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 $117 on Spirit Airlines. Other airlines that offer cheap prices include American Airlines from $258 and Delta from $268 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 $303. On average you can expect to pay $670. The most popular route, (Chicago O'Hare Intl - Saint Thomas Island Cyril E King), can usually be booked for $243.

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 195% 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 $292 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 $629 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 $606. Cheapflights users have found deals in the month of September for as cheap as $181. 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.

$516+ Flights from Chicago to the U.S. Virgin Islands

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

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

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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	$289 (Mytrip)
One-way from	$117 (Mytrip)
Popular in	March
Cheapest in	September
Average price	$537
Good round-trip deal	$736 or less
Good one-way deal	$398 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 ($44 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 3% potential price decrease ($18 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in April 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

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 April 2, 2025.

Sat 5/39:09 amORD - STT

2 stops23h 51mSpirit Airlines

Sat 5/103:49 pmSTT - ORD

1 stop9h 16mSpirit Airlines

Deal found 4/1

$289

Sat 9/65:05 amORD - STX

1 stop10h 13mSpirit Airlines

Sat 9/135:13 pmSTX - ORD

2 stops15h 27mSpirit Airlines

Deal found 3/31

$327

Sat 4/1911:45 amORD - STT

2 stops21h 15mMultiple Airlines

Sat 5/311:05 amSTT - ORD

3 stops28h 10mMultiple Airlines

Deal found 4/2

$355

Wed 6/46:51 amORD - STX

1 stop7h 34mAmerican Airlines

Fri 6/135:20 pmSTX - ORD

1 stop7h 31mAmerican Airlines

Deal found 4/1

$455

Thu 5/157:35 pmORD - STX

1 stop15h 12mMultiple Airlines

Thu 5/223:14 pmSTX - ORD

1 stop20h 11mMultiple Airlines

Deal found 3/31

$472

Thu 7/178:37 pmORD - STT

2 stops13h 08mAmerican Airlines

Mon 7/213:42 pmSTT - ORD

1 stop10h 17mAmerican Airlines

Deal found 4/1

$479

Fri 5/99:20 pmORD - STT

2 stops14h 48mUnited Airlines

Mon 5/122:10 pmSTT - ORD

1 stop10h 34mUnited Airlines

Deal found 4/1

$542

Fri 7/2510:31 amMDW - STX

2 stops28h 47mMultiple Airlines

Thu 7/315:13 pmSTX - MDW

2 stops21h 43mMultiple Airlines

Deal found 3/31

$627

Sat 8/236:00 amMDW - STT

1 stop8h 01mDelta

Sat 8/301:21 pmSTT - MDW

1 stop9h 26mDelta

Deal found 4/2

$669

Sat 6/76:00 amMDW - STX

1 stop6h 38mDelta

Sat 6/142:45 pmSTX - MDW

1 stop7h 53mDelta

Deal found 3/31

$675

Tue 6/38:10 pmORD - STX

2 stops10h 55mUnited Airlines

Tue 7/110:34 amSTX - ORD

2 stops11h 59mUnited Airlines

Deal found 3/30

$809

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 April 2, 2025.

