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Cheap flights from Milwaukee to Caribbean 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 departing on 2/7. 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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0 bags

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Frontier Logo
12:08 pm - 2:50 amMKE-SJU
12h 42m1 stop
Frontier Logo
6:00 am - 6:26 pmSJU-MKE
14h 26m1 stop
$301Frontier
Find Deal
Mon, Dec 29 - Tue, Dec 30
Multiple Airlines Logo
7:48 pm - 9:47 amMKE-SJU
11h 59m1 stop
Multiple Airlines Logo
8:40 am - 6:45 pmSJU-MKE
36h 05m2 stops
$302Multiple Airlines
Find Deal
Sat, Jan 31 - Wed, Feb 11
Multiple Airlines Logo
7:48 pm - 9:47 amMKE-SJU
11h 59m1 stop
Multiple Airlines Logo
3:55 am - 5:04 pmSJU-MKE
15h 09m1 stop
$304Multiple Airlines
Find Deal
Sat, Jan 31 - Fri, Feb 13
Delta Logo
7:00 am - 5:17 pmMKE-SJU
8h 17m1 stop
Delta Logo
7:30 am - 5:21 pmSJU-MKE
11h 51m1 stop
$305Delta
Find Deal
Sun, Feb 8 - Sat, Feb 14
American Airlines Logo
8:00 am - 8:36 pmMKE-SJU
10h 36m1 stop
American Airlines Logo
1:30 am - 11:01 amSJU-MKE
10h 31m1 stop
$308American Airlines
Find Deal
Wed, Feb 25 - Tue, Mar 10
United Airlines Logo
3:20 pm - 6:11 amMKE-SJU
12h 51m2 stops
United Airlines Logo
3:46 pm - 10:59 pmSJU-MKE
9h 13m1 stop
$309United Airlines
Find Deal
Sat, Jan 31 - Tue, Feb 10
Frontier Logo
7:48 pm - 9:54 amMKE-SJU
12h 06m1 stop
Frontier Logo
8:00 am - 6:53 pmSJU-MKE
12h 53m1 stop
$310Frontier
Find Deal
Sat, Jan 31 - Sat, Feb 7
Delta Logo
5:33 pm - 12:00 pmMKE-PLS
17h 27m2 stops
Delta Logo
1:25 pm - 10:02 amPLS-MKE
21h 37m2 stops
$354Delta
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Sun, Jan 18 - Fri, Jan 23
American Airlines Logo
6:58 pm - 2:21 pmMKE-PLS
18h 23m2 stops
American Airlines Logo
1:18 pm - 11:35 pmPLS-MKE
11h 17m2 stops
$359American Airlines
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Sun, Jan 18 - Thu, Jan 22
United Airlines Logo
6:00 am - 4:00 pmMKE-PLS
9h 00m2 stops
United Airlines Logo
5:06 pm - 3:43 pmPLS-MKE
23h 37m2 stops
$369United Airlines
Find Deal
Sun, Jan 18 - Thu, Jan 22

American Airlines flights from Milwaukee to Caribbean

Our best American Airlines deals on Milwaukee to Caribbean flight tickets
American Airlines
Jan 6
MKE6:58 pmMilwaukee-Mitchell
17h 58m
1 stop
SJU2:56 pmSan Juan Luis Munoz Marin Intl
Feb 5
SJU6:00 amSan Juan Luis Munoz Marin Intl
11h 57m
1 stop
MKE3:57 pmMilwaukee-Mitchell
$308
Find similar
American Airlines
Jan 18
MKE6:58 pmMilwaukee-Mitchell
18h 23m
2 stops
PLS2:21 pmProvidenciales
Jan 22
PLS1:18 pmProvidenciales
11h 17m
2 stops
MKE11:35 pmMilwaukee-Mitchell
$359
Find similar
American Airlines
Jan 18
MKE4:05 pmMilwaukee-Mitchell
21h 16m
2 stops
PLS2:21 pmProvidenciales
Jan 22
PLS1:18 pmProvidenciales
11h 17m
2 stops
MKE11:35 pmMilwaukee-Mitchell
$368
Find similar

Frontier flights from Milwaukee to Caribbean

Our best Frontier deals on Milwaukee to Caribbean flight tickets
Frontier
Dec 29
MKE12:08 pmMilwaukee-Mitchell
12h 42m
1 stop
SJU2:50 amSan Juan Luis Munoz Marin Intl
Dec 30
SJU6:00 amSan Juan Luis Munoz Marin Intl
14h 26m
1 stop
MKE6:26 pmMilwaukee-Mitchell
$301
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
$310
Find similar
Frontier
Dec 5
MKE6:09 pmMilwaukee-Mitchell
30h 41m
1 stop
SJU2:50 amSan Juan Luis Munoz Marin Intl
Dec 13
SJU3:55 amSan Juan Luis Munoz Marin Intl
15h 14m
1 stop
MKE5:09 pmMilwaukee-Mitchell
$311
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Milwaukee to Caribbean 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 November 26, 2025.
Use the filters below to find and compare flights from Milwaukee to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 12/29

