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Cheap flights from the U.S. Virgin Islands to Chicago from $129

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 2/13. 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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0 bags

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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

Enter your travel dates to find the best prices.
Multiple Airlines Logo
4:38 pm - 11:22 am
STX
-
ORD
20h 44m1 stop
Multiple Airlines Logo
1:13 pm - 3:43 pm
ORD
-
STX
24h 30m1 stop
$260Multiple Airlines
Mon, Jan 12 - Sun, Jan 18
Spirit Airlines Logo
4:38 pm - 11:22 am
STX
-
ORD
20h 44m1 stop
Spirit Airlines Logo
5:15 am - 3:43 pm
ORD
-
STX
8h 28m1 stop
$267Spirit Airlines
Mon, Jan 12 - Mon, Jan 19
Spirit Airlines Logo
4:38 pm - 11:46 pm
STX
-
ORD
9h 08m1 stop
Spirit Airlines Logo
8:36 pm - 3:43 pm
ORD
-
STX
17h 07m2 stops
$269Spirit Airlines
Fri, Jan 9 - Fri, Jan 16
Spirit Airlines Logo
4:38 pm - 11:46 pm
STX
-
ORD
9h 08m1 stop
Spirit Airlines Logo
5:15 am - 3:43 pm
ORD
-
STX
8h 28m1 stop
$274Spirit Airlines
Fri, Jan 9 - Fri, Jan 16
Multiple Airlines Logo
4:38 pm - 11:46 pm
STX
-
ORD
9h 08m1 stop
Multiple Airlines Logo
7:30 am - 3:43 pm
ORD
-
STX
30h 13m1 stop
$282Multiple Airlines
Fri, Jan 9 - Sun, Jan 11
Spirit Airlines Logo
4:38 pm - 11:46 pm
STX
-
ORD
9h 08m1 stop
Spirit Airlines Logo
5:15 am - 3:43 pm
ORD
-
STX
8h 28m1 stop
$290Spirit Airlines
Fri, Jan 9 - Mon, Jan 19
American Airlines Logo
1:13 pm - 6:04 pm
STT
-
ORD
5h 51mnonstop
American Airlines Logo
8:13 am - 2:01 pm
ORD
-
STT
4h 48mnonstop
$414American Airlines
Mon, Mar 16 - Thu, Mar 19
American Airlines Logo
2:43 pm - 8:39 am
STT
-
ORD
18h 56m1 stop
American Airlines Logo
8:13 am - 2:01 pm
ORD
-
STT
4h 48mnonstop
$419American Airlines
Mon, Mar 16 - Thu, Mar 19
United Airlines Logo
2:35 pm - 12:26 am
STT
-
ORD
10h 51m1 stop
United Airlines Logo
9:37 pm - 1:08 pm
ORD
-
STT
14h 31m2 stops
$548United Airlines
Wed, Mar 25 - Mon, Mar 30
United Airlines Logo
3:05 pm - 6:45 pm
STT
-
ORD
5h 40mnonstop
United Airlines Logo
9:30 am - 4:18 pm
ORD
-
STT
4h 48mnonstop
$622United Airlines
Fri, Feb 6 - Sun, Feb 8

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

Our best Spirit Airlines deals on U.S. Virgin Islands to Chicago flight tickets
Spirit Airlines
Jan 12
STX4:38 pmChristiansted Henry Rohlsen
20h 44m
1 stop
ORD11:22 amChicago O'Hare Intl
Jan 19
ORD5:15 amChicago O'Hare Intl
8h 28m
1 stop
STX3:43 pmChristiansted Henry Rohlsen
$267
Find similar
Spirit Airlines
Jan 9
STX4:38 pmChristiansted Henry Rohlsen
9h 08m
1 stop
ORD11:46 pmChicago O'Hare Intl
Jan 16
ORD8:36 pmChicago O'Hare Intl
17h 07m
2 stops
STX3:43 pmChristiansted Henry Rohlsen
$269
Find similar
Spirit Airlines
Jan 9
STX4:38 pmChristiansted Henry Rohlsen
9h 08m
1 stop
ORD11:46 pmChicago O'Hare Intl
Jan 16
ORD5:15 amChicago O'Hare Intl
8h 28m
1 stop
STX3:43 pmChristiansted Henry Rohlsen
$274
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
Mar 16
STT1:13 pmSaint Thomas Island Cyril E King
5h 51m
ORD6:04 pmChicago O'Hare Intl
Mar 19
ORD8:13 amChicago O'Hare Intl
4h 48m
STT2:01 pmSaint Thomas Island Cyril E King
$414
Find similar
American Airlines
Mar 16
STT2:43 pmSaint Thomas Island Cyril E King
18h 56m
1 stop
ORD8:39 amChicago O'Hare Intl
Mar 19
ORD8:13 amChicago O'Hare Intl
4h 48m
STT2:01 pmSaint Thomas Island Cyril E King
$419
Find similar
American Airlines
Mar 25
STT1:52 pmSaint Thomas Island Cyril E King
11h 43m
1 stop
ORD12:35 amChicago O'Hare Intl
Mar 30
ORD6:46 pmChicago O'Hare Intl
16h 19m
1 stop
STT12:05 pmSaint Thomas Island Cyril E King
$423
Find similar

