$101 Find Cheap Flights from Caribbean 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 3/10. 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

Wed, May 13 - Sun, May 17
Frontier Logo
3:08 am - 11:08 am
SJU
-
MKE
9h 00m
1 stop
Frontier Logo
12:03 pm - 2:01 am
MKE
-
SJU
12h 58m
1 stop
$223Frontier
Wed, Apr 15 - Wed, Apr 29
Delta Logo
7:30 am - 1:52 pm
SJU
-
MKE
7h 22m
1 stop
Delta Logo
2:50 pm - 11:13 pm
MKE
-
SJU
7h 23m
1 stop
$236Delta
Wed, Apr 15 - Wed, Apr 29
American Airlines Logo
11:59 pm - 10:59 am
SJU
-
MKE
12h 00m
1 stop
American Airlines Logo
6:00 am - 10:05 pm
MKE
-
SJU
15h 05m
1 stop
$243American Airlines
Thu, Apr 23 - Tue, Apr 28
American Airlines Logo
6:45 am - 10:27 pm
SJU
-
MKE
16h 42m
1 stop
American Airlines Logo
5:06 am - 6:10 pm
MKE
-
SJU
12h 04m
2 stops
$244American Airlines
Wed, Mar 11 - Sun, Mar 15
Frontier Logo
6:30 am - 5:50 pm
SJU
-
MKE
12h 20m
1 stop
Frontier Logo
7:44 pm - 2:13 am
MKE
-
SJU
29h 29m
1 stop
$249Frontier
Sat, May 23 - Sat, Jun 6
Delta Logo
6:15 am - 4:57 pm
SJU
-
MKE
11h 42m
1 stop
Delta Logo
10:22 am - 8:30 pm
MKE
-
SJU
9h 08m
1 stop
$266Delta
Wed, Apr 15 - Wed, Apr 29
American Airlines Logo
11:59 pm - 10:59 am
SJU
-
MKE
12h 00m
1 stop
American Airlines Logo
6:00 am - 10:05 pm
MKE
-
SJU
15h 05m
1 stop
$272American Airlines
Thu, Apr 9 - Thu, Apr 16
United Airlines Logo
4:12 pm - 4:47 pm
MBJ
-
MKE
24h 35m
2 stops
United Airlines Logo
7:27 pm - 3:10 pm
MKE
-
MBJ
19h 43m
2 stops
$356United Airlines
Tue, May 26 - Fri, Sep 4
United Airlines Logo
4:12 pm - 5:53 pm
MBJ
-
MKE
25h 41m
2 stops
United Airlines Logo
8:45 pm - 1:30 pm
MKE
-
MBJ
16h 45m
2 stops
$460United Airlines
Fri, Apr 10 - Fri, Apr 17
Southwest Logo
4:00 pm - 11:10 pm
PUJ
-
MKE
8h 10m
1 stop
Southwest Logo
5:30 am - 1:05 pm
MKE
-
PUJ
6h 35m
1 stop
$1,586Southwest
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$101
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 14% 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 5 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.
8.0
SouthwestOverall score based on 4299 reviews
7.5Entertainment
7.0Food
8.0Comfort
8.6Crew
8.1Boarding
Airline reviews

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

2.0 MediocreAnonymous, Feb 2026
BWI - PBI
Read more Southwest reviews

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

I have not flown Southwest in awhile and had a very pleasant experience. From ticketing to boarding to the flight. The flight left on time and landed ahead of schedule. It won't be so long next time!!

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

Great plane, great attendants,great flight crew,on time. Wonderful flight home..

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

The charges were ridiculous for an hour flight and the turbulence was very scary.

Still need to work out the kinks on the new assigned seating boarding process. Otherwise, a very good flight.

WiFi did not work. Boarding with the new seating assignments took too long. The temperature in the terminal was obnoxious. +/- 80°

2+hrs delay without any reason provided and a cramped flight

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

Flight was delayed due to crew being not on time

Flight crew issues delayed my flight by 2 1/2 hours. Causing me to miss my connection.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

Never got on it. Was re-routed through Detroit and am still in airports 12 hours later waiting for my connecting plane to arrive.

Delta has too many delays now days. It is 1:06 am now. I was supposed to land in Norfolk at 10:30 pm. I got re-booked through Detroit and I’m still in Detroit. I hope to be landed in Norfolk by 3am. I’ve been in airports for 12 hours as of right now. There is a weather delay now but most delays lately have been maintenance.

Very Very late. Subsequent flights left an hour before ours

We got delayed three hours and nobody thought to have the bathroom fixed while we were sitting waiting to board? took a full hour to have maintenance come and check it off. Had to shut the bathroom down twice so that the pilots could go to the bathroom. Everyone missed their connections.

