$163 Find Cheap Flights from Caribbean to Milwaukee - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Milwaukee departing on 8/19. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Caribbean to Milwaukee

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean to Milwaukee that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Caribbean to Milwaukee

Thu, Aug 27 - Sun, Aug 30
Southwest Logo
2:35 pm - 8:45 pm
SJU
-
MKE
7h 10m
1 stop
Southwest Logo
2:10 pm - 12:30 am
MKE
-
SJU
9h 20m
1 stop
$326Southwest
Wed, Aug 19 - Wed, Aug 26
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
Fri, Jul 31 - Sat, Aug 15
American Airlines Logo
5:14 pm - 12:22 pm
MBJ
-
MKE
19h 08m
2 stops
American Airlines Logo
6:48 pm - 1:34 pm
MKE
-
MBJ
18h 46m
2 stops
$331American Airlines
Tue, Aug 4 - Fri, Sep 4
American Airlines Logo
7:00 am - 11:08 pm
SJU
-
MKE
17h 08m
1 stop
American Airlines Logo
6:20 am - 6:34 pm
MKE
-
SJU
11h 14m
2 stops
$333American Airlines
Mon, Oct 5 - Tue, Oct 20
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
Sat, Oct 17 - Sun, Oct 25
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
Thu, Dec 3 - Sun, Dec 6
United Airlines Logo
6:32 pm - 9:46 am
PUJ
-
MKE
17h 14m
1 stop
United Airlines Logo
8:45 pm - 4:02 pm
MKE
-
PUJ
17h 17m
1 stop
$443United Airlines
Wed, Jul 15 - Sat, Jul 25
Delta Logo
4:59 pm - 11:56 pm
MBJ
-
MKE
6h 57m
1 stop
Delta Logo
6:50 am - 3:34 pm
MKE
-
MBJ
8h 44m
1 stop
$486Delta
Sat, Aug 29 - Tue, Sep 15
Multiple Airlines Logo
7:30 am - 8:18 pm
PUJ
-
MKE
13h 48m
2 stops
Multiple Airlines Logo
12:05 pm - 11:00 am
MKE
-
PUJ
21h 55m
2 stops
$1,390Multiple Airlines
Sat, Aug 29 - Tue, Sep 15
Multiple Airlines Logo
7:30 am - 8:18 pm
PUJ
-
MKE
13h 48m
2 stops
Multiple Airlines Logo
12:05 pm - 4:05 pm
MKE
-
PUJ
27h 00m
3 stops
$1,506Multiple Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$163
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from San Juan to Milwaukee

FAQs for booking flights from Caribbean to Milwaukee

  • How does KAYAK find such low prices on flights from Caribbean to Milwaukee?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Caribbean to Milwaukee.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean to Milwaukee?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Milwaukee from Caribbean is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Caribbean to Milwaukee?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Milwaukee with an airline and back to Caribbean with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean to Milwaukee?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Milwaukee from Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 4 airlines serving from Caribbean to Milwaukee

 
Need help choosing which airline to fly with from Caribbean to Milwaukee? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
SouthwestOverall score based on 4235 reviews
8.0Comfort
8.1Boarding
7.5Entertainment
7.0Food
8.6Crew
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

Gate agent showed up 20 minutes before boarding and was not at all friendly. Had to take this flight due to the one on the day before being cancelled and any later options were already full with long standby lists. Despite having paid for Delta Comfort seats, Delta did not allow me (or anyone) to choose their seat. The agent assigned them for everyone just prior to boarding. Self seat selection was allowed on the original flight. Flight staff was great - very friendly.

Crew helpful. Plenty of food although not great but ok. Good time.

Flight attendants were great. Cheerful, upbeat and friendly. Jet, in particular, was fantastic.

I have Precheck. Flew HPN to DEN and return this past weekend. Delta didn't attach my Precheck number to this trip. So it was waiting in general line especially in Denver. Unavailable.

Original flight was delayed, then cancelled and the gate staff did not expedite rebooking. Also, no instructions were given that a ticket number was needed before being called to facilitate rebooking. This could have been much more organized.

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

Five hour delays every hour, I wish it were all at once

Flight delayed four separate times. I’m now one hour hours late to landing.

worst flight ever from Delta, it got delayed and kept on delaying..

Should never have had to go to Detroit from Orlando back to Tennessee!

Airline tickets are not cheap. You expect reliable competent service. Thanks to canceled flights and botched transfers we arrived at our destination two days late. This is not acceptable

The flight got delayed. They forgot to bring the drinks when I asked for it. The toilet is messy.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

The entertainment is a bit limited, it would be better if they added some games to play besides the movies and tv shows. But the seats are comfortable and the crew is polite

This planes staff was top tier. Everything went great and had a great flight home.

Food was great. Staff was phenomenal. Seats were a bit hard and could use a lot more entertainment options as far as movies to choose from. WiFi was good. Overall great trip.

This was an overnight flight, and in the morning they did know coffee service. How you can throw passengers in a San Francisco airport at 5:40 a.m. in the morning and not giving them Coffee is a crime.

Our flight was delayed several Times due to mechanical issues. Although I understand this may happen at times, it was very inconvenient and we had to book a hotel for an overnight stay. We were traveling with my 3-yo grandson and waiting at the airport from noon until 6:30pm with no reassurance that our next rescheduled flight would depart, we had to decide what’s best for him. A day later, I found out that I may be able to demand compensation if my flight is delayed more than 4 hours. I will hav to read the fine print next time.

The pilot had to extend the flight time from san antonio to Houston to burn off fuel. This caused a lot of unnecessary stress since we had a tight connection to Aruba. And with no other flights going to Aruba we were worried about spending a night in Houston. We had to to run to our connection because of the flight crews mistake. Not happy.

Service was professional and quick. Premium economy seat was comfortable given the class

technology worked well and everything ran smoothly. The seats are quite cramped so please don't try to re-engineer the cabin to squeeze more bodies on board.

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

Flight was delayed due to connecting passengers. Lack of snack options bad. Sitting in Aisle, last cart run pulled the cart directly into my knee. Rude awakening.

We sat on plane at gate delayed without communication as to why we were just sitting there

Agency very bad had to cancelled my booking too many changes in the flight changed my flight to 1 week

Trash. Sat on the runway for 40 mins…missed connecting flight because of it now I’m stuck. Thanks…a whole fkn lot.

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The plane was comfortable but the crew wasn’t friendly.

Awfully rude American worker at door when we started boarding flight. Then, walk into a blazing hot airplane with no air conditioning until twenty minutes into the flight. Free entertainment was non existent! My husband, along with the fellow passenger in our row, and I could not get entertainment to work, no WIFI! Really?? Been flying American a long time. Was very disappointed.

Flight was delayed by 6 hours... the level of incompetence was truly astounding. I won't be flying American Airlines again. I don't care if AA is direct and there is a layover with another airline, I'll take the layover.

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