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Cheap flights from Caribbean to Milwaukee from $163

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 8/19. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Caribbean to Milwaukee

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
2:59 pm - 8:53 pm
SJU
-
MKE
6h 54m
1 stop
Delta Logo
7:03 am - 4:38 pm
MKE
-
SJU
8h 35m
1 stop
$326Delta
Thu, Aug 27 - Mon, Aug 31
American Airlines Logo
1:38 pm - 10:59 pm
SJU
-
MKE
10h 21m
2 stops
American Airlines Logo
6:28 am - 6:34 pm
MKE
-
SJU
11h 06m
2 stops
$331American Airlines
Wed, Aug 19 - Wed, Aug 26
American Airlines Logo
4:38 pm - 8:01 am
SJU
-
MKE
16h 23m
2 stops
American Airlines Logo
4:26 pm - 11:50 pm
MKE
-
SJU
6h 24m
1 stop
$333American Airlines
Mon, Sep 28 - Tue, Oct 6
American Airlines Logo
7:00 am - 11:14 pm
SJU
-
MKE
17h 14m
1 stop
American Airlines Logo
8:20 am - 11:15 pm
MKE
-
SJU
13h 55m
1 stop
$336American Airlines
Fri, Aug 14 - Sun, Aug 23
United Airlines Logo
1:00 am - 11:30 am
SJU
-
MKE
11h 30m
2 stops
United Airlines Logo
7:18 am - 8:38 pm
MKE
-
SJU
12h 20m
2 stops
$361United Airlines
Mon, Oct 5 - Tue, Oct 20
American Airlines Logo
1:38 pm - 9:47 pm
SJU
-
MKE
9h 09m
2 stops
American Airlines Logo
6:20 am - 6:34 pm
MKE
-
SJU
11h 14m
2 stops
$366American Airlines
Thu, Aug 27 - Mon, Aug 31
Southwest Logo
6:35 am - 12:05 pm
SJU
-
MKE
7h 30m
1 stop
Southwest Logo
7:55 pm - 10:00 am
MKE
-
SJU
12h 05m
1 stop
$371Southwest
Sun, Nov 1 - Fri, Nov 6
American Airlines Logo
7:00 am - 11:14 pm
SJU
-
MKE
17h 14m
1 stop
American Airlines Logo
2:49 pm - 11:59 pm
MKE
-
SJU
8h 10m
1 stop
$373American Airlines
Fri, Aug 7 - Fri, Aug 14
Delta Logo
4:59 pm - 11:49 pm
MBJ
-
MKE
6h 50m
1 stop
Delta Logo
5:45 am - 1:20 pm
MKE
-
MBJ
7h 35m
1 stop
$377Delta
Sat, Oct 17 - Sun, Oct 25
United Airlines Logo
5:20 pm - 1:43 pm
PUJ
-
MKE
22h 23m
3 stops
United Airlines Logo
7:00 am - 5:25 pm
MKE
-
PUJ
8h 25m
2 stops
$604United Airlines
Wed, Nov 11 - Sun, Nov 15

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American Airlines flights from Caribbean to Milwaukee

Our best American Airlines deals on Caribbean to Milwaukee flight tickets
American Airlines
Aug 19
SJU1:38 pmSan Juan Luis Munoz Marin Intl
10h 21m
2 stops
MKE10:59 pmMilwaukee-Mitchell
Aug 26
MKE6:28 amMilwaukee-Mitchell
11h 06m
2 stops
SJU6:34 pmSan Juan Luis Munoz Marin Intl
$331
American Airlines
Sep 28
SJU4:38 pmSan Juan Luis Munoz Marin Intl
16h 23m
2 stops
MKE8:01 amMilwaukee-Mitchell
Oct 6
MKE4:26 pmMilwaukee-Mitchell
6h 24m
1 stop
SJU11:50 pmSan Juan Luis Munoz Marin Intl
$333
American Airlines
Aug 14
SJU7:00 amSan Juan Luis Munoz Marin Intl
17h 14m
1 stop
MKE11:14 pmMilwaukee-Mitchell
Aug 23
MKE8:20 amMilwaukee-Mitchell
13h 55m
1 stop
SJU11:15 pmSan Juan Luis Munoz Marin Intl
$336

