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$80 Find cheap flights from Caribbean Islands to Milwaukee

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 5/22. 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
0 bags
Sat 6/8
Sat 6/15

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Good to know

Low season

February

High season

July

Cheapest flight

$80
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 23% increase in price.
Flight from San Juan to Milwaukee

FAQs for booking flights from Caribbean Islands to Milwaukee

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Milwaukee from Caribbean Islands 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 Islands 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 Islands with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean Islands 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 Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Caribbean Islands to Milwaukee?

Find which airlines fly direct from Caribbean Islands to Milwaukee-Mitchell, which days they fly and book direct flights.

Nonstop departures

Caribbean Islands to Milwaukee-Mitchell

Monday

ANA, Aer Lingus, Aeromexico, +27 more

ANA, Aer Lingus, +28 more

Tuesday

ANA, Aer Lingus, Aeromexico, +25 more

ANA, Aer Lingus, +26 more

Wednesday

ANA, Aer Lingus, Aeromexico, +28 more

ANA, Aer Lingus, +29 more

Thursday

ANA, Aer Lingus, Aeromexico, +27 more

ANA, Aer Lingus, +28 more

Friday

ANA, Aer Lingus, Aeromexico, +27 more

ANA, Aer Lingus, +28 more

Saturday

ANA, Aer Lingus, Aeromexico, +25 more

ANA, Aer Lingus, +26 more

Sunday

ANA, Aer Lingus, Aeromexico, +28 more

ANA, Aer Lingus, +29 more

See more direct flights

Nonstop returns

Milwaukee-Mitchell to Caribbean Islands

Monday

ANA, Aer Lingus, Aeromexico, +27 more

ANA, Aer Lingus, +28 more

Tuesday

ANA, Aer Lingus, Aeromexico, +25 more

ANA, Aer Lingus, +26 more

Wednesday

ANA, Aer Lingus, Aeromexico, +28 more

ANA, Aer Lingus, +29 more

Thursday

ANA, Aer Lingus, Aeromexico, +27 more

ANA, Aer Lingus, +28 more

Friday

ANA, Aer Lingus, Aeromexico, +27 more

ANA, Aer Lingus, +28 more

Saturday

ANA, Aer Lingus, Aeromexico, +25 more

ANA, Aer Lingus, +26 more

Sunday

ANA, Aer Lingus, Aeromexico, +28 more

ANA, Aer Lingus, +29 more

See more direct flights
See more direct flights

Top 3 airlines serving from Caribbean Islands to Milwaukee

 
Need help choosing which airline to fly with from Caribbean Islands 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.
8.0
DeltaOverall score based on 10778 reviews
7.9Comfort
7.4Food
8.0Entertainment
8.2Boarding
8.6Crew
Airline reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

Everything was great. The big planes could still stand to have a bit more leg room. Crew was amazing!!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

The flight was excellent, I recommend people to fly with Delta

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

The crew were very welcoming and helpful. I just wish economy had a bit more leg room. My knees were constantly hitting the chair in front of me.

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Check in etc was very good. As for on the plane, it was like flying in a freezer. It was so cold, i have flown for years and never been so cold on a plane. Staff on board said its always cold when flying which is a load of rubbish. They wouldnt put any heating on and now i have the flu because of this .

I’ve had a couple flights this week on United that were delayed by an hour or more

Surprisingly easy! I was hesitant to try this, but the cost swayed me. I actually felt like I had less stress than all the taxiing and possible delays that occur with short regional flights where you spend less time in the air than getting to and from the plane..

It was okay, no wifi or entertainment real disappointment. Staff onboard not very friendly.

This flight was delayed multiple times and eventually canceled around 2-3ish. Original take off time was around 10:30am. By 3, there were no other options out of Houston, so stuck in Houston for from 3pm - 11am the next day.

It started with multiple delays, cancellations, re booking, 5 hour lay over and finally on a plane from Chicago to Pittsburgh. Gates, times, etc were changed multiply times. Once on the plane, staff was fine, but built in tv did not work and could not even turn it off. Light at eye level the entire trip, so sleeping was near impossible. No snacks or drinks given.

Should have video screens Plane audio was poor and without wired connection hard to understand crew. Should serve more than just cups of water and pretzels on six hour flight. Did not see crew rest of flight. Fix charging sockets to retain charging blocks.

Only water and pretzels served on six hour flight. Did not see crew rest of flight. No video screens and so no wired audio. Poor sound on plan so did not understand anything said by crew. This is a safety issue. Electrical socket did not retain charging block so could not charge phone. No video screen so could not watch movies. Phone is not a substitute.

It was fine. Flight was on time and arrived at destination with 15 min to spare.

My bag was lost with my medicine and I am very inconvenienced. I don’t know what happened, however I want you to do a better job on getting people’s bag back

Worst situation ever! I booked my tickets for this trip on Alaska Airlines. I guess AA is a partner and we flew nonstop from Eugene to PHX on an AA jet. I had to pay for luggage from PHX to EUG. And this was an Alaska Airlines reservation paid for with Alaska airlines credit card! Got to the PHX airport and was not able to check bags because of some weird issue with the AA software. My reservation had to be the-entered by the agent. I will never pick another American Airlines flight on the Alaska Airlines website. While on vacation, I tried to upgrade our seats for the trip home. The request just buffered and never went through. I tried four times and was charged four times on my credit card. The card was charged but the seats were never changed. What a wreck!

