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Cheap flights from the U.S. Virgin Islands to Chicago from $251

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 7/14. 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.
JetBlue Logo
2:00 pm - 10:01 am
STT
-
ORD
21h 01m
2 stops
JetBlue Logo
8:10 pm - 2:03 pm
ORD
-
STT
16h 53m
1 stop
$559JetBlue
Sat, Jun 20 - Mon, Jul 20
American Airlines Logo
4:50 pm - 11:30 pm
STT
-
ORD
7h 40m
1 stop
American Airlines Logo
8:55 pm - 11:03 am
ORD
-
STT
13h 08m
2 stops
$580American Airlines
Wed, Jul 22 - Mon, Jul 27
JetBlue Logo
4:27 pm - 8:48 am
STT
-
ORD
17h 21m
2 stops
JetBlue Logo
8:20 pm - 2:03 pm
ORD
-
STT
16h 43m
1 stop
$586JetBlue
Wed, Aug 26 - Thu, Sep 3
JetBlue Logo
2:00 pm - 10:01 am
STT
-
ORD
21h 01m
2 stops
JetBlue Logo
8:10 pm - 2:03 pm
ORD
-
STT
16h 53m
1 stop
$609JetBlue
Sat, Jun 20 - Mon, Jul 20
American Airlines Logo
4:50 pm - 12:26 am
STT
-
ORD
8h 36m
1 stop
American Airlines Logo
5:07 am - 1:48 pm
ORD
-
STT
7h 41m
1 stop
$615American Airlines
Wed, Jul 8 - Sun, Jul 19
American Airlines Logo
4:49 pm - 9:08 am
STT
-
ORD
17h 19m
1 stop
American Airlines Logo
9:08 pm - 1:48 pm
ORD
-
STT
15h 40m
2 stops
$632American Airlines
Wed, Jul 1 - Tue, Jul 21
American Airlines Logo
11:44 am - 3:53 pm
STT
-
ORD
29h 09m
1 stop
American Airlines Logo
4:48 pm - 10:59 am
ORD
-
STT
17h 11m
1 stop
$643American Airlines
Wed, Jul 1 - Sat, Jul 18
American Airlines Logo
11:44 am - 3:53 pm
STT
-
ORD
29h 09m
1 stop
American Airlines Logo
4:30 pm - 10:59 am
ORD
-
STT
17h 29m
1 stop
$648American Airlines
Wed, Jul 1 - Tue, Jul 21
American Airlines Logo
1:35 pm - 11:58 pm
STT
-
ORD
11h 23m
2 stops
American Airlines Logo
6:59 am - 3:57 pm
ORD
-
STT
7h 58m
1 stop
$665American Airlines
Tue, Jun 16 - Tue, Jun 30
American Airlines Logo
4:50 pm - 12:26 am
STT
-
ORD
8h 36m
1 stop
American Airlines Logo
5:30 pm - 11:03 am
ORD
-
STT
16h 33m
2 stops
$682American Airlines
Tue, Jul 7 - Tue, Jul 21

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

Our best JetBlue deals on U.S. Virgin Islands to Chicago O'Hare Intl Airport flight tickets
JetBlue
Jun 20
STT2:00 pmSaint Thomas Island Cyril E King
21h 01m
2 stops
ORD10:01 amChicago O'Hare Intl
Jul 20
ORD8:10 pmChicago O'Hare Intl
16h 53m
1 stop
STT2:03 pmSaint Thomas Island Cyril E King
$559
JetBlue
Aug 26
STT4:27 pmSaint Thomas Island Cyril E King
17h 21m
2 stops
ORD8:48 amChicago O'Hare Intl
Sep 3
ORD8:20 pmChicago O'Hare Intl
16h 43m
1 stop
STT2:03 pmSaint Thomas Island Cyril E King
$586
JetBlue
Jun 20
STT2:00 pmSaint Thomas Island Cyril E King
21h 01m
2 stops
ORD10:01 amChicago O'Hare Intl
Jul 20
ORD8:10 pmChicago O'Hare Intl
16h 53m
1 stop
STT2:03 pmSaint Thomas Island Cyril E King
$609