Given I (and I’m assuming most people) have both carry in and a personal item included in their fare, I find it very unfair that on neither of my flights I was able to use the overhead for my small backpack because they were completely rammed with luggage, people personal items, jackets, hats and other items. So the only item I brought in had to be stuffed under my seat while they had their leg room and sat comfortable with all of their items in the overhead. This has to stop because I was uncomfortable on both flights when I only had one smaller item that could not be checked due to its contents (medication etc). Plenty of people could have checked theirs but chose not to and then took up the space allotment for 2 people.

Flight left on time and we arrived 25 minutes early! There was a gate available when we arrived so early on a busy Sunday afternoon! Flight attendants came around twice with the drinks cart.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

I couldn’t make my first flight due to weather delays trapping us in the town we were in. Then I had to buy a new ticket

Flight attendants had a little attitude. Food tastes no good.

Chargers didn’t work, no entertainment and we had to wait for taxiing for easily 40 minutes after arriving early. Bags were late too!

Everything was great except for the boarding process. Everyone is lining up all at the same time and it’s hard to tell between the groups as they are way too large.

Women boarding passengers at the gate was absolutely rude and disrespectful of passengers. The flight attendant was absolutely delightful! Smiling and connected with the passengers. So happy. The seats are cramped and uncomfortable but I guess that’s just the way it is Communication regarding flight was excellent

Overall we had a good experience during our flight from San Francisco to Houston.

Arrived early picked up my bag in a few minutes- great trip - thank you

Flight boarded, departed and landed on time. Excellent service from flight attendant in FIRST

Boarding is always an ordeal. Less dogs on flights. I am highly allergic to dogs and cats. Why are there so many animals these days?

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

Massimo, flight attendant was very authentic, attentive - wonderful. Food/wrap was just okay.

Worst experience ever. Flight could not land in Charlotte for what we were told was a ground stop. Had to be diverted to Raleigh to refuel. Strangely during ground stop, our connecting flight had no issue taking off on time causing us to miss our flight. We were told there were no other flights that day to our final destination and that two days out was the next one. The only flights to get us there were from Chicago the next morning. Completely opposite direction but it was a direct flight. So we get flown to Chicago and have to find a hotel in our own dime. The flight in the morning was also delayed. Thankfully only a short time. The non too of all this, our luggage did not arrive by the time we were there. Communication was terrible, through the entire trip. Complete incompetence. Will never fly American again.

I am an AA flyer for a very long time... AA has yet to disappoint.

Flight was delayed. Not much information on when the flight would take off. Eventually we were told it was maintenance. App was not giving updates.

We were delayed and due to lateness we were traveling from 11pm we were rerouted to FLL and couldnt deplane but stayed on the plane with no extra Service given (extra good options etc$ there Were so many things that could go wrong and did. This was not an enjoyable experience at all thoroughly exhausting

They charged late fees for selecting seats (no $0 options). They also changed my gate within the last half hour and are refusing to reimburse my costs to drive across the country with two small children in a rental car.

Seats were more spacious than other airlines. Crew kept us well informed as soon Ias we stepped into the plane.

I was waiting in line for the restroom onboard, the flight attendant told me to step back two rows and stay on the carpet. She was rude and I expected a tik tok experience with me getting thrown off the plane. She was rude and frankly there was no where else to stand.

I needed a cheaper option than Southwest who are almost as bad as Spirit...did the check in the morning of the flight and assigned the last row, middle seat. Paid 20.00 at the airport for an exit row window in 19 and all 8 rows behind me which sold occupied on their seat map were empty....so they force to you to pay for a better seat....I was alone in row 19 and shortly after take off two huge fat people came and grabbed the other seats, I rang the call button for the attendant and said I paid 20.00 for this seat and they just moved in here...I either want to be reseated, or have them take their original seats or a refund of what I paid, the attendant made them move back to their original seats. Worst, worst worst airline in the air....never again, never again, never again.

It was cancelled a few hours before take off. Spirit has yet to confirm I will be refunded for the trip

gate agents with the different rules at the different airports. made me pay for my bag as a carry on instead of a personal item, yet it fit under the seat on the way from Indy to Ft Laud

charging $3 for really bad and cold coffee on airplane flight is ridiculous.

We flew Spirit because it was cheaper but the seats were so uncomfortable. I don;t need to be fed snacks on a plane but when it's a 3-4 hour trip then at least a drink is nice. The flight attendants had nothing to do the whole flight except for gossip loudly to each other right behind our seats, and they talked so much my husband couldn't even rest! I was fine with no tv or entertainment but the seats were so uncomfortable with no recline, no padding, and I am short but even for me to leg room was tough for a 3-4 hour trip. We probably would fly spirit again if we had to, but it's definitely not our favorite!

There was absolutely nothing good about this fight. They delayed us for over 2 hours to give our plane to a flight going to Tampa. By the time we got to norfolk conditions were too bad to land so they took us to Charlotte to refuel so they could fly back to Fort lauderdale. There was almost no communication from the pilot, no wifi, no chargers, and they wouldn't even give us free water when we were stuck in Charlotte refueling.

Checking in and getting to gate fast and leasy at Laguardia airport. There is no entertainment on the plane and food was for purchase. Great experience flying with spirit

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