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Cheap flights from Caribbean to Milwaukee from $94

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 5/9. 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 Caribbean to Milwaukee

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:56 pm - 11:56 pm
SJU
-
MKE
7h 00m
1 stop
Delta Logo
12:20 pm - 10:23 pm
MKE
-
SJU
9h 03m
1 stop
$289Delta
Tue, Aug 4 - Fri, Sep 4
American Airlines Logo
12:25 pm - 10:47 pm
MBJ
-
MKE
10h 22m
1 stop
American Airlines Logo
4:33 pm - 9:10 am
MKE
-
MBJ
16h 37m
1 stop
$316American Airlines
Fri, May 8 - Thu, Sep 10
American Airlines Logo
2:29 pm - 10:47 pm
MBJ
-
MKE
8h 18m
1 stop
American Airlines Logo
4:33 pm - 10:50 am
MKE
-
MBJ
18h 17m
2 stops
$321American Airlines
Fri, May 8 - Thu, Sep 10
American Airlines Logo
10:17 am - 10:47 pm
MBJ
-
MKE
12h 30m
1 stop
American Airlines Logo
5:50 pm - 4:13 pm
MKE
-
MBJ
22h 23m
1 stop
$323American Airlines
Fri, May 15 - Fri, Sep 4
Delta Logo
5:45 pm - 11:25 pm
SJU
-
MKE
6h 40m
1 stop
Delta Logo
5:55 am - 4:35 pm
MKE
-
SJU
9h 40m
1 stop
$326Delta
Thu, Aug 27 - Mon, Aug 31
American Airlines Logo
12:56 pm - 7:41 am
MBJ
-
MKE
18h 45m
2 stops
American Airlines Logo
5:05 am - 12:31 pm
MKE
-
MBJ
7h 26m
1 stop
$326American Airlines
Thu, May 14 - Wed, Sep 2
Southwest Logo
6:50 am - 7:10 pm
SJU
-
MKE
13h 20m
1 stop
Southwest Logo
1:35 pm - 12:25 am
MKE
-
SJU
9h 50m
1 stop
$365Southwest
Mon, Jun 1 - Sun, Jun 7
United Airlines Logo
4:12 pm - 11:31 am
MBJ
-
MKE
19h 19m
2 stops
United Airlines Logo
10:38 am - 3:10 pm
MKE
-
MBJ
28h 32m
2 stops
$374United Airlines
Wed, May 13 - Sat, May 23
Southwest Logo
7:00 am - 6:50 pm
SJU
-
MKE
12h 50m
1 stop
Southwest Logo
8:15 pm - 9:00 am
MKE
-
SJU
11h 45m
1 stop
$387Southwest
Thu, Jun 11 - Mon, Jun 22
United Airlines Logo
10:30 am - 10:59 pm
CPX
-
MKE
13h 29m
2 stops
United Airlines Logo
5:56 pm - 4:13 pm
MKE
-
CPX
45h 17m
2 stops
$1,980United Airlines
Fri, May 8 - Tue, May 12

Southwest flights from Caribbean to Milwaukee

Our best Southwest deals on Caribbean to Milwaukee flight tickets
Southwest
Jun 1
SJU6:50 amSan Juan Luis Munoz Marin Intl
13h 20m
1 stop
MKE7:10 pmMilwaukee-Mitchell
Jun 7
MKE1:35 pmMilwaukee-Mitchell
9h 50m
1 stop
SJU12:25 amSan Juan Luis Munoz Marin Intl
$365
Southwest
Jun 11
SJU7:00 amSan Juan Luis Munoz Marin Intl
12h 50m
1 stop
MKE6:50 pmMilwaukee-Mitchell
Jun 22
MKE8:15 pmMilwaukee-Mitchell
11h 45m
1 stop
SJU9:00 amSan Juan Luis Munoz Marin Intl
$387
Southwest
Jul 4
SJU6:00 amSan Juan Luis Munoz Marin Intl
6h 40m
1 stop
MKE11:40 amMilwaukee-Mitchell
Jul 18
MKE2:35 pmMilwaukee-Mitchell
8h 30m
1 stop
SJU12:05 amSan Juan Luis Munoz Marin Intl
$404

