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Cheap flights from Milwaukee to Caribbean from $101

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 3/10. 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

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
7:47 pm - 1:27 pm
MKE
-
SJU
15h 40m
1 stop
Frontier Logo
3:53 am - 3:44 pm
SJU
-
MKE
13h 51m
1 stop
$255Frontier
Sat, Feb 21 - Tue, Feb 24
United Airlines Logo
9:44 am - 9:00 pm
MKE
-
SJU
9h 16m
1 stop
United Airlines Logo
8:30 am - 3:35 pm
SJU
-
MKE
9h 05m
1 stop
$256United Airlines
Mon, Mar 2 - Wed, Mar 4
Southwest Logo
3:10 pm - 12:15 am
MKE
-
SJU
8h 05m
1 stop
Southwest Logo
5:15 am - 11:35 am
SJU
-
MKE
7h 20m
1 stop
$285Southwest
Wed, Mar 11 - Wed, Mar 18
Multiple Airlines Logo
8:11 pm - 2:31 pm
MKE
-
STT
16h 20m
1 stop
Multiple Airlines Logo
2:36 pm - 7:30 am
STT
-
MKE
17h 54m
1 stop
$299Multiple Airlines
Mon, Mar 2 - Wed, Mar 11
Multiple Airlines Logo
8:11 pm - 2:31 pm
MKE
-
STT
16h 20m
1 stop
Multiple Airlines Logo
4:40 pm - 7:30 am
STT
-
MKE
15h 50m
2 stops
$326Multiple Airlines
Mon, Mar 2 - Wed, Mar 11
American Airlines Logo
3:11 pm - 12:18 pm
MKE
-
PLS
20h 07m
2 stops
American Airlines Logo
11:14 am - 5:47 pm
PLS
-
MKE
7h 33m
1 stop
$368American Airlines
Sat, Feb 28 - Fri, Mar 6
American Airlines Logo
10:00 am - 1:24 pm
MKE
-
PLS
26h 24m
1 stop
American Airlines Logo
11:14 am - 5:47 pm
PLS
-
MKE
7h 33m
1 stop
$369American Airlines
Sat, Feb 28 - Fri, Mar 6
Delta Logo
5:21 am - 11:48 am
MKE
-
NAS
5h 27m
1 stop
Delta Logo
1:13 pm - 8:35 pm
NAS
-
MKE
8h 22m
1 stop
$420Delta
Sun, Apr 26 - Wed, May 6
Delta Logo
5:25 am - 3:19 pm
MKE
-
MBJ
8h 54m
1 stop
Delta Logo
1:38 pm - 8:55 pm
MBJ
-
MKE
7h 17m
1 stop
$424Delta
Tue, Mar 3 - Wed, Mar 11
Southwest Logo
6:50 am - 6:30 pm
MKE
-
NAS
10h 40m
2 stops
Southwest Logo
2:10 pm - 10:15 pm
NAS
-
MKE
9h 05m
2 stops
$444Southwest
Mon, Apr 20 - Fri, Apr 24

Southwest flights from Milwaukee to Caribbean

Our best Southwest deals on Milwaukee to Caribbean flight tickets
Southwest
Mar 11
MKE3:10 pmMilwaukee-Mitchell
8h 05m
1 stop
SJU12:15 amSan Juan Luis Munoz Marin Intl
Mar 18
SJU5:15 amSan Juan Luis Munoz Marin Intl
7h 20m
1 stop
MKE11:35 amMilwaukee-Mitchell
$285
Southwest
Mar 2
MKE6:45 amMilwaukee-Mitchell
10h 35m
2 stops
SJU7:20 pmSan Juan Luis Munoz Marin Intl
Mar 10
SJU5:15 amSan Juan Luis Munoz Marin Intl
7h 20m
1 stop
MKE11:35 amMilwaukee-Mitchell
$314
Southwest
Mar 11
MKE3:40 pmMilwaukee-Mitchell
7h 35m
2 stops
SJU12:15 amSan Juan Luis Munoz Marin Intl
Mar 18
SJU5:15 amSan Juan Luis Munoz Marin Intl
7h 20m
1 stop
MKE11:35 amMilwaukee-Mitchell
$332

Delta flights from Milwaukee to Caribbean

Our best Delta deals on Milwaukee to Caribbean flight tickets
Delta
Mar 2
MKE5:23 amMilwaukee-Mitchell
10h 04m
1 stop
SJU5:27 pmSan Juan Luis Munoz Marin Intl
Mar 4
SJU6:37 pmSan Juan Luis Munoz Marin Intl
7h 10m
1 stop
MKE11:47 pmMilwaukee-Mitchell
$308
Delta
Mar 4
MKE10:10 amMilwaukee-Mitchell
9h 02m
1 stop
SJU9:12 pmSan Juan Luis Munoz Marin Intl
Mar 6
SJU7:30 amSan Juan Luis Munoz Marin Intl
9h 20m
1 stop
MKE2:50 pmMilwaukee-Mitchell
$318
Delta
Mar 5
MKE12:20 pmMilwaukee-Mitchell
9h 38m
1 stop
SJU11:58 pmSan Juan Luis Munoz Marin Intl
Mar 7
SJU6:15 amSan Juan Luis Munoz Marin Intl
9h 01m
1 stop
MKE1:16 pmMilwaukee-Mitchell
$360

