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. Spirit Airlines provides one of the quickest options available for as low as $500. 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 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 $283. On average you can expect to pay $1,126. The most popular route, (Chicago O'Hare Intl - Saint Thomas Island Cyril E King), can usually be booked for $236.

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 24 days early can save you up to 119% on average compared to booking a flight this week. If booking 24 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 $436 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 $631 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 $631. Cheapflights users have found deals in the month of September for as cheap as $322. 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.

$121+ Cheap Flights from Chicago to the U.S. Virgin Islands

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

Round-trip from	$226 (Cheapflightsfares)
One-way from	$121 (Kiwi.com)
Popular in	December
Cheapest in	September
Average price	$539
Good round-trip deal	$595 or less
Good one-way deal	$283 or less

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 ($41 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 3% potential price decrease ($21 potential savings vs. average RT price).

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Average for round-trip flights in September 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 September 15, 2025.

Sat 10/187:43 pmORD - STT

1 stop13h 13mSpirit Airlines

Sat 10/2511:01 amSTT - ORD

1 stop13h 44mSpirit Airlines

Deal found 9/14

$236

Wed 11/55:59 pmORD - STT

1 stop16h 29mSpirit Airlines

Tue 11/111:33 pmSTT - ORD

1 stop9h 27mSpirit Airlines

Deal found 9/13

$259

Thu 12/46:05 amORD - STT

1 stop7h 06mSpirit Airlines

Mon 12/81:33 pmSTT - ORD

1 stop12h 09mSpirit Airlines

Deal found 9/14

$260

Sun 11/27:43 pmORD - STT

1 stop13h 08mSpirit Airlines

Thu 11/64:06 pmSTT - ORD

1 stop7h 17mSpirit Airlines

Deal found 9/14

$264

Wed 10/87:43 pmORD - STT

1 stop13h 13mSpirit Airlines

Wed 10/1511:01 amSTT - ORD

1 stop13h 44mSpirit Airlines

Deal found 9/14

$266

Sat 11/85:59 pmORD - STT

1 stop16h 29mSpirit Airlines

Wed 11/121:33 pmSTT - ORD

1 stop9h 27mSpirit Airlines

Deal found 9/14

$273

Fri 11/145:59 pmORD - STX

1 stop16h 23mSpirit Airlines

Wed 11/191:17 pmSTX - ORD

1 stop9h 43mSpirit Airlines

Deal found 9/14

$304

Fri 10/245:05 amORD - STX

1 stop9h 02mSpirit Airlines

Fri 10/314:02 pmSTX - ORD

1 stop10h 01mSpirit Airlines

Deal found 9/14

$307

Wed 10/225:05 amORD - STX

1 stop9h 02mSpirit Airlines

Wed 10/294:02 pmSTX - ORD

1 stop10h 01mSpirit Airlines

Deal found 9/14

$309

Mon 10/65:05 amORD - STX

1 stop9h 02mSpirit Airlines

Wed 10/154:02 pmSTX - ORD

1 stop19h 48mSpirit Airlines

Deal found 9/15

$317

Wed 10/225:05 amORD - STX

1 stop9h 02mSpirit Airlines

Fri 10/314:02 pmSTX - ORD

1 stop19h 48mSpirit Airlines

Deal found 9/14

$320

Fri 10/245:05 amORD - STX

1 stop9h 02mSpirit Airlines

Wed 10/294:02 pmSTX - ORD

1 stop10h 01mSpirit Airlines

Deal found 9/14

$325

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 September 15, 2025.

