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Cheap flights from Caribbean Islands to Milwaukee from $111

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 Islands to Milwaukee 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.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Caribbean Islands to Milwaukee

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
2:22 pm - 9:10 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
7h 48m1 stop Philadelphia
American Airlines Logo
8:14 pm - 1:57 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
16h 43m2 stops Chicago O'Hare Intl Miami
$238American Airlines
Thu, Sep 17 - Tue, Sep 22
American Airlines Logo
3:51 pm - 11:57 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
9h 06m1 stop Charlotte Douglas
American Airlines Logo
6:27 pm - 12:09 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
16h 42m1 stop Charlotte Douglas
$238American Airlines
Fri, Oct 16 - Mon, Oct 19
Frontier Logo
2:57 am - 9:22 amSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
7h 25m1 stop Orlando
Frontier Logo
10:10 am - 5:43 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
6h 33m1 stop Orlando
$248Frontier
Sat, Sep 12 - Thu, Sep 24
Frontier Logo
2:57 am - 9:08 amSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
7h 11m1 stop Orlando
Frontier Logo
10:10 am - 11:13 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
12h 03m1 stop Orlando
$248Frontier
Wed, Sep 16 - Thu, Sep 24
Southwest Logo
6:30 am - 4:20 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
10h 50m1 stop Orlando
Southwest Logo
11:50 am - 11:55 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
11h 05m1 stop Baltimore/Washington
$292Southwest
Fri, Sep 18 - Sun, Sep 20
Southwest Logo
8:20 am - 4:20 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
9h 00m1 stop Orlando
Southwest Logo
3:00 pm - 11:45 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
7h 45m1 stop Orlando
$292Southwest
Wed, Sep 30 - Wed, Oct 14
United Airlines Logo
8:05 am - 5:43 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
11h 38m2 stops Washington, D.C. Dulles Intl Chicago O'Hare Intl
United Airlines Logo
12:03 pm - 9:00 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
6h 57m1 stop Chicago O'Hare Intl
$366United Airlines
Fri, Nov 13 - Mon, Nov 16
United Airlines Logo
1:00 am - 10:07 amSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
10h 07m2 stops Newark Chicago O'Hare Intl
United Airlines Logo
10:42 am - 11:50 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
12h 08m2 stops Chicago O'Hare Intl Newark
$392United Airlines
Wed, Oct 14 - Tue, Oct 20
Delta Logo
1:16 pm - 8:57 pmMBJ  Montego Bay Sangster Intl-MKE Milwaukee-Mitchell
7h 41m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:30 am - 11:51 amMKE  Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl
6h 21m1 stop Atlanta Hartsfield-Jackson
$462Delta
Sat, Oct 17 - Sun, Oct 25
Delta Logo
2:52 pm - 8:54 pmSTT  Saint Thomas Island Cyril E King-MKE Milwaukee-Mitchell
7h 02m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:30 am - 1:42 pmMKE  Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
7h 12m1 stop Atlanta Hartsfield-Jackson
$560Delta
Thu, Sep 24 - Tue, Sep 29

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American Airlines flights from Caribbean Islands to Milwaukee

Our best American Airlines deals on Caribbean Islands to Milwaukee flight tickets
American Airlines
Sep 17
SJU2:22 pmSan Juan Luis Munoz Marin Intl
7h 48m
1 stop
MKE9:10 pmMilwaukee-Mitchell
Sep 22
MKE8:14 pmMilwaukee-Mitchell
16h 43m
2 stops
SJU1:57 pmSan Juan Luis Munoz Marin Intl
$238
American Airlines
Oct 23
SJU2:54 pmSan Juan Luis Munoz Marin Intl
18h 13m
1 stop
MKE8:07 amMilwaukee-Mitchell
Nov 6
MKE6:31 pmMilwaukee-Mitchell
14h 13m
2 stops
SJU10:44 amSan Juan Luis Munoz Marin Intl
$243
American Airlines
Oct 23
SJU2:54 pmSan Juan Luis Munoz Marin Intl
18h 13m
1 stop
MKE8:07 amMilwaukee-Mitchell
Nov 6
MKE6:31 pmMilwaukee-Mitchell
16h 32m
1 stop
SJU1:03 pmSan Juan Luis Munoz Marin Intl
$244

