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 $151 on Spirit Airlines. Other airlines that offer cheap prices include American Airlines from $288 and Delta from $388 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 O'Hare Intl - Christiansted Henry Rohlsen or Chicago Midway - Saint Thomas Island Cyril E King 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 $263. On average you can expect to pay $953. The most popular route, (Chicago O'Hare Intl - Saint Thomas Island Cyril E King), can usually be booked for $290.

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 30 days early can save you up to 75% on average compared to booking a flight this week. If booking 30 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 $406 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 $666 for flights departing within the next 3 days.

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

September can be a great time to fly to U.S. Virgin Islands from Chicago with a flight ticket averaging about $607. Cheapflights users have found deals in the month of September for as cheap as $179. The most expensive prices can be found in the month of March.

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.

$546+ Flights from Chicago to the U.S. Virgin Islands - Compare & Save Big

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

Most accurate provider	AranGrant 3 stars
Most trusted provider	AranGrant 3 stars
Round-trip from	$297 (Mytrip)
One-way from	$151 (Cheapflightsfares)
Popular in	March
Cheapest in	September
Average price	$590
Good round-trip deal	$620 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.

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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. 11% potential increase in price ($81 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 4% potential price decrease ($24 potential savings vs. average RT price).

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Average for round-trip flights in April 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 avril 29, 2025.

mar. 6/312:41 pmORD - STT

1 stop20h 16mSpirit Airlines

sam. 6/710:52 amSTT - ORD

1 stop14h 13mSpirit Airlines

Deal found 4/28

$297

mar. 7/158:00 amORD - STX

1 stop7h 18mSpirit Airlines

lun. 7/215:13 pmSTX - ORD

1 stop17h 42mSpirit Airlines

Deal found 4/29

$317

lun. 6/27:35 pmORD - STX

2 stops22h 16mMultiple Airlines

ven. 6/612:42 pmSTX - ORD

1 stop21h 08mMultiple Airlines

Deal found 4/29

$436

jeu. 5/227:47 amORD - STT

1 stop6h 43mMultiple Airlines

lun. 5/262:41 pmSTT - ORD

1 stop10h 39mMultiple Airlines

Deal found 4/28

$461

sam. 11/86:54 pmORD - STT

1 stop14h 51mAmerican Airlines

sam. 11/153:20 pmSTT - ORD

Nonstop5h 35mAmerican Airlines

Deal found 4/29

$495

mar. 6/37:16 pmORD - STX

1 stop17h 38mAmerican Airlines

jeu. 6/123:44 pmSTX - ORD

1 stop7h 45mAmerican Airlines

Deal found 4/29

$515

lun. 7/286:00 amMDW - STT

1 stop8h 00mDelta

ven. 8/13:02 pmSTT - MDW

1 stop7h 39mDelta

Deal found 4/28

$539

dim. 10/267:25 amORD - STT

Nonstop4h 50mUnited Airlines

dim. 11/23:17 pmSTT - ORD

Nonstop5h 35mUnited Airlines

Deal found 4/29

$580

sam. 6/286:00 amMDW - STX

1 stop6h 42mDelta

sam. 7/52:45 pmSTX - MDW

1 stop8h 00mDelta

Deal found 4/27

$675

ven. 6/136:00 amORD - STX

2 stops10h 30mUnited Airlines

ven. 6/2011:20 amSTX - ORD

2 stops11h 52mUnited Airlines

Deal found 4/29

$834

lun. 12/225:40 amORD - STX

1 stop6h 40mDelta

jeu. 1/13:20 pmSTX - ORD

1 stop8h 07mDelta

Deal found 4/29

$1,485

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 avril 29, 2025.

