$214 Find Cheap Flights from Milwaukee to the Dominican Republic - Compare and Save

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Cheap Flights from Milwaukee to the Dominican Republic

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Booking Insights

Price, demand and travel trends for Milwaukee to the Dominican Republic flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

Are flights from Milwaukee to the Dominican Republic cheaper or more expensive than last year?

Fares from Milwaukee to the Dominican Republic are running about 5% higher than they were around this time last year, averaging $669 round-trip.

What are the cheapest fares from Milwaukee to the Dominican Republic right now?

Here are the cheapest round-trip fares from Milwaukee to the Dominican Republic on KAYAK in the last week:

• Punta Cana (PUJ) from $556
• Santo Domingo Las Americas (SDQ) from $660
• Santiago de los Caballeros (STI) from $662
• Puerto Plata La Union (POP) from $855

What’s the cheapest month to fly from Milwaukee to the Dominican Republic?

August is the cheapest time of year to fly, with average fares of $588. Prices are highest in March, when average flight costs increase to around $874.

When is the best time to book flights from Milwaukee to the Dominican Republic?

Book your flights 14 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 25% compared to booking last-minute (within 2 weeks of departure).

Which airport in the Dominican Republic is the cheapest to fly to from Milwaukee?

Based on KAYAK data from the past 12 months, the cheapest airports to fly into the Dominican Republic are:

• Santiago de los Caballeros (STI) (avg. price $613)
• Santo Domingo Las Americas (SDQ) (avg. price $658)
• Punta Cana (PUJ) (avg. price $673)

What’s the cheapest day to fly from Milwaukee to the Dominican Republic?

Monday tends to be the cheapest day to fly from Milwaukee to the Dominican Republic, while Thursday is the most expensive. Fares run about 9% higher that day, based on the past 12 months of KAYAK data.

What's the cheapest time of day to fly from Milwaukee to the Dominican Republic?

Data from the past 12 months shows it's cheapest to fly to the Dominican Republic during the afternoon with average prices of $588. The morning is the most expensive time to fly, with average prices of $700.

Key details for Milwaukee to the Dominican Republic flights

Low season

August

Cheapest flight

$214
Beat the crowds with an average 45% drop in travelers.
The most popular month to fly with an average 72% increase in travelers.
One-way flight from Milwaukee to Punta Cana

Your Milwaukee to the Dominican Republic flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Milwaukee to the Dominican Republic?

    Yes. Fares from Milwaukee to the Dominican Republic are low right now. As a rule of thumb, a round-trip under $558 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Milwaukee to the Dominican Republic?

    Over the past 12 months, round-trip fares from Milwaukee to the Dominican Republic have ranged from $558 to $831.

  • What are the main airports serving the Dominican Republic?

    The Dominican Republic has 7 airports. The three busiest are Punta Cana (PUJ) (74% of arrivals), Santo Domingo Las Americas (SDQ) (13%) and Puerto Plata La Union (POP) (10%).

  • What airlines fly nonstop from Milwaukee to the Dominican Republic?

    Based on the flight schedule for the next 3 months, just one airline regularly flies nonstop from Milwaukee to the Dominican Republic: Sun Country Air.

  • Where in the Dominican Republic can I fly nonstop from Milwaukee?

    Based on the flight schedule for the next 3 months, you can only fly nonstop from Milwaukee to Punta Cana.

  • Is it cheaper to fly with a layover from Milwaukee to the Dominican Republic?

    Yes. Nonstop flights from Milwaukee to the Dominican Republic average $799 over the past 12 months, but flights with a layover can cost less. The most affordable connecting airports are:

    • New York John F Kennedy Intl (JFK) (avg. price $585)
    • Orlando (MCO) (avg. price $586)
    • Charlotte Douglas (CLT) (avg. price $655)

  • How long is a flight from Milwaukee to the Dominican Republic?

    Flights from Milwaukee to the Dominican Republic take 4h 36m on average.

  • Which cabin classes are available on flights from Milwaukee to the Dominican Republic?

    On flights from Milwaukee to the Dominican Republic you can only book Economy Class.

