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Find cheap flights from Chicago to the U.S. Virgin Islands from $112

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 5/25. 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
0 bags
Sat 5/18
Sat 5/25

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Best U.S. Virgin Islands Flight Deals

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

Good to know

Low season

September

High season

March

Cheapest flight

$112
Best time to beat the crowds with an average 17% 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 to the U.S. Virgin Islands from Chicago 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 to the U.S. Virgin Islands with an airline and back to Chicago 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 to the U.S. Virgin Islands from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

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

  • Morning departure is around 52% more expensive than an evening flight, on average*.
  • 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.
See more tips
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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 11104 reviews
8.2boarding
8.6crew
8.0entertainment
7.5food
7.9comfort
Airline reviews

Everything was great except for the seat. The backrest would not stay in the upright position.

8.0 ExcellentEddie, Apr 2024SEA - PHX
Read more about Delta reviews

Everything was great except for the seat. The backrest would not stay in the upright position.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

Flight delayed about 2 hrs so it made it a VERY late night

The crew, food, and entertainment were all good. But my screen had some sort of bug where if I turned it off, it would turn back on after 2-5 minutes. At full brightness. It made it very hard to get any shut-eye on the overnight flight. Also, the older Boeing plane, while nicely cared for (and no doors fell off 😅👏) doesn't have the nice air quality of newer planes. So I felt a bit greasy by the time we landed in Sweden.

It was a crowded flight. They did the best they could.

Service was good for such a short flight. Small plane but smooth flight.

Worst flight in my life. Only was scheduled for a 45 min flight to get our connection flight. It was late by 40 minutes and we missed our connection. Delta was totally useless trying to help and unable to get my family on the next flight because they overbooked it Thus had to get a hotel at my expense and lost a day at Disney as a result. Cost me about a $1000 if you add 2 hotels meals shuttles etc to get thru the day Awful customer service by Delta in Detroit totally useless people

The experience was good and the flight departed on time and landed early

The flight was delayed but we got to our final destination.

Boarding was great. The flight landed early. It took the crew over an hour and a half to bring out drinks. I paid to upgrade my seat to Comfort+ only to be near a crying/screaming baby who was seldom quiet. Noise-cancelling earbuds didn’t even help. Waste of money to upgrade.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

my seat got changed twice after checking on then boarding it had been given to a family so by the time they found a seat for me no overhead storage left. i ended up losing my Sony Headphones case because i could even access underthe seat in front of my when deplaning.

All good, useful to have the united app from check in to boarding

All planes flying to Mexico City are very old. Seats don’t even have power outlets.

The control panel for the seat back screen did not work at all after takeoff.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

It was good, the staff was friendly and it was a typical flight to Europe.

On time and fast. Overall it was a pleasant experience.

The weight limit per bag was really low - 40 lbs - so we had to pay extra. Then, they said their carry on size was 14x18x8, and we measured our bag very carefully. It was within the limit, yet they said it was too big, so we ended up paying an extra $100 for that too!! So it wasn’t the cheap flight we thought it would be. Then, they moved up our initial flight to depart 3 hours earlier which meant we had to be out on the road by 7 am and then have a 6 hour layover and we got home at 2am. It was a grueling day. I won’t be flying with them again.

Overall it was a good experience. Stewards were very kind and professional. The departure and arrival times were as promised. Plane was clean.

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

No frills, limited comfort, no food, no entertainment, but fine

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

Flight was canceled. Knew there was weather, and were notified of 20 min delayed, and then suddenly canceled. Next reschedule was for 2 days. No help other than to refund. Thankfully full refund and appreciate that. I appreciate discounted airline but felt they could've done more for customer inconvenience.

The seat was very uncomfortable from Boston to Nashville. Otherwise the flight was excellent.

Terrible as usual!!!! Very unprofessional and rude flight attendants! You get what you pay for! HORRIBLE

There was a .79 discrepancy between the cost of the flight and what was paid. Spirit didn't let me obtain my boarding pass until the .79 (seventy nine cents) was paid. Contacting their customer service to resolve the issue was a nightmare that involved many wait minutes and two different departments. The price Kayak gave to Affirm, whom I used to pay for the tickets, and the price Spirit charged for the flight were off by the .79. I almost lost the ticket because of the hassle.