mar. 6/312:41 pmORD - STT

1 stop20h 16mSpirit Airlines

sam. 6/710:52 amSTT - ORD

1 stop14h 13mSpirit Airlines

Deal found 4/28

$297

lun. 6/27:35 pmORD - STX

2 stops22h 16mMultiple Airlines

ven. 6/612:42 pmSTX - ORD

1 stop21h 08mMultiple Airlines

Deal found 4/29

$436

jeu. 7/175:15 amORD - STT

2 stops9h 40mAmerican Airlines

mar. 7/225:05 pmSTT - ORD

1 stop16h 57mAmerican Airlines

Deal found 4/29

$499

lun. 7/286:00 amMDW - STT

1 stop8h 00mDelta

ven. 8/13:02 pmSTT - MDW

1 stop7h 39mDelta

Deal found 4/28

$539

lun. 5/129:20 pmORD - STT

2 stops17h 23mUnited Airlines

ven. 5/164:45 pmSTT - ORD

1 stop7h 30mUnited Airlines

Deal found 4/29

$628

mar. 7/158:00 amORD - STX

1 stop7h 18mSpirit Airlines

lun. 7/215:13 pmSTX - ORD

1 stop17h 42mSpirit Airlines

Deal found 4/29

$317

jeu. 5/227:47 amORD - STT

1 stop6h 43mMultiple Airlines

lun. 5/262:41 pmSTT - ORD

1 stop10h 39mMultiple Airlines

Deal found 4/28

$461

mar. 6/37:16 pmORD - STX

1 stop17h 38mAmerican Airlines

jeu. 6/123:44 pmSTX - ORD

1 stop7h 45mAmerican Airlines

Deal found 4/29

$515

sam. 6/286:00 amMDW - STX

1 stop6h 42mDelta

sam. 7/52:45 pmSTX - MDW

1 stop8h 00mDelta

Deal found 4/27

$675

ven. 6/136:00 amORD - STX

2 stops10h 30mUnited Airlines

ven. 6/2011:20 amSTX - ORD

2 stops11h 52mUnited Airlines

Deal found 4/29

$834

mer. 5/147:05 amORD - STT

1 stop7h 05mDelta

sam. 5/172:51 pmSTT - ORD

1 stop9h 26mDelta

Deal found 4/28

$804

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 avril 29, 2025 and is based on user searches.

jeu. 5/17:10 amORD - STX

3 stops27h 00mSpirit Airlines

sam. 5/1012:42 pmSTX - ORD

2 stops11h 47mSpirit Airlines

Deal found 4/28

$665

dim. 5/48:04 amORD - STT

1 stop8h 16mMultiple Airlines

dim. 5/114:35 pmSTT - ORD

2 stops17h 20mMultiple Airlines

Deal found 4/29

$641

ven. 5/97:35 pmORD - STT

1 stop13h 22mSpirit Airlines

dim. 5/184:35 pmSTT - ORD

1 stop7h 54mSpirit Airlines

Deal found 4/29

$483

ven. 5/99:20 pmORD - STT

2 stops13h 55mUnited Airlines

lun. 5/122:10 pmSTT - ORD

1 stop10h 29mUnited Airlines

Deal found 4/29

$757

ven. 5/98:52 amORD - STX

1 stop7h 38mUnited Airlines

lun. 5/126:05 pmSTX - ORD

1 stop27h 07mUnited Airlines

Deal found 4/29

$1,120

lun. 5/129:20 pmORD - STT

2 stops17h 23mUnited Airlines

ven. 5/164:45 pmSTT - ORD

1 stop7h 30mUnited Airlines

Deal found 4/29

$628

mer. 5/147:05 amORD - STT

1 stop7h 05mDelta

sam. 5/172:51 pmSTT - ORD

1 stop9h 26mDelta

Deal found 4/28

$804

mer. 5/217:47 amORD - STX

2 stops23h 33mMultiple Airlines

mer. 5/284:55 pmSTX - ORD

3 stops22h 11mMultiple Airlines

Deal found 4/28

$581

jeu. 5/227:47 amORD - STT

1 stop6h 43mMultiple Airlines

lun. 5/262:41 pmSTT - ORD

1 stop10h 39mMultiple Airlines

Deal found 4/28

$461

lun. 5/265:00 amORD - STT

2 stops10h 20mAmerican Airlines

lun. 6/25:10 pmSTT - ORD

1 stop16h 50mAmerican Airlines

Deal found 4/29

$574

lun. 5/268:49 amORD - STX

1 stop7h 41mUnited Airlines

mer. 6/43:25 pmSTX - ORD

1 stop29h 50mUnited Airlines

Deal found 4/28

$775

mer. 5/286:00 amMDW - STT

1 stop6h 41mDelta

mer. 6/41:17 pmSTT - MDW

1 stop9h 10mDelta

Deal found 4/28

$639

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 avril 29, 2025.