Fri 11/145:59 pmORD - STX

1 stop16h 23mSpirit Airlines

Wed 11/191:17 pmSTX - ORD

1 stop9h 43mSpirit Airlines

Deal found 9/14

$304

Thu 12/42:15 pmMDW - STT

1 stop22h 56mMultiple Airlines

Thu 12/111:33 pmSTT - MDW

2 stops11h 32mMultiple Airlines

Deal found 9/13

$418

Sun 2/86:00 amMDW - STX

1 stop6h 24mDelta

Fri 2/133:19 pmSTX - MDW

1 stop8h 27mDelta

Deal found 9/15

$495

Wed 1/219:30 amORD - STT

Nonstop4h 48mUnited Airlines

Wed 1/283:05 pmSTT - ORD

Nonstop5h 40mUnited Airlines

Deal found 9/14

$500

Thu 1/88:05 amORD - STT

Nonstop4h 35mAmerican Airlines

Tue 1/204:25 pmSTT - ORD

1 stop18h 05mAmerican Airlines

Deal found 9/15

$505

Tue 10/217:43 pmORD - STX

1 stop18h 24mSpirit Airlines

Wed 10/294:02 pmSTX - ORD

1 stop10h 01mSpirit Airlines

Deal found 9/14

$309

Fri 12/197:38 pmORD - STT

1 stop17h 57mSun Country Air

Sat 12/274:35 pmSTT - ORD

2 stops28h 33mSun Country Air

Deal found 9/14

$625

Tue 10/287:43 pmORD - STX

1 stop18h 24mSpirit Airlines

Mon 11/35:02 pmSTX - ORD

1 stop10h 01mSpirit Airlines

Deal found 9/14

$320

Thu 10/237:43 pmORD - STX

1 stop18h 24mSpirit Airlines

Wed 10/294:02 pmSTX - ORD

1 stop10h 01mSpirit Airlines

Deal found 9/14

$320

Tue 10/287:43 pmORD - STX

1 stop18h 24mSpirit Airlines

Fri 10/314:02 pmSTX - ORD

1 stop10h 01mSpirit Airlines

Deal found 9/14

$320

Fri 10/245:05 amORD - STX

1 stop9h 02mSpirit Airlines

Wed 10/294:02 pmSTX - ORD

1 stop19h 48mSpirit Airlines

Deal found 9/14

$325

Tue 2/106:00 amMDW - STX

1 stop6h 24mDelta

Thu 2/123:19 pmSTX - MDW

1 stop8h 27mDelta

Deal found 9/15

$495

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 September 15, 2025 and is based on user searches.

Sat 10/46:44 pmORD - STT

1 stop14h 12mSpirit Airlines

Thu 10/911:01 amSTT - ORD

1 stop13h 44mSpirit Airlines

Deal found 9/14

$278

Mon 10/65:05 amORD - STX

1 stop9h 02mSpirit Airlines

Wed 10/154:02 pmSTX - ORD

1 stop19h 48mSpirit Airlines

Deal found 9/15

$317

Wed 10/87:43 pmORD - STT

1 stop13h 13mSpirit Airlines

Wed 10/1511:01 amSTT - ORD

1 stop13h 44mSpirit Airlines

Deal found 9/14

$266

Tue 10/147:43 pmORD - STT

1 stop13h 13mSpirit Airlines

Tue 10/2111:01 amSTT - ORD

1 stop13h 44mSpirit Airlines

Deal found 9/14

$279

Wed 10/157:43 pmORD - STT

1 stop13h 13mSpirit Airlines

Wed 10/2211:01 amSTT - ORD

1 stop8h 37mSpirit Airlines

Deal found 9/15

$273

Sat 10/187:43 pmORD - STT

1 stop13h 13mSpirit Airlines

Sat 10/2511:01 amSTT - ORD

1 stop13h 44mSpirit Airlines

Deal found 9/14

$236

Wed 10/226:58 pmORD - STT

1 stop17h 01mSpirit Airlines

Sat 11/12:01 pmSTT - ORD

1 stop8h 32mSpirit Airlines

Deal found 9/15

$261

Wed 10/225:05 amORD - STX

1 stop9h 02mSpirit Airlines

Wed 10/294:02 pmSTX - ORD

1 stop10h 01mSpirit Airlines

Deal found 9/14

$309

Wed 10/225:05 amORD - STX

1 stop9h 02mSpirit Airlines

Mon 11/35:02 pmSTX - ORD

1 stop10h 01mSpirit Airlines

Deal found 9/14

$320

Thu 10/237:43 pmORD - STX

1 stop18h 24mSpirit Airlines

Fri 10/314:02 pmSTX - ORD

1 stop10h 01mSpirit Airlines

Deal found 9/14

$330

Fri 10/245:05 amORD - STX

1 stop9h 02mSpirit Airlines

Fri 10/314:02 pmSTX - ORD

1 stop10h 01mSpirit Airlines

Deal found 9/14

$307

Fri 10/245:05 amORD - STX

1 stop9h 02mSpirit Airlines

Wed 10/294:02 pmSTX - ORD

1 stop10h 01mSpirit Airlines

Deal found 9/14

$325

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 September 15, 2025.