Book cheap flights from Chicago to the U.S. Virgin Islands

Recent round-trip flight deals

5/17Fri
1 stopSpirit Airlines
14h 53mORD-STT
5/21Tue
1 stopSpirit Airlines
7h 04mSTT-ORD
$212
5/25Sat
1 stopSpirit Airlines
13h 54mORD-STT
5/29Wed
1 stopSpirit Airlines
13h 15mSTT-ORD
$214
5/15Wed
1 stop
17h 45mORD-STT
5/22Wed
3 stops
18h 08mSTT-ORD
$286
5/1Wed
2 stops
16h 19mORD-STT
5/8Wed
2 stops
16h 55mSTT-ORD
$307
5/23Thu
2 stopsAmerican Airlines
14h 17mORD-STT
5/29Wed
1 stopAmerican Airlines
10h 13mSTT-ORD
$521
5/20Mon
2 stopsAmerican Airlines
17h 27mORD-STX
6/6Thu
2 stopsAmerican Airlines
19h 55mSTX-ORD
$536
5/7Tue
1 stopDelta
6h 30mMDW-STT
5/15Wed
1 stopDelta
8h 18mSTT-MDW
$653
8/19Mon
1 stopDelta
6h 14mMDW-STT
8/25Sun
1 stopDelta
8h 23mSTT-MDW
$658
5/9Thu
1 stopUnited Airlines
7h 38mORD-STX
5/13Mon
1 stopUnited Airlines
8h 31mSTX-ORD
$703
7/5Fri
1 stopUnited Airlines
7h 38mORD-STX
7/8Mon
1 stopUnited Airlines
8h 31mSTX-ORD
$738

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Recent one-way flight deals

5/25Sat
1 stopSpirit Airlines
14h 53mORD-STT
$112
5/1Wed
2 stopsSpirit Airlines
16h 19mORD-STT
$156
5/1Wed
1 stopSpirit Airlines
13h 50mORD-STT
$162
5/1Wed
1 stopSpirit Airlines
10h 06mORD-STX
$183
5/1Wed
2 stopsSpirit Airlines
17h 06mORD-STX
$184
5/25Sat
2 stopsSpirit Airlines
18h 07mORD-STT
$184
4/24Wed
2 stopsSpirit Airlines
14h 09mORD-STT
$187
5/1Wed
3 stopsSpirit Airlines
29h 06mORD-STT
$195
4/24Wed
1 stopDelta
7h 50mMDW-STT
$412
5/25Sat
nonstopUnited Airlines
4h 59mORD-STT
$618

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Last minute flights from Chicago to the U.S. Virgin Islands

Last minute flight, train and bus deals

4/23Tue
multi-stopSpirit Airlines
18h 33mORD-STT
4/29Mon
multi-stopSpirit Airlines
8h 52mSTT-ORD
$365
4/23Tue
multi-stopSpirit Airlines
10h 32mORD-STT
4/24Wed
multi-stopSpirit Airlines
11h 10mSTT-ORD
$377
4/23Tue
multi-stopSpirit Airlines
18h 33mORD-STT
4/26Fri
multi-stopSpirit Airlines
7h 53mSTT-ORD
$390
4/23Tue
multi-stopSpirit Airlines
17h 32mORD-STT
4/26Fri
multi-stopSpirit Airlines
9h 28mSTT-ORD
$393
4/22Mon
multi-stop
15h 05mORD-STT
4/24Wed
multi-stop
17h 29mSTT-ORD
$422
4/22Mon
multi-stop
7h 35mORD-STT
4/24Wed
multi-stop
17h 29mSTT-ORD
$427
4/23Tue
multi-stopDelta
6h 23mMDW-STT
4/24Wed
multi-stopDelta
7h 11mSTT-MDW
$748
4/23Tue
multi-stopDelta
6h 23mMDW-STT
4/24Wed
multi-stopDelta
7h 11mSTT-MDW
$838
4/23Tue
multi-stopAmerican Airlines
9h 30mORD-STT
4/29Mon
multi-stopAmerican Airlines
10h 41mSTT-ORD
$843
4/23Tue
multi-stopAmerican Airlines
8h 25mORD-STT
4/26Fri
multi-stopAmerican Airlines
12h 40mSTT-ORD
$845

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Flights to the U.S. Virgin Islands

Cabin classes:

$2,193
$2,260
$2,601
$567