Cheap flights from the U.S. Virgin Islands to Chicago from $124

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 11/19. 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 the U.S. Virgin Islands to Chicago

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

Spirit Airlines Logo
11:01 am - 6:38 pmSTT-ORD
8h 37m1 stop
Spirit Airlines Logo
4:44 pm - 9:56 amORD-STT
16h 12m2 stops
$367Spirit Airlines
Find Deal
Sat, Oct 11 - Mon, Oct 13
Spirit Airlines Logo
11:01 am - 11:45 pmSTT-ORD
13h 44m1 stop
Spirit Airlines Logo
7:43 pm - 9:56 amORD-STT
13h 13m1 stop
$383Spirit Airlines
Find Deal
Sun, Oct 5 - Thu, Oct 9
Spirit Airlines Logo
2:01 pm - 11:45 pmSTT-ORD
10h 44m2 stops
Spirit Airlines Logo
4:44 pm - 9:56 amORD-STT
16h 12m2 stops
$395Spirit Airlines
Find Deal
Sat, Oct 11 - Mon, Oct 13
United Airlines Logo
5:25 pm - 11:34 pmSTT-ORD
8h 09m1 stop
United Airlines Logo
9:30 am - 4:18 pmORD-STT
4h 48mnonstop
$545United Airlines
Find Deal
Sun, Nov 23 - Sun, Nov 30
United Airlines Logo
3:35 pm - 11:15 pmSTT-ORD
9h 40m1 stop
United Airlines Logo
9:30 am - 4:18 pmORD-STT
4h 48mnonstop
$571United Airlines
Find Deal
Sat, Nov 22 - Sun, Nov 30
Delta Logo
3:19 pm - 11:54 pmSTX-ORD
10h 35m1 stop
Delta Logo
5:50 am - 1:24 pmORD-STX
6h 34m1 stop
$595Delta
Find Deal
Fri, Mar 6 - Tue, Mar 10
American Airlines Logo
6:17 pm - 7:21 amSTX-ORD
15h 04m2 stops
American Airlines Logo
8:30 pm - 2:35 pmORD-STX
17h 05m2 stops
$609American Airlines
Find Deal
Fri, Mar 6 - Tue, Mar 10
American Airlines Logo
6:36 pm - 8:47 amSTT-ORD
16h 11m1 stop
American Airlines Logo
8:13 am - 2:59 pmORD-STT
4h 46mnonstop
$615American Airlines
Find Deal
Mon, Dec 29 - Fri, Jan 2
Multiple Airlines Logo
1:33 pm - 10:46 amSTT-ORD
23h 13m2 stops
Multiple Airlines Logo
8:41 am - 12:28 pmORD-STT
25h 47m1 stop
$654Multiple Airlines
Find Deal
Mon, Dec 29 - Fri, Jan 2
Multiple Airlines Logo
1:33 pm - 9:44 amSTT-ORD
22h 11m2 stops
Multiple Airlines Logo
10:00 am - 12:28 pmORD-STT
24h 28m2 stops
$744Multiple Airlines
Find Deal
Tue, Nov 25 - Sat, Nov 29

United Airlines flights from U.S. Virgin Islands to Chicago O'Hare Intl Airport

Our best United Airlines deals on U.S. Virgin Islands to Chicago O'Hare Intl Airport flight tickets
United Airlines
Nov 23
STT5:25 pmSaint Thomas Island Cyril E King
8h 09m
1 stop
ORD11:34 pmChicago O'Hare Intl
Nov 30
ORD9:30 amChicago O'Hare Intl
4h 48m
STT4:18 pmSaint Thomas Island Cyril E King
United Airlines
Nov 22
STT3:35 pmSaint Thomas Island Cyril E King
9h 40m
1 stop
ORD11:15 pmChicago O'Hare Intl
Nov 30
ORD9:30 amChicago O'Hare Intl
4h 48m
STT4:18 pmSaint Thomas Island Cyril E King
United Airlines
Nov 22
STT3:05 pmSaint Thomas Island Cyril E King
5h 40m
ORD6:45 pmChicago O'Hare Intl
Nov 30
ORD9:30 amChicago O'Hare Intl
4h 48m
STT4:18 pmSaint Thomas Island Cyril E King

