$139 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 8/8. 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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Best U.S. Virgin Islands Flight Deals from Chicago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Cheap Flights from Chicago to the U.S. Virgin Islands

 
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

Wed, Jul 23 - Wed, Jul 30
Spirit Airlines Logo
5:40 pm - 9:48 amORD-STT
15h 08m1 stop
Spirit Airlines Logo
1:25 pm - 8:28 pmSTT-ORD
8h 03m1 stop
$256Spirit Airlines
Find Deal
Mon, Aug 18 - Fri, Aug 22
Spirit Airlines Logo
6:56 am - 3:19 pmORD-STT
7h 23m1 stop
Spirit Airlines Logo
2:43 pm - 10:22 pmSTT-ORD
8h 39m1 stop
$260Spirit Airlines
Find Deal
Mon, Aug 18 - Fri, Aug 22
Spirit Airlines Logo
6:56 am - 3:19 pmORD-STT
7h 23m1 stop
Spirit Airlines Logo
2:43 pm - 10:22 pmSTT-ORD
8h 39m1 stop
$261Spirit Airlines
Find Deal
Sat, Aug 23 - Sat, Aug 30
Spirit Airlines Logo
8:12 pm - 11:13 amORD-STT
14h 01m1 stop
Spirit Airlines Logo
2:43 pm - 10:22 pmSTT-ORD
8h 39m1 stop
$266Spirit Airlines
Find Deal
Fri, Aug 8 - Mon, Aug 11
Spirit Airlines Logo
4:37 pm - 12:30 pmORD-STT
18h 53m2 stops
Spirit Airlines Logo
12:26 pm - 11:58 pmSTT-ORD
12h 32m1 stop
$271Spirit Airlines
Find Deal
Wed, Jul 16 - Sun, Jul 20
Frontier Logo
11:28 am - 4:41 pmORD-STX
28h 13m2 stops
Frontier Logo
5:40 pm - 11:31 pmSTX-ORD
30h 51m2 stops
$401Frontier
Find Deal
Mon, Jul 21 - Thu, Jul 24
 Logo
10:31 am - 4:02 pmMDW-STX
28h 31m3 stops
 Logo
5:09 pm - 2:04 pmSTX-MDW
21h 55m2 stops
Fri, Aug 1 - Thu, Aug 7
 Logo
1:11 pm - 3:29 pmMDW-STX
25h 18m3 stops
 Logo
10:52 am - 1:56 pmSTX-MDW
28h 04m3 stops
Mon, Dec 8 - Thu, Dec 18
Delta Logo
6:00 am - 2:22 pmMDW-STT
6h 22m1 stop
Delta Logo
3:32 pm - 9:44 pmSTT-MDW
8h 12m1 stop
$509Delta
Find Deal
Sat, Aug 23 - Sat, Aug 30
Delta Logo
6:04 am - 3:10 pmMDW-STT
8h 06m1 stop
Delta Logo
3:23 pm - 9:12 pmSTT-MDW
6h 49m1 stop
$519Delta
Find Deal
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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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to the U.S. Virgin Islands.

The cheapest ticket to the U.S. Virgin Islands from Chicago found in the last 72 hours was to Christiansted, at $495 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 $510.

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 1 stop layover the cheapest option at $1,212 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 September, when tickets cost $467 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $828 and $762 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 Wednesdays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from U.S. Virgin Islands, Wednesday is the cheapest day to fly and Saturday 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 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.


Good to know

Low seasonAugust
High seasonMarch
Cheapest flight$139
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 1% 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.

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

    The cheapest time of day to fly to the U.S. Virgin Islands is generally in the evening, when round-trip flights cost $365 on average. Morning departures are around 121% more expensive than evening flights, 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 $805.

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.
8.0
DeltaOverall score based on 7975 reviews
8.5Crew
7.9Comfort
7.3Food
8.2Boarding
7.9Entertainment
Airline reviews

From Atlanta to Savannah - flight connection was way to short (we weren't even late landing ) and flight was already boarding when we landed - we were told we were the last on board and so we had to gate check our bags. Once we got on the plane, there were at least seven open bag spots so that was unnecessary delay. There should be better communication between the gate agent and the crew.

