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Cheap flights from Caribbean to Milwaukee from $105

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Caribbean to Milwaukee departing on 4/22. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
6:00 am - 9:41 pm
SJU
-
MKE
16h 41m
1 stop
American Airlines Logo
6:00 am - 2:29 pm
MKE
-
SJU
7h 29m
1 stop
$216American Airlines
qua, abr 15 - qua, abr 29
Delta Logo
12:55 pm - 11:57 pm
SJU
-
MKE
12h 02m
1 stop
Delta Logo
12:33 pm - 8:24 pm
MKE
-
SJU
6h 51m
1 stop
$236Delta
qua, abr 15 - qua, abr 29
Frontier Logo
3:08 am - 11:08 am
SJU
-
MKE
9h 00m
1 stop
Frontier Logo
12:03 pm - 2:01 am
MKE
-
SJU
12h 58m
1 stop
$244Frontier
qua, mai 13 - dom, mai 17
Delta Logo
7:30 am - 1:52 pm
SJU
-
MKE
7h 22m
1 stop
Delta Logo
12:33 pm - 8:24 pm
MKE
-
SJU
6h 51m
1 stop
$266Delta
qua, abr 15 - qua, abr 29
American Airlines Logo
6:45 am - 10:27 pm
SJU
-
MKE
16h 42m
1 stop
American Airlines Logo
6:00 am - 8:51 pm
MKE
-
SJU
13h 51m
2 stops
$270American Airlines
qui, abr 23 - ter, abr 28
Frontier Logo
3:53 am - 3:44 pm
SJU
-
MKE
13h 51m
1 stop
Frontier Logo
12:36 pm - 1:58 am
MKE
-
SJU
12h 22m
1 stop
$295Frontier
ter, mar 3 - seg, mar 9
Frontier Logo
5:30 am - 5:02 pm
SJU
-
MKE
12h 32m
1 stop
Frontier Logo
8:20 pm - 2:03 am
MKE
-
SJU
28h 43m
1 stop
$298Frontier
sex, mar 27 - seg, mar 30
Delta Logo
5:34 pm - 11:57 pm
SJU
-
MKE
7h 23m
1 stop
Delta Logo
7:10 am - 4:31 pm
MKE
-
SJU
8h 21m
1 stop
$302Delta
sex, abr 24 - qua, abr 29
United Airlines Logo
4:12 pm - 5:53 pm
MBJ
-
MKE
25h 41m
2 stops
United Airlines Logo
8:45 pm - 1:30 pm
MKE
-
MBJ
16h 45m
2 stops
$460United Airlines
ter, mai 26 - sex, set 4
United Airlines Logo
4:12 pm - 11:08 am
MBJ
-
MKE
18h 56m
2 stops
United Airlines Logo
10:45 am - 1:30 pm
MKE
-
MBJ
26h 45m
2 stops
$467United Airlines
ter, mai 26 - sex, set 4

American Airlines flights from Caribbean to Milwaukee

Our best American Airlines deals on Caribbean to Milwaukee flight tickets
American Airlines
Apr 15
SJU6:00 amSan Juan Luis Munoz Marin Intl
7h 32m
1 stop
MKE12:32 pmMilwaukee-Mitchell
Apr 29
MKE6:00 amMilwaukee-Mitchell
7h 29m
1 stop
SJU2:29 pmSan Juan Luis Munoz Marin Intl
$216
American Airlines
Apr 23
SJU6:45 amSan Juan Luis Munoz Marin Intl
16h 42m
1 stop
MKE10:27 pmMilwaukee-Mitchell
Apr 28
MKE6:00 amMilwaukee-Mitchell
13h 51m
2 stops
SJU8:51 pmSan Juan Luis Munoz Marin Intl
$270
American Airlines
Apr 23
SJU6:45 amSan Juan Luis Munoz Marin Intl
16h 42m
1 stop
MKE10:27 pmMilwaukee-Mitchell
Apr 29
MKE5:00 pmMilwaukee-Mitchell
15h 13m
2 stops
SJU9:13 amSan Juan Luis Munoz Marin Intl
$304

Frontier flights from Caribbean to Milwaukee

Our best Frontier deals on Caribbean to Milwaukee flight tickets
Frontier
May 13
SJU3:08 amSan Juan Luis Munoz Marin Intl
9h 00m
1 stop
MKE11:08 amMilwaukee-Mitchell
May 17
MKE12:03 pmMilwaukee-Mitchell
12h 58m
1 stop
SJU2:01 amSan Juan Luis Munoz Marin Intl
$244
Frontier
Mar 12
SJU3:08 amSan Juan Luis Munoz Marin Intl
17h 58m
1 stop
MKE8:06 pmMilwaukee-Mitchell
Mar 17
MKE6:35 pmMilwaukee-Mitchell
6h 28m
1 stop
SJU2:03 amSan Juan Luis Munoz Marin Intl
$270
Frontier
Mar 3
SJU3:53 amSan Juan Luis Munoz Marin Intl
13h 51m
1 stop
MKE3:44 pmMilwaukee-Mitchell
Mar 9
MKE12:36 pmMilwaukee-Mitchell
12h 22m
1 stop
SJU1:58 amSan Juan Luis Munoz Marin Intl
$295

