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Find cheap flights from Chicago to the U.S. Virgin Islands from $61

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 6/14. 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 7/6
Sat 7/13

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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
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 24% increase in price.

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 6% 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 10368 reviews
8.0Entertainment
7.4Food
7.9Comfort
8.2Boarding
8.6Crew
Airline reviews

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

8.0 Excellentmilton, Jun 2024ANC - MSP
Read more about Delta reviews

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

Standard flight experience, but there is only power at the seat to row 20 on the aircraft, on my initial check in it did not say that was the case

Energetic crew - flight full of swiftied going to Taylor's opening show in Paris! Long lines for bathroom made out kind of suck though

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

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?

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

Original flight delayed several times and finally canceled at 2:30 in the morning. Staff at the gate was not very helpful in resolving problems or communicating why there were delays. I spent 34 hours at the airport before I could leave, they couldn't book me on another early flight even after canceling my original flight. Next flight available after my original flight was canceled was 22 hours later. I will never fly American Airlines again.

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

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.

Could have TV/Movie and some water ou soda free

Flight was good and clean but delayed over an hour on the return flight.

The non stop flight and able to go into Atlantic City airport. They could lower the prices. It starts out low but then if you want to bring luggage and pick your seat the price goes up quite a bit.

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

We can’t predict circumstances like this ahead of time, but I give your staff a hats off for immediately giving us updated informations.

It was nice! There was a very unhappy child in front of us and the flight attendant did a great job calming the child. I was impressed.

The plane was not on time for boarding or departure or arrivals.

EVERYTHING WAS WONDERFUL HOSPITALITY THE HELP.THE SEATING FRIENDLY ALWAYS HAVE A GOOD RIDE NOT ONE BAD EXPERIENCE WITH THEM

This was the smoothest flight I have had in awhile. I was also offered an exit row seat for a great upgrade cost and was able to sleep almost thr whole flight due to comfort and a smooth flight. We left on time and arrived on time.

No food not even water offered unless you buy it and no usb in the seat but other than that everything was good

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

Recent round-trip flight deals

9/10Tue
1 stopSpirit Airlines
16h 25mORD-STT
9/17Tue
1 stopSpirit Airlines
11h 05mSTT-ORD
$184
9/10Tue
2 stopsSpirit Airlines
19h 52mORD-STT
9/17Tue
1 stopSpirit Airlines
11h 05mSTT-ORD
$203
6/18Tue
2 stops
19h 30mORD-STT
6/26Wed
3 stops
20h 54mSTT-ORD
$394
7/6Sat
1 stop
9h 45mORD-STX
7/13Sat
3 stops
28h 21mSTX-ORD
$419
9/14Sat
1 stopDelta
6h 14mMDW-STT
9/18Wed
1 stopDelta
8h 14mSTT-MDW
$448
8/28Wed
2 stopsAmerican Airlines
18h 09mORD-STX
9/9Mon
1 stopAmerican Airlines
7h 57mSTX-ORD
$468
11/4Mon
2 stopsAmerican Airlines
18h 38mORD-STX
11/9Sat
2 stopsAmerican Airlines
19h 01mSTX-ORD
$479
9/10Tue
1 stopDelta
6h 14mMDW-STT
9/17Tue
1 stopDelta
8h 14mSTT-MDW
$533
10/20Sun
1 stopUnited Airlines
7h 08mORD-STX
10/27Sun
1 stopUnited Airlines
8h 41mSTX-ORD
$648
10/24Thu
1 stopUnited Airlines
7h 08mORD-STX
10/30Wed
1 stopUnited Airlines
27h 06mSTX-ORD
$859

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Recent one-way flight deals

6/14Fri
1 stopFrontier
15h 26mMDW-STX
$61
6/21Fri
1 stopSpirit Airlines
14h 00mORD-STT
$164
6/20Thu
2 stopsSpirit Airlines
10h 24mORD-STT
$171
6/20Thu
1 stopSpirit Airlines
10h 39mORD-STT
$178
10/23Wed
1 stopSpirit Airlines
16h 25mORD-STT
$183
6/22Sat
1 stopSpirit Airlines
9h 45mORD-STX
$198
10/23Wed
2 stopsSpirit Airlines
19h 52mORD-STT
$209
6/21Fri
2 stopsSpirit Airlines
21h 16mORD-STT
$213
6/22Sat
3 stops
19h 23mORD-STX
$374
10/23Wed
1 stopDelta
6h 14mMDW-STT
$482

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

Last minute flight, train and bus deals

6/11Tue
multi-stopSpirit Airlines
15h 22mORD-STT
6/18Tue
multi-stopSpirit Airlines
23h 33mSTT-ORD
$480
6/8Sat
multi-stopSpirit Airlines
14h 00mORD-STT
6/15Sat
multi-stopSpirit Airlines
17h 27mSTT-ORD
$483
6/11Tue
multi-stopSpirit Airlines
15h 22mORD-STT
6/18Tue
multi-stopSpirit Airlines
17h 27mSTT-ORD
$487
6/11Tue
multi-stop
18h 20mORD-STT
6/18Tue
multi-stop
17h 40mSTT-ORD
$580
6/8Sat
multi-stop
21h 34mORD-STT
6/10Mon
multi-stop
11h 20mSTT-ORD
$591
6/8Sat
nonstopUnited Airlines
4h 59mORD-STT
6/16Sun
multi-stopUnited Airlines
10h 00mSTT-ORD
$958
6/8Sat
multi-stopDelta
9h 20mMDW-STT
6/16Sun
multi-stopDelta
9h 21mSTT-MDW
$1,008
6/8Sat
multi-stopAmerican Airlines
10h 13mORD-STT
6/16Sun
multi-stopAmerican Airlines
14h 52mSTT-ORD
$1,116
6/10Mon
multi-stopDelta
6h 49mMDW-STT
6/17Mon
multi-stopDelta
9h 21mSTT-MDW
$1,156
6/8Sat
nonstopUnited Airlines
4h 59mORD-STT
6/15Sat
multi-stopUnited Airlines
11h 51mSTT-ORD
$1,416

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Flights to the U.S. Virgin Islands

Cabin classes:

$1,192
$3,980
$1,561
$553