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 $95 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $105 and American Airlines from $258 one-way.

What is the cheapest day to fly from Chicago to U.S. Virgin Islands?

Travelers seeking maximum savings on their Chicago to U.S. Virgin Islands flight should consider departing on Wednesday mornings when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 $313. On average you can expect to pay $688. The most popular route, (Chicago O'Hare Intl - Saint Thomas Island Cyril E King), can usually be booked for $177.

What are the most popular airlines that fly from Chicago to U.S. Virgin Islands?

American Airlines, Delta and Spirit Airlines are the most popular airlines when flying from Chicago to U.S. Virgin Islands.

What is the cheapest day to fly round-trip from Chicago to U.S. Virgin Islands?

Flying to your destination on a Thursday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to U.S. Virgin Islands. Check prices with Cheapflights to find a great deal for your trip.

How far in advance should I book a flight from Chicago to U.S. Virgin Islands?

Users have found that booking a flight from Chicago to U.S. Virgin Islands at least 47 days early can save you up to 163% on average compared to booking a flight this week. If booking 47 days before your flight isn’t an option for you, users have found flights from Chicago to U.S. Virgin Islands for as little as $294 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $598 for flights departing within the next 3 days.

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

April can be a great time to fly to U.S. Virgin Islands from Chicago with a flight ticket averaging about $583. Cheapflights users have found deals in the month of April for as cheap as $181. The most expensive prices can be found in the month of December.

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.

$494+ Flights from Chicago to the U.S. Virgin Islands

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

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$255 (FlightHub)
One-way from	$95 (Kiwi.com)
Popular in	December
Cheapest in	April
Average price	$619
Good round-trip deal	$649 or less
Good one-way deal	$397 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 Chicago (CHI) to U.S. Virgin Islands

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One-way flight from Chicago (CHI) to U.S. Virgin Islands

Search Deals

Highest demand for flights based on searches. 9% potential increase in price ($61 potential increase over avg. RT price).

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Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).

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Average for round-trip flights in January 2025

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Price to beat on a round-trip flight from Chicago (CHI) to U.S. Virgin Islands.

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Price to beat on a one-way flight from Chicago (CHI) to U.S. Virgin Islands.

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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 enero 30, 2025.

mié. 5/148:00 amORD - STX

1 stop7h 18mSpirit Airlines

lun. 5/195:13 pmSTX - ORD

1 stop17h 42mSpirit Airlines

Deal found 1/29

$255

mié. 2/1912:02 pmORD - STT

2 stops20h 44mSpirit Airlines

vie. 2/2111:41 amSTT - ORD

1 stop14h 17mSpirit Airlines

Deal found 1/29

$280

dom. 3/94:02 pmORD - STT

3 stops17h 04mMultiple Airlines

dom. 3/1611:11 amSTT - ORD

2 stops23h 33mMultiple Airlines

Deal found 1/29

$414

mié. 4/97:00 amORD - STX

1 stop7h 31mAmerican Airlines

mar. 4/154:55 pmSTX - ORD

1 stop16h 53mAmerican Airlines

Deal found 1/30

$455

vie. 5/95:05 amORD - STX

1 stop10h 13mMultiple Airlines

mar. 5/139:10 amSTX - ORD

1 stop12h 40mMultiple Airlines

Deal found 1/30

$463

mar. 2/256:00 amMDW - STT

1 stop7h 49mDelta

mié. 3/54:00 pmSTT - MDW

1 stop8h 20mDelta

Deal found 1/28

$509

mar. 4/18:52 amORD - STX

1 stop7h 38mUnited Airlines

mar. 4/86:05 pmSTX - ORD

1 stop18h 50mUnited Airlines

Deal found 1/30

$775

vie. 3/285:45 amORD - STX

1 stop6h 39mDelta

vie. 4/42:27 pmSTX - ORD

1 stop7h 32mDelta

Deal found 1/30

$780

mar. 4/16:00 amMDW - STX

1 stop6h 24mDelta

vie. 4/42:27 pmSTX - MDW

1 stop8h 54mDelta

Deal found 1/30

$795

Best flights from Chicago to U.S. Virgin Islands
Discover carefully curated flight deals from Chicago to U.S. Virgin Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated enero 30, 2025.