12:08 pm-2:50 am

1 stop12h 42m

San Juan Luis Munoz Marin Intl

Tue 12/30

6:00 am-6:26 pm

1 stop14h 26m

$301

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 1/31

7:48 pm-9:47 am

1 stop11h 59m

San Juan Luis Munoz Marin Intl

Wed 2/11

8:40 am-6:45 pm

2 stops36h 05m

$302

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 1/31

7:48 pm-9:47 am

1 stop11h 59m

San Juan Luis Munoz Marin Intl

Fri 2/13

3:55 am-5:04 pm

1 stop15h 09m

$304

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 2/8

7:00 am-5:17 pm

1 stop8h 17m

San Juan Luis Munoz Marin Intl

Sat 2/14

7:30 am-5:21 pm

1 stop11h 51m

$305

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 2/25

8:00 am-8:36 pm

1 stop10h 36m

San Juan Luis Munoz Marin Intl

Tue 3/10

1:30 am-11:01 am

1 stop10h 31m

$308

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 1/31

3:20 pm-6:11 am

2 stops12h 51m

San Juan Luis Munoz Marin Intl

Tue 2/10

3:46 pm-10:59 pm

1 stop9h 13m

$309

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

$310

MilwaukeeProvidenciales

MKE - PLS

MKEPLS

Milwaukee-Mitchell

Sun 1/18

5:33 pm-12:00 pm

2 stops17h 27m

Providenciales

Fri 1/23

1:25 pm-10:02 am

2 stops21h 37m

$354

MilwaukeeProvidenciales

MKE - PLS

MKEPLS

Milwaukee-Mitchell

Sun 1/18

6:58 pm-2:21 pm

2 stops18h 23m

Providenciales

Thu 1/22

1:18 pm-11:35 pm

2 stops11h 17m

$359

MilwaukeeProvidenciales

MKE - PLS

MKEPLS

Milwaukee-Mitchell

Sun 1/18

6:00 am-4:00 pm

2 stops9h 00m

Providenciales

Thu 1/22

5:06 pm-3:43 pm

2 stops23h 37m

$369

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Milwaukee to Caribbean

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?

In general, September is the cheapest month to fly from Milwaukee to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $315. If you don’t want to visit Caribbean in September, then you should wait until October to fly from Milwaukee, when ticket prices are also cheap, with an average price of $350.

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

The cheapest day to depart from Milwaukee to Caribbean is on a Tuesday when prices can be found 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.

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

In the evening is the cheapest time of day to fly from Milwaukee to Caribbean when you can find flight prices for as low as $360. Flying to Caribbean in the evening is an ideal time because this is during off-peak travel hours. Flights at noon are often more expensive with an average ticket price of $458.

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

Fly from Milwaukee-Mitchell to Montego Bay Sangster Intl for the best Milwaukee-Mitchell - Caribbean flight prices

How far in advance should I book a flight to Caribbean?

You are more likely to see cheaper flights to Caribbean from Milwaukee when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around $436 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from Milwaukee for as low as $324 on momondo.

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

There is only 1 cabin class available to choose from on Milwaukee-Mitchell to Caribbean 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 flights?

You could potentially save up to 52% on your flight if you consider stops on a Milwaukee to Caribbean flight.

Cheap Milwaukee to Caribbean flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Milwaukee to Caribbean

Best Price Found

$324

Fastest flight time

4h 19m

Direct flights

Mon, Tue, Fri, Sat and Sun

Airports in Caribbean

1 airport
The best one-way flight to Caribbean from Milwaukee in the past 72 hours is $324. The best round-trip flight deal from Milwaukee to Caribbean found on momondo in the last 72 hours is $607.
The fastest flight from Milwaukee to Caribbean takes 4h 19m
Direct flights go from Milwaukee to Caribbean on Monday, Tuesday, Friday, Saturday and Sunday. The only airline offering direct flights is Sun Country Air.
There is 1 airport near Caribbean: Punta Cana (PUJ)
Search flight deals

  • When did momondo last update prices for flights from Milwaukee-Mitchell Airport to Caribbean?

    Prices for flights from Milwaukee-Mitchell Airport to Caribbean are updated daily.

  • How many operators does momondo search for flights from Milwaukee-Mitchell Airport to Caribbean?

  • How old do you have to be to fly from Milwaukee-Mitchell Airport to Caribbean?

    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.

  • What documentation or ID do you need to fly to Caribbean?

    The travel and health documents required for your trip to Caribbean can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Caribbean. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Milwaukee to Caribbean?

Best airlines flying from Milwaukee to Caribbean

Compare and see reviews for airlines that fly from Milwaukee to Caribbean with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $129Free CancellationRating
5.8
3,100 reviews
Search Frontier flights
United AirlinesPriceFrom $215Free CancellationRating
7.4
9,047 reviews
Search United Airlines flights
DeltaPriceFrom $215Free CancellationRating
7.9
7,998 reviews
Search Delta flights
Spirit AirlinesPriceFrom $226Free CancellationRating
6.3
8,158 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $274Free CancellationRating
7.2
11,038 reviews
Search American Airlines flights
SouthwestPriceFrom $315Free CancellationRating
8.0
4,253 reviews
Search Southwest flights
Sun Country AirPriceFrom $540Free 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?

It is quick and easy to find Milwaukee to Caribbean flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Caribbean that suits you.

Can I find flights from Milwaukee to Caribbean with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Caribbean from Milwaukee with this policy.

How can momondo help me find flights from Milwaukee to Caribbean?

Once you have performed a search for Milwaukee to Caribbean 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 right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Milwaukee to Caribbean now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Caribbean and let you know when they change.

An easier way to manage your Caribbean 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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Find better results for your trip to Caribbean

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Popular flights according to clicks in the last 7 days on momondo
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