$134 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 1/23. 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.
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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

Sat, Jan 10 - Sat, Jan 17
Spirit Airlines Logo
7:20 am - 3:43 pm
ORD
-
STX
6h 23m1 stop
Spirit Airlines Logo
4:38 pm - 11:46 pm
STX
-
ORD
9h 08m1 stop
$233Spirit Airlines
Sat, Jan 17 - Sat, Jan 24
Spirit Airlines Logo
7:20 am - 4:37 pm
ORD
-
STT
7h 17m1 stop
Spirit Airlines Logo
5:42 pm - 11:46 pm
STT
-
ORD
8h 04m1 stop
$234Spirit Airlines
Wed, Jan 21 - Mon, Jan 26
Spirit Airlines Logo
5:32 pm - 2:52 pm
ORD
-
STT
19h 20m2 stops
Spirit Airlines Logo
5:42 pm - 11:46 pm
STT
-
ORD
8h 04m1 stop
$249Spirit Airlines
Sat, Jan 17 - Mon, Jan 26
Spirit Airlines Logo
5:32 pm - 2:52 pm
ORD
-
STT
19h 20m2 stops
Spirit Airlines Logo
5:42 pm - 11:46 pm
STT
-
ORD
8h 04m1 stop
$253Spirit Airlines
Sat, Feb 21 - Sat, Feb 28
Spirit Airlines Logo
5:15 am - 4:34 pm
ORD
-
STT
9h 19m1 stop
Spirit Airlines Logo
5:40 pm - 12:18 am
STT
-
ORD
8h 38m1 stop
$273Spirit Airlines
Sat, Jan 17 - Mon, Jan 26
Spirit Airlines Logo
7:20 am - 4:37 pm
ORD
-
STT
7h 17m1 stop
Spirit Airlines Logo
5:42 pm - 11:46 pm
STT
-
ORD
8h 04m1 stop
$280Spirit Airlines
Fri, Jan 9 - Fri, Jan 16
Multiple Airlines Logo
8:27 pm - 2:52 pm
ORD
-
STT
16h 25m1 stop
Multiple Airlines Logo
3:57 pm - 2:39 pm
STT
-
ORD
24h 42m1 stop
$286Multiple Airlines
Tue, Mar 3 - Tue, Mar 10
Delta Logo
6:00 am - 2:56 pm
MDW
-
STX
6h 56m1 stop
Delta Logo
2:19 pm - 10:29 pm
STX
-
MDW
9h 10m1 stop
$615Delta
Wed, Feb 18 - Sun, Feb 22
Delta Logo
6:00 am - 2:56 pm
MDW
-
STX
6h 56m1 stop
Delta Logo
3:58 pm - 10:42 pm
STX
-
MDW
8h 44m1 stop
$640Delta
Tue, Mar 3 - Sun, Mar 8
Delta Logo
6:00 am - 2:56 pm
MDW
-
STX
6h 56m1 stop
Delta Logo
2:19 pm - 10:29 pm
STX
-
MDW
9h 10m1 stop
$700Delta
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 $332 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 $332.

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 $586 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 $539 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $879 and $759 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, Thursday 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 3 weeks before departure, which saves you about 5% 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$134
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 28% 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 108% 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 $760.

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 8009 reviews
8.1Boarding
7.9Comfort
7.3Food
8.5Crew
7.9Entertainment
Airline reviews

Left on time, a bit delayed due to headwinds most of the trip.

10.0 ExcellentCharles, Dec 2025
DTW - PHX
Read more Delta reviews

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

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

Everything was smoothly and convenient! Just stay in this way!

Cancelled my flight and the earliest that they are willing give me for the next flight which was 3 days later on a weekday. Only accommodation they are willing to give was $30 airline credit that will expire in 1 year

Terrible Airline I will never fly that airline again. Shame on you for recommending them.

Flight was canceled, huge lines to get baggage returned. Most other airlines had delays but not widespread cancellations like Spirit.

never ever fly spirit airlines you will be screwed in the end

I didn't eat, so I can't rate the food. Delayed set off was beyond

No free snacks or drinks. Freezing. Uncomfortable. No plugs or entertainment. If you fly to LA the make you change terminals with a slow bus. Awful trip that took forever. Terrible airline- maybe the worst I’ve ever flown.

I hope you continue to be one of the great company

Crew are always very angry and dismissive like they seem they are being forced to work. In addition, there was a long line for the bathrooms, and only one was allowed to be used. No reason was given for only one bathroom being available; apparently, the stewardess was more interested in using the jumpseat instead of allowing the customers to use the bathroom.

Very positive in both directions. Safe travels, nice staff, lost and found in fact found my phone under my chair! I was out of cash after my NYC trip otherwise I would've offered a reward for helping my day out immensly! Thanks you so much Spirit staff!

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.