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U.S. Virgin Islands

$91+ 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STT
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This Orbitz deal was found by Cheapflights users on 1/29. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/287:00 am
ORD
-
STX
1 stop6h 40m
Spirit Airlines
Sat 3/74:37 pm
STX
-
ORD
1 stop9h 10m
Spirit Airlines
Deal found 1/29$171
This CheapOair deal was found by Cheapflights users on 1/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/18:16 pm
ORD
-
STX
1 stop17h 24m
Spirit Airlines
Fri 3/64:37 pm
STX
-
ORD
1 stop9h 10m
Spirit Airlines
Deal found 1/28$186
This CheapOair deal was found by Cheapflights users on 1/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/158:41 pm
ORD
-
STX
1 stop16h 52m
Spirit Airlines
Mon 3/233:31 pm
STX
-
ORD
1 stop29h 15m
Spirit Airlines
Deal found 1/28$193
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/77:20 am
ORD
-
STX
1 stop6h 23m
Spirit Airlines
Sat 2/144:37 pm
STX
-
ORD
1 stop9h 10m
Spirit Airlines
Deal found 1/27$245
This CheapOair deal was found by Cheapflights users on 1/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/95:15 am
ORD
-
STX
1 stop8h 28m
Spirit Airlines
Fri 2/134:37 pm
STX
-
ORD
1 stop9h 10m
Spirit Airlines
Deal found 1/28$247
This CheapOair deal was found by Cheapflights users on 1/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/217:00 am
ORD
-
STX
1 stop6h 40m
Spirit Airlines
Sat 2/284:37 pm
STX
-
ORD
2 stops17h 17m
Spirit Airlines
Deal found 1/29$252
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/228:41 pm
ORD
-
STX
1 stop16h 52m
Spirit Airlines
Mon 3/303:31 pm
STX
-
ORD
1 stop29h 15m
Spirit Airlines
Deal found 1/27$270
This Mytrip deal was found by Cheapflights users on 1/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/47:20 am
ORD
-
STT
2 stops29h 32m
Spirit Airlines
Wed 2/115:42 pm
STT
-
ORD
3 stops26h 04m
Spirit Airlines
Deal found 1/28$392
This CheapOair deal was found by Cheapflights users on 1/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/87:20 pm
ORD
-
STT
2 stops19h 14m
Spirit Airlines
Thu 5/141:21 pm
STT
-
ORD
2 stops11h 20m
Spirit Airlines
Deal found 1/28$394
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Fri 2/134:42 pm
ORD
-
STT
2 stops21h 52m
Multiple Airlines
Sun 2/155:40 pm
STT
-
ORD
1 stop8h 07m
Multiple Airlines
Deal found 1/28$395
This Orbitz deal was found by Cheapflights users on 1/26. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/155:32 pm
ORD
-
STT
2 stops18h 59m
Multiple Airlines
Mon 5/182:45 pm
STT
-
ORD
2 stops19h 06m
Multiple Airlines
Deal found 1/26$397
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Sat 3/216:16 pm
ORD
-
STT
2 stops20h 12m
Multiple Airlines
Sun 3/292:36 pm
STT
-
ORD
1 stop19h 44m
Multiple Airlines
Deal found 1/28$399

Find 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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$171
(Orbitz)

One-way from

$91
(Expedia)

Popular in

December

Cheapest in

May

Average price

$556

Good round-trip deal

$481 or less

Good one-way deal

$328 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. 11% potential increase in price ($86 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
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

Sun 3/1

8:16 pm-3:40 pm

1 stop17h 24m

Christiansted Henry Rohlsen

Fri 3/6

4:37 pm-11:47 pm

1 stop9h 10m

$186

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Sat 3/7

7:00 am-3:40 pm

1 stop6h 40m

Christiansted Henry Rohlsen

Sat 3/14

3:31 pm-11:17 pm

1 stop8h 46m

$186

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Sun 3/15

8:41 pm-2:33 pm

1 stop16h 52m

Christiansted Henry Rohlsen

Mon 3/23

3:31 pm-4:55 pm

2 stops26h 24m

$210

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Mon 3/16

5:05 am-2:33 pm

1 stop8h 28m

Christiansted Henry Rohlsen

Mon 3/23

3:31 pm-7:46 pm

1 stop29h 15m

$250

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Sat 2/21

7:00 am-3:40 pm

1 stop6h 40m

Christiansted Henry Rohlsen

Sat 2/28

4:37 pm-7:54 am

2 stops17h 17m

$252

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Mon 2/9

5:15 am-3:43 pm

1 stop8h 28m

Christiansted Henry Rohlsen

Fri 2/13

4:37 pm-11:47 pm

1 stop9h 10m

$275

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Fri 2/27

8:16 pm-3:40 pm

1 stop17h 24m

Christiansted Henry Rohlsen

Wed 3/4

3:26 pm-11:49 am

2 stops22h 23m

$279

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Fri 5/8

7:20 pm-3:34 pm

2 stops19h 14m

Saint Thomas Island Cyril E King

Thu 5/14

1:21 pm-11:41 pm

2 stops11h 20m

$394

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Thu 3/19

2:41 pm-1:26 pm

2 stops21h 45m

Saint Thomas Island Cyril E King

Sun 3/22

2:36 pm-2:21 pm

1 stop24h 45m

$423

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Fri 5/29

5:32 pm-12:26 pm

2 stops17h 54m

Saint Thomas Island Cyril E King

Mon 6/1

2:36 pm-11:12 pm

1 stop9h 36m

$454

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 59 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 December 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 January 29, 2026.

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.

How often are flights from Chicago to the U.S. Virgin Islands delayed?

About 20% of weekly flights between Chicago and U.S. Virgin Islands have experienced delays in the past year, with the average delay time being 128 minutes.

What is the most punctual flight time for Chicago to the U.S. Virgin Islands flights?

Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to the U.S. Virgin Islands flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 16% of flights being delayed.

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 January 29, 2026.
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
8,127 reviews

Food

7.2

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.8

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,127 reviews
Delta
7.9
Good
8,127 reviews

Food

7.2

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.8

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,215 reviews
Delta
7.9
Good
8,127 reviews

Food

7.2

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.8

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,206 reviews
Delta
7.9
Good
8,127 reviews

Food

7.2

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.8

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,394 reviews
Delta
7.9
Good
8,127 reviews

Food

7.2

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.8

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 17h 24m. Spirit Airlines provides one of the quickest options available for as low as $186. There are 2159 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 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 $121 on Spirit Airlines. Other airlines that offer cheap prices include American Airlines from $205 and United Airlines from $283 one-way.

  • 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 $283. On average you can expect to pay $560. The most popular route, (Chicago O'Hare Intl - Saint Thomas Island Cyril E King), can usually be booked for $173.

  • 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 December 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$176Average$346FlexibilityNo cancel feeOn-time65%
DeltaCheapest$359Average$634FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$454Average$640FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$468Average$709FlexibilityNo cancel feeOn-time69%

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