$302 Find Cheap Flights from Milwaukee to the U.S. Virgin Islands

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 the U.S. Virgin Islands departing on 9/7. 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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Book Cheap Milwaukee to the U.S. Virgin Islands 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 the U.S. Virgin Islands 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 the U.S. Virgin Islands

Tue, Dec 1 - Tue, Dec 8
American Airlines Logo
6:48 pm - 4:58 pm
MKE
-
STT
20h 10m
2 stops
American Airlines Logo
6:17 pm - 8:20 am
STT
-
MKE
16h 03m
2 stops
$430American Airlines
Fri, Aug 21 - Mon, Aug 31
Delta Logo
5:34 am - 1:34 pm
MKE
-
STT
7h 00m
1 stop
Delta Logo
2:49 pm - 11:53 pm
STT
-
MKE
10h 04m
1 stop
$455Delta
Fri, Aug 21 - Mon, Aug 31
American Airlines Logo
7:00 pm - 12:53 pm
MKE
-
STT
16h 53m
2 stops
American Airlines Logo
3:43 pm - 10:57 am
STT
-
MKE
20h 14m
2 stops
$469American Airlines
Wed, Oct 7 - Mon, Oct 12
American Airlines Logo
4:26 pm - 12:40 pm
MKE
-
STT
19h 14m
2 stops
American Airlines Logo
5:40 pm - 12:02 pm
STT
-
MKE
19h 22m
2 stops
$474American Airlines
Thu, Jul 30 - Tue, Aug 4
American Airlines Logo
7:01 am - 8:50 pm
MKE
-
STX
12h 49m
2 stops
American Airlines Logo
9:00 am - 11:08 pm
STX
-
MKE
15h 08m
2 stops
$478American Airlines
Wed, Sep 16 - Tue, Sep 22
American Airlines Logo
5:10 pm - 3:36 pm
MKE
-
STX
21h 26m
2 stops
American Airlines Logo
5:01 pm - 11:07 am
STX
-
MKE
19h 06m
2 stops
$483American Airlines
Fri, Nov 27 - Sat, Dec 5
American Airlines Logo
2:53 pm - 12:07 pm
MKE
-
STT
19h 14m
2 stops
American Airlines Logo
6:17 pm - 10:46 am
STT
-
MKE
18h 29m
2 stops
$485American Airlines
Fri, Aug 21 - Mon, Aug 31
American Airlines Logo
7:00 pm - 12:53 pm
MKE
-
STT
16h 53m
2 stops
American Airlines Logo
3:43 pm - 10:59 pm
STT
-
MKE
8h 16m
1 stop
$491American Airlines
Thu, Sep 24 - Mon, Sep 28
American Airlines Logo
6:43 pm - 12:51 pm
MKE
-
STT
17h 08m
2 stops
American Airlines Logo
1:41 pm - 9:46 am
STT
-
MKE
21h 05m
2 stops
$508American Airlines
Fri, Aug 21 - Mon, Aug 31
Delta Logo
5:34 am - 1:34 pm
MKE
-
STT
7h 00m
1 stop
Delta Logo
2:49 pm - 11:53 pm
STT
-
MKE
10h 04m
1 stop
$529Delta
Booking Insights

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?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Milwaukee to the U.S. Virgin Islands, 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 the U.S. Virgin Islands is March, when tickets cost $165 (return) on average. On the other hand, the most expensive months are October and July, when the average cost of round-trip tickets is $683 and $670 respectively.

How far in advance should I book a flight from Milwaukee to the U.S. Virgin Islands?

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 the U.S. Virgin Islands, 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 the U.S. Virgin Islands, you should book around 3 weeks before departure, which saves you about 50% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$302
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Milwaukee to Christiansted

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.
7.9
SouthwestOverall score based on 4242 reviews
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
8.0Comfort
Airline reviews

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

2.0 MediocreIrene, Jun 2026
DEN - SFO
Read more Southwest reviews

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

Crew was rude, flight was late, wifi didn't work, no food, basically nothing about this flight was good.

It was just okay, no frills, basic transportation with no luxury. No screens on the seats, no water or drinks on a short flight. Full flight but at least it was on time.

Flight was constantly delayed with significant changes in time, it was supposed to get to Colorado Springs at 8:30 PM but it got there after midnight.

Over a 3 hour flight. The turbulence was almost imperceptible except for 2 short periods which were not bad and over quickly. The attendants claimed "Safety first" and sat looking at their phones for 3 hours with no drink or snack service. This isn't the first time with Southwest. I thinkit may be there new plan of operation. Oh, and it was June 18, Southwest's Birthday which offered free drinks. NOT.

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

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.

My flight was delayed by 4 hours in 30 minute increments. The gate agents were amazing but the communication was not. We were told that there was a maintenance issue but they didn't know what it was. That didn't inspire confidence. Then they said they found it and it was fixed and the pilot just needed to sign off. Then the pilot needed to talk to the other pilot from the arriving flight and we'd be fine. Then we were waiting for the pilot to call back. Then the maintenance issue wasn't fixed. Then they decided we were getting a new plane (why didn't they decide this earlier??). Fine. But then they announced we were changing gates AND terminals. And we were boarding in 20 minutes. So we all had to run to the new terminal gate. We could have taken off at that time, but we then had to wait for all the people who rebooked on a different flight to book this flight again. That took 30+ minutes because there was only one gate agent. When everyone ditched this flight, I saw it as an opportunity to upgrade to comfort. Delta, the greedy jerks they are, charged me $121. After their delay, their fault, their issues, couldn't even discount an upgrade. They only handed out $12 meal vouchers for the delay. I can't even get a snack from starbucks for that.

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

FA was a bit strange and dodgy not very characteristic of Delta

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.

I was exhausted from a long day. The flight was smooth. The first flight during my 3 week travel that took off on time.

Agents at gate were not immediately available to solve problems and once they did they didn’t fix all the fight connections

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

I needed internet for critical matters and it never worked.

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.

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.

Both flights were delayed. One by an hour and the other by 1 1/2 hours after boarding.

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.

Everything you need to know for your flight from Milwaukee to the U.S. Virgin Islands

Information on your arrival and departure airports