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

Our best American Airlines deals on U.S. Virgin Islands to Chicago O'Hare Intl Airport flight tickets
American Airlines
Jul 22
STT4:50 pmSaint Thomas Island Cyril E King
7h 40m
1 stop
ORD11:30 pmChicago O'Hare Intl
Jul 27
ORD8:55 pmChicago O'Hare Intl
13h 08m
2 stops
STT11:03 amSaint Thomas Island Cyril E King
$580
American Airlines
Jul 8
STT4:50 pmSaint Thomas Island Cyril E King
8h 36m
1 stop
ORD12:26 amChicago O'Hare Intl
Jul 19
ORD5:07 amChicago O'Hare Intl
7h 41m
1 stop
STT1:48 pmSaint Thomas Island Cyril E King
$615
American Airlines
Jul 1
STT4:49 pmSaint Thomas Island Cyril E King
17h 19m
1 stop
ORD9:08 amChicago O'Hare Intl
Jul 21
ORD9:08 pmChicago O'Hare Intl
15h 40m
2 stops
STT1:48 pmSaint Thomas Island Cyril E King
$632

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 May 23, 2026.
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

Cheapest round-trip

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Sat 6/20

2:00 pm-10:01 am

2 stops21h 01m

Chicago O'Hare Intl

Mon 7/20

8:10 pm-2:03 pm

1 stop16h 53m

$559

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 7/22

4:50 pm-11:30 pm

1 stop7h 40m

Chicago O'Hare Intl

Mon 7/27

8:55 pm-11:03 am

2 stops13h 08m

$580

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 8/26

4:27 pm-8:48 am

2 stops17h 21m

Chicago O'Hare Intl

Thu 9/3

8:20 pm-2:03 pm

1 stop16h 43m

$586

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Sat 6/20

2:00 pm-10:01 am

2 stops21h 01m

Chicago O'Hare Intl

Mon 7/20

8:10 pm-2:03 pm

1 stop16h 53m

$609
Quickest round-trip

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 7/8

4:50 pm-12:26 am

1 stop8h 36m

Chicago O'Hare Intl

Sun 7/19

5:07 am-1:48 pm

1 stop7h 41m

$615

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 7/1

4:49 pm-9:08 am

1 stop17h 19m

Chicago O'Hare Intl

Tue 7/21

9:08 pm-1:48 pm

2 stops15h 40m

$632

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 7/1

11:44 am-3:53 pm

1 stop29h 09m

Chicago O'Hare Intl

Sat 7/18

4:48 pm-10:59 am

1 stop17h 11m

$643

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 7/1

11:44 am-3:53 pm

1 stop29h 09m

Chicago O'Hare Intl

Tue 7/21

4:30 pm-10:59 am

1 stop17h 29m

$648

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Tue 6/16

1:35 pm-11:58 pm

2 stops11h 23m

Chicago O'Hare Intl

Tue 6/30

6:59 am-3:57 pm

1 stop7h 58m

$665

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Tue 7/7

4:50 pm-12:26 am

1 stop8h 36m

Chicago O'Hare Intl

Tue 7/21

5:30 pm-11:03 am

2 stops16h 33m

$682

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 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 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. 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 $801.

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 at noon is the least expensive time of day to depart. momondo users have found prices as low as $536 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $567. 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 Airport flights?

There are 3 cabin classes available to choose from on U.S. Virgin Islands to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport flights?

You could potentially save up to 28% on your flight if you consider stops on a U.S. Virgin Islands to Chicago O'Hare Intl Airport flight.

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 34m

Direct flights

Mon and Sun
The fastest flight from U.S. Virgin Islands to Chicago O'Hare Intl Airport takes 5h 34m
Direct flights go from U.S. Virgin Islands to Chicago O'Hare Intl Airport on Monday and Sunday. There are no airlines offering direct flights.
Search flight deals

Frequently asked questions about flying from the U.S. Virgin Islands to Chicago O'Hare Intl Airport

  • 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
American AirlinesPriceFrom $306Free CancellationRating
7.1
11,639 reviews
Search American 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
Schaumburg
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Merrillville
Gurnee
Rosemont
Naperville
Orland Park
New Buffalo
Oak Brook
Kenosha
Joliet
Aurora
Racine
Janesville
Hammond
Evanston
Elgin
Tinley Park

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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