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U.S. Virgin Islands

$111+ Cheap flights from Illinois to the U.S. Virgin Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — STT
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap flight deals from Illinois to U.S. Virgin Islands

Keep the following information in mind while searching for Illinois to U.S. Virgin Islands flight deals. Data was last updated October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$247
(American Airlines)

One-way from

$111
(Expedia)

Popular in

December

Cheapest in

September

Average price

$554

Good round-trip deal

$579 or less

Good one-way deal

$323 or less
Provider with most accurate pricing for Chicago (CHI)-Saint Thomas Island Cyril E King flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Saint Thomas Island Cyril E King flights.
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From Illinois to U.S. Virgin Islands
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One-way flight from Illinois to U.S. Virgin Islands
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Highest demand for flights based on searches. 6% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Illinois to U.S. Virgin Islands.
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Price to beat on a one-way flight from Illinois to U.S. Virgin Islands.
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Find flight deals from Illinois to U.S. Virgin Islands

Cheapest flights from Illinois to U.S. Virgin Islands
Explore the most affordable flight options available from Illinois to U.S. Virgin Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/158:05 amORD - STT
Nonstop4h 43mAmerican Airlines
Sat 11/225:10 pmSTT - ORD
1 stop15h 54mAmerican Airlines
Deal found 10/30$247
This American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/510:05 pmORD - STT
1 stop16h 46mAmerican Airlines
Mon 12/86:17 pmSTT - ORD
1 stop16h 32mAmerican Airlines
Deal found 10/30$251
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/168:10 amORD - STT
1 stop6h 47mAmerican Airlines
Sat 11/225:10 pmSTT - ORD
1 stop7h 46mAmerican Airlines
Deal found 10/28$252
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/23:43 pmORD - STT
1 stop19h 12mSpirit Airlines
Fri 12/53:54 pmSTT - ORD
1 stop7h 25mSpirit Airlines
Deal found 10/27$281
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/23:43 pmORD - STT
1 stop19h 12mSpirit Airlines
Sat 12/61:01 pmSTT - ORD
1 stop9h 00mSpirit Airlines
Deal found 10/27$285
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:23 amORD - STT
1 stop25h 05mMultiple Airlines
Wed 1/73:23 pmSTT - ORD
1 stop24h 56mMultiple Airlines
Deal found 10/30$293
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/203:26 pmORD - STT
1 stop19h 29mSpirit Airlines
Thu 11/273:25 pmSTT - ORD
1 stop9h 41mSpirit Airlines
Deal found 10/29$296
This Kiwi.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/193:26 pmORD - STT
1 stop19h 29mSpirit Airlines
Tue 11/252:00 pmSTT - ORD
1 stop8h 27mSpirit Airlines
Deal found 10/28$297
This Mytrip deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/151:55 pmORD - STT
2 stops21h 05mSpirit Airlines
Sat 11/223:25 pmSTT - ORD
1 stop9h 41mSpirit Airlines
Deal found 10/30$298
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/23:43 pmORD - STT
1 stop19h 12mSpirit Airlines
Mon 12/81:01 pmSTT - ORD
1 stop24h 12mSpirit Airlines
Deal found 10/27$302
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/24:22 pmORD - STT
2 stops18h 33mMultiple Airlines
Fri 12/53:54 pmSTT - ORD
1 stop7h 25mMultiple Airlines
Deal found 10/27$303
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/206:23 pmORD - STT
1 stop18h 07mMultiple Airlines
Mon 11/242:00 pmSTT - ORD
1 stop31h 21mMultiple Airlines
Deal found 10/30$308

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to U.S. Virgin Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 30, 2025.
Use the filters below to find and compare flights from Illinois to the U.S. Virgin Islands that are best for you.