Southwest flights from Caribbean Islands to Milwaukee

Our best Southwest deals on Caribbean Islands to Milwaukee flight tickets
Southwest
Sep 8
SJU6:00 amSan Juan Luis Munoz Marin Intl
7h 00m
1 stop
MKE12:00 pmMilwaukee-Mitchell
Sep 15
MKE2:05 pmMilwaukee-Mitchell
7h 00m
1 stop
SJU10:05 pmSan Juan Luis Munoz Marin Intl
$312
Southwest
Oct 1
SJU10:10 amSan Juan Luis Munoz Marin Intl
8h 40m
1 stop
MKE5:50 pmMilwaukee-Mitchell
Oct 14
MKE7:45 amMilwaukee-Mitchell
11h 45m
2 stops
SJU8:30 pmSan Juan Luis Munoz Marin Intl
$352
Southwest
Oct 15
SJU5:35 pmSan Juan Luis Munoz Marin Intl
7h 10m
1 stop
MKE11:45 pmMilwaukee-Mitchell
Oct 20
MKE10:20 amMilwaukee-Mitchell
10h 30m
2 stops
SJU9:50 pmSan Juan Luis Munoz Marin Intl
$366

momondo Fare Finder

 
Customize your flight search to find flights from Caribbean Islands 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 August 17, 2026.
Use the filters below to find and compare flights from Caribbean Islands to Milwaukee that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JuanMilwaukee

