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Cheap flights from Milwaukee to Caribbean from $108

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 9/16. 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

Cheap round-trip flights

American Airlines Logo
3:47 pm - 11:11 amMKE-SJU
18h 24m2 stops
American Airlines Logo
6:10 am - 11:43 pmSJU-MKE
18h 33m2 stops
$215American Airlines
Find Deal
Tue, Sep 16 - Tue, Sep 23
United Airlines Logo
6:05 am - 3:40 pmMKE-SJU
7h 35m1 stop
United Airlines Logo
2:05 am - 11:29 amSJU-MKE
11h 24m2 stops
$237United Airlines
Find Deal
Tue, Nov 11 - Wed, Nov 26
American Airlines Logo
6:00 am - 11:05 pmMKE-SJU
16h 05m1 stop
American Airlines Logo
7:10 am - 12:14 amSJU-MKE
18h 04m1 stop
$240American Airlines
Find Deal
Sat, Oct 11 - Thu, Oct 16
Southwest Logo
7:00 am - 3:10 pmMKE-SJU
7h 10m1 stop
Southwest Logo
5:50 am - 3:45 pmSJU-MKE
10h 55m1 stop
$265Southwest
Find Deal
Mon, Sep 8 - Fri, Sep 12
Delta Logo
7:00 am - 4:51 pmMKE-SJU
7h 51m1 stop
Delta Logo
6:15 am - 1:47 pmSJU-MKE
9h 32m1 stop
$274Delta
Find Deal
Mon, Feb 9 - Sat, Feb 14
Southwest Logo
6:00 am - 6:45 pmMKE-SJU
11h 45m2 stops
Southwest Logo
5:50 am - 3:45 pmSJU-MKE
10h 55m1 stop
$289Southwest
Find Deal
Fri, Sep 26 - Mon, Sep 29
Delta Logo
7:00 am - 4:51 pmMKE-SJU
7h 51m1 stop
Delta Logo
2:12 pm - 8:12 pmSJU-MKE
8h 00m1 stop
$333Delta
Find Deal
Thu, Jan 29 - Mon, Feb 2
Spirit Airlines Logo
11:57 am - 3:11 pmMKE-STT
25h 14m1 stop
Spirit Airlines Logo
4:06 pm - 12:51 pmSTT-MKE
22h 45m1 stop
$371Spirit Airlines
Find Deal
Wed, Dec 3 - Sun, Dec 7
Spirit Airlines Logo
11:57 am - 12:28 pmMKE-STT
22h 31m2 stops
Spirit Airlines Logo
4:06 pm - 12:51 pmSTT-MKE
22h 45m1 stop
$386Spirit Airlines
Find Deal
Wed, Dec 3 - Sun, Dec 7
Sun Country Air Logo
8:00 am - 2:19 pmMKE-PUJ
4h 19mnonstop
Sun Country Air Logo
3:19 pm - 6:36 pmPUJ-MKE
5h 17mnonstop
$637Sun Country Air
Find Deal
Sun, Feb 1 - Fri, Feb 6

American Airlines flights from Milwaukee to Caribbean

Our best American Airlines deals on Milwaukee to Caribbean flight tickets
American Airlines
Sep 16
MKE3:47 pmMilwaukee-Mitchell
18h 24m
2 stops
SJU11:11 amSan Juan Luis Munoz Marin Intl
Sep 23
SJU6:10 amSan Juan Luis Munoz Marin Intl
18h 33m
2 stops
MKE11:43 pmMilwaukee-Mitchell
$215
Find similar
American Airlines
Oct 11
MKE6:00 amMilwaukee-Mitchell
16h 05m
1 stop
SJU11:05 pmSan Juan Luis Munoz Marin Intl
Oct 16
SJU7:10 amSan Juan Luis Munoz Marin Intl
18h 04m
1 stop
MKE12:14 amMilwaukee-Mitchell
$240
Find similar
American Airlines
Sep 21
MKE5:05 amMilwaukee-Mitchell
17h 32m
2 stops
SJU11:37 pmSan Juan Luis Munoz Marin Intl
Sep 24
SJU4:43 pmSan Juan Luis Munoz Marin Intl
7h 17m
1 stop
MKE11:00 pmMilwaukee-Mitchell
$245
Find similar