Sat 5/39:09 amORD - STT

2 stops23h 51mSpirit Airlines

Sat 5/103:49 pmSTT - ORD

1 stop9h 16mSpirit Airlines

Deal found 4/1

$289

Mon 4/217:05 pmORD - STT

3 stops37h 55mMultiple Airlines

Sat 4/2611:05 amSTT - ORD

1 stop14h 53mMultiple Airlines

Deal found 4/2

$354

Wed 6/46:51 amORD - STX

1 stop7h 34mAmerican Airlines

Fri 6/135:20 pmSTX - ORD

1 stop7h 31mAmerican Airlines

Deal found 4/1

$455

Fri 5/99:20 pmORD - STT

2 stops14h 48mUnited Airlines

Mon 5/122:10 pmSTT - ORD

1 stop10h 34mUnited Airlines

Deal found 4/1

$542

Thu 5/154:35 pmORD - STX

2 stops18h 12mSpirit Airlines

Mon 5/1912:42 pmSTX - ORD

1 stop21h 08mSpirit Airlines

Deal found 4/1

$306

Sat 8/236:00 amMDW - STT

1 stop8h 01mDelta

Sat 8/301:21 pmSTT - MDW

1 stop9h 26mDelta

Deal found 4/2

$669

Thu 7/178:45 pmORD - STT

1 stop17h 35mAmerican Airlines

Mon 7/2111:25 amSTT - ORD

1 stop11h 00mAmerican Airlines

Deal found 4/1

$479

Thu 4/175:36 amORD - STX

1 stop28h 34mMultiple Airlines

Mon 4/218:03 pmSTX - ORD

2 stops29h 17mMultiple Airlines

Deal found 4/1

$568

Sat 6/76:00 amMDW - STX

1 stop6h 38mDelta

Sat 6/142:45 pmSTX - MDW

1 stop7h 53mDelta

Deal found 4/1

$675

Fri 7/2510:31 amMDW - STX

2 stops28h 47mMultiple Airlines

Thu 7/315:13 pmSTX - MDW

2 stops21h 43mMultiple Airlines

Deal found 3/31

$627

Wed 6/47:05 amORD - STT

1 stop7h 05mDelta

Wed 6/113:00 pmSTT - ORD

1 stop9h 59mDelta

Deal found 4/1

$729

Fri 5/98:52 amORD - STX

1 stop7h 38mUnited Airlines

Mon 5/123:25 pmSTX - ORD

1 stop29h 47mUnited Airlines

Deal found 4/1

$840

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 April 2, 2025 and is based on user searches.

Fri 4/46:00 amMDW - STX

1 stop6h 26mDelta

Fri 4/112:27 pmSTX - MDW

1 stop8h 54mDelta

Deal found 4/1

$1,010

Sun 4/66:00 amMDW - STX

1 stop6h 26mDelta

Sun 4/132:27 pmSTX - MDW

1 stop8h 50mDelta

Deal found 3/31

$1,010

Tue 4/89:08 pmORD - STT

1 stop14h 23mSpirit Airlines

Tue 4/1511:05 amSTT - ORD

1 stop14h 15mSpirit Airlines

Deal found 4/1

$351

Tue 4/85:00 amORD - STT

2 stops10h 59mAmerican Airlines

Tue 4/151:45 pmSTT - ORD

1 stop7h 16mAmerican Airlines

Deal found 4/1

$669

Tue 4/86:00 amORD - STT

1 stop8h 43mUnited Airlines

Tue 4/154:45 pmSTT - ORD

1 stop7h 44mUnited Airlines

Deal found 3/31

$752

Wed 4/95:36 amORD - STX

2 stops33h 39mMultiple Airlines

Tue 4/153:14 pmSTX - ORD

2 stops10h 06mMultiple Airlines

Deal found 3/30

$613

Wed 4/95:00 amORD - STX

1 stop8h 15mAmerican Airlines

Tue 4/153:05 pmSTX - ORD

1 stop9h 49mAmerican Airlines

Deal found 4/1

$615

Thu 4/106:03 pmORD - STT

1 stop22h 17mMultiple Airlines

Sun 4/132:10 pmSTT - ORD

Nonstop5h 30mMultiple Airlines

Deal found 4/1

$919

Sat 4/126:00 amMDW - STT

1 stop6h 44mDelta

Sat 4/193:00 pmSTT - MDW

1 stop8h 22mDelta

Deal found 4/1

$1,401

Thu 4/175:36 amORD - STX

1 stop28h 34mMultiple Airlines

Mon 4/218:03 pmSTX - ORD

2 stops29h 17mMultiple Airlines

Deal found 4/1

$568

Sat 4/1911:45 amORD - STT

2 stops21h 15mMultiple Airlines

Sat 5/311:05 amSTT - ORD

3 stops28h 10mMultiple Airlines

Deal found 4/2

$355

Wed 4/305:00 amORD - STX

1 stop8h 15mAmerican Airlines

Wed 5/72:44 pmSTX - ORD

1 stop7h 41mAmerican Airlines

Deal found 4/1

$455

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 April 2, 2025.

