What airlines fly to U.S. Virgin Islands?

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to U.S. Virgin Islands from Chicago according to our data. American Airlines is the first choice among our users, with 52% of people opting to fly with this airline when traveling to U.S. Virgin Islands. Keep in mind that there are 4 different airlines that fly to U.S. Virgin Islands on a routine basis, so you have a few additional options to choose from.

What day of the week experiences the fewest flight delays on this route?

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Monday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Chicago to the U.S. Virgin Islands flights?

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 16% of their flights experiencing any sort of delay.

How many flights depart from Chicago to U.S. Virgin Islands on average per week?

7 flights are operational weekly from Chicago to U.S. Virgin Islands as of January 2026. The most popular departure day for this route is Thu, with 29% of flights per week taking off on this day.

How many flights depart from Chicago to U.S. Virgin Islands on average per day?

1 flights are operational daily from Chicago to U.S. Virgin Islands as of January 2026. The most popular departure time for this route is 9:00AM, with 100% of flights per day taking off at noon.

What is the cheapest airline that flies from Chicago to U.S. Virgin Islands?

Spirit Airlines is the most popular carrier operating from Chicago to U.S. Virgin Islands

What is the most punctual flight time for Chicago to the U.S. Virgin Islands flights?

Generally, flights departing in the early afternoon tend to experience fewer delays. Flights in the morning have, in the past, seen delays more frequently in comparison.

When did momondo last update prices for flights from Chicago to U.S. Virgin Islands?

Prices for flights from Chicago to U.S. Virgin Islands were last updated today.

How many operators does momondo search for flights from Chicago to U.S. Virgin Islands?

As of January 2026, there are 4 operators available to choose from for flights from Chicago to U.S. Virgin Islands.

How old do you have to be to fly from Chicago to U.S. Virgin Islands?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to U.S. Virgin Islands.

What documentation or ID do you need to fly to U.S. Virgin Islands?

The travel and health documents required for your trip to U.S. Virgin Islands can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at U.S. Virgin Islands. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$91 Cheap Flights from Chicago to the U.S. Virgin Islands in 2026

Q: How often are flights from Chicago to the U.S. Virgin Islands delayed?

Historically, on average around 20% of flights between Chicago and U.S. Virgin Islands have experienced a delay on any given week. The average delay length over the past 12 months has been 128 minutes.

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Find the cheapest flights from Chicago to the U.S. Virgin Islands

