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 $128 on Spirit Airlines. Other airlines that offer cheap prices include Delta from $328 and United Airlines from $328 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 $273. On average you can expect to pay $504. The most popular route, (Chicago O'Hare Intl - Saint Thomas Island Cyril E King), can usually be booked for $274.

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 107% 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 $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 $618. Cheapflights users have found deals in the month of September for as cheap as $256. 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.

$520+ 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

Round-trip from	$261 (Cheapflightsfares)
One-way from	$128 (Cheapflightsfares)
Popular in	March
Cheapest in	September
Average price	$759
Good round-trip deal	$570 or less
Good one-way deal	$273 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. 7% potential increase in price ($52 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in June 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 June 12, 2025.

Tue 7/87:49 pmORD - STT

1 stop15h 41mSpirit Airlines

Tue 7/151:25 pmSTT - ORD

1 stop10h 46mSpirit Airlines

Deal found 6/10

$271

Sat 7/125:05 amORD - STX

1 stop9h 24mSpirit Airlines

Mon 7/145:09 pmSTX - ORD

1 stop16h 46mSpirit Airlines

Deal found 6/11

$315

Fri 7/1810:31 amMDW - STX

2 stops27h 58mMultiple Airlines

Sun 7/205:09 pmSTX - MDW

2 stops21h 55mMultiple Airlines

Deal found 6/11

$380

Fri 7/1810:31 amMDW - STT

2 stops22h 17mMultiple Airlines

Sun 7/204:05 pmSTT - MDW

2 stops22h 59mMultiple Airlines

Deal found 6/11

$389

Sat 8/25:07 pmORD - STX

2 stops22h 34mFrontier

Thu 8/75:40 pmSTX - ORD

2 stops30h 51mFrontier

Deal found 6/11

$410

Fri 7/256:23 pmORD - STX

1 stop12h 42mMultiple Airlines

Fri 8/16:05 pmSTX - ORD

2 stops15h 50mMultiple Airlines

Deal found 6/10

$444

Fri 7/256:20 amMDW - STT

2 stops9h 09mFrontier

Fri 8/15:14 pmSTT - MDW

2 stops28h 08mFrontier

Deal found 6/9

$450

Sun 9/75:00 amORD - STX

1 stop7h 03mAmerican Airlines

Sun 9/141:53 pmSTX - ORD

1 stop9h 33mAmerican Airlines

Deal found 6/11

$495

Mon 11/36:00 amMDW - STT

1 stop6h 32mDelta

Wed 11/123:32 pmSTT - MDW

1 stop8h 12mDelta

Deal found 6/9

$509

Mon 10/208:52 amORD - STX

1 stop7h 38mUnited Airlines

Mon 10/278:40 amSTX - ORD

2 stops13h 36mUnited Airlines

Deal found 6/10

$669

Sat 7/266:00 amMDW - STX

1 stop6h 30mDelta

Sat 8/22:30 pmSTX - MDW

1 stop8h 12mDelta

Deal found 6/11

$690

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 June 12, 2025.