6.0 GoodBrenda, Jul 2025SAV - ATL
Read more Delta reviews

From Atlanta to Savannah - flight connection was way to short (we weren't even late landing ) and flight was already boarding when we landed - we were told we were the last on board and so we had to gate check our bags. Once we got on the plane, there were at least seven open bag spots so that was unnecessary delay. There should be better communication between the gate agent and the crew.

Crew was excellent. Comfort seats not as nice as other kinds of planes.

Not a "Delta" issue, but a JFK issue: We booked a connecting flight with 3 1/2 hours between to clearn immigration and customs. Our inbound flight (BCN to JFK) was on the taxiway 45 minutes which ate into our layover time. Immigtration was insanely quick with the CBP MPC app; however, clearing TSA (again, after we were ALREADY cleared in Spain on the inbound international flight) took over 95 minutes. This left us with 10 minutes before boarding the connecting flight (JFK to SAN) to walk to the far end of Terminal 4 and try to find food. We didn't find any food that could promise to serve us in under 10 minutes so we boarded the Delta flight after coming off a plance and an 8-hour flight knowing that we wouldn't be served any food on the next 5 1/2 hour flight. I feel like Delta needs to put pressure on the JFK TSA to open more screening stations (by our count, we saw only 5 scanners open and a line of - as we said - over 90 minutes. The insult is that we WERE ALREADY SCREENED through TSA, but as you come off one flight into the USA, you have to go through the whole process again. It seems like if you have a connecting flight, there should be a way to pass through immigration and customs without needing to return through TSA.

It was a great flight and the stewards and stewardess were all kind and accommodating!! The seats were comfortable and entertainment screen excellent!

There are 4 flights in consecutive gates with about the same departure time. Two flights were boarding at the same time. One was delayed or boarding would be happening at the same time. I am not sure what Delta and LAX need to do to have a better layout at the end of Terminal 2

Flight was an hour late, who knows why. It was OK, nothing outstanding.

Only not having an assigned seat was an issue. Rest was great

There was a security issue at the airport and we were unable to land. We circled endlessly and then landed at another airfield for fuel. We then circled the airport again, almost landed but didn’t fully touch down before circling again. I am thankful to the crew for keeping us safe- the issue was the airline and staff at the airport getting us seats on our connecting flights. That part was hours of searching for someone and getting in double my steps.

Boarding was organised and relaxed. Crew were fantastic! Seats were lacking padding causing butt pain and stiffness.

I like for how they process during check in. It was very smoothly.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

I wanted to upgrade my seat because I’m 6’2 and never have enough leg room for my comfort. They upgraded my seat for free putting me in an emergency exit seat. I was very comfortable

I have never flown Spirit it was much better than anticipated!

Staff was very friendly. They attended to people nicely and reprimanded, in a professional way, to those who wouldn’t listen. AC wasn’t working on the flight waiting to depart in Burbank, so it was uncomfortable for a while since the flight was delayed but then better before take off.

This was the first time I use Spirit Airlines and was pleasantly surprised. It was a last-minute booking and I was happy to see there was availability on your airline for a price that was affordable. The staff was friendly. The only things I thought were missing, were the ability to recline the seats, although I don’t use that very often, and it would’ve been nice to have power access at the seats to plug in my devices.

Flight was on time and was not crowded. Flight attendants were very understanding of my wife’s back problems.

Good on that leg. When I arrived in Detroit I had to wait over an hour for luggage.

Not very good because of an almost 3 hour delay for an hour long flight.

The spirit flight was on time. The airplane itself was surprisingly very nice. We had great seats. Seems like there's more room. Only complaint is that I didn't get a full refund for my mistakenly buying the baggage twice.

We had an almost 7 hour flight delay. We left the gate twice and taxi-ed and then returned the gate twice. Finally we got a new flight crew (our third one) and then left the gate to the final time before departing at 6:45pm (original flight time was 12pm). Out of Newark.

I made it safely. The flight was delayed, though. Not upset or expect anything.

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.

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