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Find cheap flights from U.S. Virgin Islands to Chicago from $149

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 6/7. 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
Mon 6/3
Mon 6/10

Search hundreds of travel sites at once for deals on flights to Chicago

 
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
In the last 7 days travelers have searched 43,369,418 times on KAYAK, and here is why:

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Flights to O'Hare Intl - Travel Insights & Trends

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.

What is the cheapest day to fly to Chicago?

The average price of all flights to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.
Based on KAYAK data, the cheapest day to fly to Chicago is Monday where tickets can be as cheap as $293. On the other hand, the most expensive day to fly is Saturday, where prices are $683 on average.

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Chicago O'Hare Intl Airport, 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 to Chicago O'Hare Intl Airport is December, where tickets cost $303 on average for one-way flights. On the other hand, the most expensive months are May and February, where the average cost of tickets from the U.S. Virgin Islands is $899 and $864 respectively. For return trips, the best month to travel is December with an average price of $303.

What is the cheapest time of day to fly to Chicago O'Hare Intl Airport?

The average price for all flights to Chicago O'Hare Intl Airport depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to Chicago O'Hare Intl Airport is generally in the evening, when flights cost $459 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 $784.

What is a good deal for flights to Chicago O'Hare Intl Airport?

If you’re looking for cheap airfare to Chicago O'Hare Intl Airport, 25% of our users found tickets to Chicago O'Hare Intl Airport for the following prices or less: From Saint Thomas Island $405 one-way - $516 round-trip.

Which airline offers the most flights to Chicago O'Hare Intl Airport?

Of the 12 airlines that fly to Chicago O'Hare Intl Airport, United Airlines offers the most flights, with around 5,222 per week, followed by American Airlines with 2,596 flights per week.

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 Christiansted, which takes 6h 49m, and Saint Thomas Island, which takes 7h 04m.

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

There are around 1,267 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.

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

Each week there are around 8,868 direct flights from within U.S. Virgin Islands to Chicago O'Hare Intl Airport. The most common day for departures is Thursday, with 15% of flights taking off on this day.

How many long-haul flights are there to Chicago O'Hare Intl Airport each week?

There are not any long-haul (6-12 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Chicago O'Hare Intl Airport. Instead, there are 1 medium-haul flights (3-6 hour flight duration), with the most arriving from Saint Thomas Island.

How many cities have direct flights to Chicago O'Hare Intl Airport?

From the U.S. Virgin Islands, there are direct flights to Chicago O'Hare Intl Airport from 1 city. This city is Saint Thomas Island and there are 1 direct flights each week.

Good to know

Low season

February

High season

December

Cheapest flight

$149
Best time to beat the crowds but there is an average 46% increase in price.
Most popular time to fly and prices are also 49% lower on average.
Flight from Saint Thomas Island to Chicago

FAQs - booking Chicago flights

  • How far is Chicago from central Chicago?

    Chicago is 16 miles from the center of Chicago.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $499. The cheapest price found on KAYAK in the last 2 weeks cost $314 and departed from Saint Thomas Island Cyril E King Airport.

  • 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.

See more FAQs

Top tips for finding cheap flights to Chicago

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Prefer to fly non-stop to Chicago O'Hare Intl?

Find which airlines fly direct to O'Hare Intl, which days they fly and book direct flights.

Nonstop departures

U.S. Virgin Islands to Chicago O'Hare Intl

Monday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

See more direct flights

Nonstop returns

Chicago O'Hare Intl to U.S. Virgin Islands

Monday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

See more direct flights
See more direct flights

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.
7.3
United AirlinesOverall score based on 11134 reviews
7.1Entertainment
7.2Comfort
6.7Food
8.1Crew
7.7Boarding
Airline reviews

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

8.0 ExcellentAnonymous, Apr 2024YUL - ORD
Read more about United Airlines reviews

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Wifi wasn't working on one of the UA flights after boarding.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

The plane was old and in new of a cleaning up and renovating on the interior. Seats and carpets were very worn and dirty looking. Cushioning on the seats was broken down and not as comfortable as newer jet seats. Food was a little below average but okay. Staff were friendly and hard working but did not pick up debris or food they spilled when collecting from the customers. But they were very helpful and professional.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

lounge was the highlight - seats weren't that comfortable - it was a full flight but no complaints

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.

