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Cheap flights from Chicago to the U.S. Virgin Islands from $122

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 11/7. 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

Cheap round-trip flights

Spirit Airlines Logo
5:59 pm - 12:28 pmORD-STT
16h 29m1 stop
Spirit Airlines Logo
1:33 pm - 9:00 pmSTT-ORD
9h 27m1 stop
$235Spirit Airlines
Find Deal
Wed, Nov 5 - Tue, Nov 11
Spirit Airlines Logo
7:41 pm - 9:56 amORD-STT
13h 15m1 stop
Spirit Airlines Logo
11:01 am - 6:36 pmSTT-ORD
8h 35m1 stop
$244Spirit Airlines
Find Deal
Wed, Oct 15 - Wed, Oct 29
Spirit Airlines Logo
7:41 pm - 9:56 amORD-STT
13h 15m1 stop
Spirit Airlines Logo
11:01 am - 6:36 pmSTT-ORD
8h 35m1 stop
$247Spirit Airlines
Find Deal
Sat, Oct 25 - Sat, Nov 1
Spirit Airlines Logo
7:41 pm - 9:56 amORD-STT
13h 15m1 stop
Spirit Airlines Logo
11:01 am - 1:03 amSTT-ORD
15h 02m1 stop
$251Spirit Airlines
Find Deal
Wed, Oct 29 - Sat, Nov 1
Logo
5:28 pm - 12:59 pmMDW-STT
18h 31m1 stop
Logo
2:40 pm - 8:32 amSTT-MDW
18h 52m1 stop
$294
Find Deal
Fri, Oct 24 - Thu, Oct 30
Logo
5:52 pm - 12:59 pmMDW-STT
18h 07m2 stops
Logo
2:40 pm - 8:32 amSTT-MDW
18h 52m1 stop
$315
Find Deal
Fri, Oct 24 - Thu, Oct 30
American Airlines Logo
7:05 pm - 1:06 pmORD-STX
17h 01m1 stop
American Airlines Logo
3:40 pm - 10:31 pmSTX-ORD
7h 51m1 stop
$495American Airlines
Find Deal
Thu, Oct 9 - Thu, Oct 16
American Airlines Logo
9:06 pm - 1:03 pmORD-STX
14h 57m2 stops
American Airlines Logo
1:56 pm - 11:53 pmSTX-ORD
10h 57m2 stops
$499American Airlines
Find Deal
Wed, Oct 1 - Mon, Oct 6
Delta Logo
5:50 am - 2:24 pmORD-STX
6h 34m1 stop
Delta Logo
3:19 pm - 11:54 pmSTX-ORD
10h 35m1 stop
$545Delta
Find Deal
Sat, Jan 10 - Sat, Jan 17
Delta Logo
6:00 am - 2:26 pmMDW-STX
6h 26m1 stop
Delta Logo
3:24 pm - 11:32 pmSTX-MDW
10h 08m1 stop
$645Delta
Find Deal
Sat, Nov 8 - Sat, Nov 15

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
Nov 5
ORD5:59 pmChicago O'Hare Intl
16h 29m
1 stop
STT12:28 pmSaint Thomas Island Cyril E King
Nov 11
STT1:33 pmSaint Thomas Island Cyril E King
9h 27m
1 stop
ORD9:00 pmChicago O'Hare Intl
$235
Find similar
Spirit Airlines
Oct 15
ORD7:41 pmChicago O'Hare Intl
13h 15m
1 stop
STT9:56 amSaint Thomas Island Cyril E King
Oct 29
STT11:01 amSaint Thomas Island Cyril E King
8h 35m
1 stop
ORD6:36 pmChicago O'Hare Intl
$244
Find similar
Spirit Airlines
Oct 25
ORD7:41 pmChicago O'Hare Intl
13h 15m
1 stop
STT9:56 amSaint Thomas Island Cyril E King
Nov 1
STT11:01 amSaint Thomas Island Cyril E King
8h 35m
1 stop
ORD6:36 pmChicago O'Hare Intl
$247
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
Jan 10
ORD5:50 amChicago O'Hare Intl
6h 34m
1 stop
STX2:24 pmChristiansted Henry Rohlsen
Jan 17
STX3:19 pmChristiansted Henry Rohlsen
10h 35m
1 stop
ORD11:54 pmChicago O'Hare Intl
$545
Find similar
Delta
Nov 8
MDW6:00 amChicago Midway
6h 26m
1 stop
STX2:26 pmChristiansted Henry Rohlsen
Nov 15
STX3:24 pmChristiansted Henry Rohlsen
10h 08m
1 stop
MDW11:32 pmChicago Midway
$645
Find similar
Delta
Nov 10
MDW6:00 amChicago Midway
6h 40m
1 stop
STT2:40 pmSaint Thomas Island Cyril E King
Nov 18
STT3:50 pmSaint Thomas Island Cyril E King
9h 42m
1 stop
MDW11:32 pmChicago Midway
$684
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to U.S. Virgin Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 30, 2025.
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

