U.S. Virgin Islands

$162+ Cheap flights from Chicago (CHI) 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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STT
avr. 27 — mai 41
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Cheap flight deals from Chicago to U.S. Virgin Islands

Keep the following information in mind while searching for Chicago to U.S. Virgin Islands flight deals. Data was last updated avril 22, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$327
(Mytrip)

One-way from

$162
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$590

Good round-trip deal

$614 or less

Good one-way deal

$353 or less
Provider with most accurate pricing for Chicago (CHI)-Saint Thomas Island Cyril E King flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Saint Thomas Island Cyril E King flights.
From Chicago (CHI) to U.S. Virgin Islands
One-way flight from Chicago (CHI) to U.S. Virgin Islands
Highest demand for flights based on searches. 11% potential increase in price ($80 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($24 potential savings vs. average RT price).
Average for round-trip flights in April 2025
Price to beat on a round-trip flight from Chicago (CHI) to U.S. Virgin Islands.
Price to beat on a one-way flight from Chicago (CHI) to U.S. Virgin Islands.

Find flight deals from Chicago to U.S. Virgin Islands

Cheapest flights from Chicago to U.S. Virgin Islands
Explore the most affordable flight options available from Chicago to U.S. Virgin Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on avril 22, 2025.

This Mytrip deal was found by Cheapflights users on 4/22. 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.
mar. 6/174:45 pmORD - STX
1 stop22h 04mSpirit Airlines
mar. 6/244:45 pmSTX - ORD
1 stop17h 05mSpirit Airlines
Deal found 4/22$327
This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 5/187:47 amORD - STT
1 stop6h 43mSpirit Airlines
sam. 5/2410:52 amSTT - ORD
1 stop14h 13mSpirit Airlines
Deal found 4/21$329
This Trip.com deal was found by Cheapflights users on 4/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 6/149:12 pmMDW - STT
1 stop15h 46mMultiple Airlines
mer. 6/183:03 pmSTT - MDW
1 stop30h 14mMultiple Airlines
Deal found 4/21$377
This American Airlines deal was found by Cheapflights users on 4/22. 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.
mer. 6/46:51 amORD - STX
1 stop7h 34mAmerican Airlines
ven. 6/135:20 pmSTX - ORD
1 stop7h 31mAmerican Airlines
Deal found 4/22$475
This Delta deal was found by Cheapflights users on 4/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/156:00 amMDW - STT
1 stop6h 39mDelta
ven. 9/192:49 pmSTT - MDW
1 stop7h 55mDelta
Deal found 4/20$479
This American Airlines deal was found by Cheapflights users on 4/21. 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.
ven. 9/265:15 amORD - STT
2 stops9h 45mAmerican Airlines
sam. 10/41:50 pmSTT - ORD
2 stops11h 07mAmerican Airlines
Deal found 4/21$479
This United Airlines deal was found by Cheapflights users on 4/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 6/218:48 amORD - STT
Nonstop5h 06mUnited Airlines
mer. 6/254:45 pmSTT - ORD
1 stop7h 45mUnited Airlines
Deal found 4/21$495
This Mytrip deal was found by Cheapflights users on 4/22. 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.
ven. 5/237:47 amORD - STX
2 stops27h 00mMultiple Airlines
lun. 5/264:55 pmSTX - ORD
3 stops31h 09mMultiple Airlines
Deal found 4/22$546
This Delta deal was found by Cheapflights users on 4/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 6/125:35 amORD - STT
1 stop7h 14mDelta
mar. 6/171:19 pmSTT - ORD
1 stop11h 40mDelta
Deal found 4/20$564
This Delta deal was found by Cheapflights users on 4/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 6/76:00 amMDW - STX
1 stop6h 38mDelta
sam. 6/142:45 pmSTX - MDW
1 stop8h 00mDelta
Deal found 4/22$675
This United Airlines deal was found by Cheapflights users on 4/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/68:52 amORD - STX
1 stop7h 38mUnited Airlines
ven. 5/1611:20 amSTX - ORD
1 stop9h 52mUnited Airlines
Deal found 4/22$800

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago 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 avril 22, 2025.
Use the filters below to find and compare flights from Chicago to the U.S. Virgin Islands that are best for you.

