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Cheap flights from the U.S. Virgin Islands to Chicago from $215

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from the U.S. Virgin Islands to Chicago departing on 8/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

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

Enter your travel dates to find the best prices.
Multiple Airlines Logo
4:55 pm - 11:27 pm
STX
-
ORD
7h 32m
1 stop
Multiple Airlines Logo
12:44 am - 4:15 pm
ORD
-
STX
14h 31m
1 stop
$584Multiple Airlines
Thu, Sep 3 - Sat, Sep 5
American Airlines Logo
1:49 pm - 10:31 pm
STT
-
ORD
9h 42m
1 stop
American Airlines Logo
8:55 pm - 12:51 pm
ORD
-
STT
14h 56m
2 stops
$585American Airlines
Wed, Sep 2 - Wed, Sep 9
JetBlue Logo
4:44 pm - 8:52 am
STX
-
ORD
17h 08m
2 stops
JetBlue Logo
8:20 pm - 3:36 pm
ORD
-
STX
18h 16m
2 stops
$611JetBlue
Thu, Sep 3 - Sun, Sep 6
Multiple Airlines Logo
8:39 am - 11:27 pm
STT
-
ORD
15h 48m
1 stop
Multiple Airlines Logo
12:44 am - 2:35 pm
ORD
-
STT
12h 51m
1 stop
$628Multiple Airlines
Thu, Aug 20 - Mon, Aug 24
American Airlines Logo
4:40 pm - 7:25 am
STX
-
ORD
15h 45m
2 stops
American Airlines Logo
6:50 pm - 3:39 pm
ORD
-
STX
19h 49m
2 stops
$638American Airlines
Tue, Sep 22 - Sat, Oct 3
American Airlines Logo
4:40 pm - 5:59 am
STX
-
ORD
14h 19m
2 stops
American Airlines Logo
6:50 pm - 3:39 pm
ORD
-
STX
19h 49m
2 stops
$640American Airlines
Mon, Sep 21 - Sat, Oct 3
Multiple Airlines Logo
8:39 am - 11:27 pm
STT
-
ORD
15h 48m
1 stop
Multiple Airlines Logo
12:44 am - 10:14 am
ORD
-
STT
8h 30m
1 stop
$651Multiple Airlines
Thu, Aug 13 - Wed, Aug 19
American Airlines Logo
8:04 am - 8:03 pm
STX
-
ORD
12h 59m
1 stop
American Airlines Logo
5:00 am - 8:43 pm
ORD
-
STX
14h 43m
1 stop
$656American Airlines
Thu, Aug 6 - Mon, Aug 10
American Airlines Logo
4:40 pm - 7:25 am
STX
-
ORD
15h 45m
2 stops
American Airlines Logo
8:45 pm - 3:39 pm
ORD
-
STX
17h 54m
2 stops
$659American Airlines
Wed, Sep 16 - Sat, Oct 3
United Airlines Logo
4:45 pm - 11:31 pm
STT
-
ORD
7h 46m
1 stop
United Airlines Logo
5:30 am - 3:43 pm
ORD
-
STT
9h 13m
1 stop
$731United Airlines
Wed, Jul 22 - Mon, Jul 27

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

Our best United Airlines deals on U.S. Virgin Islands to Chicago flight tickets
United Airlines
Jul 22
STT4:45 pmSaint Thomas Island Cyril E King
7h 46m
1 stop
ORD11:31 pmChicago O'Hare Intl
Jul 27
ORD5:30 amChicago O'Hare Intl
9h 13m
1 stop
STT3:43 pmSaint Thomas Island Cyril E King
$731
United Airlines
Jul 22
STT4:45 pmSaint Thomas Island Cyril E King
7h 46m
1 stop
ORD11:31 pmChicago O'Hare Intl
Jul 27
ORD9:41 pmChicago O'Hare Intl
13h 39m
2 stops
STT12:20 pmSaint Thomas Island Cyril E King
$855
United Airlines
Jul 30
STT1:22 pmSaint Thomas Island Cyril E King
10h 53m
1 stop
ORD11:15 pmChicago O'Hare Intl
Aug 6
ORD9:25 pmChicago O'Hare Intl
13h 55m
2 stops
STT12:20 pmSaint Thomas Island Cyril E King
$915