Delta flights from Caribbean to Milwaukee

Our best Delta deals on Caribbean to Milwaukee flight tickets
Delta
Aug 27
SJU2:59 pmSan Juan Luis Munoz Marin Intl
6h 54m
1 stop
MKE8:53 pmMilwaukee-Mitchell
Aug 31
MKE7:03 amMilwaukee-Mitchell
8h 35m
1 stop
SJU4:38 pmSan Juan Luis Munoz Marin Intl
$326
Delta
Oct 17
MBJ4:59 pmMontego Bay Sangster Intl
6h 50m
1 stop
MKE11:49 pmMilwaukee-Mitchell
Oct 25
MKE5:45 amMilwaukee-Mitchell
7h 35m
1 stop
MBJ1:20 pmMontego Bay Sangster Intl
$377
Delta
Aug 5
SJU5:49 pmSan Juan Luis Munoz Marin Intl
7h 04m
1 stop
MKE11:53 pmMilwaukee-Mitchell
Aug 14
MKE12:51 pmMilwaukee-Mitchell
8h 38m
1 stop
SJU10:29 pmSan Juan Luis Munoz Marin Intl
$401

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 June 18, 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

Cheapest round-trip

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 8/27

2:59 pm-8:53 pm

1 stop6h 54m

Milwaukee-Mitchell

Mon 8/31

7:03 am-4:38 pm

1 stop8h 35m

$326

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 8/19

1:38 pm-10:59 pm

2 stops10h 21m

Milwaukee-Mitchell

Wed 8/26

6:28 am-6:34 pm

2 stops11h 06m

$331

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Mon 9/28

4:38 pm-8:01 am

2 stops16h 23m

Milwaukee-Mitchell

Tue 10/6

4:26 pm-11:50 pm

1 stop6h 24m

$333

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Fri 8/14

7:00 am-11:14 pm

1 stop17h 14m

Milwaukee-Mitchell

Sun 8/23

8:20 am-11:15 pm

1 stop13h 55m

$336

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Mon 10/5

1:00 am-11:30 am

2 stops11h 30m

Milwaukee-Mitchell

Tue 10/20

7:18 am-8:38 pm

2 stops12h 20m

$361

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 8/27

1:38 pm-9:47 pm

2 stops9h 09m

Milwaukee-Mitchell

Mon 8/31

6:20 am-6:34 pm

2 stops11h 14m

$366

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Sun 11/1

6:35 am-12:05 pm

1 stop7h 30m

Milwaukee-Mitchell

Fri 11/6

7:55 pm-10:00 am

1 stop12h 05m

$371

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Fri 8/7

7:00 am-11:14 pm

1 stop17h 14m

Milwaukee-Mitchell

Fri 8/14

2:49 pm-11:59 pm

1 stop8h 10m

$373
Quickest round-trip

Montego BayMilwaukee

MBJ - MKE

MBJMKE

Montego Bay Sangster Intl

Sat 10/17

4:59 pm-11:49 pm

1 stop6h 50m

Milwaukee-Mitchell

Sun 10/25

5:45 am-1:20 pm

1 stop7h 35m

$377

Punta CanaMilwaukee

PUJ - MKE

PUJMKE

Punta Cana

Wed 11/11

5:20 pm-1:43 pm

3 stops22h 23m

Milwaukee-Mitchell

Sun 11/15

7:00 am-5:25 pm

2 stops8h 25m

$604

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 May. Flight prices, which tend to average around $98, are often lower during this time because this is during the off-season. The month of October is another great option to travel to Milwaukee, with average flight prices from Caribbean averaging around $108.

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 from Caribbean 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 $385 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 $215 on momondo.

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

There is only 1 cabin class available to choose from on Caribbean to Milwaukee 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 66% 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

6h 54m

Direct flights

None
The fastest flight from Caribbean to Milwaukee takes 6h 54m
There are no direct flights from Caribbean to Milwaukee. There are no popular flight routes from Caribbean to Milwaukee.
Search flight deals

Frequently asked questions about flying from Caribbean to Milwaukee

  • 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
7.8
8,417 reviews
Search Delta flights
United AirlinesPriceFrom $235Free CancellationRating
7.4
9,860 reviews
Search United Airlines flights
American AirlinesPriceFrom $235Free CancellationRating
7.1
11,703 reviews
Search American Airlines flights
SouthwestPriceFrom $256Free CancellationRating
7.9
4,239 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
West Bend
Port Washington
Kohler
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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