$244 Find Cheap Flights from Chicago 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 Chicago to the U.S. Virgin Islands departing on 8/10. 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.
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Book Cheap Chicago 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 Chicago 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 Chicago to the U.S. Virgin Islands

Thu, Jul 30 - Tue, Aug 4
JetBlue Logo
8:20 pm - 2:03 pm
ORD
-
STT
16h 43m
1 stop
JetBlue Logo
2:58 pm - 10:06 am
STT
-
ORD
20h 08m
2 stops
$475JetBlue
Tue, Aug 25 - Tue, Sep 1
JetBlue Logo
2:35 pm - 3:32 pm
ORD
-
STT
23h 57m
2 stops
JetBlue Logo
2:58 pm - 10:06 am
STT
-
ORD
20h 08m
2 stops
$487JetBlue
Tue, Aug 11 - Tue, Aug 18
JetBlue Logo
2:35 pm - 3:32 pm
ORD
-
STT
23h 57m
2 stops
JetBlue Logo
2:58 pm - 10:06 am
STT
-
ORD
20h 08m
2 stops
$489JetBlue
Thu, Aug 20 - Tue, Aug 25
JetBlue Logo
8:20 pm - 2:03 pm
ORD
-
STT
16h 43m
1 stop
JetBlue Logo
2:58 pm - 10:06 am
STT
-
ORD
20h 08m
2 stops
$495JetBlue
Thu, Jun 11 - Sat, Jun 20
JetBlue Logo
8:20 pm - 2:35 pm
ORD
-
STT
17h 15m
1 stop
JetBlue Logo
2:00 pm - 10:01 am
STT
-
ORD
21h 01m
2 stops
$506JetBlue
Mon, Aug 24 - Fri, Aug 28
American Airlines Logo
9:15 pm - 12:52 pm
ORD
-
STT
14h 37m
2 stops
American Airlines Logo
4:42 pm - 6:10 am
STT
-
ORD
14h 28m
2 stops
$521American Airlines
Sun, Aug 16 - Sun, Aug 30
American Airlines Logo
8:37 am - 8:38 pm
ORD
-
STX
11h 01m
1 stop
American Airlines Logo
3:54 pm - 12:31 am
STX
-
ORD
9h 37m
1 stop
$536American Airlines
Tue, Sep 22 - Tue, Sep 29
Delta Logo
6:00 am - 1:44 pm
MDW
-
STT
6h 44m
1 stop
Delta Logo
2:54 pm - 9:46 pm
STT
-
MDW
7h 52m
1 stop
$580Delta
Sun, Aug 16 - Sat, Aug 29
Delta Logo
6:05 am - 1:34 pm
MDW
-
STT
6h 29m
1 stop
Delta Logo
4:13 pm - 10:36 pm
STT
-
MDW
7h 23m
1 stop
$585Delta
Sat, Sep 19 - Sat, Sep 26
Southwest Logo
5:05 pm - 1:25 pm
MDW
-
STT
19h 20m
2 stops
Southwest Logo
2:05 pm - 8:55 pm
STT
-
MDW
7h 50m
1 stop
$677Southwest
Booking Insights

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

Get data-powered insights and trends into flights from Chicago 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 Chicago to the U.S. Virgin Islands flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to the U.S. Virgin Islands from Chicago found in the last 72 hours was to Saint Thomas Island, at $575 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Saint Thomas Island (STT), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $575.

What is the cheapest time of day to fly to the U.S. Virgin Islands?

The average price for all round-trip flights from Chicago to the U.S. Virgin Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to the U.S. Virgin Islands is generally in the morning, when round-trip flights cost $702 on average. The most expensive time of day to fly to the U.S. Virgin Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $702.

Can I save money by flying with a layover from Chicago to the U.S. Virgin Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $622 on average.

What is the cheapest month to fly from Chicago 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 Chicago 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 Chicago to the U.S. Virgin Islands is April, when tickets cost $80 (return) on average. On the other hand, the most expensive months are September and November, when the average cost of round-trip tickets is $261 and $251 respectively.

What’s the cheapest day of the week to fly from Chicago to U.S. Virgin Islands?

The average price of all round-trip flights from Chicago to the U.S. Virgin Islands clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago to U.S. Virgin Islands, look for departures on Thursdays and avoid leaving on a Saturday, as it's usually the priciest day. When flying back from U.S. Virgin Islands, Sunday is the cheapest day to fly and Friday is the most expensive.

How far in advance should I book a flight from Chicago 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 Chicago 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 Chicago to the U.S. Virgin Islands, you should book around 4 weeks before departure, which saves you about 37% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$244
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 13% increase in price.
Flight from Chicago O'Hare Airport to Saint Thomas Island

FAQs - booking U.S. Virgin Islands flights

  • Does either of the Chicago airports have an on-site hotel?

    Yes. You can find the Hilton Chicago O'Hare Airport hotel, located at ORD across from Terminal 2. This hotel is connected to all the terminals in ORD by way of an underground walkway, and you can get a free shuttle to terminal 5. Amenities of this accommodation include a number of restaurants, room service, Wi-Fi, an indoor pool, and much more.

  • Does either ORD or MDW have private facilities for nursing moms?

    Both O'Hare and Midway provide private facilities for traveling moms who either want to breastfeed their babies in private or who need to express their breast milk. ORD has a mother's room in each terminal as well as a lactation suite. MDW has a freestanding lactation suite located on Concourse A and a mother's room on Concourse C.

  • Where else can I fly to in the Caribbean from STT?

    From STT, you can take a flight on Air Sunshine to islands such as Anguilla, St. Croix, St. Kitts, or Nevis. You can take an LIAT flight to Antigua or a Trade Wind Aviation flight to St. Barthelemy. These are just a few examples of the many inter-Caribbean flights you can take from STT.