  • What are some popular landmarks in the Dominican Republic?

    KAYAK travelers' favorite landmarks in the Dominican Republic include:

    • Playa Dorada
    • Catedral Primada de América
    • Playa Juanillo
    • Centro Olimpico Juan Pablo Duarte

  • What are the earliest and latest flights from Milwaukee to the Dominican Republic?

    The earliest nonstop flight from Milwaukee to the Dominican Republic departs at 8:00 am and the latest departs at 8:05 am. Nonstop flights take about 4h 36m.

Your guide to booking Milwaukee to the Dominican Republic flights

Get tips on when to book, when to fly and what to know before your trip.
  • If you can plan ahead, the sweet spot for booking your flight is 14 weeks before your trip. KAYAK data shows fares in this window are around 25% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • If your travel dates are flexible, book your trip for August when flights are typically cheapest and avoid March when prices are at their highest.
  • Flying on Monday is usually the cheapest. Flights on Thursday cost about 9% more on average, so being flexible with your travel dates could help you save.
  • If you're looking to save, Santiago de los Caballeros (STI) is the cheapest airport to fly into from Milwaukee. If you have onward travel, don't forget to factor in the cost of your journey by train, bus or domestic flight.
  • Start your trip in Punta Cana, which is the most popular destination in the Dominican Republic. From there, it's easy to continue on to other popular destinations such as Puerto Plata, Santo Domingo and La Romana.
  • If you want the shortest trip, choose the Milwaukee to the Dominican Republic nonstop route. If you'd rather save money, the route via New York John F Kennedy Intl (JFK) is usually the cheapest.

Reviews of the top 5 airlines serving from Milwaukee to the Dominican Republic

 
Need help choosing which airline to fly with from Milwaukee to the Dominican Republic? 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 4223 reviews
7.4Entertainment
8.6Crew
7.0Food
8.0Comfort
8.1Boarding
Airline reviews

On time departure and arrival. Had to be the oldest plane in the SWA fleet but it got me where I needed to be.

8.0 ExcellentJohn, Oct 2026
Read more Southwest reviews

On time departure and arrival. Had to be the oldest plane in the SWA fleet but it got me where I needed to be.

Flight was delayed out of BWI unexpectedly / without a reason given but otherwise ok.

I got a bit sick on the flight, and was so grateful when the male flight attendant explained to me they keep the back row open for cases like mine. He took such great care of me! I was incredibly grateful.

Friendly crew. Snacks were carb-heavy. Flight was quite delaye

The service was fine, about the same as you get on most lower end airlines. I dont understand the perks of flying them much anymore for the cost.

the flight was significantly delayed. Not much was done by the airline to compensate passengers

the flight itself was totally fine. The crew were great and very helpful. The flight was delayed, however, over an hour without a lot of information as to why.

Flight time kept changing and so did the gate. It was very frustrating

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

We were headed for Florida and anxious to get there. Everything was absolutely the best. This is our first time with Southwest and it’s now our go to airline. Best ever.

The flights were on time; all went as expected which is a big positive! No delays! There was no food or drink service in any legs, which I understand due to the short flight time.

The Delta assistsed services were awesome for my aunt. So very helpful.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

None of the airplane features were available during the flight.

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Pretty standard flight. Delta has a good selection of movies.

The flight was so late that I had to change connecting flights, turning a five-hour trip into a fourteen-hour nightmare.

Despite being delayed, we would still give a high score for this flight experience. For the first time in quite some time we had excellent customer service throughout our entire round trip. The flight attendants were the most polite we have experienced in our last ten flights at least (non of which were Delta and include business class). The food offered was a better selection than most—we just didn’t have any of it. Overall, almost as good as flying used to be. Thank you to Delta.

The boarding agent and checked bag agent were both rude. It only takes a second to be kind. However, the flight crew was amazing. I got a turkey sandwich and it wasn't bad---not great but not bad. The internet was my biggest problem. This was a work trip and I REALLY needed the internet to meet a deadline but it didn't work for 80% of the trip. Very disappointing.