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:00 am - 3:40 pm

ORD

STX

6h 40m

1 stop

4:37 pm - 11:47 pm

STX

ORD

9h 10m

1 stop

$171Spirit Airlines

Sat, Feb 28 - Sat, Mar 7

8:16 pm - 3:40 pm

ORD

STX

17h 24m

1 stop

4:37 pm - 11:47 pm

STX

ORD

9h 10m

1 stop

$186Spirit Airlines

Sun, Mar 1 - Fri, Mar 6

8:41 pm - 2:33 pm

ORD

STX

16h 52m

1 stop

3:31 pm - 11:21 am

STX

ORD

20h 50m

1 stop

$193Spirit Airlines

Sun, Mar 15 - Mon, Mar 23

8:16 pm - 3:40 pm

ORD

STX

17h 24m

1 stop

4:37 pm - 5:46 pm

STX

ORD

27h 09m

2 stops

$210Spirit Airlines

Sun, Mar 1 - Fri, Mar 6

4:42 pm - 4:34 pm

ORD

STT

21h 52m

2 stops

5:40 pm - 11:47 pm

STT

ORD

8h 07m

1 stop

$395Multiple Airlines

Fri, Feb 13 - Sun, Feb 15

5:32 pm - 1:31 pm

ORD

STT

18h 59m

2 stops

2:45 pm - 8:51 am

STT

ORD

19h 06m

2 stops

$397Multiple Airlines

Fri, May 15 - Mon, May 18

5:15 pm - 2:55 pm

MDW

STT

19h 40m

2 stops

2:10 pm - 7:15 pm

STT

MDW

7h 05m

1 stop

$468Southwest

Mon, Feb 23 - Thu, Feb 26

6:00 am - 2:20 pm

MDW

STT

7h 20m

1 stop

1:50 pm - 7:45 am

STT

MDW

18h 55m

2 stops

$484Southwest

Tue, Mar 17 - Mon, Mar 23

6:00 am - 2:56 pm

MDW

STX

6h 56m

1 stop

3:58 pm - 10:31 pm

STX

MDW

8h 33m

1 stop

$496Delta

Sun, Mar 1 - Fri, Mar 6

6:00 am - 2:56 pm

MDW

STX

6h 56m

1 stop

3:58 pm - 10:31 pm

STX

MDW

8h 33m

1 stop

$521Delta

Tue, Mar 3 - Sat, Mar 7

Delta flights from Chicago to U.S. Virgin Islands

Our best Delta deals on Chicago to U.S. Virgin Islands flight tickets

Delta

Mar 1

MDW6:00 amChicago Midway

6h 56m

1 stop

STX2:56 pmChristiansted Henry Rohlsen

Mar 6

STX3:58 pmChristiansted Henry Rohlsen

8h 33m

1 stop

MDW10:31 pmChicago Midway

$496

Delta

Mar 3

MDW6:00 amChicago Midway

6h 56m

1 stop

STX2:56 pmChristiansted Henry Rohlsen

Mar 7

STX3:58 pmChristiansted Henry Rohlsen

8h 33m

1 stop

MDW10:31 pmChicago Midway

$521

Delta

Apr 17

MDW6:00 amChicago Midway

7h 48m

1 stop

STT2:48 pmSaint Thomas Island Cyril E King

Apr 24

STT1:54 pmSaint Thomas Island Cyril E King

9h 34m

1 stop

MDW10:28 pmChicago Midway

$535

Southwest flights from Chicago to U.S. Virgin Islands

Our best Southwest deals on Chicago to U.S. Virgin Islands flight tickets

Southwest

Feb 23

MDW5:15 pmChicago Midway

19h 40m

2 stops

STT2:55 pmSaint Thomas Island Cyril E King

Feb 26

STT2:10 pmSaint Thomas Island Cyril E King

7h 05m

1 stop

MDW7:15 pmChicago Midway

$468

Southwest

Mar 17

MDW6:00 amChicago Midway

7h 20m

1 stop

STT2:20 pmSaint Thomas Island Cyril E King

Mar 23

STT1:50 pmSaint Thomas Island Cyril E King

18h 55m

2 stops

MDW7:45 amChicago Midway

$484

Southwest

Feb 19

MDW5:30 amChicago Midway

7h 25m

1 stop

STT2:55 pmSaint Thomas Island Cyril E King

Feb 27

STT2:10 pmSaint Thomas Island Cyril E King

12h 45m

2 stops

MDW12:55 amChicago Midway

$499

momondo 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

Sat 2/28

7:00 am-3:40 pm

1 stop6h 40m

Christiansted Henry Rohlsen

Sat 3/7

4:37 pm-11:47 pm

1 stop9h 10m

$171

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Sun 3/1

8:16 pm-3:40 pm

1 stop17h 24m

Christiansted Henry Rohlsen

Fri 3/6

4:37 pm-11:47 pm

1 stop9h 10m

$186

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Sun 3/15

8:41 pm-2:33 pm

1 stop16h 52m

Christiansted Henry Rohlsen

Mon 3/23

3:31 pm-11:21 am

1 stop20h 50m

$193

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Sun 3/1

8:16 pm-3:40 pm

1 stop17h 24m

Christiansted Henry Rohlsen

Fri 3/6

4:37 pm-5:46 pm

2 stops27h 09m

$210

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Fri 2/13

4:42 pm-4:34 pm

2 stops21h 52m

Saint Thomas Island Cyril E King

Sun 2/15

5:40 pm-11:47 pm

1 stop8h 07m

$395

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Fri 5/15

5:32 pm-1:31 pm

2 stops18h 59m

Saint Thomas Island Cyril E King

Mon 5/18

2:45 pm-8:51 am

2 stops19h 06m

$397

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 2/23

5:15 pm-2:55 pm

2 stops19h 40m

Saint Thomas Island Cyril E King

Thu 2/26

2:10 pm-7:15 pm

1 stop7h 05m

$468

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 3/17

6:00 am-2:20 pm

1 stop7h 20m

Saint Thomas Island Cyril E King

Mon 3/23

1:50 pm-7:45 am

2 stops18h 55m

$484

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

Sun 3/1

6:00 am-2:56 pm

1 stop6h 56m

Christiansted Henry Rohlsen