Sat 10/117:43 pmORD - STT

1 stop13h 13mSpirit Airlines

Deal found 9/15

$121

Fri 11/145:59 pmORD - STT

1 stop16h 29mSpirit Airlines

Deal found 9/14

$128

Sun 11/165:59 pmORD - STT

1 stop16h 29mSpirit Airlines

Deal found 9/15

$133

Fri 10/177:43 pmORD - STT

1 stop13h 13mSpirit Airlines

Deal found 9/15

$135

Fri 12/125:59 pmORD - STX

1 stop16h 23mSpirit Airlines

Deal found 9/13

$136

Mon 11/106:05 amORD - STT

1 stop7h 06mSpirit Airlines

Deal found 9/13

$136

Tue 10/147:43 pmORD - STT

1 stop13h 13mSpirit Airlines

Deal found 9/15

$140

Mon 10/137:43 pmORD - STT

1 stop13h 13mSpirit Airlines

Deal found 9/15

$144

Sat 11/17:43 pmORD - STT

1 stop14h 08mSpirit Airlines

Deal found 9/15

$147

Fri 11/145:59 pmORD - STX

1 stop16h 23mSpirit Airlines

Deal found 9/14

$151

Sat 2/76:05 amORD - STT

1 stop7h 06mSpirit Airlines

Deal found 9/15

$154

Tue 10/147:43 pmORD - STX

1 stop18h 24mSpirit Airlines

Deal found 9/13

$155

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

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Fri 11/14

5:59 pm-12:22 pm

1 stop16h 23m

Christiansted Henry Rohlsen

Wed 11/19

1:17 pm-9:00 pm

1 stop9h 43m

$304

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Tue 10/21

7:43 pm-3:07 pm

1 stop18h 24m

Christiansted Henry Rohlsen

Wed 10/29

4:02 pm-1:03 am

1 stop10h 01m

$309

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Tue 10/28

7:43 pm-3:07 pm

1 stop18h 24m

Christiansted Henry Rohlsen

Mon 11/3

5:02 pm-1:03 am

1 stop10h 01m

$320

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Thu 10/23

7:43 pm-3:07 pm

1 stop18h 24m

Christiansted Henry Rohlsen

Wed 10/29

4:02 pm-1:03 am

1 stop10h 01m

$320

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Tue 10/28

7:43 pm-3:07 pm

1 stop18h 24m

Christiansted Henry Rohlsen

Fri 10/31

4:02 pm-1:03 am

1 stop10h 01m

$320

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Fri 10/24

5:05 am-3:07 pm

1 stop9h 02m

Christiansted Henry Rohlsen

Wed 10/29

4:02 pm-10:50 am

1 stop19h 48m

$325

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Sun 10/26

7:43 pm-3:07 pm

1 stop18h 24m

Christiansted Henry Rohlsen

Fri 10/31

4:02 pm-1:03 am

1 stop10h 01m

$330

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Mon 10/27

5:05 am-3:07 pm

1 stop9h 02m

Christiansted Henry Rohlsen

Fri 10/31

4:02 pm-1:03 am

1 stop10h 01m

$330

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Thu 10/23

7:43 pm-3:07 pm

1 stop18h 24m

Christiansted Henry Rohlsen

Mon 11/3

5:02 pm-1:03 am

1 stop10h 01m

$330

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Mon 10/27

5:05 am-3:07 pm

1 stop9h 02m

Christiansted Henry Rohlsen

Mon 11/3

5:02 pm-1:03 am

1 stop10h 01m

$330

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 59 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 $433). Flying from Chicago to U.S. Virgin Islands in June is currently the most expensive (average of $643). 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

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

8.0

Very good

7,954 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Delta

8.0

Very good

7,954 reviews

Delta

8.0

Very good

7,954 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

United Airlines

7.4

Good

8,929 reviews

Delta

8.0

Very good

7,954 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

7,954 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Spirit Airlines

6.3

Okay

8,015 reviews

Delta

8.0

Very good

7,954 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

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. Spirit Airlines provides one of the quickest options available for as low as $500. 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 $283. On average you can expect to pay $1,126. The most popular route, (Chicago O'Hare Intl - Saint Thomas Island Cyril E King), can usually be booked for $236.
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 $643). 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$182	Average$311	FlexibilityNo cancel fee	On-time65%
Delta	Cheapest$359	Average$652	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$454	Average$622	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$479	Average$729	FlexibilityNo cancel fee	On-time69%

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$121+ 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 10/11. 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 September 15, 2025.

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 September 15, 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 September 15, 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 September 15, 2025.

Reviews of airlines servicing U.S. Virgin Islands

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.

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?

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 September 15, 2025.