Sat 5/175:05 amORD - STT

1 stop8h 49mSpirit Airlines

Deal found 3/31

$117

Wed 4/3011:53 amORD - STX

3 stops46h 17mSpirit Airlines

Deal found 4/1

$223

Wed 6/46:51 amORD - STX

1 stop7h 34mAmerican Airlines

Deal found 4/1

$258

Fri 5/166:00 amMDW - STT

1 stop8h 10mDelta

Deal found 3/31

$268

Sat 7/128:37 pmORD - STT

2 stops13h 08mAmerican Airlines

Deal found 4/1

$274

Wed 4/98:04 amORD - STX

1 stop23h 16mMultiple Airlines

Deal found 4/1

$298

Sat 5/1010:57 amORD - STT

Nonstop5h 03mUnited Airlines

Deal found 4/1

$308

Fri 7/116:00 amORD - STT

1 stop8h 01mDelta

Deal found 4/2

$838

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

Sat 5/3

9:09 am-10:00 am

2 stops23h 51m

Saint Thomas Island Cyril E King

Sat 5/10

3:49 pm-12:05 am

1 stop9h 16m

$289

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Fri 5/16

7:35 pm-11:47 am

1 stop15h 12m

Christiansted Henry Rohlsen

Fri 5/23

12:42 pm-8:03 pm

2 stops32h 21m

$351

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Mon 4/21

7:05 pm-10:00 am

3 stops37h 55m

Saint Thomas Island Cyril E King

Sat 4/26

11:05 am-12:58 am

1 stop14h 53m

$354

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Wed 6/4

6:51 am-3:25 pm

1 stop7h 34m

Christiansted Henry Rohlsen

Fri 6/13

5:20 pm-11:51 pm

1 stop7h 31m

$455

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Thu 5/15

7:35 pm-11:47 am

1 stop15h 12m

Christiansted Henry Rohlsen

Thu 5/22

3:14 pm-10:25 am

1 stop20h 11m

$472

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Thu 7/17

8:45 pm-3:20 pm

1 stop17h 35m

Saint Thomas Island Cyril E King

Mon 7/21

11:25 am-9:25 pm

1 stop11h 00m

$479

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Fri 5/9

9:20 pm-1:08 pm

2 stops14h 48m

Saint Thomas Island Cyril E King

Mon 5/12

2:10 pm-11:44 pm

1 stop10h 34m

$542

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sat 8/23

6:00 am-3:01 pm

1 stop8h 01m

Saint Thomas Island Cyril E King

Sat 8/30

1:21 pm-9:47 pm

1 stop9h 26m

$669

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

Sat 6/7

6:00 am-1:38 pm

1 stop6h 38m

Christiansted Henry Rohlsen

Sat 6/14

2:45 pm-9:38 pm

1 stop7h 53m

$675

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Wed 6/4

7:05 am-3:10 pm

1 stop7h 05m

Saint Thomas Island Cyril E King

Wed 6/11

3:00 pm-11:59 pm

1 stop9h 59m

$729

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 19 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 $640). 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

7,898 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

7,898 reviews

Delta

8.0

Very good

7,898 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

8,615 reviews

Delta

8.0

Very good

7,898 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

7,898 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

7,886 reviews

Delta

8.0

Very good

7,898 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 $117 on Spirit Airlines. Other airlines that offer cheap prices include American Airlines from $258 and Delta from $268 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 $303. On average you can expect to pay $670. The most popular route, (Chicago O'Hare Intl - Saint Thomas Island Cyril E King), can usually be booked for $243.
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 $640). 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

O'Hare Intl to Luis Munoz Marin Intl flights

O'Hare Intl to Punta Cana flights

Midway to Luis Munoz Marin Intl flights

O'Hare Intl to Montego Bay flights

O'Hare Intl to Oranjestad flights

Midway to Punta Cana flights

Midway to Montego Bay flights

O'Hare Intl to Nassau flights

O'Hare Intl to Saint Thomas Island flights

Midway to Oranjestad flights

St. Louis to Luis Munoz Marin Intl flights

O'Hare Intl to Simpson Bay flights

O'Hare Intl to Santo Domingo flights

O'Hare Intl to Willemstad flights

O'Hare Intl to Castries flights

St. Louis to Punta Cana flights

O'Hare Intl to Christiansted flights

Midway to Nassau flights

St. Louis to Saint Thomas Island flights

O'Hare Intl to George Town flights

St. Louis to Montego Bay flights

O'Hare Intl to Puerto Plata flights

Midway to Saint Thomas Island flights

Midway to Santo Domingo flights

O'Hare Intl to Providenciales flights

O'Hare Intl to Bridgetown flights

O'Hare Intl to Kingston flights

O'Hare Intl to Ponce flights

St. Louis to Nassau flights

Midway to Providenciales flights

St. Louis to Providenciales flights

Moline to Montego Bay flights

St. Louis to Oranjestad flights

St. Louis to George Town flights

St. Louis to Christiansted flights

O'Hare Intl to Road Town flights

Midway to Simpson Bay flights

St. Louis to Castries flights

O'Hare Intl to St. John's flights

O'Hare Intl to Gregory Town flights

Midway to George Town flights

O'Hare Intl to Santiago de los Caballeros flights

O'Hare Intl to Port of Spain flights

St. Louis to Simpson Bay flights

O'Hare Intl to Basseterre flights

O'Hare Intl to St. George's flights

Moline to Punta Cana flights

O'Hare Intl to Freeport flights

O'Hare Intl to Castries flights

St. Louis to Willemstad flights

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

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$163	Average$320	FlexibilityNo cancel fee	On-time65%
Delta	Cheapest$402	Average$734	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$447	Average$619	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$483	Average$755	FlexibilityNo cancel fee	On-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

$117+ 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 5/17. 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

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

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 April 2, 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 April 2, 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 April 2, 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 April 2, 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

100% Free

Book with Flexibility

Travel Smart

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 April 2, 2025.