mié. 5/148:00 amORD - STX

1 stop7h 18mSpirit Airlines

lun. 5/195:13 pmSTX - ORD

1 stop17h 42mSpirit Airlines

Deal found 1/29

$255

dom. 3/94:02 pmORD - STT

3 stops17h 04mMultiple Airlines

dom. 3/1611:11 amSTT - ORD

2 stops23h 33mMultiple Airlines

Deal found 1/29

$414

mié. 4/97:00 amORD - STX

1 stop7h 31mAmerican Airlines

mar. 4/154:55 pmSTX - ORD

1 stop16h 53mAmerican Airlines

Deal found 1/30

$455

mar. 3/116:00 amMDW - STT

1 stop6h 41mDelta

mar. 3/183:00 pmSTT - MDW

1 stop8h 23mDelta

Deal found 1/30

$509

sáb. 3/17:07 amORD - STT

3 stops25h 39mSpirit Airlines

sáb. 3/812:11 pmSTT - ORD

2 stops22h 33mSpirit Airlines

Deal found 1/30

$273

jue. 5/15:15 amORD - STX

2 stops11h 15mUnited Airlines

jue. 5/86:05 pmSTX - ORD

2 stops15h 35mUnited Airlines

Deal found 1/29

$819

mar. 3/254:32 pmORD - STX

2 stops26h 06mMultiple Airlines

lun. 3/313:34 pmSTX - ORD

2 stops18h 10mMultiple Airlines

Deal found 1/29

$472

mié. 2/125:45 amORD - STX

1 stop6h 38mDelta

mié. 3/192:25 pmSTX - ORD

1 stop7h 33mDelta

Deal found 1/29

$795

mar. 4/16:00 amMDW - STX

1 stop6h 24mDelta

vie. 4/42:27 pmSTX - MDW

1 stop8h 54mDelta

Deal found 1/30

$795

Last-minute flights from Chicago to U.S. Virgin Islands
Discover last-minute flight deals from Chicago to U.S. Virgin Islands. Data last updated enero 30, 2025 and is based on user searches.

mar. 2/49:00 amORD - STX

1 stop6h 30mUnited Airlines

dom. 2/93:25 pmSTX - ORD

2 stops9h 50mUnited Airlines

Deal found 1/29

$1,024

mié. 2/55:11 amORD - STX

1 stop8h 49mSpirit Airlines

sáb. 2/85:05 pmSTX - ORD

1 stop8h 27mSpirit Airlines

Deal found 1/29

$500

mié. 2/56:00 amMDW - STT

1 stop7h 49mDelta

jue. 2/274:00 pmSTT - MDW

1 stop8h 20mDelta

Deal found 1/29

$629

mié. 2/58:50 amORD - STT

Nonstop4h 50mUnited Airlines

mié. 2/263:00 pmSTT - ORD

Nonstop5h 35mUnited Airlines

Deal found 1/29

$710

vie. 2/712:25 pmORD - STX

2 stops22h 05mMultiple Airlines

mar. 2/113:14 pmSTX - ORD

2 stops21h 26mMultiple Airlines

Deal found 1/29

$603

vie. 2/77:04 amORD - STX

1 stop7h 59mAmerican Airlines

mar. 2/116:20 pmSTX - ORD

1 stop8h 07mAmerican Airlines

Deal found 1/29

$655

vie. 2/76:00 amMDW - STX

1 stop6h 23mDelta

mar. 2/113:25 pmSTX - MDW

1 stop8h 55mDelta

Deal found 1/29

$920

sáb. 2/83:56 pmORD - STT

1 stop16h 50mSpirit Airlines

mié. 2/122:33 pmSTT - ORD

2 stops24h 04mSpirit Airlines

Deal found 1/29

$319

sáb. 2/88:35 amORD - STT

Nonstop4h 45mAmerican Airlines

sáb. 2/155:40 pmSTT - ORD

1 stop19h 06mAmerican Airlines

Deal found 1/28

$797

dom. 2/95:45 amORD - STX

1 stop6h 38mDelta

mié. 3/192:25 pmSTX - ORD

1 stop7h 33mDelta

Deal found 1/29

$800

mié. 2/125:45 amORD - STX

1 stop6h 38mDelta

mié. 3/192:25 pmSTX - ORD

1 stop7h 33mDelta

Deal found 1/29

$795

jue. 2/139:00 amORD - STX

1 stop23h 45mSilver Airways

dom. 2/163:25 pmSTX - ORD

1 stop6h 46mSilver Airways

Deal found 1/28

$1,262

One-way flights from Chicago to U.S. Virgin Islands
Search for one-way flight options from Chicago to U.S. Virgin Islands. Find affordable one-way fares based on user searches. Data last updated enero 30, 2025.