United Airlines flights from Milwaukee to Caribbean

Our best United Airlines deals on Milwaukee to Caribbean flight tickets
United Airlines
Nov 11
MKE6:05 amMilwaukee-Mitchell
7h 35m
1 stop
SJU3:40 pmSan Juan Luis Munoz Marin Intl
Nov 26
SJU2:05 amSan Juan Luis Munoz Marin Intl
11h 24m
2 stops
MKE11:29 amMilwaukee-Mitchell
$237
Find similar
United Airlines
Jan 31
MKE12:14 pmMilwaukee-Mitchell
10h 22m
2 stops
SJU12:36 amSan Juan Luis Munoz Marin Intl
Feb 6
SJU2:05 amSan Juan Luis Munoz Marin Intl
9h 41m
1 stop
MKE9:46 amMilwaukee-Mitchell
$258
Find similar
United Airlines
Jan 31
MKE12:14 pmMilwaukee-Mitchell
10h 22m
2 stops
SJU12:36 amSan Juan Luis Munoz Marin Intl
Feb 6
SJU2:05 amSan Juan Luis Munoz Marin Intl
9h 41m
1 stop
MKE9:46 amMilwaukee-Mitchell
$292
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 August 15, 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

Tue 9/16

3:47 pm-11:11 am

2 stops18h 24m

San Juan Luis Munoz Marin Intl

Tue 9/23

6:10 am-11:43 pm

2 stops18h 33m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 11/11

6:05 am-3:40 pm

1 stop7h 35m

San Juan Luis Munoz Marin Intl

Wed 11/26

2:05 am-11:29 am

2 stops11h 24m

$237

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 10/11

6:00 am-11:05 pm

1 stop16h 05m

San Juan Luis Munoz Marin Intl

Thu 10/16

7:10 am-12:14 am

1 stop18h 04m

$240

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 9/8

7:00 am-3:10 pm

1 stop7h 10m

San Juan Luis Munoz Marin Intl

Fri 9/12

5:50 am-3:45 pm

1 stop10h 55m

$265

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 2/9

7:00 am-4:51 pm

1 stop7h 51m

San Juan Luis Munoz Marin Intl

Sat 2/14

6:15 am-1:47 pm

1 stop9h 32m

$274

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Fri 9/26

6:00 am-6:45 pm

2 stops11h 45m

San Juan Luis Munoz Marin Intl

Mon 9/29

5:50 am-3:45 pm

1 stop10h 55m

$289

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Thu 1/29

7:00 am-4:51 pm

1 stop7h 51m

San Juan Luis Munoz Marin Intl

Mon 2/2

2:12 pm-8:12 pm

1 stop8h 00m

$333

MilwaukeeSaint Thomas Island

MKE - STT

MKESTT

Milwaukee-Mitchell

Wed 12/3

11:57 am-3:11 pm

1 stop25h 14m

Saint Thomas Island Cyril E King

Sun 12/7

4:06 pm-12:51 pm

1 stop22h 45m

$371

MilwaukeeSaint Thomas Island

MKE - STT

MKESTT

Milwaukee-Mitchell

Wed 12/3

11:57 am-12:28 pm

2 stops22h 31m

Saint Thomas Island Cyril E King

Sun 12/7

4:06 pm-12:51 pm

1 stop22h 45m

$386

MilwaukeePunta Cana

MKE - PUJ

MKEPUJ

Milwaukee-Mitchell

Sun 2/1

8:00 am-2:19 pm

Nonstop4h 19m

Punta Cana

Fri 2/6

3:19 pm-6:36 pm

Nonstop5h 17m

$637

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 $325. 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 $347.

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 $438 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 $357 on momondo.

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

There are 1 cabin classes 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 64% 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

$108

Fastest flight time

4h 19m

Direct flights

Mon, Fri and Sun

Airports in Caribbean

8 airports
The best one-way flight to Caribbean from Milwaukee in the past 72 hours is $108. The best round-trip flight deal from Milwaukee to Caribbean found on momondo in the last 72 hours is $215.
The fastest flight from Milwaukee to Caribbean takes 4h 19m
Direct flights go from Milwaukee to Caribbean on Monday, Friday and Sunday. The only airline offering direct flights is Sun Country Air.
There are 8 airports near Caribbean: George Town Owen Roberts Intl (GCM), Santo Domingo Las Americas (SDQ), Nassau Intl (NAS), Saint Thomas Island Cyril E King (STT), Punta Cana (PUJ), Montego Bay Sangster Intl (MBJ), Providenciales (PLS), San Juan Luis Munoz Marin Intl (SJU)
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  • 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
3,217 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $208Free CancellationRating
6.3
8,046 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $215Free CancellationRating
7.4
8,915 reviews
Search United Airlines flights
DeltaPriceFrom $225Free CancellationRating
8.0
7,982 reviews
Search Delta flights
American AirlinesPriceFrom $275Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $323Free CancellationRating
8.0
4,244 reviews
Search Southwest flights
Sun Country AirPriceFrom $519Free 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

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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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