momondo Fare Finder

 
Customize your flight search to find flights from Caribbean to Milwaukee 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 março 1, 2026.
Use the filters below to find and compare flights from Caribbean to Milwaukee that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

qua 4/15

6:00 am-9:41 pm

1 stop16h 41m

Milwaukee-Mitchell

qua 4/29

6:00 am-2:29 pm

1 stop7h 29m

$216

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

qua 4/15

12:55 pm-11:57 pm

1 stop12h 02m

Milwaukee-Mitchell

qua 4/29

12:33 pm-8:24 pm

1 stop6h 51m

$236

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

qua 5/13

3:08 am-11:08 am

1 stop9h 00m

Milwaukee-Mitchell

dom 5/17

12:03 pm-2:01 am

1 stop12h 58m

$244

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

qua 4/15

7:30 am-1:52 pm

1 stop7h 22m

Milwaukee-Mitchell

qua 4/29

12:33 pm-8:24 pm

1 stop6h 51m

$266

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

qui 4/23

6:45 am-10:27 pm

1 stop16h 42m

Milwaukee-Mitchell

ter 4/28

6:00 am-8:51 pm

2 stops13h 51m

$270

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

ter 3/3

3:53 am-3:44 pm

1 stop13h 51m

Milwaukee-Mitchell

seg 3/9

12:36 pm-1:58 am

1 stop12h 22m

$295

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

sex 3/27

5:30 am-5:02 pm

1 stop12h 32m

Milwaukee-Mitchell

seg 3/30

8:20 pm-2:03 am

1 stop28h 43m

$298

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

sex 4/24

5:34 pm-11:57 pm

1 stop7h 23m

Milwaukee-Mitchell

qua 4/29

7:10 am-4:31 pm

1 stop8h 21m

$302

Montego BayMilwaukee

MBJ - MKE

MBJMKE

Montego Bay Sangster Intl

ter 5/26

4:12 pm-5:53 pm

2 stops25h 41m

Milwaukee-Mitchell

sex 9/4

8:45 pm-1:30 pm

2 stops16h 45m

$460

Montego BayMilwaukee

MBJ - MKE

MBJMKE

Montego Bay Sangster Intl

ter 5/26

4:12 pm-11:08 am

2 stops18h 56m

Milwaukee-Mitchell

sex 9/4

10:45 am-1:30 pm

2 stops26h 45m

$467

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 Milwaukee from

How to get the cheapest flight ticket from Caribbean to Milwaukee

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 Milwaukee?

The cheapest month to fly to Milwaukee from Caribbean is in January. Flight prices, which tend to average around $253, are often lower during this time because this is during the off-season. The month of February is another great option to travel to Milwaukee, with average flight prices from Caribbean averaging around $286.

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

Fly from Punta Cana to Milwaukee-Mitchell for the best Caribbean - Milwaukee-Mitchell flight prices

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

You are more likely to see cheaper flights to Milwaukee from Caribbean when booking weeks ahead of your departure date. In general, you can expect to find flights to Milwaukee for around $376 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Milwaukee from Caribbean for as low as $262 on momondo.

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

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

You could potentially save up to 64% on your flight if you consider stops on a Caribbean to Milwaukee flight.

Cheap Caribbean to Milwaukee flight deals and tips

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

Fastest flight time

5h 16m

Direct flights

Tue, Fri, Sat and Sun

Airports in Milwaukee

1 airport
The fastest flight from Caribbean to Milwaukee takes 5h 16m
Direct flights go from Caribbean to Milwaukee on Tuesday, Friday, Saturday and Sunday. The only airline offering direct flights is Sun Country Air.
There is 1 airport in Milwaukee. From Caribbean there are direct flights to Milwaukee-Mitchell (MKE).
Search flight deals

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

    Prices for flights from Caribbean to Milwaukee-Mitchell Airport are refreshed on a daily basis.

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Caribbean to Milwaukee-Mitchell Airport.

  • What documentation or ID do you need to fly to Milwaukee-Mitchell Airport?

    The travel and health documents required for your trip to Milwaukee-Mitchell Airport 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 Milwaukee-Mitchell Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Caribbean to Milwaukee

Compare and see reviews for airlines that fly from Caribbean to Milwaukee with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $112Free CancellationRating
7.9
8,244 reviews
Search Delta flights
Spirit AirlinesPriceFrom $140Free CancellationRating
6.3
8,490 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $215Free CancellationRating
7.4
9,370 reviews
Search United Airlines flights
American AirlinesPriceFrom $235Free CancellationRating
7.1
11,370 reviews
Search American Airlines flights
SouthwestPriceFrom $256Free CancellationRating
8.0
4,303 reviews
Search Southwest flights

Traveling to a place near Milwaukee?

Book flights to Milwaukee if you plan to visit one of these locations
Sheboygan
Waukesha
Wauwatosa
Oak Creek
Mequon
Glendale
Pewaukee
Kohler
Port Washington
West Bend
New Berlin
Grafton

Why use momondo?

Why should I use momondo to find a flight deal from Caribbean to Milwaukee?

Finding the right flight to Milwaukee from Caribbean is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Milwaukee quick and easy, saving you time and money.

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

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

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Milwaukee from Caribbean.

I’m not ready to book a flight from Caribbean to Milwaukee right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Caribbean to Milwaukee flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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