Fly from

Illinois

Fly to

U.S. Virgin Islands

Route

Depart

Return

Price

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Thu 1/22

6:00 am-3:04 pm

1 stop7h 04m

Saint Thomas Island Cyril E King

Mon 1/26

4:15 pm-10:26 pm

1 stop8h 11m

$251

St. LouisSaint Thomas Island

STL - STT

STLSTT

Lambert-St Louis

Wed 1/21

5:11 pm-3:11 pm

1 stop20h 00m

Saint Thomas Island Cyril E King

Thu 1/29

4:06 pm-10:33 pm

1 stop8h 27m

$307

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Thu 1/8

9:30 am-4:18 pm

Nonstop4h 48m

Saint Thomas Island Cyril E King

Thu 1/15

3:05 pm-6:45 pm

Nonstop5h 40m

$332

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 1/6

6:45 am-3:04 pm

1 stop6h 19m

Saint Thomas Island Cyril E King

Fri 1/16

4:15 pm-10:09 pm

1 stop7h 54m

$345

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 1/19

6:00 am-4:10 pm

1 stop8h 10m

Saint Thomas Island Cyril E King

Fri 1/23

3:10 pm-10:26 pm

1 stop9h 16m

$345

St. LouisSaint Thomas Island

STL - STT

STLSTT

Lambert-St Louis

Sun 11/16

6:21 pm-1:00 pm

1 stop16h 39m

Saint Thomas Island Cyril E King

Sat 11/22

5:54 pm-10:03 am

1 stop18h 09m

$350

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Sat 11/15

5:10 am-4:46 pm

1 stop9h 36m

Christiansted Henry Rohlsen

Wed 11/19

5:41 pm-9:17 am

1 stop17h 36m

$372

St. LouisSaint Thomas Island

STL - STT

STLSTT

Lambert-St Louis

Thu 1/8

5:11 pm-3:11 pm

1 stop20h 00m

Saint Thomas Island Cyril E King

Thu 1/15

4:06 pm-7:54 am

1 stop17h 48m

$395

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 12/13

9:30 am-4:18 pm

Nonstop4h 48m

Saint Thomas Island Cyril E King

Thu 12/18

3:05 pm-6:45 pm

Nonstop5h 40m

$396

St. LouisSaint Thomas Island

STL - STT

STLSTT

Lambert-St Louis

Wed 11/26

7:03 pm-2:30 pm

2 stops41h 27m

Saint Thomas Island Cyril E King

Wed 12/3

2:00 pm-1:52 pm

1 stop25h 52m

$406

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 60 results
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Best time to book a flight from Illinois to U.S. Virgin Islands

Have a flexible travel schedule? Discover the best time to fly to U.S. Virgin Islands from Illinois with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Illinois to the U.S. Virgin Islands

What is the cheapest month to book a flight from Illinois to U.S. Virgin Islands?

Currently, June is the cheapest month in which you can book a flight from Illinois to U.S. Virgin Islands (average of $171). Flying from Illinois to U.S. Virgin Islands in March is currently the most expensive (average of $438). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from IL to VI?

Find hourly flight availability from Illinois to U.S. Virgin Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

It’s typically best to fly out from Illinois to U.S. Virgin Islands in the evening. Doing so could potentially save you 45% on the flight price compared to flying in the morning, which is usually more expensive.

Related info for your journey

Find useful and relevant information for your journey from Illinois to U.S. Virgin Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Illinois to U.S. Virgin Islands?

    There are many flights that can get you from Illinois to U.S. Virgin Islands in 4h 48m. Fly via Delta, United Airlines, or Spirit Airlines to get the fastest option. Airlines will cover a distance of 2116 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • Can I find deals for flights from Illinois to U.S. Virgin Islands that include hotel bookings?

    Yes. In addition to deals on Illinois to U.S. Virgin Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to U.S. Virgin Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to U.S. Virgin Islands.

  • Can I find deals for business class flights from Illinois to U.S. Virgin Islands?

    Yes. Cheapflights offers flight deals from Illinois to U.S. Virgin Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Illinois to U.S. Virgin Islands?

    Currently, June is the cheapest month in which you can book a flight from Illinois to U.S. Virgin Islands (average of $171). Flying from Illinois to U.S. Virgin Islands in March is currently the most expensive (average of $438). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Illinois to U.S. Virgin Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Illinois to U.S. Virgin Islands

Discover the top 4 airlines that operate flights from Illinois to U.S. Virgin Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$182Average$319FlexibilityNo cancel feeOn-time65%
DeltaCheapest$359Average$651FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$454Average$662FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$474Average$727FlexibilityNo cancel feeOn-time69%

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