$149 Find Cheap Flights from Milwaukee to the U.S. Virgin Islands - Compare and Save

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KAYAK's insights & trends for Milwaukee to the U.S. Virgin Islands flights

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

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

The cheapest month for flights from Milwaukee to the U.S. Virgin Islands is August, when tickets cost $242 (return) on average. On the other hand, the most expensive months are May and October, when the average cost of round-trip tickets is $830 and $796 respectively.

Good to know

Low season

August

Cheapest flight

$149
Best time to beat the crowds with an average 64% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Milwaukee to Saint Thomas Island

FAQs - booking U.S. Virgin Islands flights

  • How does KAYAK find such low prices on flights from Milwaukee to the U.S. Virgin Islands?

    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 the U.S. Virgin Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Milwaukee to the U.S. Virgin Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Milwaukee to the U.S. Virgin Islands 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 the U.S. Virgin Islands?

    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 the U.S. Virgin Islands 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 the U.S. Virgin Islands?

    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 the U.S. Virgin Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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 4200 reviews
8.6Crew
8.1Boarding
8.0Comfort
7.5Entertainment
7.0Food
Airline reviews

Delayed and once landed waited very long for the luggage

6.0 GoodIngeborg, Sep 2026
Read more Southwest reviews

Delayed and once landed waited very long for the luggage

Nice managed … it was a smaller plane, so the seating wasn’t as comfortable.

The Southwest airline was ok. A big thank you to Kayak team (David), who worked with me on Sunday afternoon to rebook my travel from Burbank, CA, to CVG. My original flight on Sunday was delayed, so I had to cancel Sunday flight and rebook my travel to Monday. Could not have done it without help from David from Kayak team. Ante Soda GE Aerospace

Seated at front bulkhead for a smidge extra leg room away from home and on flight back home. Away crew was very proactive about assuring our carryons had space close behind us (because no seat in front of us our personal items had to be in a small bin overhead). They actively required passengers place overhead luggage on its side so more items could fit in bins. Home crew made no such efforts. I had to struggle back rows to get overhead bags upon landing, no crew help then either, and some disgruntled passengers as I and others retrieved our bags. There was a system that worked pretty well. The home bound crew just didn't feel like working.

Southwest has inacted unfriendly customer policies like other airlines. Watch the fine print very carefully if you are having to alter flight arrangements. Rules are now complicated and very stilted to travelers sacrificing travel funds (unlike before where the simple, straight forward flight change policy was worth the extra premium for ticket price.) On the positive side, SW Flight crews are still wonderfully helpful.

Flight left on time and was early landing. Seats not comfortable and not enough space…

Flight left on time. Seat spacing is way too small…

It would have been better if the flight was on time

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.

Both legs on the way were smaller planes, each had a mechanical issue causing a delay

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.

Upset about cancel to St. John’s and no overnight accomodation

The crew was great. The food was typical, but decent. Everything else - mediocre to poor. The flight was late arriving - happily for us and our 49 minute connection (what idiot came up with that?)- in another concourse - that concourse changed before we arrived (ticket and app was showing the incorrect gate - when we boarded at the correct gate - known by the airport person pushing my assistance cart). Had I walked and read the screens or United app I would have missed the flight! May other people arrived late to the correct gate, having been victims of a last minute gate change, were also relieved the flight arrived late. The aircraft (Boeing 757) was a sardine-can due to an uncomfortable seat pitch distance. The material or seat was beyond not comfortable, but I'm sure they made a lot of money with that aircraft type. I spent a lot of time standing in the back (in the middle of the night/morning to rest my back). I learned my lesson - any trans-oceanic fight - avoid United or American Airlines - and look for Airbus or Boeing 737, 767, 777. Also, pay for business class or premium coach seating.

Great Brasilia aircraft - not a Boeing 757 like the next part of the flight. Flight from MCI to IAD was great, on-time, comfortable, did I mention that? The flight from IAD to EDI was painful. One of the reasons I won't fly United again? Boeing 757, with a seat pitch and material that was horrendous. Worst aircraft ever, made worse by United sardine-can tight seating. Oh, and the connection window, 45 minutes, really? At IAD, in different concourses? What idiot came up with that flight scenario? Happily, (for me and my travel insurance people) the flight was late (reminiscent of American Airlines). The crew was professional and courteous.

Crew was great. Seats are cramped and uncomfortable and I’m a small person.

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.

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.

Flight delayed 3 times due to maintenance (on exact same plane that had just brought us from Boston to Miami). Eventually changed to a different plane and gate.

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.

Boarding was relatively fast and easy and the crew was attentive throughout.

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