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 December 15, 2025.
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

ChristianstedChicago

STX - ORD

STXORD

Christiansted Henry Rohlsen

Mon 1/12

4:38 pm-11:22 am

1 stop20h 44m

Chicago O'Hare Intl

Sun 1/18

1:13 pm-3:43 pm

1 stop24h 30m

$260

ChristianstedChicago

STX - ORD

STXORD

Christiansted Henry Rohlsen

Mon 1/12

4:38 pm-11:22 am

1 stop20h 44m

Chicago O'Hare Intl

Mon 1/19

5:15 am-3:43 pm

1 stop8h 28m

$267

ChristianstedChicago

STX - ORD

STXORD

Christiansted Henry Rohlsen

Fri 1/9

4:38 pm-11:46 pm

1 stop9h 08m

Chicago O'Hare Intl

Fri 1/16

8:36 pm-3:43 pm

2 stops17h 07m

$269

ChristianstedChicago

STX - ORD

STXORD

Christiansted Henry Rohlsen

Fri 1/9

4:38 pm-11:46 pm

1 stop9h 08m

Chicago O'Hare Intl

Fri 1/16

5:15 am-3:43 pm

1 stop8h 28m

$274

ChristianstedChicago

STX - ORD

STXORD

Christiansted Henry Rohlsen

Fri 1/9

4:38 pm-11:46 pm

1 stop9h 08m

Chicago O'Hare Intl

Sun 1/11

7:30 am-3:43 pm

1 stop30h 13m

$282

ChristianstedChicago

STX - ORD

STXORD

Christiansted Henry Rohlsen

Fri 1/9

4:38 pm-11:46 pm

1 stop9h 08m

Chicago O'Hare Intl

Mon 1/19

5:15 am-3:43 pm

1 stop8h 28m

$290

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Mon 3/16

1:13 pm-6:04 pm

Nonstop5h 51m

Chicago O'Hare Intl

Thu 3/19

8:13 am-2:01 pm

Nonstop4h 48m

$414

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Mon 3/16

2:43 pm-8:39 am

1 stop18h 56m

Chicago O'Hare Intl

Thu 3/19

8:13 am-2:01 pm

Nonstop4h 48m

$419

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 3/25

2:35 pm-12:26 am

1 stop10h 51m

Chicago O'Hare Intl

Mon 3/30

9:37 pm-1:08 pm

2 stops14h 31m

$548

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Fri 2/6

3:05 pm-6:45 pm

Nonstop5h 40m

Chicago O'Hare Intl

Sun 2/8

9:30 am-4:18 pm

Nonstop4h 48m

$622

Flights are sorted by cheapest round-trip flights first.

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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 Thursday when prices can be found for as low as $479. This is often the case because there is less demand to fly during this day of the week. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from U.S. Virgin Islands to Chicago for around $813.

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 $606.

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

Fastest flight time

5h 40m

Direct flights

Mon, Tue, Wed, Thu, Sat and Sun

Airports in Chicago

3 airports
The fastest flight from U.S. Virgin Islands to Chicago takes 5h 40m
Direct flights go from U.S. Virgin Islands to Chicago on Monday, Tuesday, Wednesday, Thursday, 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

  • 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
Spirit AirlinesPriceFrom $227Free CancellationRating
6.3
8,187 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $306Free CancellationRating
7.2
11,051 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
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
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