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 9% of their flights experiencing any sort of delay.

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

Spirit Airlines and Delta are the most popular carriers operating from Chicago to U.S. Virgin Islands

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 51% 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 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 December 2025, 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.

$100 Cheap Flights from Chicago to the U.S. Virgin Islands in 2025/26

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

Historically, on average around 12% 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 138 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.

5:32 pm - 2:52 pm

ORD

STT

19h 20m2 stops

5:42 pm - 11:46 pm

STT

ORD

8h 04m1 stop

$212Spirit Airlines

Sat, Jan 17 - Sat, Jan 24

9:09 pm - 2:28 pm

ORD

STT

15h 19m2 stops

5:42 pm - 11:46 pm

STT

ORD

8h 04m1 stop

$226Spirit Airlines

Tue, Jan 6 - Sat, Jan 17

7:20 am - 3:43 pm

ORD

STX

6h 23m1 stop

4:38 pm - 11:46 pm

STX

ORD

9h 08m1 stop

$233Spirit Airlines

Sat, Jan 10 - Sat, Jan 17

7:20 am - 4:37 pm

ORD

STT

7h 17m1 stop

5:42 pm - 11:46 pm

STT

ORD

8h 04m1 stop

$234Spirit Airlines

Sat, Jan 17 - Sat, Jan 24

7:20 am - 4:37 pm

ORD

STT

7h 17m1 stop

5:42 pm - 11:46 pm

STT

ORD

8h 04m1 stop

$235Spirit Airlines

Sat, Jan 17 - Sat, Jan 24

5:32 pm - 2:52 pm

ORD

STT

19h 20m2 stops

5:40 pm - 12:18 am

STT

ORD

8h 38m1 stop

$237Spirit Airlines

Sat, Feb 7 - Sat, Feb 14

5:32 pm - 2:52 pm

ORD

STT

19h 20m2 stops

3:56 pm - 11:10 pm

STT

ORD

9h 14m2 stops

$241Multiple Airlines

Sat, Feb 7 - Sat, Feb 14

6:00 am - 2:56 pm

MDW

STX

6h 56m1 stop

2:19 pm - 10:29 pm

STX

MDW

9h 10m1 stop

$615Delta

Tue, Mar 3 - Tue, Mar 10

6:00 am - 2:33 pm

MDW

STX

6h 33m1 stop

3:33 pm - 10:22 pm

STX

MDW

8h 49m1 stop

$640Delta

Tue, Jan 27 - Sat, Jan 31

6:00 am - 2:56 pm

MDW

STX

6h 56m1 stop

2:19 pm - 10:29 pm

STX

MDW

9h 10m1 stop

$700Delta

Tue, Mar 3 - Sun, Mar 8

Spirit Airlines flights from Chicago to U.S. Virgin Islands

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

Spirit Airlines

Jan 17

ORD5:32 pmChicago O'Hare Intl

19h 20m

2 stops

STT2:52 pmSaint Thomas Island Cyril E King

Jan 24

STT5:42 pmSaint Thomas Island Cyril E King

8h 04m

1 stop

ORD11:46 pmChicago O'Hare Intl

$212

Find similar

Spirit Airlines

Jan 6

ORD9:09 pmChicago O'Hare Intl

15h 19m

2 stops

STT2:28 pmSaint Thomas Island Cyril E King

Jan 17

STT5:42 pmSaint Thomas Island Cyril E King

8h 04m

1 stop

ORD11:46 pmChicago O'Hare Intl

$226

Find similar

Spirit Airlines

Jan 10

ORD7:20 amChicago O'Hare Intl

6h 23m

1 stop

STX3:43 pmChristiansted Henry Rohlsen

Jan 17

STX4:38 pmChristiansted Henry Rohlsen

9h 08m

1 stop

ORD11:46 pmChicago O'Hare Intl

$233

Find similar

Delta flights from Chicago to U.S. Virgin Islands

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

Delta

Mar 3

MDW6:00 amChicago Midway

6h 56m

1 stop

STX2:56 pmChristiansted Henry Rohlsen

Mar 10

STX2:19 pmChristiansted Henry Rohlsen

9h 10m

1 stop

MDW10:29 pmChicago Midway

$615

Find similar

Delta

Jan 27

MDW6:00 amChicago Midway

6h 33m

1 stop

STX2:33 pmChristiansted Henry Rohlsen

Jan 31

STX3:33 pmChristiansted Henry Rohlsen

8h 49m

1 stop

MDW10:22 pmChicago Midway

$640

Find similar

Delta

Mar 3

MDW6:00 amChicago Midway

6h 56m

1 stop

STX2:56 pmChristiansted Henry Rohlsen

Mar 8

STX2:19 pmChristiansted Henry Rohlsen

9h 10m

1 stop

MDW10:29 pmChicago Midway

$700

Find similar

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

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 1/17

5:32 pm-2:52 pm

2 stops19h 20m

Saint Thomas Island Cyril E King

Sat 1/24

5:42 pm-11:46 pm

1 stop8h 04m

$212

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Tue 1/6

9:09 pm-2:28 pm

2 stops15h 19m

Saint Thomas Island Cyril E King

Sat 1/17

5:42 pm-11:46 pm

1 stop8h 04m

$226

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Sat 1/10

7:20 am-3:43 pm

1 stop6h 23m

Christiansted Henry Rohlsen

Sat 1/17

4:38 pm-11:46 pm

1 stop9h 08m

$233

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 1/17

7:20 am-4:37 pm

1 stop7h 17m

Saint Thomas Island Cyril E King

Sat 1/24

5:42 pm-11:46 pm

1 stop8h 04m

$234

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 1/17

7:20 am-4:37 pm

1 stop7h 17m

Saint Thomas Island Cyril E King

Sat 1/24

5:42 pm-11:46 pm

1 stop8h 04m

$235

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 2/7

5:32 pm-2:52 pm

2 stops19h 20m

Saint Thomas Island Cyril E King

Sat 2/14

5:40 pm-12:18 am

1 stop8h 38m

$237

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 2/7

5:32 pm-2:52 pm

2 stops19h 20m