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!

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

Had to board plan 2x due to lack of security check after 1st boarding

Miserable. The crew was rude, the flight was delayed 5 hours for mechanical reasons and then “weather” even though other planes were leaving.

They kept Changing the flight times. It was delayed several times and at one point it was supposed to depart at 3.40am! At which point we ended up staying overnight and booked long a separate United flight for early morning departure. The spirit flight then got moved up and left at 1.30 in the morning when it was supposed to leave at 9.40pm the night before.

Flight was delayed...not horribly late. Just before push back engine shut down for a quick replacement item that took about five minutes. After that, everything was smooth and the pilot was able to make up time in the air so that our arrival time was not too far off the original anticipated arrival time.

Only inflight purchases for food and water. Nothing comes with ticket price. Have to purchase bags, food...

The flight was delayed almost two hours on the front end, and an hour on the backend once we landed and waited for a gate to open up. We were told to remain in our seats during that whole delay and I had to go to the bathroom badly. I was unable to hold it and was forced to urinate in my pants while in my seat. I then had to sit in it until we finally deboarded and I was able to change my clothes.

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

Recent round-trip flight deals

 
These are the cheapest round-trip flights to Chicago found on KAYAK in the last 72 hours.
5/28Tue
1 stopSpirit Airlines
24h 10mSTT-ORD
6/2Sun
1 stopSpirit Airlines
14h 53mORD-STT
$212
5/28Tue
2 stopsSpirit Airlines
25h 58mSTT-ORD
6/2Sun
1 stopSpirit Airlines
14h 53mORD-STT
$235
6/1Sat
1 stopSpirit Airlines
14h 03mSTT-ORD
6/8Sat
1 stopSpirit Airlines
10h 39mORD-STT
$250
5/28Tue
2 stopsSpirit Airlines
25h 58mSTT-ORD
6/2Sun
2 stopsSpirit Airlines
17h 21mORD-STT
$264
6/1Sat
2 stopsSpirit Airlines
19h 15mSTT-ORD
6/8Sat
1 stopSpirit Airlines
10h 39mORD-STT
$297
5/28Tue
2 stopsSpirit Airlines
25h 58mSTT-ORD
6/2Sun
3 stopsSpirit Airlines
18h 20mORD-STT
$307
6/1Sat
2 stopsSpirit Airlines
19h 15mSTT-ORD
6/8Sat
2 stopsSpirit Airlines
21h 32mORD-STT
$350
6/1Sat
2 stopsSpirit Airlines
21h 04mSTT-ORD
6/8Sat
3 stopsSpirit Airlines
36h 01mORD-STT
$363
6/1Sat
nonstopUnited Airlines
5h 22mSTT-ORD
6/8Sat
nonstopUnited Airlines
4h 59mORD-STT
$3,334

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best deals for one-way flights to Chicago found on KAYAK in the last 72 hours.
6/7Fri
1 stopSpirit Airlines
15h 25mSTT-ORD
$149
5/10Fri
3 stopsSpirit Airlines
34h 38mSTT-ORD
$168
10/19Sat
1 stopSpirit Airlines
7h 35mSTT-ORD
$171
5/10Fri
2 stopsSpirit Airlines
29h 26mSTT-ORD
$174
5/10Fri
1 stopSpirit Airlines
8h 30mSTT-ORD
$180
6/7Fri
3 stopsSpirit Airlines
25h 41mSTT-ORD
$225
10/19Sat
2 stopsSpirit Airlines
28h 10mSTT-ORD
$247
6/7Fri
2 stopsAmerican Airlines
19h 57mSTT-ORD
$840
6/7Fri
1 stopUnited Airlines
7h 45mSTT-ORD
$934
10/19Sat
3 stopsUnited Airlines
18h 04mSTT-ORD
$1,491

Search by stops

Search by airline

Search by price

Flights to Chicago

Destination:

Chicago (ORD)United States

Return flight deals:

Chicago - U.S. Virgin Islands

Cabin classes:

$2,265
$1,561
$468