JetBlue flights from U.S. Virgin Islands to Chicago

Our best JetBlue deals on U.S. Virgin Islands to Chicago flight tickets
JetBlue
Sep 3
STX4:44 pmChristiansted Henry Rohlsen
17h 08m
2 stops
ORD8:52 amChicago O'Hare Intl
Sep 6
ORD8:20 pmChicago O'Hare Intl
18h 16m
2 stops
STX3:36 pmChristiansted Henry Rohlsen
$611
JetBlue
Jul 16
STX4:37 pmChristiansted Henry Rohlsen
17h 15m
2 stops
ORD8:52 amChicago O'Hare Intl
Jul 21
ORD6:30 pmChicago O'Hare Intl
20h 17m
2 stops
STX3:47 pmChristiansted Henry Rohlsen
$749
JetBlue
Jul 22
STT3:38 pmSaint Thomas Island Cyril E King
9h 06m
2 stops
ORD11:44 pmChicago O'Hare Intl
Jul 27
ORD8:10 pmChicago O'Hare Intl
16h 53m
1 stop
STT2:03 pmSaint Thomas Island Cyril E King
$791

momondo Fare Finder

 
Customize your flight search to find flights from U.S. Virgin Islands to Chicago 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 July 2, 2026.
Use the filters below to find and compare flights from the U.S. Virgin Islands to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChristianstedChicago

STX - ORD

STXORD

Christiansted Henry Rohlsen

Thu 9/3

4:55 pm-11:27 pm

1 stop7h 32m

Chicago O'Hare Intl

Sat 9/5

12:44 am-4:15 pm

1 stop14h 31m

$584

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 9/2

1:49 pm-10:31 pm

1 stop9h 42m

Chicago O'Hare Intl

Wed 9/9

8:55 pm-12:51 pm

2 stops14h 56m

$585

ChristianstedChicago

STX - ORD

STXORD

Christiansted Henry Rohlsen

Thu 9/3

4:44 pm-8:52 am

2 stops17h 08m

Chicago O'Hare Intl

Sun 9/6

8:20 pm-3:36 pm

2 stops18h 16m

$611

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Thu 8/20

8:39 am-11:27 pm

1 stop15h 48m

Chicago O'Hare Intl

Mon 8/24

12:44 am-2:35 pm

1 stop12h 51m

$628

ChristianstedChicago

STX - ORD

STXORD

Christiansted Henry Rohlsen

Tue 9/22

4:40 pm-7:25 am

2 stops15h 45m

Chicago O'Hare Intl

Sat 10/3

6:50 pm-3:39 pm

2 stops19h 49m

$638

ChristianstedChicago

STX - ORD

STXORD

Christiansted Henry Rohlsen

Mon 9/21

4:40 pm-5:59 am

2 stops14h 19m

Chicago O'Hare Intl

Sat 10/3

6:50 pm-3:39 pm

2 stops19h 49m

$640

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Thu 8/13

8:39 am-11:27 pm

1 stop15h 48m

Chicago O'Hare Intl

Wed 8/19

12:44 am-10:14 am

1 stop8h 30m

$651

ChristianstedChicago

STX - ORD

STXORD

Christiansted Henry Rohlsen

Thu 8/6

8:04 am-8:03 pm

1 stop12h 59m

Chicago O'Hare Intl

Mon 8/10

5:00 am-8:43 pm

1 stop14h 43m

$656

ChristianstedChicago

STX - ORD

STXORD

Christiansted Henry Rohlsen

Wed 9/16

4:40 pm-7:25 am

2 stops15h 45m

Chicago O'Hare Intl

Sat 10/3

8:45 pm-3:39 pm

2 stops17h 54m

$659
Quickest round-trip

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 7/22

4:45 pm-11:31 pm

1 stop7h 46m

Chicago O'Hare Intl

Mon 7/27

5:30 am-3:43 pm

1 stop9h 13m

$731

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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2

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?

The cheapest day to depart on your flight to Chicago is on a Sunday when prices can be found for as low as $505. 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 $801.

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 at noon. Flights from U.S. Virgin Islands to Chicago during this time can be as low as $540. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $567.

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

Fly from Christiansted Henry Rohlsen 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 2 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 28% 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

Fastest flight time

7h 32m

Direct flights

Mon, Tue, Wed, Sat and Sun

Airports in Chicago

3 airports
The fastest flight from U.S. Virgin Islands to Chicago takes 7h 32m
Direct flights go from U.S. Virgin Islands to Chicago on Monday, Tuesday, Wednesday, Saturday and Sunday. There are no airlines offering direct flights.
There are 3 airports in Chicago. From U.S. Virgin Islands there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from the 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?

  • 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?

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
American AirlinesPriceFrom $306Free CancellationRating
7.1
11,769 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Crown Point
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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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
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport