$127 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 2/7. 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
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
$295
Spirit Airlines
Sat 5/2Sat 5/9
STX - ORD • 1 stop
Cheapest non-stop
$501
United Airlines
Thu 2/12Mon 2/16
STT - ORD • Non-stop
Top airlines
United Airlines
Most flights • 6 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

Sat, May 2 - Sat, May 9
Spirit Airlines Logo
3:37 pm - 11:41 pm
STX
-
ORD
9h 04m1 stop
Spirit Airlines Logo
7:05 am - 2:40 pm
ORD
-
STX
6h 35m1 stop
$295Spirit Airlines
Tue, Feb 24 - Sun, Mar 1
Spirit Airlines Logo
5:40 pm - 11:47 pm
STT
-
ORD
8h 07m1 stop
Spirit Airlines Logo
4:43 pm - 4:34 pm
ORD
-
STT
21h 51m1 stop
$295Spirit Airlines
Mon, Feb 9 - Mon, Feb 16
Spirit Airlines Logo
4:38 pm - 11:47 pm
STX
-
ORD
9h 09m1 stop
Spirit Airlines Logo
7:00 am - 3:40 pm
ORD
-
STX
6h 40m1 stop
$302Spirit Airlines
Tue, Feb 24 - Sun, Mar 1
Spirit Airlines Logo
3:36 pm - 11:47 pm
STT
-
ORD
10h 11m2 stops
Spirit Airlines Logo
7:00 am - 4:34 pm
ORD
-
STT
7h 34m1 stop
$305Spirit Airlines
Thu, Feb 12 - Mon, Feb 16
Multiple Airlines Logo
5:40 pm - 11:03 pm
STT
-
ORD
31h 23m1 stop
Multiple Airlines Logo
9:41 pm - 2:31 pm
ORD
-
STT
14h 50m1 stop
$310Multiple Airlines
Tue, Feb 24 - Sun, Mar 1
Spirit Airlines Logo
3:36 pm - 11:47 pm
STT
-
ORD
10h 11m2 stops
Spirit Airlines Logo
8:16 pm - 2:31 pm
ORD
-
STT
16h 15m2 stops
$313Spirit Airlines
Thu, Feb 12 - Mon, Feb 16
Spirit Airlines Logo
3:36 pm - 11:47 pm
STT
-
ORD
10h 11m2 stops
Spirit Airlines Logo
4:43 pm - 2:31 pm
ORD
-
STT
19h 48m2 stops
$334Spirit Airlines
Thu, Feb 12 - Mon, Feb 16
Spirit Airlines Logo
3:36 pm - 11:47 pm
STT
-
ORD
10h 11m2 stops
Spirit Airlines Logo
5:15 am - 4:34 pm
ORD
-
STT
9h 19m1 stop
$337Spirit Airlines
Mon, Feb 9 - Mon, Feb 16
American Airlines Logo
8:30 am - 7:29 pm
STX
-
ORD
12h 59m2 stops
American Airlines Logo
5:00 am - 5:37 pm
ORD
-
STX
10h 37m2 stops
$568American Airlines
Sat, Mar 7 - Sat, Mar 14
American Airlines Logo
3:50 pm - 7:41 pm
STX
-
ORD
5h 51mnonstop
American Airlines Logo
6:59 pm - 12:56 pm
ORD
-
STX
16h 57m1 stop
$636American 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 $264 one-way - $346 round-trip.

Good to know

Low seasonDecember
Cheapest flight$131
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 $512. The cheapest price found on KAYAK in the last 2 weeks cost $148 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 $479. On the other hand, the most expensive day to fly is Saturday, where prices are $813 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 evening, when flights cost $537 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 $541.

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 $305
  • 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 11111 reviews
7.5Boarding
6.4Food
6.9Entertainment
8.0Crew
7.2Comfort
Airline reviews

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

10.0 ExcellentAnonymous, Jan 2026
SEA - ORD
Read more American Airlines reviews

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.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

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.

Bought round trip tickets. Ended up upgrading to first class. Both flights were new planes but hadn’t been equipped with WiFi and there were no charging ports at my seat despite it being new and first class accommodations.

Like: seats that don't move; fast boarding; engaging crew; low-prices; individual gate at LGA; access to restrooms at the gate Dislike: no water on the flight

To be Honest they canceled my flight and didn't have other options. Until 4 says later and I have a 2yr old very disappointed.

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