$496 Find Cheap Flights from Milwaukee to the U.S. Virgin Islands - Compare and Save

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Price, demand and travel trends for Milwaukee to the U.S. Virgin Islands 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 U.S. Virgin Islands cheaper or more expensive than last year?

Fares from Milwaukee to the U.S. Virgin Islands are running about 7% higher than they were around this time last year, averaging $668 round-trip.

What are the cheapest fares from Milwaukee to the U.S. Virgin Islands right now?

The cheapest fares from Milwaukee to the U.S. Virgin Islands on KAYAK in the last week were to Saint Thomas Island Cyril E King (STT) from $496 round-trip, and to Christiansted Henry Rohlsen (STX) from $582 round-trip.

What’s the cheapest month to fly from Milwaukee to the U.S. Virgin Islands?

January is the cheapest time of year to fly, with average fares of $519. Prices are highest in September, when average flight costs increase to around $1,077.

Which airport in the U.S. Virgin Islands is the cheapest to fly to from Milwaukee?

Based on KAYAK data from the past 12 months, the cheapest airports to fly into the U.S. Virgin Islands are:

• Christiansted Henry Rohlsen (STX) from $565
• Saint Thomas Island Cyril E King (STT) from $690

What’s the cheapest day to fly from Milwaukee to the U.S. Virgin Islands?

Thursday tends to be the cheapest day to fly from Milwaukee to the U.S. Virgin Islands, while Sunday is the most expensive. Fares run about 31% 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 U.S. Virgin Islands?

Data from the past 12 months shows it's cheapest to fly to the U.S. Virgin Islands during the afternoon with average prices of $604. The morning is the most expensive time to fly, with average prices of $683.

Key details for Milwaukee to the U.S. Virgin Islands flights

Low season

August

Cheapest flight

$496
Beat the crowds with an average 80% drop in travelers.
The most popular month to fly with an average 142% increase in travelers.
Round-trip flight from Milwaukee to Saint Thomas Island

Your Milwaukee to the U.S. Virgin Islands 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 U.S. Virgin Islands?

    Yes. Fares from Milwaukee to the U.S. Virgin Islands are low right now. As a rule of thumb, a round-trip under $526 (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 U.S. Virgin Islands?

    Over the past 12 months, round-trip fares from Milwaukee to the U.S. Virgin Islands have ranged from $526 to $801.

  • What airlines fly nonstop from Milwaukee to the U.S. Virgin Islands?

    Based on the flight schedule for the next 3 months, no airline regularly operates nonstop flights from Milwaukee to the U.S. Virgin Islands. One-stop options include:

    • Delta
    • Southwest
    • American Airlines

  • Which cabin classes are available on flights from Milwaukee to the U.S. Virgin Islands?

    On flights from Milwaukee to the U.S. Virgin Islands you can book Economy Class or First Class.

  • What are some popular landmarks in the U.S. Virgin Islands?

    KAYAK travelers' favorite landmarks in the U.S. Virgin Islands include:

    • Sapphire Beach
    • Coki Beach
    • 99 Steps
    • Blackbeard's Castle

Your guide to booking Milwaukee to the U.S. Virgin Islands flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your travel dates are flexible, book your trip for January when flights are typically cheapest and avoid September when prices are at their highest.
  • Flying on Thursday is usually the cheapest. Flights on Sunday cost about 31% more on average, so being flexible with your travel dates could help you save.
  • If you're looking to save, Christiansted Henry Rohlsen (STX) 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 Saint Thomas Island, which is the most popular destination in the U.S. Virgin Islands. From there, it's easy to continue on to other popular destinations such as St. John, Christiansted and Kingshill.

Reviews of the top 4 airlines serving from Milwaukee to the U.S. Virgin Islands

 
Need help choosing which airline to fly with from Milwaukee to the U.S. Virgin Islands? 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 4215 reviews
7.5Entertainment
7.0Food
8.6Crew
8.0Comfort
8.1Boarding
Airline reviews

Flight boarded 2.5 hours late (my second southwest flight of the day with late departure), the gate agent was grumpy and unhelpful. Said she was "tired so we aren't going to follow normal boarding order". No complaints about the actual flight crew.

2.0 MediocreBrittney, Oct 2026
Read more Southwest reviews

Flight boarded 2.5 hours late (my second southwest flight of the day with late departure), the gate agent was grumpy and unhelpful. Said she was "tired so we aren't going to follow normal boarding order". No complaints about the actual flight crew.

Your computers were down and took a long time to check baggage

Southwest has lost most of what made it special. The flight attendants all used to seem fun and like they were having fun. Now they seem just miserable. They do NOT seem happy to give you your pretzels and drinks. They stick it in your hand or on your tray like it's an annoyance. They bark safety instructions at you. It's not just this flight but the last few SW flights I've had to SNA and SAN as well and it's not just me. I've informally surveyed my colleagues (business and leisure travelers) and these feelings are consistent. The tickets are similarly priced to other carriers and the seat assignments make boarding slower. The free luggage and free ability to change flights is still a differentiator. You lose that and there's virtually nothing special left.

Flight attendant skipped about 6 rows for drink service. I got a side eye when I asked for a drink - like it was an inconvenience or my mistake. He shouldn't be on a flight if he doesn't like his job and doesn't have customer service first attitude.

The entire crew were wonderful but 1 flight attendant stood out with his sense of humor on the microphone. I told him as much as I exited the plane.

They did not fix the wifi that they knew was an issue on an earlier flight. The flight was filled with business people that were clearly frustrated not being able to work. That can’t happen on a 3 1/2 hour flight. Would rather have been delayed a bit.

The WiFi did not work three hours of productivity lost. 15 people from the firm were on the flight. Loss of revenue

Very rude stewardess; there was a senior citizen woman next to me who asked the stewardess for help getting her purse out of the overhead bin, and it was as though she asked the stewardess for $1M . . . . I was shocked how rude that stewardess was. The stewardess also refused to get the senior citizen woman a drink about half way thru the flight, telling her that we were almost landing . . . . that stewardess made my flight (and in particular the flight of the senior citizen next to me) very uncomfortable

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

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.

On time, quick boarding, so nice of them to honor active and retired military with early boarding. Attendants were nice . Plane was clean. A bit crowded like all flights.

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

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.

A couple flight attendants in business class had bad attitudes and provided poor service. They did provide drinks or refill drinks. They talked to certain passengers for long periods of time and ignored others.

I especially enjoyed having a lightly packed flight which enabled me and my wife to occupy a three seat area with nobody in the middle seat.

Fantastic experience once again flying with United! There was great communication from the cockpit and one of the flight attendants went out of her way to get my two little kids some special treats which elevated our travel experience coming home.

Good, our flight was delayed but that was totally out of their control due to weather and a presidential visit.

The flight was delayed by two de-icings. The seatbelt did not work correctly. It did not stay tight.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

It was literally one of the worst travel experiences ever. My flight got delayed by over an hour and there was no communication of this from the gate staff. I realized it by checking the screen periodically. Once on board the flight attendants continued to serve alcohol to a man who was clearly already drunk and that was making a bunch of commotion. Never again will I fly United!

At least the delays were short. Business class, even in the new planes is very crowded now with crappy tray tables

All good except paid for wifi that did not work

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

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.

More options for your flight from Milwaukee to the U.S. Virgin Islands

Complete your trip to the U.S. Virgin Islands with a hotel stay or car rental