How long does it take to fly to Chicago?

Average flight duration from U.S. Virgin Islands to Chicago depends on which airport you fly into and out of. Flying from Saint Thomas Island to Chicago O'Hare Intl Airport is 5h 40m on average, while flying from Christiansted to Chicago O'Hare Intl Airport is 5h 40m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

What airlines fly to Chicago?

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Chicago from U.S. Virgin Islands according to our data. American Airlines is the first choice among our users, with 60% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

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

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

Prices for flights from U.S. Virgin Islands to Chicago are refreshed on a daily basis.

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

As of July 2025, there are 3 operators available to choose from for flights from U.S. Virgin Islands to Chicago.

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

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from U.S. Virgin Islands to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents required for your trip to Chicago 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 Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$130 Cheap Flights from the U.S. Virgin Islands to Chicago in 2025

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

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One-way

Direct

Recent round-trip flight deals from the U.S. Virgin Islands to Chicago

9:40 am - 5:37 pmSTT-ORD

8h 57m1 stop

5:13 pm - 8:45 amORD-STT

14h 32m2 stops

$285Spirit Airlines

Find Deal

Wed, Oct 15 - Mon, Oct 20

2:43 pm - 10:22 pmSTT-ORD

8h 39m1 stop

8:12 pm - 11:13 amORD-STT

14h 01m1 stop

$305Spirit Airlines

Find Deal

Sun, Aug 24 - Wed, Aug 27

5:40 pm - 10:14 amSTX-ORD

41h 34m2 stops

5:01 am - 4:41 pmORD-STX

10h 40m2 stops

$402Frontier

Find Deal

Sun, Jul 27 - Sun, Aug 3

5:40 pm - 11:31 pmSTX-ORD

30h 51m2 stops

5:05 pm - 4:41 pmORD-STX

22h 36m2 stops

$433Frontier

Find Deal

Sun, Jul 27 - Sat, Aug 9

3:20 pm - 11:58 pmSTX-ORD

10h 38m1 stop

5:40 am - 2:20 pmORD-STX

6h 40m1 stop

$495Delta

Find Deal

Tue, Dec 23 - Wed, Dec 31

4:30 pm - 11:56 pmSTX-ORD

9h 26m1 stop

6:00 am - 5:35 pmORD-STX

9h 35m2 stops

$499American Airlines

Find Deal

Thu, Dec 25 - Thu, Jan 1

3:55 pm - 10:14 pmSTT-ORD

7h 19m1 stop

5:30 am - 1:33 pmORD-STT

7h 03m1 stop

$514Delta

Find Deal

Sat, Sep 20 - Tue, Sep 23

3:55 pm - 7:35 pmSTX-ORD

5h 40mnonstop

6:55 pm - 2:05 pmORD-STX

17h 10m1 stop

$515American Airlines

Find Deal

Sat, Dec 20 - Wed, Dec 31

10:49 am - 10:34 amSTT-ORD

24h 45m3 stops

6:30 am - 11:50 amORD-STT

28h 20m2 stops

$602

Find Deal

Sat, Sep 20 - Tue, Sep 23

10:49 am - 10:34 amSTT-ORD

24h 45m3 stops

6:30 am - 1:53 pmORD-STT

30h 23m3 stops

$727

Find Deal

Sat, Sep 20 - Tue, Sep 23

Frontier flights from U.S. Virgin Islands to Chicago

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

Frontier

Jul 27

STX5:40 pmChristiansted Henry Rohlsen

41h 34m

2 stops

ORD10:14 amChicago O'Hare Intl

Aug 3

ORD5:01 amChicago O'Hare Intl

10h 40m

2 stops

STX4:41 pmChristiansted Henry Rohlsen

$399

Find similar

Frontier

Jul 27

STX5:40 pmChristiansted Henry Rohlsen

41h 34m

2 stops

ORD10:14 amChicago O'Hare Intl

Aug 3

ORD5:01 amChicago O'Hare Intl

10h 40m

2 stops

STX4:41 pmChristiansted Henry Rohlsen

$402

Find similar

Frontier

Jul 27

STX5:40 pmChristiansted Henry Rohlsen

30h 51m

2 stops

ORD11:31 pmChicago O'Hare Intl

Aug 9

ORD5:05 pmChicago O'Hare Intl

22h 36m

2 stops

STX4:41 pmChristiansted Henry Rohlsen

$433

Find similar

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

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

American Airlines

Dec 25

STX4:30 pmChristiansted Henry Rohlsen

9h 26m

1 stop

ORD11:56 pmChicago O'Hare Intl

Jan 1

ORD6:00 amChicago O'Hare Intl

9h 35m

2 stops

STX5:35 pmChristiansted Henry Rohlsen

$499

Find similar

American Airlines

Dec 20

STX3:55 pmChristiansted Henry Rohlsen

5h 40m

ORD7:35 pmChicago O'Hare Intl

Dec 31

ORD6:55 pmChicago O'Hare Intl

17h 10m

1 stop

STX2:05 pmChristiansted Henry Rohlsen

$515

Find similar

American Airlines

Nov 1

STX3:40 pmChristiansted Henry Rohlsen

17h 34m

2 stops

ORD8:14 amChicago O'Hare Intl

Nov 15

ORD8:27 pmChicago O'Hare Intl

15h 18m

2 stops

STX1:45 pmChristiansted Henry Rohlsen

$524

Find similar

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

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

Other information

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $557. This is often the case because there is less demand to fly during this day of the week. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from U.S. Virgin Islands to Chicago for around $1,141.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from U.S. Virgin Islands to Chicago during this time can be as low as $383. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $609.

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

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

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

