$88 Find Cheap Flights from Milwaukee to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Milwaukee to Caribbean departing on 5/17. 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 Milwaukee to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$274
Santo Domingo
Santo Domingo1 stop$521
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$657
Nassau
Nassau1 stop$558
Kingston
Kingston2 stops$779
Simpson Bay
Simpson Bay1 stop$483
Providenciales
Providenciales1 stop$524
George Town
George Town1 stop$461
Willemstad
Willemstad2 stops$696
Puerto Plata
Puerto Plata2 stops$675
Aguadilla
Aguadilla1 stop$206
St. John's
St. John's2 stops$684
Punta Cana
Punta Cana1 stop$274
Santo Domingo
Santo Domingo1 stop$521
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$657
Nassau
Nassau1 stop$558
Kingston
Kingston2 stops$779
Simpson Bay
Simpson Bay1 stop$483
Providenciales
Providenciales1 stop$524
George Town
George Town1 stop$461
Willemstad
Willemstad2 stops$696
Puerto Plata
Puerto Plata2 stops$675
Aguadilla
Aguadilla1 stop$206
St. John's
St. John's2 stops$684

Book Cheap Milwaukee to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Milwaukee to Caribbean 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 Milwaukee to Caribbean

Fri, May 15 - Fri, May 22
Frontier Logo
12:09 pm - 2:24 pm
MKE
-
PUJ
25h 15m
1 stop
Frontier Logo
3:35 pm - 11:34 am
PUJ
-
MKE
20h 59m
1 stop
$274Frontier
Fri, May 1 - Thu, May 7
Frontier Logo
5:13 pm - 1:54 pm
MKE
-
PUJ
19h 41m
1 stop
Frontier Logo
3:35 pm - 11:14 am
PUJ
-
MKE
20h 39m
1 stop
$284Frontier
Mon, Aug 24 - Fri, Aug 28
Delta Logo
5:55 am - 1:30 pm
MKE
-
SJU
6h 35m
1 stop
Delta Logo
7:30 am - 1:43 pm
SJU
-
MKE
7h 13m
1 stop
$326Delta
Wed, Aug 12 - Tue, Aug 18
American Airlines Logo
2:46 pm - 11:59 pm
MKE
-
SJU
8h 13m
1 stop
American Airlines Logo
6:51 am - 11:23 pm
SJU
-
MKE
17h 32m
1 stop
$331American Airlines
Mon, May 25 - Wed, May 27
American Airlines Logo
6:00 am - 1:55 pm
MKE
-
MBJ
7h 55m
1 stop
American Airlines Logo
12:47 pm - 11:34 pm
MBJ
-
MKE
10h 47m
1 stop
$352American Airlines
Sat, May 16 - Sat, May 23
United Airlines Logo
5:10 am - 12:50 pm
MKE
-
MBJ
7h 40m
1 stop
United Airlines Logo
2:40 pm - 10:45 pm
MBJ
-
MKE
8h 05m
1 stop
$432United Airlines
Tue, Sep 1 - Tue, Sep 8
Delta Logo
5:55 am - 11:41 am
MKE
-
GCM
5h 46m
1 stop
Delta Logo
12:56 pm - 11:25 pm
GCM
-
MKE
10h 29m
1 stop
$461Delta
Mon, May 11 - Thu, May 14
United Airlines Logo
5:56 pm - 1:30 pm
MKE
-
MBJ
19h 34m
2 stops
United Airlines Logo
2:40 pm - 11:31 am
MBJ
-
MKE
20h 51m
2 stops
$467United Airlines
Sun, May 31 - Sun, Jun 7
Southwest Logo
5:00 am - 2:25 pm
MKE
-
SXM
8h 25m
1 stop
Southwest Logo
1:55 pm - 10:40 pm
SXM
-
MKE
9h 45m
1 stop
$539Southwest
Fri, May 15 - Sat, May 23
Southwest Logo
12:40 pm - 12:25 pm
MKE
-
SXM
22h 45m
2 stops
Southwest Logo
2:35 pm - 10:55 pm
SXM
-
MKE
9h 20m
1 stop
$594Southwest
Booking Insights

KAYAK's insights & trends for Milwaukee to Caribbean flights

Get data-powered insights and trends into flights from Milwaukee to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Milwaukee to Caribbean flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean from Milwaukee found in the last 72 hours was to Montego Bay, at $540 round-trip. The most popular route is from Milwaukee (MKE) to Punta Cana (PUJ), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $628.

