$91 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 2/28. 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, Feb 28 - Sat, Mar 7
Spirit Airlines Logo
7:00 am - 3:40 pm
ORD
-
STX
6h 40m
1 stop
Spirit Airlines Logo
4:37 pm - 11:47 pm
STX
-
ORD
9h 10m
1 stop
$171Spirit Airlines
Sun, Mar 1 - Fri, Mar 6
Spirit Airlines Logo
8:16 pm - 3:40 pm
ORD
-
STX
17h 24m
1 stop
Spirit Airlines Logo
4:37 pm - 11:47 pm
STX
-
ORD
9h 10m
1 stop
$186Spirit Airlines
Sun, Mar 15 - Mon, Mar 23
Spirit Airlines Logo
8:41 pm - 2:33 pm
ORD
-
STX
16h 52m
1 stop
Spirit Airlines Logo
3:31 pm - 7:46 pm
STX
-
ORD
29h 15m
1 stop
$193Spirit Airlines
Sun, Mar 1 - Fri, Mar 6
Spirit Airlines Logo
8:16 pm - 3:40 pm
ORD
-
STX
17h 24m
1 stop
Spirit Airlines Logo
4:37 pm - 5:46 pm
STX
-
ORD
27h 09m
2 stops
$210Spirit Airlines
Fri, Feb 13 - Sun, Feb 15
Multiple Airlines Logo
4:42 pm - 4:34 pm
ORD
-
STT
21h 52m
2 stops
Multiple Airlines Logo
5:40 pm - 11:47 pm
STT
-
ORD
8h 07m
1 stop
$395Multiple Airlines
Fri, May 15 - Mon, May 18
Multiple Airlines Logo
5:32 pm - 1:31 pm
ORD
-
STT
18h 59m
2 stops
Multiple Airlines Logo
2:45 pm - 8:51 am
STT
-
ORD
19h 06m
2 stops
$397Multiple Airlines
Mon, Feb 23 - Thu, Feb 26
Southwest Logo
5:15 pm - 2:55 pm
MDW
-
STT
19h 40m
2 stops
Southwest Logo
2:10 pm - 7:15 pm
STT
-
MDW
7h 05m
1 stop
$468Southwest
Tue, Mar 17 - Mon, Mar 23
Southwest Logo
6:00 am - 2:20 pm
MDW
-
STT
7h 20m
1 stop
Southwest Logo
1:50 pm - 7:45 am
STT
-
MDW
18h 55m
2 stops
$484Southwest
Sun, Mar 1 - Fri, Mar 6
Delta Logo
6:00 am - 2:56 pm
MDW
-
STX
6h 56m
1 stop
Delta Logo
3:58 pm - 10:31 pm
STX
-
MDW
8h 33m
1 stop
$496Delta
Tue, Mar 3 - Sat, Mar 7
Delta Logo
6:00 am - 2:56 pm
MDW
-
STX
6h 56m
1 stop
Delta Logo
3:58 pm - 10:31 pm
STX
-
MDW
8h 33m
1 stop
$521Delta
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 $414 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 $414.

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 $613 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 $546 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $980 and $774 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 11% 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$91
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly with an average 27% 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 morning, when round-trip flights cost $732 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 $732.

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 8127 reviews
7.9Comfort
8.5Crew
8.1Boarding
7.8Entertainment
7.2Food
Airline reviews

Timing, quality of service, promptness and courtesy of the staff

10.0 ExcellentAjai, Jan 2026
DFW - ATL
Read more Delta reviews

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The flight was comfortable and uneventful, which is what I desire

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

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. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

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.

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.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

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.

I know it's a low-cost airline. However, the seats are very basic, so after two hours of travel, they feel very uncomfortable and cannot be reclined. The two flights from Bogota to Orlando and the return flight were very punctual. The check-in process on the app works very well. I really liked the self-check-in process for luggage at the Orlando airport; it was quick, easy, and very convenient.

The entire experience was so surprisingly pleasant. And the blocked extra seat between us was such an amazing and nice bonus. Great experience all around and I can’t wait to fly with spirit again!

Everything was OK, the deicing took a long time, our connections were almost missed.

All very good except they didn’t load our walker so haven’t gotten it yet

Flight was cancelled. But kayak thought it was still on time.

For the cost you can't e too critical, but the inablitiy to recline the seat and minimal cushioning in the seats made for a less than comfortable flight. Other than that we had an ealry departure and arrival, boarding was smooth.

The flight was delayed by 2 hours and we had no food or water or chargers

Spirit was on time. They maintained updates and information. The crew was friendly and professional. Because this is a budget friendly airline, they have dispensed with a lot of frills and part of that comes with a price, for example, the seats are not quite as comfortable as others. I am ok with a pay for beverage and snack service as I prefer my own anyway so this was not a concern. I thought overall, having a great flight crew and on time service was definitely worth losing some of the frills from other carriers.

Nothing everything cost money a bottle of water is 5 dollars and there wasn't even an outlet to plug 🔌 in my 📱 phone

You can’t beat Spirit’s prices on tickets, especially with the positive experience that comes with it! I appreciated the timeliness of Spirit airlines. The crew in the airport was very kind and wished you a good flight by name. The crew on the flight was attentive and friendly. Overall, I am very pleased with my experience with Spirit.

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.