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U.S. Virgin Islands

$111+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STT
nov. 29 — déc. 61
sam. 11/29
sam. 12/6
1 adult, Economy
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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 octobre 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.
sam. 11/158:05 amORD - STT
Nonstop4h 43mAmerican Airlines
sam. 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.
ven. 12/510:05 pmORD - STT
1 stop16h 46mAmerican Airlines
lun. 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.
dim. 11/168:10 amORD - STT
1 stop6h 47mAmerican Airlines
sam. 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.
mar. 12/23:43 pmORD - STT
1 stop19h 12mSpirit Airlines
ven. 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.
mar. 12/23:43 pmORD - STT
1 stop19h 12mSpirit Airlines
sam. 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.
mer. 12/3111:23 amORD - STT
1 stop25h 05mMultiple Airlines
mer. 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.
jeu. 11/203:26 pmORD - STT
1 stop19h 29mSpirit Airlines
jeu. 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.
mer. 11/193:26 pmORD - STT
1 stop19h 29mSpirit Airlines
mar. 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.
sam. 11/151:55 pmORD - STT
2 stops21h 05mSpirit Airlines
sam. 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.
mar. 12/23:43 pmORD - STT
1 stop19h 12mSpirit Airlines
lun. 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.
mar. 12/24:22 pmORD - STT
2 stops18h 33mMultiple Airlines
ven. 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.
jeu. 11/206:23 pmORD - STT
1 stop18h 07mMultiple Airlines
lun. 11/242:00 pmSTT - ORD
1 stop31h 21mMultiple Airlines
Deal found 10/30$308

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

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 octobre 30, 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

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

jeu. 1/22

6:00 am-3:04 pm

1 stop7h 04m

Saint Thomas Island Cyril E King

lun. 1/26

4:15 pm-10:26 pm

1 stop8h 11m

$251

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

jeu. 1/8

9:30 am-4:18 pm

Nonstop4h 48m

Saint Thomas Island Cyril E King

jeu. 1/15

3:05 pm-6:45 pm

Nonstop5h 40m

$332

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

mar. 1/6

6:45 am-3:04 pm

1 stop6h 19m

Saint Thomas Island Cyril E King

ven. 1/16

4:15 pm-10:09 pm

1 stop7h 54m

$345

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

lun. 1/19

6:00 am-4:10 pm

1 stop8h 10m

Saint Thomas Island Cyril E King

ven. 1/23

3:10 pm-10:26 pm

1 stop9h 16m

$345

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

sam. 11/15

5:10 am-4:46 pm

1 stop9h 36m

Christiansted Henry Rohlsen

mer. 11/19

5:41 pm-9:17 am

1 stop17h 36m

$372

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

sam. 12/13

9:30 am-4:18 pm

Nonstop4h 48m

Saint Thomas Island Cyril E King

jeu. 12/18

3:05 pm-6:45 pm

Nonstop5h 40m

$396

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

ven. 1/9

6:45 am-4:10 pm

1 stop7h 25m

Saint Thomas Island Cyril E King

ven. 1/16

4:15 pm-10:09 pm

1 stop7h 54m

$410

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

lun. 1/19

9:30 am-4:18 pm

Nonstop4h 48m

Saint Thomas Island Cyril E King

ven. 1/23

1:02 pm-6:37 pm

1 stop7h 35m

$424

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

dim. 11/30

5:30 pm-12:55 pm

2 stops17h 25m

Saint Thomas Island Cyril E King

ven. 12/5

3:54 pm-10:39 pm

1 stop8h 45m

$471

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

lun. 1/12

9:30 am-4:18 pm

Nonstop4h 48m

Saint Thomas Island Cyril E King

lun. 1/19

3:05 pm-6:45 pm

Nonstop5h 40m

$476

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 52 results
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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, June is the cheapest month in which you can book a flight from Chicago to U.S. Virgin Islands (average of $171). Flying from Chicago 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 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 octobre 30, 2025.

It’s optimal to fly from Chicago to U.S. Virgin Islands in the afternoon. By choosing this option you can save up to 54% on the cost of your flight, compared to a flight in the morning.

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 octobre 30, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Chicago to the U.S. Virgin Islands. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,998 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,035 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Spirit Airlines
6.3
Okay
8,116 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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.

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

    A quick flight from Chicago to U.S. Virgin Islands can take about 4h 48m. United Airlines provides one of the quickest options available for as low as $332. There are 2116 mi between Chicago and U.S. Virgin Islands. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    When deciding which route to take from Chicago to U.S. Virgin Islands consider Chicago O'Hare Intl - Saint Thomas Island Cyril E King, Chicago Midway - Saint Thomas Island Cyril E King or Chicago O'Hare Intl - Christiansted Henry Rohlsen as they are the most popular.

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

    The cheapest flight price from Chicago to U.S. Virgin Islands is $246. On average you can expect to pay $590. The most popular route, (Chicago O'Hare Intl - Saint Thomas Island Cyril E King), can usually be booked for $242.

  • 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, June is the cheapest month in which you can book a flight from Chicago to U.S. Virgin Islands (average of $171). Flying from Chicago 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

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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.
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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 octobre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$182Average$319FlexibilityNo cancel feeOn-time65%
DeltaCheapest$359Average$659FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$454Average$642FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$474Average$727FlexibilityNo cancel feeOn-time69%

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