What is the cheapest month to fly from Milwaukee to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Milwaukee to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Milwaukee to Caribbean is September, when tickets cost $315 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $675 and $519 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Milwaukee to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Milwaukee to Caribbean, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Good to know

Low seasonJuly
Cheapest flight$88
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 12% increase in price.
Flight from Milwaukee to San Juan

FAQs - booking Caribbean flights

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

    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 Milwaukee to Caribbean.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Milwaukee to 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 Milwaukee to Caribbean?

    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 from Milwaukee to Caribbean with an airline and back with another airline.

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

    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 from Milwaukee to 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 Milwaukee to Caribbean

 
Need help choosing which airline to fly with from Milwaukee to Caribbean? 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 4330 reviews
7.5Entertainment
7.0Food
8.0Comfort
8.1Boarding
8.6Crew
Airline reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

4.0 OkayDavid, Apr 2026
COS - DAL
Read more Southwest reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

The seat was not comfortable. 1D. My back was sore all night and the next day.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Great flight from Seattle to Phoenix and to Chicago-Midway from Phoenix

The new boarding process was easy and straightforward. Very pleasant.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

Everything went smoothly, although the usual gripes about airline travel were still present: the boarding process is inefficient, the snack selection is limited, and so on. Since there was extra space on the flight, the gate agent rearranged many people's seats to put people on the aisles and windows, leaving the middle seats empty, as much as possible, which was pretty great.

Landed without a gate ready. Plane is extremely old and dirty.

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

Very old plane with no inflight entertainment. I purchased the internet pass and it was nearly unusable.

My tray was broken so i had no place to work or eat except my lap. Flight attendant said I would get an email with some credit or miles, it was a complete waste of time as I could only function at about 20% of normal. I have not received anything yet.

Short trip, no food and therefore no expectation for much interaction with staff who were pleasant and professional. My critique is on comfort of the seats. Exit rows and comfort seats do not provide enough personal space for 3 side-by-side seats, especially when in the middle row. Some passengers are not considerate of the middle seat and there should be signs that state something to the effect of: "please consider giving middle seats use of the armrests."

My flight yesterday evening was delayed 3.5 hours with no water or food service. Poor experience

Transparency from pilots, quick boarding and exiting the plane, staff greeted to each and everyone,

Didn't like sitting on the waiting pad for 30 minutes right after departing the gate. If you're going to do that, just don't board so people can still get up and walk around in the terminal. My luggage was damaged by the baggage handlers.

Pilots lied about waiting on “paperwork”. Sat in the plane for over an hour, waiting on some papers to be printed according to the pilot and then all of a sudden he says good news maintenance is finally on their way. Maybe they can fix it before we get our paperwork. Ended up missing my connection in LaGuardia and as a result, had a fly home to Lexington instead of the Louisville airport. Then paid $100 to uber to Louisville since it was midnight by the time I got in. I wish they would just be transparent with passengers sometimes and not try to beat around the bush on why things are delayed.

Putting people that close to the bathroom, where you have to look into the bathroom as people are exiting and entering was not great and the smell was also not great. I know the airlines are desperate for more chairs, but that seat is a crime.

My bags were misplaced!!! Im in a foreign country with no bags

The entertainment options on the seat back video boards were nice.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

Due to cancellation of connecting flight (Lufthansa) I didn’t fly with United

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

It was a red-eye, but the flight felt surprisingly quick. The seats were very comfortable, and that made resting much easier. I also want to thank the gentleman seated next to me, who graciously moved so my mom could sit beside me. We slept almost the entire way. The cabin crew was respectful in not disturbing us, while also being courteous and professional throughout. Thank you, United.

Flight: Started on time. Comfortable flight. Arrived on time. Crew: Very cordial and helpful. Drinks and snack was served with a smile. Overall enjoyed the trip. Regards, Hari Doss Chanchala Doss

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Early departure meant on time arrival. Only real problem was free internet had issues, although chatting with the internet help desk (you can do this via aainflight.com) got the issue resolved.

It was really a terrific experience both going and returning on AA. Staff and crew were professional.

The business class layout of chairs was weired. You are sitting directly across stranger.,

Flights on time w/o delays. However, my baggage was damaged. Ground crew, throws baggage from plane to the baggage carrier, carelessly.

I’m sure Business Class would be excellent. I feel like I got what I paid for. Overall it was good and well worth it. I would do it again.

