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Flight Deals
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, Jan 19 - Mon, Jan 25
5:15 am - 2:55 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
7h 40m1 stop Orlando
2:10 pm - 10:00 pmSTT Saint Thomas Island Cyril E King-MKE Milwaukee-Mitchell
9h 50m1 stop Orlando
$484Southwest
Tue, Jan 19 - Mon, Jan 25
5:15 am - 2:55 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
7h 40m1 stop Orlando
2:10 pm - 10:10 pmSTT Saint Thomas Island Cyril E King-MKE Milwaukee-Mitchell
10h 00m2 stops Orlando Nashville Intl
$484Southwest
Mon, Apr 19 - Tue, Apr 27
5:55 am - 2:45 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
7h 50m1 stop Atlanta Hartsfield-Jackson
1:25 pm - 9:08 pmSTT Saint Thomas Island Cyril E King-MKE Milwaukee-Mitchell
8h 43m1 stop Atlanta Hartsfield-Jackson
$520Delta
Sun, Apr 25 - Wed, Apr 28
7:00 am - 2:45 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
6h 45m1 stop Atlanta Hartsfield-Jackson
1:25 pm - 11:49 pmSTT Saint Thomas Island Cyril E King-MKE Milwaukee-Mitchell
11h 24m1 stop Atlanta Hartsfield-Jackson
$520Delta
Mon, Jan 4 - Wed, Jan 13
5:00 am - 2:31 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
7h 31m1 stop Chicago O'Hare Intl
3:00 pm - 10:31 pmSTT Saint Thomas Island Cyril E King-MKE Milwaukee-Mitchell
9h 31m1 stop Chicago O'Hare Intl
$522United Airlines
Mon, Jan 4 - Wed, Jan 13
5:00 am - 5:50 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
10h 50m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl
1:07 pm - 10:31 pmSTT Saint Thomas Island Cyril E King-MKE Milwaukee-Mitchell
11h 24m2 stops Washington, D.C. Dulles Intl Chicago O'Hare Intl
$522United Airlines
Sun, Nov 29 - Fri, Dec 4
7:33 pm - 3:58 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
18h 25m2 stops Chicago O'Hare Intl Miami
4:38 pm - 11:55 pmSTT Saint Thomas Island Cyril E King-MKE Milwaukee-Mitchell
9h 17m1 stop Charlotte Douglas
$528American Airlines
Fri, Dec 4 - Mon, Dec 7
8:12 pm - 4:30 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
18h 18m2 stops Chicago O'Hare Intl Miami
4:53 pm - 11:50 amSTT Saint Thomas Island Cyril E King-MKE Milwaukee-Mitchell
20h 57m2 stops Miami Charlotte Douglas
$528American Airlines
Thu, Nov 19 - Mon, Nov 23
10:15 am - 1:55 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
25h 40m3 stops Orlando Philadelphia San Juan Luis Munoz Marin Intl
12:01 pm - 5:26 pmSTT Saint Thomas Island Cyril E King-MKE Milwaukee-Mitchell
31h 25m3 stops San Juan Luis Munoz Marin Intl Chicago O'Hare Intl Orlando
$889Multiple Airlines
Thu, Nov 19 - Mon, Nov 23
10:15 am - 8:43 amMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
20h 28m2 stops Orlando San Juan Luis Munoz Marin Intl
12:01 pm - 5:26 pmSTT Saint Thomas Island Cyril E King-MKE Milwaukee-Mitchell
31h 25m3 stops San Juan Luis Munoz Marin Intl Chicago O'Hare Intl Orlando
$923Multiple Airlines
Recent one-way flight deals from Milwaukee to the U.S. Virgin Islands
Mon, Feb 15
6:10 pm - 1:20 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
17h 10m2 stops Nashville Intl Baltimore/Washington
$240Southwest
Tue, Feb 16
5:15 am - 2:55 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
7h 40m1 stop Orlando
$240Southwest
Mon, Feb 1
5:30 am - 3:49 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
8h 19m1 stop Atlanta Hartsfield-Jackson
$258Delta
Mon, Feb 15
7:00 am - 4:15 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
7h 15m1 stop Atlanta Hartsfield-Jackson
$258Delta
Sat, Jan 23
5:00 am - 5:50 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
10h 50m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl
$259United Airlines
Sat, Jan 23
5:00 am - 2:31 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