American Airlines flights from Caribbean to Milwaukee

Our best American Airlines deals on Caribbean to Milwaukee flight tickets
American Airlines
May 8
MBJ12:25 pmMontego Bay Sangster Intl
10h 22m
1 stop
MKE10:47 pmMilwaukee-Mitchell
Sep 10
MKE4:33 pmMilwaukee-Mitchell
16h 37m
1 stop
MBJ9:10 amMontego Bay Sangster Intl
$316
American Airlines
May 8
MBJ12:56 pmMontego Bay Sangster Intl
18h 45m
2 stops
MKE7:41 amMilwaukee-Mitchell
Sep 10
MKE4:33 pmMilwaukee-Mitchell
18h 17m
2 stops
MBJ10:50 amMontego Bay Sangster Intl
$321
American Airlines
May 15
MBJ10:17 amMontego Bay Sangster Intl
12h 30m
1 stop
MKE10:47 pmMilwaukee-Mitchell
Sep 4
MKE5:50 pmMilwaukee-Mitchell
22h 23m
1 stop
MBJ4:13 pmMontego Bay Sangster Intl
$323

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 April 21, 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
Quickest round-trip

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Tue 8/4

5:56 pm-11:56 pm

1 stop7h 00m

Milwaukee-Mitchell

Fri 9/4

12:20 pm-10:23 pm

1 stop9h 03m

$289

Montego BayMilwaukee

MBJ - MKE

MBJMKE

Montego Bay Sangster Intl

Fri 5/8

12:25 pm-10:47 pm

1 stop10h 22m

Milwaukee-Mitchell

Thu 9/10

4:33 pm-9:10 am

1 stop16h 37m

$316

Montego BayMilwaukee

MBJ - MKE

MBJMKE

Montego Bay Sangster Intl

Fri 5/8

2:29 pm-10:47 pm

1 stop8h 18m

Milwaukee-Mitchell

Thu 9/10

4:33 pm-10:50 am

2 stops18h 17m

$321

Montego BayMilwaukee

MBJ - MKE

MBJMKE

Montego Bay Sangster Intl

Fri 5/15

10:17 am-10:47 pm

1 stop12h 30m

Milwaukee-Mitchell

Fri 9/4

5:50 pm-4:13 pm

1 stop22h 23m

$323

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 8/27

5:45 pm-11:25 pm

1 stop6h 40m

Milwaukee-Mitchell

Mon 8/31

5:55 am-4:35 pm

1 stop9h 40m

$326

Montego BayMilwaukee

MBJ - MKE

MBJMKE

Montego Bay Sangster Intl

Thu 5/14

12:56 pm-7:41 am

2 stops18h 45m

Milwaukee-Mitchell

Wed 9/2

5:05 am-12:31 pm

1 stop7h 26m

$326

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Mon 6/1

6:50 am-7:10 pm

1 stop13h 20m

Milwaukee-Mitchell

Sun 6/7

1:35 pm-12:25 am

1 stop9h 50m

$365

Montego BayMilwaukee

MBJ - MKE

MBJMKE

Montego Bay Sangster Intl

Wed 5/13

4:12 pm-11:31 am

2 stops19h 19m

Milwaukee-Mitchell

Sat 5/23

10:38 am-3:10 pm

2 stops28h 32m

$374

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 6/11

7:00 am-6:50 pm

1 stop12h 50m

Milwaukee-Mitchell

Mon 6/22

8:15 pm-9:00 am

1 stop11h 45m

$387

CulebraMilwaukee

CPX - MKE

CPXMKE

Culebra

Fri 5/8

10:30 am-10:59 pm

2 stops13h 29m

Milwaukee-Mitchell

Tue 5/12

5:56 pm-4:13 pm

2 stops45h 17m

$1,980

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 $294.

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 $371 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-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 74% 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 41m

Direct flights

None
The fastest flight from Caribbean to Milwaukee takes 6h 41m
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
7.9
8,434 reviews
Search Delta flights
United AirlinesPriceFrom $235Free CancellationRating
7.4
9,613 reviews
Search United Airlines flights
American AirlinesPriceFrom $235Free CancellationRating
7.1
11,645 reviews
Search American Airlines flights
SouthwestPriceFrom $256Free CancellationRating
8.0
4,331 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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