mar. 7/295:05 amORD - STX

1 stop10h 13mSpirit Airlines

Deal found 4/29

$151

dim. 5/187:47 amORD - STT

1 stop6h 43mSpirit Airlines

Deal found 4/29

$208

mar. 5/2711:30 amORD - STX

1 stop19h 50mMultiple Airlines

Deal found 4/28

$244

mar. 7/295:15 amORD - STX

2 stops10h 11mAmerican Airlines

Deal found 4/29

$288

dim. 5/188:17 pmORD - STT

2 stops13h 38mAmerican Airlines

Deal found 4/29

$374

sam. 5/106:00 amMDW - STT

1 stop6h 41mDelta

Deal found 4/29

$388

sam. 5/1010:57 amORD - STT

Nonstop5h 03mUnited Airlines

Deal found 4/29

$408

mar. 7/299:42 pmORD - STX

3 stops40h 08mUnited Airlines

Deal found 4/29

$729

ven. 7/115:35 amORD - STT

1 stop7h 17mDelta

Deal found 4/29

$863

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago to the U.S. Virgin Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

mar. 6/3

12:41 pm-9:57 am

1 stop20h 16m

Saint Thomas Island Cyril E King

sam. 6/7

10:52 am-12:05 am

1 stop14h 13m

$297

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

mar. 7/15

8:00 am-4:18 pm

1 stop7h 18m

Christiansted Henry Rohlsen

lun. 7/21

5:13 pm-9:55 am

1 stop17h 42m

$317

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

lun. 6/2

7:35 pm-6:51 pm

2 stops22h 16m

Christiansted Henry Rohlsen

ven. 6/6

12:42 pm-8:50 am

1 stop21h 08m

$436

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

jeu. 5/22

7:47 am-3:30 pm

1 stop6h 43m

Saint Thomas Island Cyril E King

lun. 5/26

2:41 pm-12:20 am

1 stop10h 39m

$461

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

jeu. 7/17

5:15 am-3:55 pm

2 stops9h 40m

Saint Thomas Island Cyril E King

mar. 7/22

5:05 pm-9:02 am

1 stop16h 57m

$499

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

mar. 6/3

7:16 pm-1:54 pm

1 stop17h 38m

Christiansted Henry Rohlsen

jeu. 6/12

3:44 pm-10:29 pm

1 stop7h 45m

$515

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

lun. 7/28

6:00 am-3:00 pm

1 stop8h 00m

Saint Thomas Island Cyril E King

ven. 8/1

3:02 pm-9:41 pm

1 stop7h 39m

$539

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

lun. 5/12

9:20 pm-3:43 pm

2 stops17h 23m

Saint Thomas Island Cyril E King

ven. 5/16

4:45 pm-11:15 pm

1 stop7h 30m

$628

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

sam. 6/28

6:00 am-1:42 pm

1 stop6h 42m

Christiansted Henry Rohlsen

sam. 7/5

2:45 pm-9:45 pm

1 stop8h 00m

$675

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

mer. 5/14

7:05 am-3:10 pm

1 stop7h 05m

Saint Thomas Island Cyril E King

sam. 5/17

2:51 pm-11:17 pm

1 stop9h 26m

$804

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 17 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.

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 $432). Flying from Chicago to U.S. Virgin Islands in June is currently the most expensive (average of $627). 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

7,936 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

7,936 reviews

Delta

8.0

Very good

7,936 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

8,696 reviews

Delta

8.0

Very good

7,936 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

7,936 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

7,961 reviews

Delta

8.0

Very good

7,936 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 $151 on Spirit Airlines. Other airlines that offer cheap prices include American Airlines from $288 and Delta from $388 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 O'Hare Intl - Christiansted Henry Rohlsen or Chicago Midway - Saint Thomas Island Cyril E King 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 $263. On average you can expect to pay $953. The most popular route, (Chicago O'Hare Intl - Saint Thomas Island Cyril E King), can usually be booked for $290.
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 $432). Flying from Chicago to U.S. Virgin Islands in June is currently the most expensive (average of $627). 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$324	FlexibilityNo cancel fee	On-time65%
American Airlines	Cheapest$447	Average$599	FlexibilityNo cancel fee	On-time71%
Delta	Cheapest$467	Average$728	FlexibilityNo cancel fee	On-timeN/A
United Airlines	Cheapest$481	Average$810	FlexibilityNo cancel fee	On-time69%

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$151+ 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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chicago to U.S. Virgin Islands with Cheapflights

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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 29, 2025.

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

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 avril 29, 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 avril 29, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago to the U.S. Virgin Islands that are best for you.

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.

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?

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 29, 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?

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 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

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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 avril 29, 2025.