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Cheap flights from Caribbean to Milwaukee 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 Caribbean to Milwaukee 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.
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0 bags

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Find the cheapest flights from Caribbean to Milwaukee

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
8:00 am - 6:01 pm
SJU
-
MKE
12h 01m1 stop
Frontier Logo
7:28 pm - 3:26 pm
MKE
-
SJU
17h 58m1 stop
$215Frontier
Wed, Jan 28 - Fri, Feb 6
American Airlines Logo
2:31 pm - 10:49 pm
SJU
-
MKE
10h 18m1 stop
American Airlines Logo
6:06 am - 8:50 pm
MKE
-
SJU
12h 44m1 stop
$235American Airlines
Tue, Jan 13 - Wed, Jan 21
American Airlines Logo
6:30 am - 8:24 pm
SJU
-
MKE
15h 54m1 stop
American Airlines Logo
12:07 pm - 10:26 pm
MKE
-
SJU
8h 19m1 stop
$243American Airlines
Wed, Jan 21 - Wed, Jan 28
Frontier Logo
3:55 am - 11:13 am
SJU
-
MKE
9h 18m1 stop
Frontier Logo
12:08 pm - 2:50 am
MKE
-
SJU
12h 42m1 stop
$284Frontier
Sun, Dec 28 - Mon, Jan 5
Multiple Airlines Logo
5:09 pm - 7:03 pm
SJU
-
MKE
27h 54m1 stop
Multiple Airlines Logo
8:15 pm - 10:33 am
MKE
-
SJU
12h 18m1 stop
$305Multiple Airlines
Fri, Dec 19 - Wed, Dec 31
Southwest Logo
10:20 am - 7:55 pm
SJU
-
MKE
11h 35m2 stops
Southwest Logo
11:25 am - 10:25 pm
MKE
-
SJU
9h 00m1 stop
$313Southwest
Wed, Jan 28 - Fri, Feb 6
United Airlines Logo
12:56 pm - 10:56 pm
PUJ
-
MKE
12h 00m2 stops
United Airlines Logo
2:32 pm - 4:14 pm
MKE
-
PUJ
23h 42m2 stops
$445United Airlines
Thu, Jan 22 - Fri, Feb 6
Delta Logo
3:45 pm - 11:46 pm
PUJ
-
MKE
10h 01m1 stop
Delta Logo
7:05 am - 4:21 pm
MKE
-
PUJ
7h 16m1 stop
$487Delta
Wed, Jan 21 - Wed, Feb 4
United Airlines Logo
4:25 pm - 10:13 pm
PUJ
-
MKE
7h 48m1 stop
United Airlines Logo
5:00 am - 2:22 pm
MKE
-
PUJ
7h 22m1 stop
$514United Airlines
Mon, Dec 29 - Thu, Jan 1
Delta Logo
4:55 pm - 11:27 pm
MBJ
-
MKE
6h 32m1 stop
Delta Logo
5:55 am - 1:16 pm
MKE
-
MBJ
7h 21m1 stop
$519Delta
Fri, May 22 - Fri, May 29

Spirit Airlines flights from Caribbean to Milwaukee

Our best Spirit Airlines deals on Caribbean to Milwaukee flight tickets
Spirit Airlines
Dec 22
SJU11:38 amSan Juan Luis Munoz Marin Intl
9h 42m
1 stop
MKE7:20 pmMilwaukee-Mitchell
Jan 3
MKE8:15 pmMilwaukee-Mitchell
12h 18m
1 stop
SJU10:33 amSan Juan Luis Munoz Marin Intl
$342
Find similar
Spirit Airlines
Dec 23
SJU11:38 amSan Juan Luis Munoz Marin Intl
9h 42m
1 stop
MKE7:20 pmMilwaukee-Mitchell
Jan 3
MKE8:15 pmMilwaukee-Mitchell
16h 05m
1 stop
SJU2:20 pmSan Juan Luis Munoz Marin Intl
$344
Find similar
Spirit Airlines
Dec 19
SJU11:38 amSan Juan Luis Munoz Marin Intl
9h 42m
1 stop
MKE7:20 pmMilwaukee-Mitchell
Dec 31
MKE8:15 pmMilwaukee-Mitchell
23h 50m
2 stops
SJU10:05 pmSan Juan Luis Munoz Marin Intl
$378
Find similar