SJU San Juan Luis Munoz Marin Intl - MKE Milwaukee-Mitchell

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 9/17

2:22 pm-9:10 pm

1 stop7h 48m

Milwaukee-Mitchell

Tue 9/22

8:14 pm-1:57 pm

2 stops16h 43m

$238

San JuanMilwaukee

SJU San Juan Luis Munoz Marin Intl - MKE Milwaukee-Mitchell

SJUMKE

San Juan Luis Munoz Marin Intl

Fri 10/16

3:51 pm-11:57 pm

1 stop9h 06m

Milwaukee-Mitchell

Mon 10/19

6:27 pm-12:09 pm

1 stop16h 42m

$238
Quickest round-trip

San JuanMilwaukee

SJU San Juan Luis Munoz Marin Intl - MKE Milwaukee-Mitchell

SJUMKE

San Juan Luis Munoz Marin Intl

Sat 9/12

2:57 am-9:22 am

1 stop7h 25m

Milwaukee-Mitchell

Thu 9/24

10:10 am-5:43 pm

1 stop6h 33m

$248

San JuanMilwaukee

SJU San Juan Luis Munoz Marin Intl - MKE Milwaukee-Mitchell

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 9/16

2:57 am-9:08 am

1 stop7h 11m

Milwaukee-Mitchell

Thu 9/24

10:10 am-11:13 pm

1 stop12h 03m

$248

San JuanMilwaukee

SJU San Juan Luis Munoz Marin Intl - MKE Milwaukee-Mitchell

SJUMKE

San Juan Luis Munoz Marin Intl

Fri 9/18

6:30 am-4:20 pm

1 stop10h 50m

Milwaukee-Mitchell

Sun 9/20

11:50 am-11:55 pm

1 stop11h 05m

$292

San JuanMilwaukee

SJU San Juan Luis Munoz Marin Intl - MKE Milwaukee-Mitchell

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 9/30

8:20 am-4:20 pm

1 stop9h 00m

Milwaukee-Mitchell

Wed 10/14

3:00 pm-11:45 pm

1 stop7h 45m

$292

San JuanMilwaukee

SJU San Juan Luis Munoz Marin Intl - MKE Milwaukee-Mitchell

SJUMKE

San Juan Luis Munoz Marin Intl

Fri 11/13

8:05 am-5:43 pm

2 stops11h 38m

Milwaukee-Mitchell

Mon 11/16

12:03 pm-9:00 pm

1 stop6h 57m

$366

San JuanMilwaukee

SJU San Juan Luis Munoz Marin Intl - MKE Milwaukee-Mitchell

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 10/14

1:00 am-10:07 am

2 stops10h 07m

Milwaukee-Mitchell

Tue 10/20

10:42 am-11:50 pm

2 stops12h 08m

$392

Montego BayMilwaukee

MBJ Montego Bay Sangster Intl - MKE Milwaukee-Mitchell

MBJMKE

Montego Bay Sangster Intl

Sat 10/17

1:16 pm-8:57 pm

1 stop7h 41m

Milwaukee-Mitchell

Sun 10/25

5:30 am-11:51 am

1 stop6h 21m

$462

Saint Thomas IslandMilwaukee

STT Saint Thomas Island Cyril E King - MKE Milwaukee-Mitchell

STTMKE

Saint Thomas Island Cyril E King

Thu 9/24

2:52 pm-8:54 pm

1 stop7h 02m

Milwaukee-Mitchell

Tue 9/29

5:30 am-1:42 pm

1 stop7h 12m

$560

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 Islands 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 Islands is in August. Flight prices, which tend to average around $0, are often lower during this time because this is during the off-season. The month of July is another great option to travel to Milwaukee, with average flight prices from Caribbean Islands averaging around $0.

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

You are more likely to see cheaper flights to Milwaukee from Caribbean Islands when booking weeks ahead of your departure date. In general, you can expect to find flights to Milwaukee for around $381 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Milwaukee from Caribbean Islands for as low as $215 on momondo.

Can stopping save me money on Caribbean Islands to Milwaukee flights?

No. A direct flight is the cheapest option for a flight between Caribbean Islands to Milwaukee.

Cheap Caribbean Islands to Milwaukee flight deals and tips

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

Fastest flight time

6h 49m

Direct flights

Sat

Airports in Milwaukee

1 airport
The fastest flight from Caribbean Islands to Milwaukee takes 6h 49m
Direct flights go from Caribbean Islands to Milwaukee on Saturday. There are no airlines offering direct flights.
There is 1 airport in Milwaukee. From Caribbean Islands there are direct flights to Milwaukee-Mitchell (MKE).
Search flight deals

Frequently asked questions about flying from Caribbean Islands to Milwaukee

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

    Prices for flights from Caribbean Islands to Milwaukee-Mitchell Airport are updated daily.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Caribbean Islands to Milwaukee-Mitchell Airport.

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

    The travel and health documents you'll need for your trip to Milwaukee-Mitchell Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Milwaukee-Mitchell Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Caribbean Islands to Milwaukee?

Best airlines flying from Caribbean Islands to Milwaukee

Compare and see reviews for airlines that fly from Caribbean Islands to Milwaukee with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $118Free CancellationRating
7.8
8,503 reviews
Search Delta flights
United AirlinesPriceFrom $235Free CancellationRating
7.4
10,106 reviews
Search United Airlines flights
American AirlinesPriceFrom $235Free CancellationRating
7.1
11,944 reviews
Search American Airlines flights
SouthwestPriceFrom $256Free CancellationRating
8.0
4,218 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
West Bend
Port Washington
Kohler
Pewaukee
New Berlin
Grafton

Why use momondo?

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

Finding the right flight to Milwaukee from Caribbean Islands 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 Islands to Milwaukee with flexible booking policies on momondo?

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

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

momondo provides multiple filters to help you find the best flight to Milwaukee from Caribbean Islands. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

If you are simply researching potential flights to Milwaukee, momondo offers a useful price alert feature which will track prices for flights to Milwaukee from Caribbean Islands and alert you when they change.

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