Wed 11/5

5:59 pm-12:28 pm

1 stop16h 29m

Saint Thomas Island Cyril E King

Tue 11/11

1:33 pm-9:00 pm

1 stop9h 27m

$235

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Wed 10/15

7:41 pm-9:56 am

1 stop13h 15m

Saint Thomas Island Cyril E King

Wed 10/29

11:01 am-6:36 pm

1 stop8h 35m

$244

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 10/25

7:41 pm-9:56 am

1 stop13h 15m

Saint Thomas Island Cyril E King

Sat 11/1

11:01 am-6:36 pm

1 stop8h 35m

$247

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Wed 10/29

7:41 pm-9:56 am

1 stop13h 15m

Saint Thomas Island Cyril E King

Sat 11/1

11:01 am-1:03 am

1 stop15h 02m

$251

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 10/24

5:28 pm-12:59 pm

1 stop18h 31m

Saint Thomas Island Cyril E King

Thu 10/30

2:40 pm-8:32 am

1 stop18h 52m

$294

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 10/24

5:52 pm-12:59 pm

2 stops18h 07m

Saint Thomas Island Cyril E King

Thu 10/30

2:40 pm-8:32 am

1 stop18h 52m

$315

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Thu 10/9

7:05 pm-1:06 pm

1 stop17h 01m

Christiansted Henry Rohlsen

Thu 10/16

3:40 pm-10:31 pm

1 stop7h 51m

$495

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Wed 10/1

9:06 pm-1:03 pm

2 stops14h 57m

Christiansted Henry Rohlsen

Mon 10/6

1:56 pm-11:53 pm

2 stops10h 57m

$499

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Sat 1/10

5:50 am-2:24 pm

1 stop6h 34m

Christiansted Henry Rohlsen

Sat 1/17

3:19 pm-11:54 pm

1 stop10h 35m

$545

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

Sat 11/8

6:00 am-2:26 pm

1 stop6h 26m

Christiansted Henry Rohlsen

Sat 11/15

3:24 pm-11:32 pm

1 stop10h 08m

$645

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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?

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 $473. If you aren’t able to travel to U.S. Virgin Islands during the month of September, then flying in November is also cheap. Prices for this month can be found on momondo for an average of $529.

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

According to our data, Wednesday is the cheapest day to fly to U.S. Virgin Islands from Chicago. The lowest ticket price found for a Wednesday departure recently was $634. 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, Friday 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 $1,160.

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 $773.

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 $641 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 $489 on momondo.

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

There are 3 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 3% 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

$428

Fastest flight time

4h 35m

Direct flights

Mon, Wed, Thu, Fri, Sat and Sun

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 $428. The best round-trip flight deal from Chicago to U.S. Virgin Islands found on momondo in the last 72 hours is $535.
The fastest flight from Chicago to U.S. Virgin Islands takes 4h 35m
Direct flights go from Chicago to U.S. Virgin Islands on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. The only airline offering direct flights is United Airlines.
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?

  • 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?

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 AirlinesPriceFrom $182Free CancellationRating
6.3
8,019 reviews
Search Spirit Airlines flights
DeltaPriceFrom $359Free CancellationRating
7.9
7,978 reviews
Search Delta flights
American AirlinesPriceFrom $454Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $479Free CancellationRating
7.4
8,941 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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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
Flights to Saint Thomas Islandfrom $153