41m1 stop
$253United Airlines
Tue, Jan 13 - Tue, Jan 20
American Airlines Logo
6:00 am - 8:50 pm
MKE
-
SJU
12h 50m2 stops
American Airlines Logo
1:24 pm - 11:23 pm
SJU
-
MKE
11h 59m2 stops
$260American Airlines
Sun, Jan 18 - Wed, Jan 21
American Airlines Logo
5:00 am - 1:24 pm
MKE
-
PLS
7h 24m1 stop
American Airlines Logo
3:30 pm - 4:56 pm
PLS
-
MKE
26h 26m1 stop
$372American Airlines
Sun, Mar 8 - Mon, Mar 30
United Airlines Logo
5:00 am - 2:32 pm
MKE
-
NAS
8h 32m2 stops
United Airlines Logo
3:35 pm - 9:44 pm
NAS
-
MKE
7h 09m1 stop
$393United Airlines
Tue, Feb 3 - Thu, Feb 12
Multiple Airlines Logo
7:30 pm - 2:52 pm
MKE
-
STT
17h 22m1 stop
Multiple Airlines Logo
3:57 pm - 6:52 pm
STT
-
MKE
28h 55m1 stop
$422Multiple Airlines
Thu, Jan 8 - Thu, Jan 15
Multiple Airlines Logo
3:10 pm - 2:52 pm
MKE
-
STT
21h 42m1 stop
Multiple Airlines Logo
3:57 pm - 9:58 am
STT
-
MKE
20h 01m2 stops
$439Multiple Airlines
Wed, Jan 7 - Sun, Jan 11

Delta flights from Milwaukee to Caribbean Islands

Our best Delta deals on Milwaukee to Caribbean Islands flight tickets
Delta
Mar 4
MKE1:35 pmMilwaukee-Mitchell
8h 23m
1 stop
SJU11:58 pmSan Juan Luis Munoz Marin Intl
Mar 11
SJU7:30 amSan Juan Luis Munoz Marin Intl
10h 59m
1 stop
MKE5:29 pmMilwaukee-Mitchell
$235
Find similar
Delta
Jan 13
MKE7:00 amMilwaukee-Mitchell
8h 17m
1 stop
SJU5:17 pmSan Juan Luis Munoz Marin Intl
Jan 23
SJU6:09 amSan Juan Luis Munoz Marin Intl
7h 01m
1 stop
MKE11:10 amMilwaukee-Mitchell
$317
Find similar
Delta
Jan 30
MKE5:45 pmMilwaukee-Mitchell
17h 15m
1 stop
PLS12:00 pmProvidenciales
Feb 12
PLS2:10 pmProvidenciales
7h 03m
1 stop
MKE8:13 pmMilwaukee-Mitchell
$364
Find similar

Frontier flights from Milwaukee to Caribbean Islands

Our best Frontier deals on Milwaukee to Caribbean Islands flight tickets
Frontier
Jan 18
MKE7:42 pmMilwaukee-Mitchell
11h 43m
1 stop
SJU9:25 amSan Juan Luis Munoz Marin Intl
Jan 21
SJU8:00 amSan Juan Luis Munoz Marin Intl
12h 01m
1 stop
MKE6:01 pmMilwaukee-Mitchell
$236
Find similar
Frontier
Jan 31
MKE7:48 pmMilwaukee-Mitchell
12h 06m
1 stop
SJU9:54 amSan Juan Luis Munoz Marin Intl
Feb 7
SJU8:00 amSan Juan Luis Munoz Marin Intl
12h 53m
1 stop
MKE6:53 pmMilwaukee-Mitchell
$247
Find similar
Frontier
Jan 8
MKE7:30 pmMilwaukee-Mitchell
11h 24m
1 stop
SJU8:54 amSan Juan Luis Munoz Marin Intl
Jan 17
SJU8:57 amSan Juan Luis Munoz Marin Intl
11h 50m
1 stop
MKE6:47 pmMilwaukee-Mitchell
$249
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 December 17, 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

Wed 3/4

1:35 pm-11:58 pm

1 stop8h 23m

San Juan Luis Munoz Marin Intl

Tue 3/10

5:10 pm-11:51 pm

1 stop7h 41m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 1/18

7:42 pm-9:25 am

1 stop11h 43m

San Juan Luis Munoz Marin Intl

Wed 1/21

8:00 am-6:01 pm

1 stop12h 01m

$236

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 1/31

7:48 pm-9:54 am

1 stop12h 06m

San Juan Luis Munoz Marin Intl

Sat 2/7

8:00 am-6:53 pm

1 stop12h 53m

$247

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Thu 1/8

7:30 pm-8:54 am

1 stop11h 24m

San Juan Luis Munoz Marin Intl

Sat 1/17

8:57 am-6:47 pm

1 stop11h 50m

$249

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 1/13

8:33 am-9:26 pm

2 stops10h 53m

San Juan Luis Munoz Marin Intl

Tue 1/20

2:05 am-10:46 am

1 stop10h 41m

$253

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 1/18

6:00 am-8:50 pm

2 stops12h 50m

San Juan Luis Munoz Marin Intl

Wed 1/21

1:24 pm-11:23 pm

2 stops11h 59m

$260

MilwaukeeProvidenciales

MKE - PLS

MKEPLS

Milwaukee-Mitchell

Sun 3/8

5:00 am-1:24 pm

1 stop7h 24m

Providenciales

Mon 3/30

3:30 pm-4:56 pm

1 stop26h 26m

$372

MilwaukeeNassau

MKE - NAS

MKENAS

Milwaukee-Mitchell

Tue 2/3

5:00 am-2:32 pm

2 stops8h 32m

Nassau Intl

Thu 2/12

3:35 pm-9:44 pm

1 stop7h 09m

$393

MilwaukeeSaint Thomas Island

MKE - STT

MKESTT

Milwaukee-Mitchell

Thu 1/8

7:30 pm-2:52 pm

1 stop17h 22m

Saint Thomas Island Cyril E King

Thu 1/15

3:57 pm-6:52 pm

1 stop28h 55m

$422

MilwaukeeSaint Thomas Island

MKE - STT

MKESTT

Milwaukee-Mitchell

Wed 1/7

3:10 pm-2:52 pm

1 stop21h 42m

Saint Thomas Island Cyril E King

Sun 1/11

3:57 pm-9:58 am

2 stops20h 01m

$439

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 $315. The month of October is another great option to travel to Caribbean Islands, with average flight prices from Milwaukee averaging around $350.

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 $434 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 $343 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

99 airports
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 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?

  • 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
3,081 reviews
Search Frontier flights
DeltaPriceFrom $191Free CancellationRating
7.9
8,007 reviews
Search Delta flights
United AirlinesPriceFrom $215Free CancellationRating
7.4
9,091 reviews
Search United Airlines flights
Spirit AirlinesPriceFrom $226Free CancellationRating
6.3
8,190 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $274Free CancellationRating
7.2
11,054 reviews
Search American Airlines flights
SouthwestPriceFrom $315Free CancellationRating
7.9
4,250 reviews
Search Southwest flights
Sun Country AirPriceFrom $497Free CancellationRating
6.9
333 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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