7h 31m1 stop Chicago O'Hare Intl
$259United Airlines
Mon, Feb 1
2:09 pm - 12:24 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
20h 15m2 stops Dallas/Fort Worth Miami
$262American Airlines
Tue, Feb 16
5:40 pm - 12:22 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
16h 42m2 stops Charlotte Douglas Miami
$262American Airlines
Tue, Feb 16
8:15 am - 2:50 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
28h 35m3 stops Orlando Atlanta Hartsfield-Jackson Tampa
$355Multiple Airlines
Sat, Jan 23
6:00 am - 5:01 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
33h 01m3 stops Cancun Punta Cana San Juan Luis Munoz Marin Intl
$976Multiple Airlines
Recent last minute flight deals from Milwaukee to the U.S. Virgin Islands
Thu, Nov 5 - Thu, Nov 12
7:00 am - 3:53 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
6h 53m1 stop Charlotte Douglas
3:15 pm - 7:48 amSTT Saint Thomas Island Cyril E King-MKE Milwaukee-Mitchell
18h 33m2 stops Miami Chicago O'Hare Intl
$575American Airlines
Thu, Nov 5 - Thu, Nov 12
7:00 am - 3:53 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
6h 53m1 stop Charlotte Douglas
4:33 pm - 11:56 pmSTT Saint Thomas Island Cyril E King-MKE Milwaukee-Mitchell
9h 23m1 stop Charlotte Douglas
$575American Airlines
Thu, Nov 5 - Thu, Nov 12
7:29 pm - 2:23 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
16h 54m2 stops Chicago O'Hare Intl Miami
4:33 pm - 11:55 pmSTT Saint Thomas Island Cyril E King-MKE Milwaukee-Mitchell
9h 22m2 stops Charlotte Douglas Washington, D.C. Reagan-National
$575American Airlines
Thu, Nov 5 - Thu, Nov 12
5:30 am - 2:37 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
7h 07m1 stop Atlanta Hartsfield-Jackson
3:53 pm - 11:54 pmSTT Saint Thomas Island Cyril E King-MKE Milwaukee-Mitchell
10h 01m1 stop Atlanta Hartsfield-Jackson
$669Delta
Thu, Nov 5 - Thu, Nov 12
5:30 am - 2:37 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
7h 07m1 stop Atlanta Hartsfield-Jackson
3:53 pm - 11:54 pmSTT Saint Thomas Island Cyril E King-MKE Milwaukee-Mitchell
10h 01m1 stop Atlanta Hartsfield-Jackson
$689Delta
Thu, Nov 5 - Thu, Nov 12
5:30 am - 2:37 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
7h 07m1 stop Atlanta Hartsfield-Jackson
3:53 pm - 11:54 pmSTT Saint Thomas Island Cyril E King-MKE Milwaukee-Mitchell
10h 01m1 stop Atlanta Hartsfield-Jackson
$732Delta
Thu, Nov 5 - Thu, Nov 12
5:08 pm - 1:38 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
18h 30m2 stops Washington, D.C. Reagan-National Charlotte Douglas
1:07 pm - 10:37 pmSTT Saint Thomas Island Cyril E King-MKE Milwaukee-Mitchell
11h 30m2 stops Miami Chicago O'Hare Intl
$791American Airlines
Thu, Nov 5 - Thu, Nov 12
7:29 pm - 2:23 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
16h 54m2 stops Chicago O'Hare Intl Miami
4:33 pm - 11:55 pmSTT Saint Thomas Island Cyril E King-MKE Milwaukee-Mitchell
9h 22m2 stops Charlotte Douglas Washington, D.C. Reagan-National
$791American Airlines
Thu, Nov 5 - Thu, Nov 12
7:00 am - 3:53 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
6h 53m1 stop Charlotte Douglas
3:15 pm - 7:48 amSTT Saint Thomas Island Cyril E King-MKE Milwaukee-Mitchell
18h 33m2 stops Miami Chicago O'Hare Intl
$791American Airlines
Thu, Nov 5 - Thu, Nov 12
7:00 am - 3:53 pmMKE Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
6h 53m1 stop Charlotte Douglas
3:15 pm - 7:48 amSTT Saint Thomas Island Cyril E King-MKE Milwaukee-Mitchell
18h 33m2 stops Miami Chicago O'Hare Intl
$811American Airlines
Booking Insights
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.
Prices
Airlines
More
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 $484 round-trip, and to Christiansted Henry Rohlsen (STX) from $574 round-trip.
