$308 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 11/23. 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, Oct 6 - Thu, Oct 15
American Airlines Logo
4:26 pm - 12:40 pm
MKE
-
STT
19h 14m
2 stops
American Airlines Logo
1:50 pm - 11:47 pm
STT
-
MKE
10h 57m
2 stops
$420American Airlines
Fri, Sep 18 - Fri, Sep 25
American Airlines Logo
5:53 pm - 12:51 pm
MKE
-
STT
17h 58m
2 stops
American Airlines Logo
1:41 pm - 9:46 am
STT
-
MKE
21h 05m
2 stops
$485American Airlines
Fri, Jul 17 - Thu, Jul 23
American Airlines Logo
6:03 pm - 11:57 am
MKE
-
STT
16h 54m
2 stops
American Airlines Logo
4:50 pm - 8:02 am
STT
-
MKE
16h 12m
2 stops
$520American Airlines
Fri, Jul 17 - Thu, Jul 23
Delta Logo
6:50 am - 3:20 pm
MKE
-
STT
7h 30m
1 stop
Delta Logo
1:21 pm - 8:54 pm
STT
-
MKE
8h 33m
1 stop
$535Delta
Thu, Sep 24 - Mon, Sep 28
American Airlines Logo
5:53 pm - 12:51 pm
MKE
-
STT
17h 58m
2 stops
American Airlines Logo
1:41 pm - 9:46 am
STT
-
MKE
21h 05m
2 stops
$550American Airlines
Fri, Jul 17 - Thu, Jul 23
American Airlines Logo
6:03 pm - 11:57 am
MKE
-
STT
16h 54m
2 stops
American Airlines Logo
11:43 am - 9:54 pm
STT
-
MKE
11h 11m
1 stop
$560American Airlines
Wed, Nov 11 - Sun, Nov 15
American Airlines Logo
6:48 pm - 12:07 pm
MKE
-
STT
15h 19m
2 stops
American Airlines Logo
12:57 pm - 8:00 am
STT
-
MKE
21h 03m
2 stops
$565American Airlines
Fri, Sep 18 - Fri, Sep 25
Delta Logo
5:30 am - 1:44 pm
MKE
-
STT
7h 14m
1 stop
Delta Logo
2:54 pm - 8:52 pm
STT
-
MKE
6h 58m
1 stop
$572Delta
Fri, Sep 18 - Fri, Sep 25
Southwest Logo
6:20 pm - 1:20 pm
MKE
-
STT
18h 00m
2 stops
Southwest Logo
2:35 pm - 8:45 pm
STT
-
MKE
7h 10m
1 stop
$590Southwest
Sun, Nov 22 - Tue, Dec 1
American Airlines Logo
2:53 pm - 12:07 pm
MKE
-
STT
19h 14m
2 stops
American Airlines Logo
12:57 pm - 9:45 am
STT
-
MKE
22h 48m
2 stops
$605American Airlines
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 September, when the average cost of round-trip tickets is $683 and $666 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 2 weeks before departure, which saves you about 31% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$308
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 3% lower on average.
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 5 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 4262 reviews
8.6Crew
8.0Comfort
7.5Entertainment
7.0Food
8.1Boarding
Airline reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

4.0 OkayAnonymous, May 2026
MDW - LAX
Read more Southwest reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

Clean planes and not take my comfort class seat away.

The crew were efficient. The pilots seemed professional. It was a bit chilly in our seats. The sheet provided weren’t very helpful.

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

Planes were clean, no water or snacks on either flight.

Free & relatively fast Wi-Fi. Would've liked a wider drink selection.

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

The Boarding process was great. Particularly since my wife and I require assistance. The flight attendants were amazing. We travel frequently; they honestly were a cut above. 😀

Enjoyed it very much. Especially liked the free WiFi that Delta offers.

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

It was a short flight so I was expecting too much

Horrifying Almost 2 million miles. Bring your own food and drink. One coffee or drink every three hours. Have to order meals on app more than 24 hours ahead Tiny and dirty bathrooms

Flight was delayed but more than 90 minutes. This caused me to miss my available windows for pick-up by a friend. I had to pay $125 for an uber back home from the airport which was an added expense that I had not budgeted for my trip. Staff was friendly.

I felt scammed. The priced advertised was different than what I paid. I paid the whole some online. I then got a call 20 minutes later saying I need to paid 70 more person. She said the price online is not the guaranteed price.

Seat pitch is horrible especially on the 15 hour flight. Gate crew at SFO was Outstanding. The flight crew was also great.

Easy of boarding, helpfully staff at check in, surprisingly comfortable seating

Check in was chaotic with only one counter for business class and first class. The luggage conveyor belt at JFK airport was broken so the flight departure was delayed which made the flight stressful as I had a tight connection. Although the captain said they could make up the delay, they didn’t do so.

Had a one hour delay due to mechanical issue. I didn’t think I’d be able to make my connecting flight, but they waited for me and greeted me when I arrived to help things run smooth.

Lost of requested seat assignments. Lost my husband's meal choice

Was put into a seat right behind the toilet that had no entertainment possible but did have plenty of leg room over noisy part of plane.

B-class on an old plane with antiquated amenities and poor service. Landed in Rome w/o bag that didn’t make the connection (plenty of time in London). Bag will come to hotel NOT the day it lands but the following night!! Still waiting for bag…BA had nothing to offer in support and couldn’t even tell me their comp, told to submit receipts and then I’ll learn what is or isn’t covered.

Movies on my phone are great. It would be nice to have a gluten free snack option.

It was what i expected. I like the movies you can access from your phone. It would be nice if there was a gluten free snack offered. But I did bring my own snack knowing there would not be a gluten free option

The flight was peaceful, just s slight turbulence, pilots and crews were all nice and made a great job! Arrived safely in the Philippines. Thank you ya’ll!

Ontario airport boarding was very easy to park and access, is clean and TSA took 10 minutes total. Check-in was a breeze and cruise was very nice.

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

The flight attendants were very friendly, efficient, and helpful. The plane was ahead of schedule, and it all went very smoothly. Thank you.

They lost my baggage and I am still struggling to the information and update

My flight today was cancelled because it was Spirit Airlines but have received no refund.

THEY WENT OUT OF BUSINESS AND CANCELED FLIGHT. REPLACEMENT FLIGHTS WERE 300% HIGHER SO MY FAMILY COULD NOT GET TOGETHER. WHY AM I GETTING THIS SURVEY?????

If there WAS a flight it would have been EXCELENT..Maybe?

It would have been better IF IT HAD NOT BEEN CANCELED!!!!

There was no flight. Spirit went bankrupt Right before my departure and kayak did not refund me any money. I would like my refund kayak. How can I get it? Please let me know. Thank you

Flights were canceled due to airline shutting down and haven’t received a reimbursement. Had to book last minute new flights which were expensive

My flight was canceled the morning of the flight. I had to rebook a flight with a different airline that cost me $900 out of my pocket

Are you serious? I know this is an automated message but how can you not update the system?

Had a flight change had to get a credit.will I get my money back.

Shut down without prior notice End up with spending lots of extra $$$

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

Information on your arrival and departure airports