Fly from

Chicago

Fly to

U.S. Virgin Islands

Route

Depart

Return

Price

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

mar. 6/17

4:45 pm-3:49 pm

1 stop22h 04m

Christiansted Henry Rohlsen

mar. 6/24

4:45 pm-8:50 am

1 stop17h 05m

$327

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

dim. 5/18

7:47 am-3:30 pm

1 stop6h 43m

Saint Thomas Island Cyril E King

sam. 5/24

10:52 am-12:05 am

1 stop14h 13m

$329

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

sam. 6/14

9:12 pm-1:58 pm

1 stop15h 46m

Saint Thomas Island Cyril E King

mer. 6/18

3:03 pm-8:17 pm

1 stop30h 14m

$377

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

mer. 6/4

6:51 am-3:25 pm

1 stop7h 34m

Christiansted Henry Rohlsen

ven. 6/13

5:20 pm-11:51 pm

1 stop7h 31m

$475

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

lun. 9/15

6:00 am-1:39 pm

1 stop6h 39m

Saint Thomas Island Cyril E King

ven. 9/19

2:49 pm-9:44 pm

1 stop7h 55m

$479

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

ven. 9/26

5:15 am-4:00 pm

2 stops9h 45m

Saint Thomas Island Cyril E King

sam. 10/4

1:50 pm-11:57 pm

2 stops11h 07m

$479

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

sam. 6/21

8:48 am-2:54 pm

Nonstop5h 06m

Saint Thomas Island Cyril E King

mer. 6/25

4:45 pm-11:30 pm

1 stop7h 45m

$495

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

ven. 5/23

7:47 am-11:47 am

2 stops27h 00m

Christiansted Henry Rohlsen

lun. 5/26

4:55 pm-11:04 pm

3 stops31h 09m

$546

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

jeu. 6/12

5:35 am-1:49 pm

1 stop7h 14m

Saint Thomas Island Cyril E King

mar. 6/17

1:19 pm-11:59 pm

1 stop11h 40m

$564

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

sam. 6/7

6:00 am-1:38 pm

1 stop6h 38m

Christiansted Henry Rohlsen

sam. 6/14

2:45 pm-9:45 pm

1 stop8h 00m

$675

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 18 results
1
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Best time to book a flight from Chicago to U.S. Virgin Islands

Have a flexible travel schedule? Discover the best time to fly to U.S. Virgin Islands from Chicago 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 Chicago to the U.S. Virgin Islands

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

Currently, September is the cheapest month in which you can book a flight from Chicago to U.S. Virgin Islands (average of $433). Flying from Chicago to U.S. Virgin Islands in June is currently the most expensive (average of $640). 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 CHI to VI?

Find hourly flight availability from Chicago 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 avril 22, 2025.

When flying from Chicago to U.S. Virgin Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing U.S. Virgin Islands

Get insights into the airlines that provide service to U.S. Virgin Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to U.S. Virgin Islands. Reviews last updated avril 22, 2025.
See what other customers who have flown with Delta, United Airlines and American Airlines from Chicago to U.S. Virgin Islands have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.0
Very good

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
8.0
Very good
8.0
Very good

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
8.0
Very good

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
8.0
Very good

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
8.0
Very good

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

Find useful and relevant information for your journey from Chicago 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.
  • What are the cheapest airlines to fly from Chicago to U.S. Virgin Islands one-way?

    One-way options have recently been found by users for as low as $162 on Spirit Airlines. Other airlines that offer cheap prices include American Airlines from $268 and Delta from $268 one-way.

  • What are the most popular routes from Chicago to U.S. Virgin Islands?

  • What are the cheapest flights from Chicago to U.S. Virgin Islands?

    The cheapest flight price from Chicago to U.S. Virgin Islands is $263. On average you can expect to pay $620. The most popular route, (Chicago O'Hare Intl - Saint Thomas Island Cyril E King), can usually be booked for $310.

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago 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 Chicago to U.S. Virgin Islands?

    Currently, September is the cheapest month in which you can book a flight from Chicago to U.S. Virgin Islands (average of $433). Flying from Chicago to U.S. Virgin Islands in June is currently the most expensive (average of $640). 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

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Alternative routes for Chicago to U.S. Virgin Islands

See prices for flight routes from nearby airports that may be better suited for you.

Top 4 airlines flying from Chicago to U.S. Virgin Islands

Discover the top 4 airlines that operate flights from Chicago 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 avril 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$163Average$325FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$447Average$600FlexibilityNo cancel feeOn-time71%
DeltaCheapest$467Average$717FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$481Average$804FlexibilityNo cancel feeOn-time69%

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