Left from gate 30 minutes before flight. Never been late to a flight ever. It says 15 minutes before explicitly on the ticket.

I like the boarding process, it was fast. The seat doesn’t have a TV for a long flight and food wasn’t served, just snacks.

Left on time. Arrived early. Turbulence coming in and gate not open due to early arrival but expected.

Use planes with TVs on flights over 4 hours. The free entertainment was a cheap in between solution for a very long flight that you don't even bother providing meals or decent snacks.

Even though we left CMI late, we mostly made up the time.

Delayed almost 4 hours for a 45 minute flight with no explanation.

Again, multiple delays and I eventually just canceled and drove!

Great crew. We were delayed so that late passengers could get on the flight. Love the bedding in business class. Good food. Great experience.

The CX617 from HK to BKK was delayed more than 1.5 hours.

Book cheap flights from Caribbean Islands to Milwaukee

Recent round-trip flight deals

7/17Wed
1 stopFrontier
10h 08mSJU-MKE
7/23Tue
1 stopFrontier
12h 06mMKE-SJU
$290
6/13Thu
1 stopAmerican Airlines
17h 33mSJU-MKE
6/23Sun
1 stopAmerican Airlines
16h 56mMKE-SJU
$296
7/18Thu
1 stopSpirit Airlines
6h 56mSJU-MKE
7/23Tue
1 stopSpirit Airlines
6h 51mMKE-SJU
$313
6/6Thu
1 stopSpirit Airlines
9h 21mSJU-MKE
6/11Tue
1 stopSpirit Airlines
8h 36mMKE-SJU
$317
6/6Thu
2 stops
17h 22mSJU-MKE
6/11Tue
1 stop
8h 36mMKE-SJU
$332
6/12Wed
1 stop
21h 24mSJU-MKE
6/23Sun
1 stop
23h 00mMKE-SJU
$356
7/25Thu
1 stopDelta
8h 52mSJU-MKE
8/3Sat
1 stopDelta
8h 59mMKE-SJU
$389
6/14Fri
1 stopDelta
7h 39mSJU-MKE
6/22Sat
1 stopDelta
7h 29mMKE-SJU
$424
6/7Fri
1 stopUnited Airlines
7h 04mMBJ-MKE
6/14Fri
2 stopsUnited Airlines
28h 25mMKE-MBJ
$436
6/7Fri
2 stopsUnited Airlines
21h 23mMBJ-MKE
6/14Fri
2 stopsUnited Airlines
28h 25mMKE-MBJ
$481

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Recent one-way flight deals

5/22Wed
1 stopFrontier
28h 57mSJU-MKE
$80
5/28Tue
1 stopSpirit Airlines
17h 51mSJU-MKE
$115
5/22Wed
2 stopsFrontier
49h 09mSJU-MKE
$127
5/21Tue
1 stop
21h 51mSJU-MKE
$151
5/21Tue
1 stop
21h 51mSJU-MKE
$153
6/2Sun
2 stopsAmerican Airlines
27h 23mSTX-MKE
$186
6/14Fri
1 stopAmerican Airlines
16h 09mSJU-MKE
$188
5/21Tue
2 stopsUnited Airlines
11h 22mSJU-MKE
$222
8/1Thu
1 stopDelta
8h 26mSTT-MKE
$304
6/19Wed
2 stopsUnited Airlines
16h 30mSJU-MKE
$446

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Last minute flights from Caribbean Islands to Milwaukee

Last minute flight, train and bus deals

5/13Mon
multi-stopJetBlue
8h 16mSJU-MKE
5/15Wed
multi-stopJetBlue
8h 35mMKE-SJU
$445
5/14Tue
multi-stopJetBlue
7h 30mSJU-MKE
5/15Wed
multi-stopJetBlue
8h 35mMKE-SJU
$455
5/14Tue
multi-stopUnited Airlines
7h 38mSJU-MKE
5/15Wed
multi-stopUnited Airlines
10h 47mMKE-SJU
$519
5/13Mon
multi-stopJetBlue
8h 16mSJU-MKE
5/15Wed
multi-stopJetBlue
8h 35mMKE-SJU
$530
5/13Mon
multi-stopAmerican Airlines
10h 51mSJU-MKE
5/15Wed
multi-stopAmerican Airlines
18h 35mMKE-SJU
$567
5/14Tue
multi-stopUnited Airlines
10h 14mSJU-MKE
5/15Wed
multi-stopUnited Airlines
8h 27mMKE-SJU
$579
5/13Mon
multi-stopAmerican Airlines
16h 52mSJU-MKE
5/15Wed
multi-stopAmerican Airlines
11h 03mMKE-SJU
$618
5/10Fri
multi-stopSpirit Airlines
13h 16mSJU-MKE
5/13Mon
multi-stopSpirit Airlines
16h 54mMKE-SJU
$648
5/10Fri
multi-stopAmerican Airlines
11h 27mSJU-MKE
5/13Mon
multi-stopAmerican Airlines
12h 50mMKE-SJU
$666
5/13Mon
multi-stopUnited Airlines
11h 22mSJU-MKE
5/15Wed
multi-stopUnited Airlines
11h 57mMKE-SJU
$729

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Flights to Milwaukee