$111 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 2/20. 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, 0 bags

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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Everything you should know

Cheapest round-trip
$266
Multiple Airlines
Thu 2/19Wed 2/25
STT - ORD • 1 stop
Cheapest non-stop
$521
United Airlines
Thu 3/19Tue 3/24
STT - ORD • Non-stop
Top airlines
American Airlines
Most flights • 13 per week
American Airlines
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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We hope you love your trip to O'Hare Intl!
Flight Deals
Booking Insights
Flight Deals

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

Thu, Feb 19 - Wed, Feb 25
Multiple Airlines Logo
5:40 pm - 11:03 pm
STT
-
ORD
31h 23m
1 stop
Multiple Airlines Logo
5:15 am - 4:34 pm
ORD
-
STT
9h 19m
1 stop
$266Multiple Airlines
Fri, Feb 6 - Tue, Feb 10
Spirit Airlines Logo
5:42 pm - 11:47 pm
STT
-
ORD
8h 05m
1 stop
Spirit Airlines Logo
5:32 pm - 4:37 pm
ORD
-
STT
21h 05m
1 stop
$272Spirit Airlines
Fri, Feb 6 - Tue, Feb 10
Spirit Airlines Logo
5:42 pm - 9:12 am
STT
-
ORD
17h 30m
2 stops
Spirit Airlines Logo
8:37 pm - 4:37 pm
ORD
-
STT
18h 00m
2 stops
$285Spirit Airlines
Thu, Feb 19 - Wed, Feb 25
Multiple Airlines Logo
3:36 pm - 11:47 pm
STT
-
ORD
10h 11m
2 stops
Multiple Airlines Logo
12:59 pm - 2:35 pm
ORD
-
STT
23h 36m
2 stops
$287Multiple Airlines
Thu, Feb 19 - Wed, Feb 25
Multiple Airlines Logo
5:40 pm - 11:47 pm
STT
-
ORD
8h 07m
1 stop
Multiple Airlines Logo
12:59 pm - 2:35 pm
ORD
-
STT
23h 36m
2 stops
$290Multiple Airlines
Sat, Mar 7 - Sun, Mar 8
Spirit Airlines Logo
4:37 pm - 11:47 pm
STX
-
ORD
9h 10m
1 stop
Spirit Airlines Logo
8:16 pm - 2:40 pm
ORD
-
STX
17h 24m
1 stop
$308Spirit Airlines
Sat, Mar 7 - Sun, Mar 8
American Airlines Logo
3:50 pm - 7:41 pm
STX
-
ORD
5h 51mnonstop
American Airlines Logo
5:00 am - 12:56 pm
ORD
-
STX
6h 56m
1 stop
$631American Airlines
Sat, Mar 7 - Fri, Mar 20
American Airlines Logo
3:50 pm - 7:41 pm
STX
-
ORD
5h 51mnonstop
American Airlines Logo
6:00 am - 4:27 pm
ORD
-
STX
9h 27m
1 stop
$696American Airlines
Sat, Mar 7 - Fri, Mar 20
JetBlue Logo
3:26 pm - 10:48 am
STX
-
ORD
21h 22m
2 stops
JetBlue Logo
5:00 pm - 8:55 am
ORD
-
STX
14h 55m
2 stops
$783JetBlue
Sat, Mar 7 - Sun, Mar 8
United Airlines Logo
9:20 am - 11:08 pm
STX
-
ORD
15h 48m
2 stops
United Airlines Logo
8:10 pm - 8:55 am
ORD
-
STX
11h 45m
2 stops
$1,665United Airlines
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.

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 $377 one-way - $346 round-trip.

Good to know

Low seasonDecember
Cheapest flight$116
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Christiansted 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 $571. The cheapest price found on KAYAK in the last 2 weeks cost $178 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 tickets can be as cheap as $372. On the other hand, the most expensive day to fly is Saturday, where prices are $718 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 afternoon, when flights cost $541 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 $606.

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 $362
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Reviews of the top airlines flying 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.
7.2
American AirlinesOverall score based on 11173 reviews
7.2Comfort
7.5Boarding
6.9Entertainment
6.4Food
8.0Crew
Airline reviews

Little warm on the plane and delayed for an hour

8.0 ExcellentHoward, Jan 2026
FLL - ORD
Read more American Airlines reviews

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Flight, food and crew were all good, friendly and very satisfactory.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

Not seat assigned because overbooking. We could go because some people decided to give their seats.

Even though there was a delay the crew was exeptional

The flights were very uncomfortable the seats don't have much leg room at all and they are pretty hard as well.

Our outgoing flight was cancelled two hours before boarding and Spirit was not able to get us onto another flight. Their customer service was slow and unhelpful.

spirit delayed my first flight 9 hours and then cancelled my flight back home. Very disappointed with their service.

Late taking off. ATC sent us circling around Chicago for almost an hour, after landing taxied for 40 minutes.

I waited for 4+ extra hours to even board when i was fighting off a cold. So i was sitting there in the airport with a fever and chills while spirit wasted my time. Then once on the plane we had at least an extra hour of taxiing before and after takeoff. Really poor airline, no amenities to speak of, and a lack of organization that will just ruin your experience.

Terrible. They cancelled the flight at the last minute after I had checked in at the airport and then told me they could only put me on a flight after 7 days. Pathetic.

Seats are too close. Bags are too expensive. One bag should always be free.

Flight was on time. Friendly crew. Gate agents in the other hand were very unfriendly.

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
Merrillville
Oak Brook
Saint Joseph
Tinley Park
Elk Grove Village
Des Plaines
Hoffman Estates
Hammond
Willowbrook
Portage
South Holland
Delavan
Northbrook
Pleasant Prairie
Lansing
Elmhurst
Lisle
Valparaiso

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

Information on the airport you'll fly into in Chicago