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 February 11, 2026.
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

Sat 2/21

7:47 pm-1:27 pm

1 stop15h 40m

San Juan Luis Munoz Marin Intl

Tue 2/24

3:53 am-3:44 pm

1 stop13h 51m

$255

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 3/2

9:44 am-9:00 pm

1 stop9h 16m

San Juan Luis Munoz Marin Intl

Wed 3/4

8:30 am-3:35 pm

1 stop9h 05m

$256

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 3/11

3:10 pm-12:15 am

1 stop8h 05m

San Juan Luis Munoz Marin Intl

Wed 3/18

5:15 am-11:35 am

1 stop7h 20m

$285

MilwaukeeSaint Thomas Island

MKE - STT

MKESTT

Milwaukee-Mitchell

Mon 3/2

8:11 pm-2:31 pm

1 stop16h 20m

Saint Thomas Island Cyril E King

Wed 3/11

2:36 pm-7:30 am

1 stop17h 54m

$299

MilwaukeeSaint Thomas Island

MKE - STT

MKESTT

Milwaukee-Mitchell

Mon 3/2

8:11 pm-2:31 pm

1 stop16h 20m

Saint Thomas Island Cyril E King

Wed 3/11

4:40 pm-7:30 am

2 stops15h 50m

$326

MilwaukeeProvidenciales

MKE - PLS

MKEPLS

Milwaukee-Mitchell

Sat 2/28

3:11 pm-12:18 pm

2 stops20h 07m

Providenciales

Fri 3/6

11:14 am-5:47 pm

1 stop7h 33m

$368

MilwaukeeProvidenciales

MKE - PLS

MKEPLS

Milwaukee-Mitchell

Sat 2/28

10:00 am-1:24 pm

1 stop26h 24m

Providenciales

Fri 3/6

11:14 am-5:47 pm

1 stop7h 33m

$369

MilwaukeeNassau

MKE - NAS

MKENAS

Milwaukee-Mitchell

Sun 4/26

5:21 am-11:48 am

1 stop5h 27m

Nassau Intl

Wed 5/6

1:13 pm-8:35 pm

1 stop8h 22m

$420

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Tue 3/3

5:25 am-3:19 pm

1 stop8h 54m

Montego Bay Sangster Intl

Wed 3/11

1:38 pm-8:55 pm

1 stop7h 17m

$424

MilwaukeeNassau

MKE - NAS

MKENAS

Milwaukee-Mitchell

Mon 4/20

6:50 am-6:30 pm

2 stops10h 40m

Nassau Intl

Fri 4/24

2:10 pm-10:15 pm

2 stops9h 05m

$444

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 $317.

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

Fly from Milwaukee-Mitchell to Punta Cana 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 $444 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 $383 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 56% 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

$230

Fastest flight time

4h 19m

Direct flights

Mon, Tue, Fri, Sat and Sun

Airports in Caribbean

195 airports
The best one-way flight to Caribbean from Milwaukee in the past 72 hours is $230. The best round-trip flight deal from Milwaukee to Caribbean found on momondo in the last 72 hours is $628.
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 are 195 airports in Caribbean. 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?

    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 $85Free CancellationRating
5.7
3,052 reviews
Search Frontier flights
DeltaPriceFrom $118Free CancellationRating
7.9
8,180 reviews
Search Delta flights
United AirlinesPriceFrom $182Free CancellationRating
7.4
9,274 reviews
Search United Airlines flights
Spirit AirlinesPriceFrom $195Free CancellationRating
6.3
8,444 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $266Free CancellationRating
7.2
11,266 reviews
Search American Airlines flights
SouthwestPriceFrom $315Free CancellationRating
8.0
4,280 reviews
Search Southwest flights
Sun Country AirPriceFrom $547Free CancellationRating
6.8
342 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

Popular cities in Caribbean

Popular flights according to clicks in the last 7 days on momondo
Flights to San Juanfrom $92
Flights to Punta Canafrom $186
Flights to Santo Domingofrom $193
Flights to Montego Bayfrom $219
Flights to Oranjestadfrom $190
Flights to Nassaufrom $245
Flights to Santiago de los Caballerosfrom $203
Flights to Saint Thomas Islandfrom $120
Flights to Kingstonfrom $286
Flights to Simpson Bayfrom $174
Flights to Willemstadfrom $230
Flights to Port of Spainfrom $242