I am writing to share detailed feedback regarding my recent journey with American Airlines on the New York (JFK) to New Delhi (DEL) sector, which was ultimately diverted to Jaipur (JAI) due to weather conditions. At the outset, I would like to acknowledge that this was a full long-haul flight of approximately 14–15 hours, and while the journey fulfilled its primary transport objective, several aspects of the experience warrant both recognition and constructive feedback. 1. Cabin Crew Conduct and Service Consistency While the majority of the cabin crew maintained a polite and professional demeanor, one flight attendant’s conduct was notably inconsistent with expected service standards. The tone was often directive and lacked the warmth and guest-centric engagement typically associated with long-haul service. This created a perceptible imbalance in the cabin experience. Although other crew members acknowledged and apologized for the behavior, it highlighted a gap in service standardization and supervisory oversight. 2. Inflight Experience (IFE & Comfort) The inflight entertainment system was unreliable, with content failing to load consistently throughout the journey. Seating comfort in economy class was below expectations when compared with other international long-haul carriers. Cabin environment management at times felt unsettled, with noticeable noise and movement in the aisles. 3. Disruption Handling and Communication (DEL Diversion to JAI) The diversion to Jaipur due to weather was understandably beyond the airline’s control. However, the handling of post-diversion communication and guest management was an area of concern: Information during and after the diversion was fragmented and lacked clarity Limited guidance was provided upon disembarkation regarding next steps (transport, accommodation, onward travel) Ground coordination appeared inconsistent, with hotel partners and passengers receiving incomplete or delayed updates Communication the following morning remained unclear, including last-minute changes to transfer timings This resulted in avoidable uncertainty during a critical disruption phase. 4. Positive Acknowledgment – Ground Recovery Arrangements It is important to recognize that despite the initial communication gaps, the overall recovery framework was eventually well executed: Hotel accommodation was arranged efficiently Meal vouchers were provided appropriately Transfers between airport and hotel were organized in a structured manner Given the sudden and large-scale disruption, these arrangements were commendable and reflect the airline’s ability to operationally recover once systems were in place. 5. Recommendations for Improvement In the interest of strengthening the overall customer experience, I would respectfully propose the following: Service Delivery Reinforce consistent cabin crew service standards, particularly for long-haul sectors Enhance supervisory presence to address outlier behaviors in real time Inflight Product Improve reliability of inflight entertainment systems Reassess economy seating comfort for ultra-long-haul routes Disruption Management Establish a more visible “Care & Coordination Team” during irregular operations Ensure clear, centralized communication (single source of truth) for passengers and ground partners Provide structured briefing points to hotel and transport vendors to avoid information gaps Introduce proactive guest engagement (clear next steps, timelines, reassurance) Closing Reflection: While the journey was impacted by both controllable and uncontrollable factors, the overall experience would have been significantly enhanced through greater consistency in service delivery and more structured communication during disruption. I appreciate the efforts made by the broader team in arranging accommodation and onward logistics under challenging circumstances. With improved coordination and alignment, the experience can be elevated to match the expectations of a global long-haul carrier. Thank you for your attention to this feedback. I trust it will be received constructively and contribute to ongoing service improvement. Warm regards, Soosnata Chowdhury Convert effective for airlines) Or tailor tone

This short sector between Miami and JFK was undertaken purely for business purposes, with efficiency as the primary objective rather than a full inflight experience. Overall, the journey met its intended purpose; however, the ground experience at Miami stood out significantly. During check-in, I was unable to link my frequent flyer details from Qatar Airways (oneworld alliance) through either the self-service kiosk or web check-in. The situation was handled exceptionally well by the check-in agent, who demonstrated remarkable ownership. She coordinated across multiple counters, ensured my frequent flyer number was correctly reflected, reissued the boarding pass, and confirmed that mileage accrual would be recognized. Additionally, she ensured the boarding pass reflected priority status, enabling a seamless priority check-in experience without delays. This level of proactive service was both commendable and impactful. Boarding and the inflight experience, operated by American Airlines under a codeshare arrangement, were efficient but largely transactional. While operational delivery was smooth, there was no visible recognition of oneworld frequent flyer status onboard. In comparison to the consistently personalized engagement typically experienced with Qatar Airways, this absence was noticeable—though understandably a potential limitation of codeshare alignment rather than a direct service shortfall. In summary, while the flight itself fulfilled its operational intent, the exceptional professionalism and commitment demonstrated at the Miami check-in counter was the defining highlight of this journey. Greater consistency in elite recognition across partner airlines would further enhance the overall experience.

I was able to get the AA customer Service desk to put me on an earlier flight without any issues.

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports