$124 Find Cheap Flights from U.S. Virgin Islands to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to O'Hare Intl departing on 10/16. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
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Cheap Flights from the U.S. Virgin Islands to O'Hare Intl

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from the U.S. Virgin Islands to O'Hare Intl 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 the U.S. Virgin Islands to O'Hare Intl

Sat, Oct 11 - Mon, Oct 13
Spirit Airlines Logo
2:01 pm - 9:33 pmSTT-ORD
8h 32m1 stop
Spirit Airlines Logo
4:53 pm - 9:56 amORD-STT
16h 03m1 stop
$278Spirit Airlines
Find Deal
Sat, Oct 11 - Mon, Oct 13
Spirit Airlines Logo
2:01 pm - 11:45 pmSTT-ORD
10h 44m2 stops
Spirit Airlines Logo
4:53 pm - 9:56 amORD-STT
16h 03m1 stop
$285Spirit Airlines
Find Deal
Mon, Oct 27 - Mon, Nov 3
Spirit Airlines Logo
11:01 am - 1:03 amSTT-ORD
15h 02m1 stop
Spirit Airlines Logo
2:14 pm - 10:51 amORD-STT
18h 37m1 stop
$293Spirit Airlines
Find Deal
Thu, Oct 2 - Mon, Oct 6
Multiple Airlines Logo
7:50 am - 10:48 pmSTX-ORD
15h 58m2 stops
Multiple Airlines Logo
5:05 am - 3:07 pmORD-STX
9h 02m1 stop
$489Multiple Airlines
Find Deal
Sat, Dec 13 - Sat, Apr 25
American Airlines Logo
3:01 pm - 6:41 pmSTX-ORD
5h 40mnonstop
American Airlines Logo
7:17 pm - 12:40 pmORD-STX
16h 23m1 stop
$515American Airlines
Find Deal
Sat, Dec 13 - Sat, Feb 28
American Airlines Logo
4:07 pm - 10:57 pmSTX-ORD
8h 50m1 stop
American Airlines Logo
7:09 pm - 2:00 pmORD-STX
16h 51m1 stop
$520American Airlines
Find Deal
Thu, Oct 2 - Mon, Oct 6
Multiple Airlines Logo
4:10 pm - 11:56 pmSTX-ORD
8h 46m1 stop
Multiple Airlines Logo
5:05 am - 3:07 pmORD-STX
9h 02m1 stop
$576Multiple Airlines
Find Deal
Fri, Mar 6 - Tue, Mar 10
Delta Logo
3:19 pm - 11:54 pmSTX-ORD
10h 35m1 stop
Delta Logo
5:50 am - 1:24 pmORD-STX
6h 34m1 stop
$595Delta
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Sat, Nov 22 - Sun, Nov 30
United Airlines Logo
3:35 pm - 12:15 amSTT-ORD
10h 40m1 stop
United Airlines Logo
9:30 am - 4:18 pmORD-STT
4h 48mnonstop
$624United Airlines
Find Deal
Wed, Nov 26 - Sun, Nov 30
United Airlines Logo
1:02 pm - 6:30 pmSTT-ORD
7h 28m1 stop
United Airlines Logo
9:30 am - 4:18 pmORD-STT
4h 48mnonstop
$649United Airlines
Find Deal

Everything you should know

Cheapest round-trip
$278
Spirit Airlines
Sat 10/11Mon 10/13
STT - ORD • 1 stop
Cheapest non-stop
$536
American Airlines
Sat 12/13Sat 2/28
STX - ORD • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to O'Hare Intl!
Booking Insights

KAYAK's insights & trends for flights to O'Hare Intl

Get data-powered insights and trends for flights to O'Hare Intl to help you find the cheapest flights, the best time to fly and much more.

How long is the flight to Chicago O'Hare Intl Airport?

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously, any flights that include a layover will also be longer. The most popular routes to Chicago on KAYAK are from Saint Thomas Island, which takes 5h 40m, and Christiansted, which takes 10h 35m.

How many direct flights to Chicago O'Hare Intl Airport are there each day?

There are around 1,454 direct flights from within U.S. Virgin Islands to Chicago O'Hare Intl Airport every day. Most flights depart in the morning, with 6:00 am the most common departure time and 52% of flights departing in the morning.