I tried to check in beforehand from Ireland. The Jet Blue website sent me to the Aer Lingus website and vice versa. I tried to get a boarding pass at Dublin Airport as well, but they said they couldn't help me either. I had to wait until I arrived at the gate in Boston to secure a boarding pass...it was a bit nerve wracking.

Great flight. Best in years. Very clean craft. Easy boarding. Communicative pilot. Friendly flight attendants. Absolutely smooth take off, in flight and landing. Very comfortable seats. Smoothest flight I've experienced in years. THANK YOU JET BLUE!

I was asked to pony up an additional $239 (over the $735 paid originally) for a one way middle seat, which was very uncomfortable. Where did you expect me to sit?

Jet Blue sevice was good. Just don't understand why they charge for earphones to listen to flight entertainment. Other than that, everything was excellent.

Mostly good, flight take off in time and land earlier I can’t ask for more..

All the TV screens in my rows was non functional . The map shown for an international route was antiqued..

There was a fowl odour coming from the lavatory the entire flight

The flights are back on time and everything else runs perfectly.

Surly, unhelpful ground staff at JFK. There was a complete lack of empathy—a flawed check-in ordeal caused us to miss our flight. All airlines that I have ever flown would have worked to help me solve the ticket problem. Instead, frontline employees shrugged their shoulders and pointed fingers at us for having made an error. I will do anything to avoid EVER flying on Jet Blue again. It well deserves its low rank among airlines.

My luggage was lost at some point during my layover between Chicago and LHR. I landed Tuesday morning, and did not get it until Thursday night. Ironically, the people at the ticket desk had added a “priority” sticker to my tracking tag.

The flight was delayed multiple times. Breakfast was not served and only an apology given and statement that we could find better pastries in Paris. Seats were extremely narrow and uncomfortable.

The flight could have actually taken place. Canceled flight and no option to rebook that day.

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

There were several different delays but we ended up being delayed a total of 40 mins or so. It was annoying we had a gate change which made it take longer to leave DFW, and we had to check our carry on. Ugh

The counter/baggage counter was busy and so many people missed flights. We got stuck sitting on the plane over 2 hours at the gate while they were doing an inspection is wrong. Many of us missed our connecting flights because of it.

Our flight was changed from Madison to DC to Madison to Charlotte.

We were told we had no flights before our flight was continually delayed then cancelled.

The flight was cancelled without compensation on hotel lodging near MSP. We had to buy tickets from another airlines to fly home.

My seat was comfortable and I had plenty of leg room.

Boarding and crew were great, but seats are terribly uncomfortable. No food or entertainment options.

Everything went very smoothly! Thanks for a great first experience flying with small children!

Crew members great. Everything else a 0! Got on plane at 530am. Got de boarded for mechanical issue. Supposed to leave by 830 am. Zero communication from gate agents. Then supposed to leave by 230pm. Then delayed till 330pm. Still zero communication with gate agents. All they would say is if you have an issue call the 1800 number. You call and sit on hold minimum 45 minutes for zero answer. Finally board at 345pm didn’t take off till after 4pm! Sat in airport for 11 hours with 4 adults and 3 kids. Finally offered a $100 (we are sorry) voucher for next trip. Missed whole day in Florida had to change reservations in Florida! Absolute joke of an airline! And I usually really like sun country.

Booked through Kayak for $236. They canceled the flight unknown to me; retaining $100 for canceling it. Found out when I went to check in. Rebooked the same flight for $400. Incredibly disappointed. The Sun Country part was as to be expected. Crowded, no food, no arm room but got me where I wanted to go.

3 seperate extremely rude unhelpful staff. Delayed flight. Lost my bag

Sat between 2 big men. I was uncomfortable. Flight was delayed twice. About 2 hours altogether.

It was a good experience. I do wish the seats were roomier. Also, I did not like being charged for my carry on bag

Exceptional take off and landing in snow and wind…thank you to the well skilled pilots!

More options for your flight from Milwaukee to the Dominican Republic

Complete your trip to the Dominican Republic with a hotel stay or car rental