What’s the cheapest month to fly from Milwaukee to the U.S. Virgin Islands?
These monthly figures are based on KAYAK fares from the past 12 months, with extreme outliers removed so each month's typical price is accurate.
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.
What are the cheapest airlines to fly with from Milwaukee to the U.S. Virgin Islands?
Fares reflect aggregated pricing data and may not include every trip type.
Looking at KAYAK data from the last 12 months, the cheapest airlines to fly with from Milwaukee to the U.S. Virgin Islands are:
• JetBlue (avg. price $460)
• American Airlines (avg. price $638)
• United Airlines (avg. price $692)
• Delta (avg. price $703)
• Southwest (avg. price $810)
What's the most popular airline to fly with from Milwaukee to the U.S. Virgin Islands?
Drawing on KAYAK data from the past three months, the most popular airlines to fly with from Milwaukee to the U.S. Virgin Islands are:
• American Airlines
• Delta
• United Airlines
• Southwest
What are the most popular regions in the U.S. Virgin Islands?
Saint Croix is the most popular region with KAYAK travelers, making up 20% of all interest in visiting the U.S. Virgin Islands, based on the past three months of KAYAK data.
What are the most popular flight destinations in the U.S. Virgin Islands?
Saint Thomas Island and Christiansted are the most popular flight destinations in the U.S. Virgin Islands, based on KAYAK data. Saint Thomas Island is the clear favorite, making up 80% of that interest.
Key details for Milwaukee to the U.S. Virgin Islands flights
Low season | August |
|---|---|
High season | February |
Cheapest flight | $240 |
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.
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.Reviews of the top 4 airlines serving from Milwaukee to the U.S. Virgin Islands
8.0
SouthwestOverall score based on 4219 reviews
7.5Entertainment
7.0Food
8.0Comfort
8.6Crew
8.1Boarding
Airline reviews
When I made my reservation it would have been nice if kayak would have included my luggage. Unaware that I had to pay $45 each way. Should have asked at reservation time if luggage was being checked
8.0 ExcellentJeremy, Nov 2026
When I made my reservation it would have been nice if kayak would have included my luggage. Unaware that I had to pay $45 each way. Should have asked at reservation time if luggage was being checked
Crew was a little surly. But plane left on time and arrived early. All one can ask for. New 737 Max was nice.
Flight was delayed about 50 minutes and completely full. they did the usual demand for people to check carry-ons. they called all groups to board very fast only to stand in the gangway after having boarding passes scanned. Why don't airlines board from the back to front - since they now have assigned seats? our stewardess got drink orders confused, so she just called out "cranberry". etc.,.. I wish they wouldn't serve pretzels snacks with a powdered coating, as it sticks to your hands and they don't have wet wipes. don't want to lick my fingers after hanging out in the terminal for over an hour.
Delayed over 3 hours, extremely rough landing on all four flights. Would not recommend
Boarding, crew and inflight entertainment was great. Could have better food options for a long flight. Paid money and got a seat with extra leg space but was asked to keep my carry on under the seat in front of me which defeats the purpose of buying a extra space seat.
On time departure and arrival. Had to be the oldest plane in the SWA fleet but it got me where I needed to be.
Flight was delayed out of BWI unexpectedly / without a reason given but otherwise ok.
I got a bit sick on the flight, and was so grateful when the male flight attendant explained to me they keep the back row open for cases like mine. He took such great care of me! I was incredibly grateful.
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.
I used by Skymiles to upgrade to First so that I could comfortably work using my laptop. But WiFi was intermittent and unavailable for long periods. I feel like I wasted 70,000 miles :(
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.
Terrible boarding - 4 flights boarded from the same gate. Chaos there; long ramps to the plane.
Flight delay in lax which delayed our connecting flight to Copenhagen. Was placed on standby the following day and got delayed again at Scandinavian air. Bad bad counter service at ar Canada in Toronto by the name of Camilla who said that she was doing us a courtesy for even finding a earlier flight for us after we the customer are the ones being inconvenient by the cancellation of our flight. Btw, we are going on a tour. Air Canada is the worse
The flight itself was ok, but one member of the crew was miserable
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
Information on your arrival and departure airports
Cabin class types available on flights to the U.S. Virgin Islands
Cabin classes available on flights to the U.S. Virgin Islands. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights from other airports in Milwaukee to the U.S. Virgin Islands
Flights from all airports in Milwaukee to the U.S. Virgin Islands. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights to other popular destinations
The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.