Saint Thomas Island Cyril E King

Sat 2/14

3:56 pm-11:10 pm

2 stops9h 14m

$241

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

Tue 3/3

6:00 am-2:56 pm

1 stop6h 56m

Christiansted Henry Rohlsen

Tue 3/10

2:19 pm-10:29 pm

1 stop9h 10m

$615

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

Tue 1/27

6:00 am-2:33 pm

1 stop6h 33m

Christiansted Henry Rohlsen

Sat 1/31

3:33 pm-10:22 pm

1 stop8h 49m

$640

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

Tue 3/3

6:00 am-2:56 pm

1 stop6h 56m

Christiansted Henry Rohlsen

Sun 3/8

2:19 pm-10:29 pm

1 stop9h 10m

$700

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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, September 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 $539. If you aren’t able to travel to U.S. Virgin Islands during the month of September, then flying in January is also cheap. Prices for this month can be found on momondo for an average of $564.

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 $610. 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 $924.

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

In the afternoon is the cheapest time of day to fly from Chicago to U.S. Virgin Islands when you can find flight prices for as low as $365. Flying to U.S. Virgin Islands in the afternoon is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $760.

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 $646 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 $455 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.

Can stopping save me money on Chicago to U.S. Virgin Islands flights?

You could potentially save up to 54% on your flight if you consider stops on a Chicago to U.S. Virgin Islands flight.

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	$323
Fastest flight time	4h 42m
Direct flights	Every day
Airports in U.S. Virgin Islands	2 airports

The best one-way flight to U.S. Virgin Islands from Chicago in the past 72 hours is $323. The best round-trip flight deal from Chicago to U.S. Virgin Islands found on momondo in the last 72 hours is $564.

The fastest flight from Chicago to U.S. Virgin Islands takes 4h 42m

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

There are 2 airports near U.S. Virgin Islands: 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 December 2025, 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 53.72% of the total bookings. Other popular models include Airbus A319 with 36.97%, Boeing 737-800 with 7.71%, and Boeing 737-700 with 0.53%.

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 $182	Free Cancellation	Rating 6.3 8,157 reviews	Search Spirit Airlines flights
Delta	PriceFrom $359	Free Cancellation	Rating 7.9 8,011 reviews	Search Delta flights
American Airlines	PriceFrom $454	Free Cancellation	Rating 7.2 11,047 reviews	Search American Airlines flights
United Airlines	PriceFrom $474	Free Cancellation	Rating 7.4 9,066 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

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.

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

Popular cities in the U.S. Virgin Islands

Flights to Saint Thomas Islandfrom $166

U.S. Virgin Islands flight routes

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

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

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

Flights from Newark to Saint Thomas Island Cyril E King

Flights from Chicago O'Hare Intl to Saint Thomas Island Cyril E King

Cheap flights from Chicago to the U.S. Virgin Islands from $100

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to the U.S. Virgin Islands departing on 2/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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

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Spirit Airlines flights from Chicago to U.S. Virgin Islands

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

Delta flights from Chicago to U.S. Virgin Islands

Our best Delta 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

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

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 time of 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.

Can stopping save me money on Chicago to U.S. Virgin Islands flights?

You could potentially save up to 54% on your flight if you consider stops on a Chicago to U.S. Virgin Islands flight.

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

Spirit Airlines and Delta are the most popular carriers 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 12% 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 138 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 9% of their flights experiencing any sort of delay.

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