Fri 3/6

3:58 pm-10:31 pm

1 stop8h 33m

$496

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

Tue 3/3

6:00 am-2:56 pm

1 stop6h 56m

Christiansted Henry Rohlsen

Sat 3/7

3:58 pm-10:31 pm

1 stop8h 33m

$521

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How to get the cheapest flight ticket from Chicago to U.S. Virgin Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Delays

Other information

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

In general, May is the cheapest month to fly from Chicago to U.S. Virgin Islands. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $546. If you aren’t able to travel to U.S. Virgin Islands during the month of May, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $549.

What is the cheapest day to depart on your flight to U.S. Virgin Islands?

According to our data, Thursday is the cheapest day to fly to U.S. Virgin Islands from Chicago. The lowest ticket price found for a Thursday departure recently was $609. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Saturday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $860.

What is the cheapest Chicago to U.S. Virgin Islands flight route?

Fly from Chicago O'Hare Intl to Saint Thomas Island Cyril E King for the best Chicago - U.S. Virgin Islands flight prices

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

You are more likely to see cheaper flights to U.S. Virgin Islands from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to U.S. Virgin Islands for around $650 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to U.S. Virgin Islands from Chicago for as low as $507 on momondo.

What cabin class options are available on Chicago to U.S. Virgin Islands flights?

There are 2 cabin classes available to choose from on Chicago to U.S. Virgin Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap Chicago to U.S. Virgin Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to U.S. Virgin Islands

Best Price Found	$328
Fastest flight time	4h 48m
Direct flights	Every day
Airports in U.S. Virgin Islands	6 airports

The best one-way flight to U.S. Virgin Islands from Chicago in the past 72 hours is $328. The best round-trip flight deal from Chicago to U.S. Virgin Islands found on momondo in the last 72 hours is $481.

The fastest flight from Chicago to U.S. Virgin Islands takes 4h 48m

Direct flights go from Chicago to U.S. Virgin Islands every day.

There are 6 airports in U.S. Virgin Islands. From Chicago there are direct flights to Saint Thomas Island Cyril E King (STT), Christiansted Henry Rohlsen (STX).

Search flight deals

When did momondo last update prices for flights from Chicago to U.S. Virgin Islands?
Prices for flights from Chicago to U.S. Virgin Islands were last updated today.
How many operators does momondo search for flights from Chicago to U.S. Virgin Islands?
As of January 2026, there are 4 operators available to choose from for flights from Chicago to U.S. Virgin Islands.
How old do you have to be to fly from Chicago to U.S. Virgin Islands?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to U.S. Virgin Islands.
What documentation or ID do you need to fly to U.S. Virgin Islands?
The travel and health documents required for your trip to U.S. Virgin Islands can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at U.S. Virgin Islands. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to U.S. Virgin Islands?
Based on momondo bookings for flights between Chicago and U.S. Virgin Islands, the leading plane model is Boeing 737 MAX 8, making up 54.34% of the total bookings. Other popular models include Airbus A319 with 38.75%, Boeing 737-800 with 5.12%, and Airbus A320-100/200 with 0.89%.

Best airlines flying from Chicago to U.S. Virgin Islands

Compare and see reviews for airlines that fly from Chicago to U.S. Virgin Islands with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $176	Free Cancellation	Rating 6.3 8,394 reviews	Search Spirit Airlines flights
Delta	PriceFrom $359	Free Cancellation	Rating 7.9 8,127 reviews	Search Delta flights
American Airlines	PriceFrom $454	Free Cancellation	Rating 7.2 11,206 reviews	Search American Airlines flights
United Airlines	PriceFrom $468	Free Cancellation	Rating 7.4 9,215 reviews	Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to U.S. Virgin Islands?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to U.S. Virgin Islands for you.