Good to know

Cheapest flight$124
Flight from Saint Thomas Island to Chicago

FAQs - booking Chicago flights

  • How far is Chicago O'Hare Intl Airport from central Chicago?

    Chicago O'Hare Intl Airport is 16 miles from the center of Chicago.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $420. The cheapest price found on KAYAK in the last 2 weeks cost $287 and departed from Saint Thomas Island Cyril E King Airport.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Thursday where round-trip tickets can be as cheap as $202. On the other hand, the most expensive day to fly is Friday, where round-trip prices are $661 on average.

  • How does KAYAK find such low prices on flights to Chicago?

    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 to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to 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 to Chicago?

    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 Chicago 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 to Chicago?

    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 Chicago 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 Chicago O'Hare Intl Airport?

    The cheapest time of day to fly to Chicago O'Hare Intl Airport is generally in the morning, when round-trip flights cost $430 on average. The most expensive time of day to fly to Chicago O'Hare Intl Airport is generally in the evening, which is peak travel time and where the average cost of a ticket is $612.

  • How many direct flights to Chicago O'Hare Intl Airport are there each week?

    Each week there are around 10,178 direct flights from within U.S. Virgin Islands to Chicago O'Hare Intl Airport. The most common day for departures is Sunday, with 15% of flights taking off on this day.

Top tips for finding cheap flights to Chicago

  • Looking for cheap airfare to Chicago? 25% of our users found round-trip tickets to Chicago for the following prices or less: From Saint Thomas Island $382
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Reviews of the top 3 airlines serving from the U.S. Virgin Islands to O'Hare Intl

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from the U.S. Virgin Islands to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to O'Hare Intl? 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.
7.4
United AirlinesOverall score based on 8926 reviews
7.1Entertainment
7.3Comfort
6.6Food
7.7Boarding
8.1Crew
Airline reviews

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

8.0 ExcellentAnonymous, Aug 2025YOW - ORD
Read more United Airlines reviews

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Inoperable monitor left no entert for 9 hours. Crew was not helpful Food was awful.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

Lost bag and 2 days no word leaving for cruise no clothes or stuff

The flight was on time and crew were nice, seats were tight and there was entertainment available

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

They should have MSNBC available on board. A 4- hour flight should provide more than a cookie.

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Just total easy flight experience!! What could you do better..? Hmmm..? There was nothing I can remember. Spirit was a far more comfortable and easy process than American, United & Delta. I'll always look for Spirit and I've told a few people about, since flying this past trip!! I'm a SPIRIT FAN!! Thank You, SPIRIT AIRLINES!! Very, VERY well done, 100%!! See you...SOON!! -Best, Linda R.

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.

As expected. Nothing jumps out at me as bad or wrong, but the flight was fine. No complaints with pilot or crew. The flight left on time and arrived earlier than stated. Overall, I will continue to plan on flying with Spirit.

Horrible considering I didn’t go and I bought travel insurance and I didn’t receive a refund.

While on the flight we had a delay and had to sit on the plane while maintenance fixed it. It’s ended up taking an hour and a half longer to leave than expected. I had an unruly passenger sitting behind me that vaped during the flight and was rude and loud for the majority of the flight.

Spirit is by far the worst airline to travel with, period. Seats are cardboard, flight attendants need anger management and if you ask for water, you’re basically a criminal. I don’t care how much it costs but I will travel with an airline who actually cares about their customers. Oh and one more thing, the next time your gate agent puts his foot on someone’s baggage's scale, I hope they get what’s coming next, a viral video of your scams. You suck Spirit, do better.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

Traveling to a place near O'Hare Intl?

Book flights to O'Hare Intl if you plan to visit one of these locations
Gurnee
South Haven
Oak Brook
Merrillville
Saint Joseph
Tinley Park
Elk Grove Village
Hoffman Estates
Des Plaines
Hammond
Willowbrook
Portage
Delavan
Northbrook
Elmhurst
South Holland
Lisle
Pleasant Prairie
Valparaiso
Lansing

Everything you need to know for your flight to O'Hare Intl

Information on the airport you'll fly into in Chicago

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