There are 4 cabin classes available to choose from on U.S. Virgin Islands to Chicago 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 U.S. Virgin Islands to Chicago flights?

You could potentially save up to 21% on your flight if you consider stops on a U.S. Virgin Islands to Chicago flight.

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

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

Best Price Found	$130
Fastest flight time	5h 30m
Direct flights	Mon, Tue and Sun
Airports in Chicago	1 airport

The best one-way flight to Chicago from U.S. Virgin Islands in the past 72 hours is $130. The best round-trip flight deal from U.S. Virgin Islands to Chicago found on momondo in the last 72 hours is $285.

The fastest flight from U.S. Virgin Islands to Chicago takes 5h 30m

Direct flights go from U.S. Virgin Islands to Chicago on Monday, Tuesday and Sunday. Airlines offering direct flights are: United Airlines and American Airlines.

There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

Search flight deals

When did momondo last update prices for flights from U.S. Virgin Islands to Chicago?
Prices for flights from U.S. Virgin Islands to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from U.S. Virgin Islands to Chicago?
As of July 2025, there are 3 operators available to choose from for flights from U.S. Virgin Islands to Chicago.
How old do you have to be to fly from U.S. Virgin Islands to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from U.S. Virgin Islands to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago 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 Chicago. 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 U.S. Virgin Islands to Chicago?
momondo data reveals that the most frequently booked plane model on the route from U.S. Virgin Islands to Chicago is Boeing 737 MAX 8, representing 40.00% of all bookings. The subsequent popular models are Airbus A319 at 20.00%, Boeing 737-700 at 20.00%, and Boeing 737-800 at 20.00%.

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

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

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $200	Free Cancellation	Rating 6.3 8,043 reviews	Search Spirit Airlines flights
American Airlines	PriceFrom $453	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $509	Free Cancellation	Rating 7.4 8,863 reviews	Search United Airlines flights

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Crown Point

Munster

Monticello

Chesterton

Porter

Griffith

Saint John

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from U.S. Virgin Islands to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

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

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from U.S. Virgin Islands.

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

Yes. momondo can track prices for U.S. Virgin Islands to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Cheap flights from the U.S. Virgin Islands to Chicago from $130

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

Recent round-trip flight deals from the U.S. Virgin Islands to Chicago

Recent one-way flight deals from the U.S. Virgin Islands to Chicago

Recent direct flight deals from the U.S. Virgin Islands to Chicago

Frontier flights from U.S. Virgin Islands to Chicago

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

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

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

See travel insights to Chicago from

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

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 day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from U.S. Virgin Islands to Chicago during this time can be as low as $383. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $609.

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

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

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

There are 4 cabin classes available to choose from on U.S. Virgin Islands to Chicago 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 U.S. Virgin Islands to Chicago flights?

You could potentially save up to 21% on your flight if you consider stops on a U.S. Virgin Islands to Chicago flight.

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

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

What airlines fly to Chicago?

How long does it take to fly to Chicago?

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

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

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

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

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

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

What documentation or ID do you need to fly to Chicago?

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

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

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

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago 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 United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago