$255 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 7/21. 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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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

Fri, Sep 4 - Tue, Sep 8
American Airlines Logo
3:43 pm - 5:30 am
STT
-
ORD
14h 47m
2 stops
American Airlines Logo
9:15 pm - 12:51 pm
ORD
-
STT
14h 36m
2 stops
$520American Airlines
Fri, Sep 4 - Tue, Sep 8
JetBlue Logo
2:58 pm - 9:08 am
STT
-
ORD
19h 10m
3 stops
JetBlue Logo
2:35 pm - 2:41 pm
ORD
-
STT
23h 06m
2 stops
$555JetBlue
Thu, Aug 27 - Mon, Aug 31
American Airlines Logo
4:42 pm - 7:34 am
STT
-
ORD
15h 52m
1 stop
American Airlines Logo
9:15 pm - 12:53 pm
ORD
-
STT
14h 38m
2 stops
$579American Airlines
Thu, Aug 27 - Mon, Aug 31
American Airlines Logo
4:42 pm - 12:35 am
STT
-
ORD
8h 53m
1 stop
American Airlines Logo
6:00 am - 3:52 pm
ORD
-
STT
8h 52m
1 stop
$580American Airlines
Fri, Sep 4 - Tue, Sep 8
American Airlines Logo
4:42 pm - 7:34 am
STT
-
ORD
15h 52m
1 stop
American Airlines Logo
9:15 pm - 12:51 pm
ORD
-
STT
14h 36m
2 stops
$588American Airlines
Sat, Nov 21 - Sun, Nov 29
United Airlines Logo
3:00 pm - 6:45 pm
STT
-
ORD
5h 45mnonstop
United Airlines Logo
6:00 am - 4:20 pm
ORD
-
STT
8h 20m
1 stop
$614United Airlines
Sat, Aug 1 - Sat, Aug 15
United Airlines Logo
4:00 pm - 12:45 am
STT
-
ORD
9h 45m
1 stop
United Airlines Logo
5:00 am - 3:43 pm
ORD
-
STT
9h 43m
1 stop
$630United Airlines
Thu, Aug 6 - Sun, Aug 9
American Airlines Logo
3:54 pm - 11:30 pm
STX
-
ORD
8h 36m
1 stop
American Airlines Logo
6:00 am - 8:43 pm
ORD
-
STX
13h 43m
1 stop
$656American Airlines
Wed, Jul 22 - Sun, Jul 26
United Airlines Logo
4:45 pm - 11:31 pm
STT
-
ORD
7h 46m
1 stop
United Airlines Logo
5:30 am - 3:43 pm
ORD
-
STT
9h 13m
1 stop
$657United Airlines
Thu, Aug 6 - Sun, Aug 9
American Airlines Logo
3:54 pm - 11:30 pm
STX
-
ORD
8h 36m
1 stop
American Airlines Logo
8:00 am - 8:43 pm
ORD
-
STX
11h 43m
2 stops
$660American 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 the cheapest flight to Chicago?

These are the best round-trip prices found by users searching on KAYAK in the last 5 days.

In the last 5 days, the cheapest flight deal to Chicago was found on the route from Saint Thomas Island, at $520 return. The most popular connection is from Christiansted to Chicago and KAYAK users have found round-trip deals for as low as $656 in the last 5 days.

What is the cheapest day to fly to Chicago?

The average price of all round-trip 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 Sunday where round-trip tickets can be as cheap as $505. On the other hand, the most expensive day to fly is Friday, where round-trip prices are $801 on average.

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

The average price for all round-trip 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 afternoon, when round-trip flights cost $540 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 $567.

Good to know

Cheapest flight$255
Flight from Saint Thomas Island to Chicago

FAQs - booking Chicago flights

  • What is the cheapest flight to Chicago?

    In the last 5 days, the cheapest flight deal to Chicago was found on the route from Saint Thomas Island, at $520 return. The most popular connection is from Christiansted to Chicago and KAYAK users have found round-trip deals for as low as $656 in the last 5 days.

  • 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 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.

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

    Each week there are around 34,947 direct flights from within U.S. Virgin Islands to Chicago O'Hare Intl Airport. The most common day for departures is Sunday, with 16% of flights taking off on this day.

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.

Reviews of the top airline 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.
7.1
American AirlinesOverall score based on 11751 reviews
6.8Entertainment
7.2Comfort
7.5Boarding
7.9Crew
6.4Food
Airline reviews

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

6.0 GoodHardin, Jun 2026
ICT - ORD
Read more American Airlines reviews

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

weather delay of almost 2 hours then we landed and our gate wasn't available so we waited another 30 min

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

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
Hammond
Elk Grove Village
Des Plaines
Hoffman Estates
Portage
South Holland
Willowbrook
Delavan
Lansing
Northbrook
Lisle
Elmhurst
Alsip
Pleasant Prairie

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

Information on the airport you'll fly into in Chicago