Frontier flights from Caribbean to Milwaukee

Our best Frontier deals on Caribbean to Milwaukee flight tickets
Frontier
Jan 28
SJU8:00 amSan Juan Luis Munoz Marin Intl
12h 01m
1 stop
MKE6:01 pmMilwaukee-Mitchell
Feb 6
MKE7:28 pmMilwaukee-Mitchell
17h 58m
1 stop
SJU3:26 pmSan Juan Luis Munoz Marin Intl
$215
Find similar
Frontier
Dec 11
SJU5:09 pmSan Juan Luis Munoz Marin Intl
26h 00m
1 stop
MKE5:09 pmMilwaukee-Mitchell
Dec 14
MKE6:09 pmMilwaukee-Mitchell
13h 46m
1 stop
SJU9:55 amSan Juan Luis Munoz Marin Intl
$268
Find similar
Frontier
Dec 28
SJU3:55 amSan Juan Luis Munoz Marin Intl
9h 18m
1 stop
MKE11:13 amMilwaukee-Mitchell
Jan 5
MKE12:08 pmMilwaukee-Mitchell
12h 42m
1 stop
SJU2:50 amSan Juan Luis Munoz Marin Intl
$284
Find similar

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 December 9, 2025.
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

Wed 1/28

8:00 am-6:01 pm

1 stop12h 01m

Milwaukee-Mitchell

Fri 2/6

7:28 pm-3:26 pm

1 stop17h 58m

$215

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Tue 1/13

2:31 pm-10:49 pm

1 stop10h 18m

Milwaukee-Mitchell

Wed 1/21

6:06 am-8:50 pm

1 stop12h 44m

$235

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 1/21

6:30 am-8:24 pm

1 stop15h 54m

Milwaukee-Mitchell

Wed 1/28

12:07 pm-10:26 pm

1 stop8h 19m

$243

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Sun 12/28

3:55 am-11:13 am

1 stop9h 18m

Milwaukee-Mitchell

Mon 1/5

12:08 pm-2:50 am

1 stop12h 42m

$284

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Fri 12/19

5:09 pm-7:03 pm

1 stop27h 54m

Milwaukee-Mitchell

Wed 12/31

8:15 pm-10:33 am

1 stop12h 18m

$305

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 1/28

10:20 am-7:55 pm

2 stops11h 35m

Milwaukee-Mitchell

Fri 2/6

11:25 am-10:25 pm

1 stop9h 00m

$313

Punta CanaMilwaukee

PUJ - MKE

PUJMKE

Punta Cana

Thu 1/22

12:56 pm-10:56 pm

2 stops12h 00m

Milwaukee-Mitchell

Fri 2/6

2:32 pm-4:14 pm

2 stops23h 42m

$445

Punta CanaMilwaukee

PUJ - MKE

PUJMKE

Punta Cana

Wed 1/21

3:45 pm-11:46 pm

1 stop10h 01m

Milwaukee-Mitchell

Wed 2/4

7:05 am-4:21 pm

1 stop7h 16m

$487

Punta CanaMilwaukee

PUJ - MKE

PUJMKE

Punta Cana

Mon 12/29

4:25 pm-10:13 pm

1 stop7h 48m

Milwaukee-Mitchell

Thu 1/1

5:00 am-2:22 pm

1 stop7h 22m

$514

Montego BayMilwaukee

MBJ - MKE

MBJMKE

Montego Bay Sangster Intl

Fri 5/22

4:55 pm-11:27 pm

1 stop6h 32m

Milwaukee-Mitchell

Fri 5/29

5:55 am-1:16 pm

1 stop7h 21m

$519

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 September. Flight prices, which tend to average around $298, 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 $301.

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

According to our data, Thursday is the cheapest day to fly to Milwaukee from Caribbean. The lowest ticket price found for a Thursday departure recently was $331. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. Flights from Caribbean to Milwaukee on a Sunday will generally be more expensive and average around $624. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

In the evening is the cheapest time of day to fly from Caribbean to Milwaukee when you can find flight prices for as low as $404. Flying to Milwaukee in the evening is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Milwaukee, so prices are often more expensive at around $429 per ticket.

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 $383 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 $286 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 62% 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 30m

Direct flights

Mon, Fri and Sun

Airports in Milwaukee

1 airport
The fastest flight from Caribbean to Milwaukee takes 6h 30m
Direct flights go from Caribbean to Milwaukee on Monday, Friday and Sunday. There are no airlines offering direct flights.
There is 1 airport near Milwaukee: 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 $118Free CancellationRating
7.9
8,007 reviews
Search Delta flights
Spirit AirlinesPriceFrom $182Free CancellationRating
6.3
8,174 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $215Free CancellationRating
7.4
9,092 reviews
Search United Airlines flights
American AirlinesPriceFrom $235Free CancellationRating
7.2
11,048 reviews
Search American Airlines flights
SouthwestPriceFrom $305Free CancellationRating
7.9
4,253 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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