$271 Find Cheap Flights from the U.S. Virgin Islands to Illinois - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 26% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from the U.S. Virgin Islands to Illinois

 
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 Illinois

Sun, Dec 20 - Mon, Jan 4
United Airlines Logo
3:00 pm - 6:45 pmSTT  Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl
5h 45mnonstop
United Airlines Logo
7:40 am - 2:31 pmORD  Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King
4h 51mnonstop
$646United Airlines
Sun, Dec 20 - Mon, Jan 4
United Airlines Logo
3:35 pm - 12:44 amSTT  Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl
11h 09m1 stop Houston George Bush Intcntl
United Airlines Logo
7:40 am - 2:31 pmORD  Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King
4h 51mnonstop
$651United Airlines
Sun, Dec 20 - Mon, Jan 4
United Airlines Logo
5:25 pm - 12:01 amSTT  Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl
8h 36m1 stop Washington, D.C. Dulles Intl
United Airlines Logo
7:04 am - 5:50 pmORD  Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King
8h 46m1 stop Washington, D.C. Dulles Intl
$655United Airlines
Sun, Dec 20 - Mon, Jan 4
American Airlines Logo
3:54 pm - 7:43 pmSTT  Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl
5h 49mnonstop
American Airlines Logo
8:25 am - 3:14 pmORD  Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King
4h 49mnonstop
$661American Airlines
Sun, Dec 20 - Mon, Jan 4
Delta Logo
3:20 pm - 12:02 amSTT  Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl
10h 42m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:30 am - 2:53 pmORD  Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King
7h 23m1 stop Atlanta Hartsfield-Jackson
$665Delta
Tue, Nov 24 - Thu, Nov 26
Multiple Airlines Logo
11:17 am - 10:21 pmSTX  Christiansted Henry Rohlsen-ORD Chicago O'Hare Intl
13h 04m1 stop San Juan Luis Munoz Marin Intl
Multiple Airlines Logo
11:53 pm - 8:50 amORD  Chicago O'Hare Intl-STX Christiansted Henry Rohlsen
6h 57m1 stop San Juan Luis Munoz Marin Intl
$666Multiple Airlines
Sun, Dec 20 - Mon, Jan 4
Multiple Airlines Logo
5:28 pm - 1:33 amSTT  Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl
10h 05m1 stop San Juan Luis Munoz Marin Intl
Multiple Airlines Logo
4:59 pm - 2:50 pmORD  Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King
43h 51m2 stops Atlanta Hartsfield-Jackson Tampa
$678Multiple Airlines
Sun, Dec 20 - Mon, Jan 4
JetBlue Logo
1:00 pm - 6:58 pmSTT  Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl
31h 58m2 stops San Juan Luis Munoz Marin Intl Boston Logan Intl
JetBlue Logo
7:00 am - 1:41 pmORD  Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King
28h 41m2 stops Fort Lauderdale San Juan Luis Munoz Marin Intl
$684JetBlue
Wed, Nov 25 - Thu, Nov 26
Multiple Airlines Logo
5:23 pm - 1:44 pmSTX  Christiansted Henry Rohlsen-ORD Chicago O'Hare Intl
22h 21m2 stops San Juan Luis Munoz Marin Intl Atlanta Hartsfield-Jackson
Multiple Airlines Logo
11:53 pm - 2:10 pmORD  Chicago O'Hare Intl-STX Christiansted Henry Rohlsen
12h 17m1 stop San Juan Luis Munoz Marin Intl
$691Multiple Airlines
Sun, Jan 24 - Wed, Jan 27
American Airlines Logo
3:50 pm - 7:38 pmSTT  Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl
5h 48mnonstop
American Airlines Logo
9:30 pm - 1:17 pmORD  Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King
13h 47m1 stop Philadelphia
$763American Airlines
Booking Insights

KAYAK's insights & trends for flights to Illinois

Get data-powered insights and trends for flights to Illinois to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest flight to Illinois?