Tue 7/87:49 pmORD - STT

1 stop15h 41mSpirit Airlines

Sat 7/194:05 pmSTT - ORD

1 stop8h 22mSpirit Airlines

Deal found 6/12

$261

Fri 7/1810:31 amMDW - STX

2 stops27h 58mMultiple Airlines

Sun 7/205:09 pmSTX - MDW

2 stops21h 55mMultiple Airlines

Deal found 6/11

$380

Sat 8/25:07 pmORD - STX

2 stops22h 34mFrontier

Thu 8/75:40 pmSTX - ORD

2 stops30h 51mFrontier

Deal found 6/11

$410

Sun 9/75:00 amORD - STX

1 stop7h 03mAmerican Airlines

Sun 9/141:53 pmSTX - ORD

1 stop8h 29mAmerican Airlines

Deal found 6/12

$495

Wed 8/136:04 amMDW - STT

1 stop7h 06mDelta

Mon 8/183:23 pmSTT - MDW

1 stop7h 26mDelta

Deal found 6/10

$514

Tue 7/225:05 amORD - STX

1 stop9h 57mSpirit Airlines

Sat 7/264:35 pmSTX - ORD

1 stop8h 18mSpirit Airlines

Deal found 6/12

$300

Mon 10/208:52 amORD - STX

1 stop7h 38mUnited Airlines

Mon 10/278:40 amSTX - ORD

2 stops13h 36mUnited Airlines

Deal found 6/10

$669

Fri 7/1810:31 amMDW - STT

2 stops22h 17mMultiple Airlines

Sun 7/204:05 pmSTT - MDW

2 stops22h 59mMultiple Airlines

Deal found 6/11

$389

Fri 7/256:20 amMDW - STT

2 stops9h 09mFrontier

Fri 8/15:14 pmSTT - MDW

2 stops28h 08mFrontier

Deal found 6/9

$450

Fri 7/256:23 pmORD - STX

1 stop12h 42mMultiple Airlines

Fri 8/16:05 pmSTX - ORD

2 stops15h 50mMultiple Airlines

Deal found 6/10

$444

Sat 7/266:00 amMDW - STX

1 stop6h 30mDelta

Sat 8/22:30 pmSTX - MDW

1 stop8h 12mDelta

Deal found 6/11

$690

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 June 12, 2025 and is based on user searches.

Sat 6/1410:05 pmORD - STX

2 stops15h 49mAmerican Airlines

Sat 6/213:45 pmSTX - ORD

1 stop18h 20mAmerican Airlines

Deal found 6/12

$784

Sun 6/154:04 pmORD - STT

2 stops23h 23mFrontier

Fri 6/205:12 pmSTT - ORD

2 stops16h 01mFrontier

Deal found 6/10

$452

Tue 6/174:45 pmORD - STX

1 stop22h 04mSpirit Airlines

Tue 6/244:48 pmSTX - ORD

1 stop17h 02mSpirit Airlines

Deal found 6/10

$463

Tue 6/1712:03 pmORD - STX

1 stop25h 47mMultiple Airlines

Tue 6/246:05 pmSTX - ORD

1 stop18h 01mMultiple Airlines

Deal found 6/11

$506

Tue 6/175:29 amORD - STX

2 stops10h 01mAmerican Airlines

Tue 6/243:44 pmSTX - ORD

2 stops10h 15mAmerican Airlines

Deal found 6/10

$869

Wed 6/184:45 pmORD - STT

1 stop16h 03mSpirit Airlines

Mon 6/233:03 pmSTT - ORD

2 stops19h 35mSpirit Airlines

Deal found 6/9

$431

Wed 6/186:00 amORD - STT

1 stop8h 43mUnited Airlines

Wed 6/254:45 pmSTT - ORD

1 stop7h 45mUnited Airlines

Deal found 6/11

$799

Wed 6/188:49 amORD - STX

1 stop7h 41mUnited Airlines

Wed 6/256:05 pmSTX - ORD

1 stop18h 50mUnited Airlines

Deal found 6/10

$1,090

Wed 6/186:00 amMDW - STT

1 stop6h 49mDelta

Sun 6/223:00 pmSTT - MDW

1 stop7h 45mDelta

Deal found 6/10

$1,785

Thu 6/196:16 pmORD - STT

2 stops21h 11mFrontier

Mon 6/235:12 pmSTT - ORD

2 stops18h 05mFrontier

Deal found 6/10

$461

Thu 6/199:45 pmORD - STT

2 stops15h 13mMultiple Airlines

Mon 6/232:05 pmSTT - ORD

3 stops20h 33mMultiple Airlines

Deal found 6/10

$617

Sat 6/216:00 amMDW - STX

1 stop6h 42mDelta

Sat 6/282:45 pmSTX - MDW

1 stop8h 00mDelta

Deal found 6/12

$1,305

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 June 12, 2025.