mié. 2/263:14 pmORD - STT

1 stop17h 32mSpirit Airlines

Deal found 1/30

$95

dom. 3/28:14 amORD - STT

2 stops26h 35mFrontier

Deal found 1/30

$105

dom. 3/212:43 pmMDW - STT

2 stops22h 06mFrontier

Deal found 1/30

$127

dom. 4/2010:19 amORD - STX

1 stop27h 10mSpirit Airlines

Deal found 1/29

$195

mié. 4/95:00 amORD - STX

1 stop9h 31mAmerican Airlines

Deal found 1/30

$258

mar. 4/16:17 pmORD - STT

2 stops20h 26mUnited Airlines

Deal found 1/29

$258

dom. 3/26:00 amMDW - STT

1 stop7h 49mDelta

Deal found 1/30

$268

vie. 3/288:33 pmORD - STX

3 stops22h 05mMultiple Airlines

Deal found 1/29

$401

sáb. 3/298:05 amORD - STT

Nonstop4h 35mAmerican Airlines

Deal found 1/29

$485

dom. 4/209:50 pmORD - STX

2 stops18h 40mUnited Airlines

Deal found 1/29

$593

Find flights from Chicago to U.S. Virgin Islands within your budget

Fly from

Fly to

Route

Depart

Return

Price

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

mié. 5/14

8:00 am-4:18 pm

1 stop7h 18m

Christiansted Henry Rohlsen

lun. 5/19

5:13 pm-9:55 am

1 stop17h 42m

$255

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

sáb. 3/1

7:07 am-10:46 am

3 stops25h 39m

Saint Thomas Island Cyril E King

sáb. 3/8

12:11 pm-8:44 am

2 stops22h 33m

$273

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

dom. 3/9

4:02 pm-10:06 am

3 stops17h 04m

Saint Thomas Island Cyril E King

dom. 3/16

11:11 am-9:44 am

2 stops23h 33m

$414

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

mié. 4/9

7:00 am-3:31 pm

1 stop7h 31m

Christiansted Henry Rohlsen

mar. 4/15

4:55 pm-8:48 am

1 stop16h 53m

$455

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

mar. 3/25

4:32 pm-7:38 pm

2 stops26h 06m

Christiansted Henry Rohlsen

lun. 3/31

3:34 pm-8:44 am

2 stops18h 10m

$472

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

mar. 2/25

6:00 am-3:49 pm

1 stop7h 49m

Saint Thomas Island Cyril E King

mié. 3/5

4:00 pm-10:20 pm

1 stop8h 20m

$509

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

mié. 2/12

5:45 am-2:23 pm

1 stop6h 38m

Christiansted Henry Rohlsen

mié. 3/19

2:25 pm-8:58 pm

1 stop7h 33m

$795

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

mar. 4/1

6:00 am-1:24 pm

1 stop6h 24m

Christiansted Henry Rohlsen

vie. 4/4

2:27 pm-10:21 pm

1 stop8h 54m

$795

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

jue. 5/1

5:15 am-5:30 pm

2 stops11h 15m

Christiansted Henry Rohlsen

jue. 5/8

6:05 pm-8:40 am

2 stops15h 35m

$819

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

mié. 3/26

7:21 pm-10:06 am

1 stop13h 45m

$90

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/30

Showing 1-10 of 20 results

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.

Travel insights for flights from Chicago to U.S. Virgin Islands

Get recent, data-driven insights about flights from Chicago to U.S. Virgin Islands including ideal travel times, pricing trends, and more.

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 $658). 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?

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

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.

Delta

8.0

Very good

8,454 reviews

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.

Delta

8.0

Very good

8,454 reviews

Delta

8.0

Very good

8,454 reviews

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.

United Airlines

7.4

Good

8,913 reviews

Delta

8.0

Very good

8,454 reviews

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.

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

8,454 reviews

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.

Spirit Airlines

6.3

Okay

8,083 reviews

Delta

8.0

Very good

8,454 reviews

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.

Frontier

6.0

Okay

3,424 reviews

Delta

8.0

Very good

8,454 reviews

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

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 $95 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $105 and American Airlines from $258 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 $313. On average you can expect to pay $688. The most popular route, (Chicago O'Hare Intl - Saint Thomas Island Cyril E King), can usually be booked for $177.
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 $658). 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

Alternative routes for Chicago to U.S. Virgin Islands

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

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$163	Average$334	FlexibilityNo cancel fee	On-time65%
American Airlines	Cheapest$447	Average$647	FlexibilityNo cancel fee	On-time71%
Delta	Cheapest$467	Average$817	FlexibilityNo cancel fee	On-timeN/A
United Airlines	Cheapest$478	Average$813	FlexibilityNo cancel fee	On-time69%

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$90+ 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 3/26. Fares are subject to change and may not be available on all flights or dates of travel.

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

Cheapest flights from Chicago to U.S. Virgin IslandsExplore 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 enero 30, 2025.

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 enero 30, 2025.

Find flights from Chicago to U.S. Virgin Islands within your budget

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.

Travel insights for flights from Chicago to U.S. Virgin Islands

Get recent, data-driven insights about flights from Chicago to U.S. Virgin Islands including ideal travel times, pricing trends, and more.

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

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 enero 30, 2025.

Reviews of airlines servicing U.S. Virgin Islands

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.

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?

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?

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

How can I 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?

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

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Alternative routes for Chicago to U.S. Virgin Islands

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

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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 enero 30, 2025.