$126 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 4/5. 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

KAYAK searches hundreds of travel sites at once for deals on flights to the U.S. Virgin Islands

Travelers love KAYAK
41 299 237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

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

Mon, May 18 - Fri, May 29
Spirit Airlines Logo
5:05 am - 4:35 pm
ORD
-
STX
10h 30m
1 stop
Spirit Airlines Logo
5:30 pm - 12:24 am
STX
-
ORD
7h 54m
1 stop
$236Spirit Airlines
Tue, Apr 7 - Tue, Apr 14
Spirit Airlines Logo
5:05 am - 3:28 pm
ORD
-
STT
9h 23m
1 stop
Spirit Airlines Logo
4:35 pm - 9:36 am
STT
-
ORD
18h 01m
1 stop
$268Spirit Airlines
Fri, Apr 10 - Mon, Apr 13
Spirit Airlines Logo
4:36 pm - 3:28 pm
ORD
-
STT
21h 52m
1 stop
Spirit Airlines Logo
4:35 pm - 5:15 pm
STT
-
ORD
25h 40m
1 stop
$269Spirit Airlines
Fri, Apr 10 - Tue, Apr 14
Spirit Airlines Logo
4:36 pm - 3:28 pm
ORD
-
STT
21h 52m
1 stop
Spirit Airlines Logo
4:35 pm - 9:36 am
STT
-
ORD
18h 01m
1 stop
$271Spirit Airlines
Tue, Apr 14 - Tue, Apr 21
Spirit Airlines Logo
4:36 pm - 9:54 am
ORD
-
STT
16h 18m
2 stops
Spirit Airlines Logo
5:10 pm - 12:24 am
STT
-
ORD
8h 14m
1 stop
$272Spirit Airlines
Mon, Apr 6 - Mon, Apr 13
Spirit Airlines Logo
6:10 pm - 3:28 pm
ORD
-
STT
20h 18m
1 stop
Spirit Airlines Logo
4:35 pm - 7:51 pm
STT
-
ORD
28h 16m
1 stop
$273Spirit Airlines
Tue, Apr 14 - Thu, Apr 23
Multiple Airlines Logo
5:05 am - 3:28 pm
ORD
-
STT
9h 23m
1 stop
Multiple Airlines Logo
10:49 am - 9:30 pm
STT
-
ORD
11h 41m
1 stop
$276Multiple Airlines
Sat, Aug 1 - Sat, Aug 8
Delta Logo
6:00 am - 1:57 pm
MDW
-
STX
6h 57m
1 stop
Delta Logo
2:45 pm - 9:45 pm
STX
-
MDW
8h 00m
1 stop
$626Delta
Tue, Mar 31 - Tue, Apr 7
Delta Logo
6:00 am - 1:18 pm
MDW
-
STX
6h 18m
1 stop
Delta Logo
2:24 pm - 10:31 pm
STX
-
MDW
9h 07m
1 stop
$869Delta
Tue, Mar 31 - Tue, Apr 7
Delta Logo
6:00 am - 1:18 pm
MDW
-
STX
6h 18m
1 stop
Delta Logo
2:24 pm - 10:31 pm
STX
-
MDW
9h 07m
1 stop
$889Delta
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 $531 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 $531.

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 $720 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 $720.

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 May, when tickets cost $399 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $1,000 and $683 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 Saturday, 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, which saves you about 13% 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$126
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 9% 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 8276 reviews
8.1Boarding
7.2Food
7.8Entertainment
8.5Crew
7.9Comfort
Airline reviews

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

8.0 ExcellentMary, Mar 2026
LGA - MKE
Read more Delta reviews

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

Extremely disappointed with Delta. They canceled flight last minute and then I rebooked the other flights and with which were delayed as well

Could not get my connecting flight boarding pass until four hrs before departure! Ver annoying especially since the staff could not explain why!

The flight was flying with 30% capacity. The flight my seat from preferred seating to back of the seat. Even though i can understand that this was to balance the flight weight. The flight attendance decided to do the serving near my seat and in the middle , their noices woke me up from sleep , when i realized that the service has ended and when they were going back asked for a coffee, for which they answered they have completed teh service in my location. That really upset me as they woke me up and also rejected the coffee i asked. I ended up landing with a headache, thanks to the crew that screwed up my travel

Delayed. Hot. Passenger next to me was so large I couldn’t move.

Same experience as the flight from Norfolk to Atlanta where people are boarded in zones that don't make sense. People behind you on the plane will get on before you and they take the luggage space on your row.

The boarding process doesn't make sense since some people that will sit behind your rows are boarded before you and then they take up the luggage space above your head. I then have to wait for people to get off the plane before I can go back to get my luggage.

Good flight. Connector flight was delayed so made a short turnaround in Atlanta which was stressful. Otherwise, great crew, Staff in ATL was very informative about the delay and ensured people their connections were fine. Notified the ones that were not. Great communication.

The flight went very well, but the flight attendants didn't serve and food or drinks other than 1st class due to rough air but to be honest it wasn't that bumpy and I felt that they could've at least offered water and coffee perhaps. Also serving 1st class only is a bad look. I've been in 1st class many times and I would've felt that if the turbulence was too rough for the main cabin, it would be too rough for 1st class too.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

Delayed both in takeoff and landing, trash plane no amenities, I've said it before but I'll never fly Spirit again.

My flight was delayed by over an hour and the turbulance was horrible.

Everything is an additional fee. No one said anything when I checking in and got my boarding pass about my small carry on suitcase. Charged me $100 at the gate for that little bag that I still had to take with me. Delays for both flights for no reason and then when I asked everyone said something different. Never flying spirit again. If it was just one thing maybe. This was a show from the minute I got to the airport.

I had a great experience from booking to boarding to landing. This was the best experience from all the flights I’ve had with Spirit so far! The price and times were affordable and perfect. I will fly with them again soon!

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

First off, I had a conversation with a flight attendant that was working this flight. I overheard her telling another flight attendant while we were in line for Chic-Fil-A that the flight was not going to land until 12:47 pm. I found this odd since the flight was to take off at 1:03. I commented to the flight attendant that was going to mess up the on-time take-off She said. if you fly alot you will notice that it's a good thing if the flight even arrives at all. I said that was a low bar. I think that flight attendants represent their airlines whether on board or in the airport ordering food. I was surprised to hear such negativity. However, I have noticed that Spirit flight attendants are usually in a sour mood.. Eventually the flight arrived and I boarded and the flight took off an hour late. There was no direction about the on-board wi-fi. Nor was there any info in the seat back pocket. I don't know if there was wi-fi or not, There were no complimentary snacks or drinks for my row 36 as there was turbulence and the captain asked the flight attendants to stop serving just as they were close to my row. When the turbulence stopped, they did have time to serve us but they did not. Upon arriving, the flight attendant asked anyone not having to catch a flight to Ft. Laudersle which was a tight connection to sit down and let those people pass. I complied but I could not help thinking that if Spirit would have took off on time that they would not have to inconvenience their passengers. All in all, I think Spirit is a mediocre airline at best. There are so many things they could do to improve. Yet, since I only fly Spirit infrequently preferring Southwest and Delta, I like to see if they are improving and sadly no, they are not. One good thing - nice modern seats and interiors.

I have to wait for the flight for 3 hours. The gate was switching for 5 times. Made feel frustrated. Delays took all my sleep. I went to work without any sleep.

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

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.