$258 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 $520 round-trip, and to Christiansted Henry Rohlsen (STX) from $558 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 $479. 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) (avg. price $563)
• Saint Thomas Island Cyril E King (STT) (avg. price $675)

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

Monday 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 27% 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 evening is the most expensive time to fly, with average prices of $680.

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

Low season

August

Cheapest flight

$258
Beat the crowds with an average 77% drop in travelers.
The most popular month to fly with an average 121% increase in travelers.
One-way 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?

    Fares from Milwaukee to the U.S. Virgin Islands are around their usual level right now. A round-trip under $516 is considered a good deal, so it's worth keeping an eye out, or setting a Price Alert to catch price changes.

  • 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 $516 to $791.

  • 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
    • American Airlines
    • Southwest

  • 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 Monday is usually the cheapest. Flights on Sunday cost about 27% 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 Cruz Bay.

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.
8.0
SouthwestOverall score based on 4220 reviews
8.6Crew
8.1Boarding
7.0Food
8.0Comfort
7.5Entertainment
Airline reviews

Terrible, decided to delay our flight since another flight require a flight captain

2.0 MediocreChih Hsuan, Nov 2026
Read more Southwest reviews

Terrible, decided to delay our flight since another flight require a flight captain

staff and crew were great but the flight delays for the last few flights are insane. After a long day of work and you will get a notification of flights delay is not the message we want to see. And for some reason it keeps happening often this year.

I love southwest. I can not wait until all the planes convert to the upgraded planes. I love the charging option and the newer seats. Thank you from a very loyal Southwest customer.

My return flight was much better than the flight there! I paid for seat to Veagas but not the return. Thankgoodness they assigned me a seat with additional leg room as I have back and leg problems. I really appreciate it. With the flight already being super expensive due to gas prices and having to pay for bags (now) I needed to save some money.

My first flight from LGA to STL was not good. They didn't do service until over halfway through the flight, the internet didn't really work, and the crew all seemed like they didn't want to be there.

We were stressed about landing as our connecting flight was about to start boarding, being unfamiliar with the airport or where the gates were. We exited the plane to discover we were at the gate we needed. We would be getting back on the same plane but nobody told us we could have just stayed onboard. My wife and I were seated on aisle seats across from each other. We asked if there was a way we could sit together. Once we were at cruising altitude they let us move to an unoccupied row so that was nice.

It’s Southwest. The seats are small, the snacks are meh, it’s $50 to check a bag. It’s exactly fine. Could have been better. Could have been worse. It’s not Spirit

They delayed my flight all day but didn't try to reschedule me until all other options were gone. Ended up on a red eye. Not happy. Lesson learned, don't book the last flight from SJC to RDU.

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.

As an Elevance employee, don't we get priority boarding? Also, I boarded zone 5 and could not get normal carry on in luggage space. There were many Delta employees on the flight and their bags, which were large and could only fit two bags per compartment, got preference over customers so I had to check my bag.

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.

We left nearly 3 hours late...so that was not a good experience. We boarded and then ended up about 1 hour stuck at the gate. Not a good experience.

It is completely insane to me that first class does not include WiFi. Also does not include lounge access. Port for phone charging did not work. The crew was absolutely lovely, and the food was excellent.

I appreciate how quickly and kindly the people at the gate at DCA accommodated several of us who wanted to switch from the 6pm flight to the 5pm flight at the last minute. The flight crew was helpful to us too (dealing with luggage).

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