The cheapest ticket to Illinois from the U.S. Virgin Islands found in the last 5 days was to Chicago O'Hare Intl Airport, at $472 round-trip. The most popular route is Saint Thomas Island (STT) to Chicago O'Hare Intl Airport (ORD) and the cheapest round-trip airline ticket found on this route in the last 5 days was $472.

What is the cheapest month to fly from the U.S. Virgin Islands to Illinois?

The cheapest month for flights from the U.S. Virgin Islands to Illinois is May, when tickets cost $236 (return) on average. On the other hand, the most expensive months are June and January, when the average cost of round-trip tickets is $597 and $565 respectively.

What is the cheapest time of day to fly to Illinois?

The cheapest time of day to fly to Illinois is generally in the evening, when round-trip flights cost $486 on average. The most expensive time of day to fly to Illinois is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $580.

Which is the cheapest airport to fly into in Illinois?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Illinois is Chicago O'Hare Intl Airport (ORD), with an average flight price of $666.

Find deals

FAQs for booking flights from the U.S. Virgin Islands to Illinois

  • How does KAYAK find such low prices on flights from the U.S. Virgin Islands to Illinois?

    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 from the U.S. Virgin Islands to Illinois.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from the U.S. Virgin Islands to Illinois?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from the U.S. Virgin Islands to Illinois is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from the U.S. Virgin Islands to Illinois?

    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 from the U.S. Virgin Islands to Illinois 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 from the U.S. Virgin Islands to Illinois?

    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 from the U.S. Virgin Islands to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest day to fly to Illinois?

    Based on KAYAK data, the cheapest day to fly to Illinois is Thursday where round-trip tickets can be as cheap as $537. On the other hand, the most expensive day to fly is Tuesday, where round-trip prices are $677 on average.

Reviews of the top airline flying from the U.S. Virgin Islands to Illinois

 
Need help choosing which airline to fly with from the U.S. Virgin Islands to Illinois? 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.
7.0
American AirlinesOverall score based on 12225 reviews
6.4Food
7.9Crew
7.4Boarding
7.2Comfort
6.8Entertainment
Airline reviews

WiFi broken, very long wait for valet bags, and the typical long wait at O'Hare on a thursday to get clearance to take off and then again long taxi and wait for the gate.

6.0 GoodJulie, Nov 2026
Read more American Airlines reviews

WiFi broken, very long wait for valet bags, and the typical long wait at O'Hare on a thursday to get clearance to take off and then again long taxi and wait for the gate.

Another American flight, another significant non weather related delay. Was delayed over 90 minutes on both legs of the round trip.

The now boarding notification was not updated in the app until I was actually on the plan. This si a massive fail considering my flight was delayed several times. These types of failures add stress that could be avoided since I no longer feel comfortable leaving the boarding area to get food or visit a lounge. Had I used the notification from the app, I would have missed my flight. The secondly, the process of connecting to wifi on aa flights is clunky and could be streamlined better. the copy and past process feels like MVP, and you are well beyond that stage.

Both flights were late leaving due to repairs/switching gates. The crew and pilots, however, were professional and courteous. Most importantly, we arrived at our destination safely. The seats were comforable. That size should be standard for all economy class. American could improve its boarding process. I am not sure why you need 9 groups for a small regional plane.

It was close to its perfect the flake could be took off early, landed early, didn’t have to wait for my daughter stroller luggage came out quick, very efficient, very good flight

The amount of gate changes and delays is completely unacceptable. This has happened on 3 of 4 trips between Chicago and Dallas in 2026.

The delay update was very late. I had a stressful short connection and RAN through Chicago to get to the next flight, only to find the plane wasn't at the gate yet an nobody was boarding. I would not have had to run if the delay was updated earlier.

No flight delays. No need to rebook to make connections. Enjoyed second leg of flight on Iberia.

Same the delay was not ideal and the credits to move flights was not sufficient

No food on 4.5 hour flight, wi-fi did not work. Terrible experience for a long haul flight.

More options for your flight to Illinois

Complete your trip to Illinois with a hotel stay or car rental

Car rentals in Illinois
Hotels in Illinois
Vacations in Illinois