Spirit Airlines flights from U.S. Virgin Islands to Chicago O'Hare Intl Airport

Our best Spirit Airlines deals on U.S. Virgin Islands to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines
Oct 11
STT11:01 amSaint Thomas Island Cyril E King
8h 37m
1 stop
ORD6:38 pmChicago O'Hare Intl
Oct 13
ORD4:44 pmChicago O'Hare Intl
16h 12m
2 stops
STT9:56 amSaint Thomas Island Cyril E King
Spirit Airlines
Oct 5
STT11:01 amSaint Thomas Island Cyril E King
13h 44m
1 stop
ORD11:45 pmChicago O'Hare Intl
Oct 9
ORD7:43 pmChicago O'Hare Intl
13h 13m
1 stop
STT9:56 amSaint Thomas Island Cyril E King
Spirit Airlines
Oct 11
STT2:01 pmSaint Thomas Island Cyril E King
10h 44m
2 stops
ORD11:45 pmChicago O'Hare Intl
Oct 13
ORD4:44 pmChicago O'Hare Intl
16h 12m
2 stops
STT9:56 amSaint Thomas Island Cyril E King

momondo Fare Finder

 
Customize your flight search to find flights from U.S. Virgin Islands to Chicago O'Hare Intl Airport 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 September 21, 2025.
Use the filters below to find and compare flights from the U.S. Virgin Islands to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Sat 10/11

11:01 am-6:38 pm

1 stop8h 37m

Chicago O'Hare Intl

Mon 10/13

4:44 pm-9:56 am

2 stops16h 12m

$367

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Sun 10/5

11:01 am-11:45 pm

1 stop13h 44m

Chicago O'Hare Intl

Thu 10/9

7:43 pm-9:56 am

1 stop13h 13m

$383

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Sat 10/11

2:01 pm-11:45 pm

2 stops10h 44m

Chicago O'Hare Intl

Mon 10/13

4:44 pm-9:56 am

2 stops16h 12m

$395

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Sun 11/23

5:25 pm-11:34 pm

1 stop8h 09m

Chicago O'Hare Intl

Sun 11/30

9:30 am-4:18 pm

Nonstop4h 48m

$545

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Sat 11/22

3:35 pm-11:15 pm

1 stop9h 40m

Chicago O'Hare Intl

Sun 11/30

9:30 am-4:18 pm

Nonstop4h 48m

$571

ChristianstedChicago

STX - ORD

STXORD

Christiansted Henry Rohlsen

Fri 3/6

3:19 pm-11:54 pm

1 stop10h 35m

Chicago O'Hare Intl

Tue 3/10

5:50 am-1:24 pm

1 stop6h 34m

$595

ChristianstedChicago

STX - ORD

STXORD

Christiansted Henry Rohlsen

Fri 3/6

6:17 pm-7:21 am

2 stops15h 04m

Chicago O'Hare Intl

Tue 3/10

8:30 pm-2:35 pm

2 stops17h 05m

$609

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Mon 12/29

6:36 pm-8:47 am

1 stop16h 11m

Chicago O'Hare Intl

Fri 1/2

8:13 am-2:59 pm

Nonstop4h 46m

$615

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Mon 12/29

1:33 pm-10:46 am

2 stops23h 13m

Chicago O'Hare Intl

Fri 1/2

8:41 am-12:28 pm

1 stop25h 47m

$654

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Tue 11/25

1:33 pm-9:44 am

2 stops22h 11m

Chicago O'Hare Intl

Sat 11/29

10:00 am-12:28 pm

2 stops24h 28m

$744

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 O'Hare Intl Airport

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 O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport 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. On the other hand, Friday is the most expensive day to depart from U.S. Virgin Islands because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $1,176.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from U.S. Virgin Islands in the morning is the least expensive time of day to depart. momondo users have found prices as low as $430 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $612. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest U.S. Virgin Islands to Chicago O'Hare Intl flight route?

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

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

There are 4 cabin classes available to choose from on U.S. Virgin Islands to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap U.S. Virgin Islands to Chicago O'Hare Intl Airport flight deals and tips

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

Fastest flight time

5h 32m

Direct flights

Every day
The fastest flight from U.S. Virgin Islands to Chicago O'Hare Intl Airport takes 5h 32m
Direct flights go from U.S. Virgin Islands to Chicago O'Hare Intl Airport every day.
  • When did momondo last update prices for flights from U.S. Virgin Islands to Chicago O'Hare Intl Airport?

    Prices for flights from U.S. Virgin Islands to Chicago O'Hare Intl Airport are updated daily.

  • How many operators does momondo search for flights from U.S. Virgin Islands to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from U.S. Virgin Islands to Chicago O'Hare Intl Airport?

    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 U.S. Virgin Islands to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from U.S. Virgin Islands to Chicago O'Hare Intl Airport?

Best airlines flying from U.S. Virgin Islands to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from U.S. Virgin Islands to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $204Free CancellationRating
6.3
8,031 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $453Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $509Free CancellationRating
7.4
8,922 reviews
Search United Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
South Haven
Rockford
Schaumburg
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Orland Park
Tinley Park
Elgin
Aurora
Janesville
Benton Harbor

Why use momondo?

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

Finding the right flight to Chicago from U.S. Virgin Islands is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

Yes. momondo enables you to select and highlight flights to Chicago from U.S. Virgin Islands with this policy.

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

Once you have performed a search for U.S. Virgin Islands to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from U.S. Virgin Islands and alert you when they change.

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Tue 10/21
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