Tue 7/87:49 pmORD - STT

1 stop15h 41mSpirit Airlines

Deal found 6/11

$128

Mon 9/225:05 amORD - STX

1 stop10h 13mSpirit Airlines

Deal found 6/12

$161

Sat 7/266:00 amMDW - STT

1 stop8h 00mDelta

Deal found 6/11

$328

Sat 7/268:48 amORD - STT

Nonstop5h 06mUnited Airlines

Deal found 6/11

$328

Fri 11/215:00 amORD - STT

1 stop7h 00mAmerican Airlines

Deal found 6/12

$588

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

Tue 7/8

7:49 pm-12:30 pm

1 stop15h 41m

Saint Thomas Island Cyril E King

Tue 7/15

1:25 pm-11:11 pm

1 stop10h 46m

$271

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Sat 7/12

5:05 am-3:29 pm

1 stop9h 24m

Christiansted Henry Rohlsen

Mon 7/14

5:09 pm-8:55 am

1 stop16h 46m

$315

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

Fri 7/18

10:31 am-3:29 pm

2 stops27h 58m

Christiansted Henry Rohlsen

Sun 7/20

5:09 pm-2:04 pm

2 stops21h 55m

$380

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 7/18

10:31 am-9:48 am

2 stops22h 17m

Saint Thomas Island Cyril E King

Sun 7/20

4:05 pm-2:04 pm

2 stops22h 59m

$389

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Sat 8/2

5:07 pm-4:41 pm

2 stops22h 34m

Christiansted Henry Rohlsen

Thu 8/7

5:40 pm-11:31 pm

2 stops30h 51m

$410

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Fri 7/25

6:23 pm-8:05 am

1 stop12h 42m

Christiansted Henry Rohlsen

Fri 8/1

6:05 pm-8:55 am

2 stops15h 50m

$444

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 7/25

6:20 am-4:29 pm

2 stops9h 09m

Saint Thomas Island Cyril E King

Fri 8/1

5:14 pm-8:22 pm

2 stops28h 08m

$450

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Sun 9/7

5:00 am-1:03 pm

1 stop7h 03m

Christiansted Henry Rohlsen

Sun 9/14

1:53 pm-10:26 pm

1 stop9h 33m

$495

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 11/3

6:00 am-2:32 pm

1 stop6h 32m

Saint Thomas Island Cyril E King

Wed 11/12

3:32 pm-9:44 pm

1 stop8h 12m

$509

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

Sat 7/26

6:00 am-1:30 pm

1 stop6h 30m

Christiansted Henry Rohlsen

Sat 8/2

2:30 pm-9:42 pm

1 stop8h 12m

$690

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 16 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 $650). 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

7,950 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

7,950 reviews

Delta

8.0

Very good

7,950 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

8,790 reviews

Delta

8.0

Very good

7,950 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

7,950 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

8,052 reviews

Delta

8.0

Very good

7,950 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!

Frontier

5.9

Fair

3,295 reviews

Delta

8.0

Very good

7,950 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

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 $128 on Spirit Airlines. Other airlines that offer cheap prices include Delta from $328 and United Airlines from $328 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 $273. On average you can expect to pay $504. The most popular route, (Chicago O'Hare Intl - Saint Thomas Island Cyril E King), can usually be booked for $274.
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 $650). 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

O'Hare Intl to Saint Thomas Island flights

O'Hare Intl to Castries flights

Midway to Montego Bay flights

O'Hare Intl to Nassau flights

St. Louis to Luis Munoz Marin Intl flights

O'Hare Intl to Willemstad flights

O'Hare Intl to Providenciales flights

O'Hare Intl to Santo Domingo flights

O'Hare Intl to Simpson Bay flights

O'Hare Intl to Bridgetown flights

O'Hare Intl to Puerto Plata flights

O'Hare Intl to George Town flights

St. Louis to Punta Cana flights

St. Louis to Saint Thomas Island flights

Midway to Saint Thomas Island flights

Midway to Oranjestad flights

St. Louis to Montego Bay flights

O'Hare Intl to Christiansted flights

Midway to Nassau flights

St. Louis to Nassau flights

St. Louis to Oranjestad flights

Midway to Providenciales flights

O'Hare Intl to Kingston flights

Midway to Santo Domingo flights

O'Hare Intl to Santiago de los Caballeros flights

St. Louis to Santo Domingo flights

Midway to George Town flights

O'Hare Intl to St. John's flights

St. Louis to Willemstad flights

St. Louis to Castries flights

O'Hare Intl to Road Town flights

O'Hare Intl to Basseterre flights

St. Louis to George Town flights

O'Hare Intl to St. George's flights

O'Hare Intl to Port of Spain flights

O'Hare Intl to Castries flights

St. Louis to Simpson Bay flights

St. Louis to Providenciales flights

O'Hare Intl to Pointe-à-Pitre flights

Moline to Saint Thomas Island flights

O'Hare Intl to Aguadilla flights

O'Hare Intl to Havana flights

St. Louis to Christiansted flights

Midway to Simpson Bay flights

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

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$163	Average$351	FlexibilityNo cancel fee	On-time65%
American Airlines	Cheapest$453	Average$597	FlexibilityNo cancel fee	On-time71%
Delta	Cheapest$467	Average$686	FlexibilityNo cancel fee	On-timeN/A
United Airlines	Cheapest$481	Average$751	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.

$128+ 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 7/8. 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 June 12, 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 June 12, 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 June 12, 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 June 12, 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 June 12, 2025.