  • Is STX a small airport?

    Yes. STX is a small airport that services North American flights as well as inter-island flights. The check-in area is open air and the few amenities include one restaurant and two shops. This airport also includes a VIP lounge, car rentals, luggage lockers, and taxis that can take you into the city.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago 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 Chicago 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 Chicago 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 Chicago 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 Chicago 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.

Top tips for finding cheap flights to the U.S. Virgin Islands

  • The primary airport serving Chicago, the Chicago O'Hare International Airport (ORD) is located to the northwest of Chicago. The second major airport to serve the Chicago metropolitan area is Midway International Airport (MDW), located about an hour to the southeast of O'Hare. Both ORD and MDW have flights to the US Virgin Islands.
  • The Cyril E. King Airport (STT) is on the island of St. Thomas in the US Virgin Islands. You can get one-stop flights from ORD to STT on airlines such as Spirit, American, United, and others. Some layover cities include Miami, New York, Charlotte. You can find a one-stop flight from Midway to STT on Delta or a two-stop flight on Frontier.
  • If you want to fly to the island of St. Croix, you’ll most likely be landing at the Henry E. Rohlsen Airport (STX), located in the town of Christiansted. Airlines such as Spirit, American, Delta, and United offer flights from ORD to STX with one stop, often in Fort Lauderdale, Miami, or Atlanta. Frontier and Delta offer one-stop flights from MDW to STX, which stops in Atlanta or Fort Lauderdale.
  • Several flights from Chicago to the US Virgin Islands require you to check in again for each leg of your flight or to change airports in a layover city. Before you book a ticket with these requirements, make sure the itinerary leaves you enough time. Also make sure that you have enough of the right kind of money if you need to travel across a foreign city in order to change airports.
  • If you want to stretch out your muscles before your flight to the US Virgin Islands, you can take advantage of the Yoga Room in both ORD and MDW. You can indulge in some low-key stretching as you follow poses displayed on wall mounted TVs. Open every day from 6 in the morning until 10 at night, these rooms do not have locker rooms.

Reviews of the top 4 airlines serving from Chicago to the U.S. Virgin Islands

 
Need help choosing which airline to fly with from Chicago 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
DeltaOverall score based on 8454 reviews
7.2Food
8.1Boarding
7.8Entertainment
8.5Crew
7.8Comfort
Airline reviews

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

10.0 ExcellentBenjamin, May 2026
CLT - MSP
Read more Delta reviews

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

Smooth flight. Left on time, and got in 15 minutes early. Onboard video was great

For some reason, TSA Atlanta didn’t have my bag on the flight on time and they don’t have to provide Delta a reason for that.

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Delta does a great job with entertainment and free wifi. I can still be in touch with my colleagues while in the air.

Aside from a completely packed plane, I really have no complaints.

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

It was a pleasant surprise to have complimentary Wi-Fi on the flight

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

The boarding timing needs to be improved. The flight was delayed again because it took way too long to board. I was already exhausted from sleeping at the airport and spending all day there due to delay from my previous flight that connected in Chicago.

Great until we got to FRA. The next trip leg we were put in Business Class where seats had minimal padding!!!! They were awful and United Airlines needs to have their Lufthansa partner up their game or I won’t fly with them again!!

Our flight was cancelled while we are on our way to the airport. So, no notice. We were rescheduled to another airline with a 2 hour later takeoff and so arrived at our destination on time. We pre-paid American Airlines $190 to upgrade our seats. No refund. So no use for AA or Kayak.

Terrible, horrible, disappointing- without telling us they changed planes and moved and separated our seats to opposite sides - said they changed seats putting us together - got to airport to find no, they did not - we sat opposing sides of plane - food overly salty to inedible, never saw stewardess but once - it was terrible

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

The airline cancel mi flight, lost a lot of money!!!

Paid for WiFi and the connection was basically nonexistent. Was pleasantly surprised with everything else. Staff was great. Boarding was easy. Plane was clean. Overall, a very pleasant experience

They cancelled our flight. 2 hours before we were supposed to take off and offered us nothing! We got our money back and that was it. No other flight to get to our cruise no working with another airline or with us to get there. Terrible customer service, no apology.

We get stuck in the plane when landed during 45min and no communication from the crew People were listening to their phone and music out loud and nobody told them anything I definitely want stop booking spirit flight it is a disaster

Good: It was cheap and they got us to our destination safely. Not so Good: Gates experience with many, many nauseatingly (almost) threatening announcements about bags size and how much they were going to charge us if our bag was too big, even to the point of having a gate agent roaming around through the passengers eyeballing bags size and making people go check their bags in the sizers.

Terrible. The flight was randomly delayed in Chicago causing us to miss our connection and they offered us a flight the next day at 6 am and it would have taken till 345 to get to Pensacola. They didn’t cover any fees. Our bags also supposedly were on the flight to Pensacola and we tried to get them yesterday after driving 6 hours and nobody was available. Worst company ever and will never use them again. Had to pay for a rental. Spirit is claiming in climate weather for the delay but there wasn’t any weather issuesz it’s a bunch of bullshit and I am not happy

Checking in at desk in Chicago was horrible. Person was not friendly never smiled and said my flight was not paid for so I had to give another credit card. Then it ended up that I was charged twice. Then after arriving at my destination had to wait on the phone a long time to speak to a person to fix the double charge! Thank goodness the flight was perfect.

Flight was delayed for 12 h. They should stop overlooking flights.

All of our flights were canceled, though every other airline was flying out and in

it was terrible. flight was cancelled hours before the flight without a given reason and no other booking available .

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

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.