$133 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 5/31. 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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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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Flights Deals

Cheap Flight Deals 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.

Recent round-trip flight deals from the U.S. Virgin Islands to O'Hare Intl

KAYAK's recommended round-trip deals from the most popular airlines that fly from the U.S. Virgin Islands to O'Hare Intl.
Discover the best prices for you by selecting your travel dates on KAYAK.
Spirit Airlines Logo
1:24 pm - 8:23 pmSTT-ORD
7h 59m1 stop
Spirit Airlines Logo
5:15 am - 12:29 pmORD-STT
6h 14m1 stop
$325Spirit Airlines
Find Deal
Thu, Jun 19 - Sun, Jun 22
Spirit Airlines Logo
1:24 pm - 8:23 pmSTT-ORD
7h 59m1 stop
Spirit Airlines Logo
10:15 pm - 12:29 pmORD-STT
13h 14m2 stops
$369Spirit Airlines
Find Deal
Thu, Jun 19 - Sun, Jun 22
Spirit Airlines Logo
10:47 am - 11:45 pmSTT-ORD
13h 58m1 stop
Spirit Airlines Logo
5:15 am - 1:58 pmORD-STT
7h 43m1 stop
$373Spirit Airlines
Find Deal
Thu, Jun 19 - Sun, Jun 22
American Airlines Logo
3:50 pm - 10:34 pmSTX-ORD
7h 44m1 stop
American Airlines Logo
6:55 pm - 12:50 pmORD-STX
16h 55m1 stop
$515American Airlines
Find Deal
Thu, Oct 16 - Sat, Oct 25
American Airlines Logo
3:50 pm - 9:02 amSTX-ORD
18h 12m1 stop
American Airlines Logo
8:35 pm - 12:50 pmORD-STX
15h 15m2 stops
$519American Airlines
Find Deal
Thu, Oct 16 - Sat, Oct 25
American Airlines Logo
4:55 pm - 9:00 amSTX-ORD
17h 05m1 stop
American Airlines Logo
6:00 am - 4:30 pmORD-STX
9h 30m1 stop
$570American Airlines
Find Deal
Sun, Jun 1 - Mon, Jun 9
American Airlines Logo
4:55 pm - 9:00 amSTX-ORD
17h 05m1 stop
American Airlines Logo
9:36 pm - 2:54 pmORD-STX
16h 18m2 stops
$575American Airlines
Find Deal
Sun, Jun 1 - Mon, Jun 9
American Airlines Logo
4:55 pm - 12:18 pmSTX-ORD
20h 23m2 stops
American Airlines Logo
5:29 am - 4:30 pmORD-STX
10h 01m2 stops
$594American Airlines
Find Deal
Sun, Jun 1 - Mon, Jun 9
American Airlines Logo
3:50 pm - 10:34 pmSTX-ORD
7h 44m1 stop
American Airlines Logo
8:45 pm - 12:50 pmORD-STX
15h 05m2 stops
$604American Airlines
Find Deal
Thu, Oct 16 - Fri, Oct 24
American Airlines Logo
3:50 pm - 9:02 amSTX-ORD
18h 12m1 stop
American Airlines Logo
5:00 am - 12:50 pmORD-STX
6h 50m1 stop
$615American Airlines
Find Deal
Thu, Oct 16 - Fri, Oct 24
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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 7h 59m, and Christiansted, which takes 12h 23m.

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

There are around 1,297 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 51% of flights departing in the morning.


Good to know

Low seasonSeptember
High seasonMay
Cheapest flight$133
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 32% lower on average.
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 $577. The cheapest price found on KAYAK in the last 2 weeks cost $365 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 Friday where round-trip tickets can be as cheap as $249. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $676 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 afternoon, which is peak travel time and where the average cost of a ticket is $683.

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

    Each week there are around 9,079 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 $427
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

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 8696 reviews
8.1Crew
7.3Comfort
6.6Food
7.1Entertainment
7.7Boarding
Airline reviews

So far so good but food and entertainment are not available for this flight

8.0 ExcellentAnonymous, Apr 2025YUL - ORD
Read more United Airlines reviews

So far so good but food and entertainment are not available for this flight

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

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

Terrible-extreme delay with very little communication, plane was overfull, luggage was returned on baggage claim in filthy condition.

Lower cost is the reason to fly Spirit. Should give free baggage with credit card.

Very difficult. Flew out on Dec 24th and it was a mess. They know it is going to be the busiest time of the year and they had no organization. Finally they called for people going on certiam flights so they could get them thru thw line then we had to rush to our gate to get in li e to board.We missed our flight do to being stuck at the border of Mexico. They would not work with us to make an affordable price so we had to wait a day with no where to go and pay 280 more for our flights. I would think that a complimentary drink would be nice. But we had to pay 4.49 for a coke. Not an overall good experience

I very late and supose be in home at 12 pm from yesterday but I stiill in detroi airport

I’ve now flown Spirit a few times and while the general perception of Spirit I feel is poor, I’ve had a great experience each time. They do charge extra for everything but you should know that going in

Horrible. Take off was delayed by an hour. They were letting people board d the plane right before takeoff. I was delayed an hour when I arrived and late for my meeting. Spirit is NEVER on time.

The flight landed with a delay and we had to wait almost an hour to be off boarded. So typical of spirit.

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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