Can I find flights from Chicago to U.S. Virgin Islands with flexible booking policies on momondo?

momondo does allow users to show only those flights to U.S. Virgin Islands from Chicago which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Chicago to U.S. Virgin Islands?

Once all potential Chicago to U.S. Virgin Islands flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to U.S. Virgin Islands right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to U.S. Virgin Islands from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your U.S. Virgin Islands trip

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Popular cities in the U.S. Virgin Islands

Flights to Saint Thomas Islandfrom $113

U.S. Virgin Islands flight routes

Flights from Boston Logan Intl to Saint Thomas Island Cyril E King

Flights from New York John F Kennedy Intl to Saint Thomas Island Cyril E King

Flights from Newark to Saint Thomas Island Cyril E King

Flights from Washington, D.C. Dulles Intl to Saint Thomas Island Cyril E King

Flights from Orlando to Saint Thomas Island Cyril E King

Cheap flights from Chicago to the U.S. Virgin Islands from $91

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Delta flights from Chicago to U.S. Virgin Islands

Our best Delta deals on Chicago to U.S. Virgin Islands flight tickets

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Our best Southwest deals on Chicago to U.S. Virgin Islands flight tickets

momondo Fare Finder

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

See travel insights to the U.S. Virgin Islands from

How to get the cheapest flight ticket from Chicago to U.S. Virgin Islands

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

What is the cheapest day to depart on your flight to U.S. Virgin Islands?

What is the cheapest Chicago to U.S. Virgin Islands flight route?

Fly from Chicago O'Hare Intl to Saint Thomas Island Cyril E King for the best Chicago - U.S. Virgin Islands flight prices

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

What cabin class options are available on Chicago to U.S. Virgin Islands flights?

There are 2 cabin classes available to choose from on Chicago to U.S. Virgin Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

What is the cheapest airline that flies from Chicago to U.S. Virgin Islands?

Spirit Airlines is the most popular carrier operating from Chicago to U.S. Virgin Islands

What airlines fly to U.S. Virgin Islands?

How often are flights from Chicago to the U.S. Virgin Islands delayed?

Historically, on average around 20% of flights between Chicago and U.S. Virgin Islands have experienced a delay on any given week. The average delay length over the past 12 months has been 128 minutes.

What is the most punctual flight time for Chicago to the U.S. Virgin Islands flights?

Generally, flights departing in the early afternoon tend to experience fewer delays. Flights in the morning have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Monday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Chicago to the U.S. Virgin Islands flights?

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 16% of their flights experiencing any sort of delay.

How many flights depart from Chicago to U.S. Virgin Islands on average per day?

1 flights are operational daily from Chicago to U.S. Virgin Islands as of January 2026. The most popular departure time for this route is 9:00AM, with 100% of flights per day taking off at noon.

How many flights depart from Chicago to U.S. Virgin Islands on average per week?

7 flights are operational weekly from Chicago to U.S. Virgin Islands as of January 2026. The most popular departure day for this route is Thu, with 29% of flights per week taking off on this day.

Cheap Chicago to U.S. Virgin Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to U.S. Virgin Islands

Best Price Found

Fastest flight time

Direct flights

Airports in U.S. Virgin Islands

When did momondo last update prices for flights from Chicago to U.S. Virgin Islands?

How many operators does momondo search for flights from Chicago to U.S. Virgin Islands?

How old do you have to be to fly from Chicago to U.S. Virgin Islands?

What documentation or ID do you need to fly to U.S. Virgin Islands?

What is the most popular plane model from Chicago to U.S. Virgin Islands?

Best airlines flying from Chicago to U.S. Virgin Islands

Compare and see reviews for airlines that fly from Chicago to U.S. Virgin Islands with momondo

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to U.S. Virgin Islands?

Can I find flights from Chicago to U.S. Virgin Islands with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to U.S. Virgin Islands?

I’m not ready to book a flight from Chicago to U.S. Virgin Islands right now. Can momondo alert me if prices change?

An easier way to manage your U.S. Virgin Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the U.S. Virgin Islands

Popular cities in the U.S. Virgin Islands

Popular flights according to clicks in the last 7 days on momondo