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Cheap flights from the U.S. Virgin Islands to Chicago from $110

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 3/10. 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.
Spirit Airlines Logo
4:35 pm - 11:17 pm
STT
-
ORD
7h 42m
1 stop
Spirit Airlines Logo
5:05 am - 3:28 pm
ORD
-
STT
9h 23m
1 stop
$225Spirit Airlines
Wed, Mar 18 - Tue, Mar 24
Spirit Airlines Logo
4:35 pm - 11:17 pm
STT
-
ORD
7h 42m
1 stop
Spirit Airlines Logo
6:10 pm - 3:28 pm
ORD
-
STT
20h 18m
1 stop
$242Spirit Airlines
Wed, Mar 18 - Tue, Mar 24
Spirit Airlines Logo
4:35 pm - 11:17 pm
STT
-
ORD
7h 42m
1 stop
Spirit Airlines Logo
4:36 pm - 1:26 pm
ORD
-
STT
19h 50m
2 stops
$246Spirit Airlines
Wed, Mar 18 - Tue, Mar 24
Spirit Airlines Logo
4:35 pm - 11:17 pm
STT
-
ORD
7h 42m
1 stop
Spirit Airlines Logo
8:58 pm - 3:28 pm
ORD
-
STT
17h 30m
2 stops
$249Spirit Airlines
Wed, Mar 25 - Mon, Mar 30
Multiple Airlines Logo
5:40 pm - 11:05 pm
STT
-
ORD
31h 25m
1 stop
Multiple Airlines Logo
3:40 pm - 4:34 pm
ORD
-
STT
22h 54m
1 stop
$250Multiple Airlines
Wed, Feb 25 - Sun, Mar 1
Spirit Airlines Logo
4:35 pm - 11:17 pm
STT
-
ORD
7h 42m
1 stop
Spirit Airlines Logo
6:10 pm - 1:26 pm
ORD
-
STT
18h 16m
2 stops
$256Spirit Airlines
Wed, Mar 18 - Tue, Mar 24
Spirit Airlines Logo
5:40 pm - 11:47 pm
STT
-
ORD
8h 07m
1 stop
Spirit Airlines Logo
5:15 am - 3:34 pm
ORD
-
STT
9h 19m
1 stop
$259Spirit Airlines
Thu, Mar 5 - Sun, Mar 8
Spirit Airlines Logo
5:40 pm - 11:47 pm
STT
-
ORD
8h 07m
1 stop
Spirit Airlines Logo
5:15 am - 3:34 pm
ORD
-
STT
9h 19m
1 stop
$269Spirit Airlines
Thu, Mar 5 - Sun, Mar 8
Spirit Airlines Logo
4:35 pm - 11:17 pm
STT
-
ORD
7h 42m
1 stop
Spirit Airlines Logo
8:58 pm - 3:28 pm
ORD
-
STT
17h 30m
2 stops
$270Spirit Airlines
Wed, Mar 25 - Mon, Mar 30
Multiple Airlines Logo
4:37 pm - 11:24 pm
STX
-
ORD
8h 47m
1 stop
Multiple Airlines Logo
4:44 pm - 3:40 pm
ORD
-
STX
20h 56m
2 stops
$317Multiple Airlines
Fri, Feb 27 - Fri, Mar 6

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
Mar 18
STT4:35 pmSaint Thomas Island Cyril E King
7h 42m
1 stop
ORD11:17 pmChicago O'Hare Intl
Mar 24
ORD5:05 amChicago O'Hare Intl
9h 23m
1 stop
STT3:28 pmSaint Thomas Island Cyril E King
$225
Spirit Airlines
Mar 18
STT4:35 pmSaint Thomas Island Cyril E King
7h 42m
1 stop
ORD11:17 pmChicago O'Hare Intl
Mar 24
ORD6:10 pmChicago O'Hare Intl
20h 18m
1 stop
STT3:28 pmSaint Thomas Island Cyril E King
$242
Spirit Airlines
Mar 18
STT4:35 pmSaint Thomas Island Cyril E King
7h 42m
1 stop
ORD11:17 pmChicago O'Hare Intl
Mar 24
ORD4:36 pmChicago O'Hare Intl
19h 50m
2 stops
STT1:26 pmSaint Thomas Island Cyril E King
$246

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
Mar 28
STX5:32 pmChristiansted Henry Rohlsen
16h 21m
1 stop
ORD8:53 amChicago O'Hare Intl
Apr 4
ORD6:59 pmChicago O'Hare Intl
16h 57m
1 stop
STX12:56 pmChristiansted Henry Rohlsen
$581
American Airlines
May 5
STX5:14 pmChristiansted Henry Rohlsen
15h 10m
2 stops
ORD7:24 amChicago O'Hare Intl
May 23
ORD6:56 amChicago O'Hare Intl
12h 45m
2 stops
STX8:41 pmChristiansted Henry Rohlsen
$585
American Airlines
May 5
STX5:14 pmChristiansted Henry Rohlsen
18h 50m
1 stop
ORD11:04 amChicago O'Hare Intl
May 23
ORD7:09 amChicago O'Hare Intl
12h 32m
2 stops
STX8:41 pmChristiansted Henry Rohlsen
$593

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 February 12, 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

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 3/18

4:35 pm-11:17 pm

1 stop7h 42m

Chicago O'Hare Intl

Tue 3/24

5:05 am-3:28 pm

1 stop9h 23m

$225

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 3/18

4:35 pm-11:17 pm

1 stop7h 42m

Chicago O'Hare Intl

Tue 3/24

6:10 pm-3:28 pm

1 stop20h 18m

$242

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 3/18

4:35 pm-11:17 pm

1 stop7h 42m

Chicago O'Hare Intl

Tue 3/24

4:36 pm-1:26 pm

2 stops19h 50m

$246

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 3/25

4:35 pm-11:17 pm

1 stop7h 42m

Chicago O'Hare Intl

Mon 3/30

8:58 pm-3:28 pm

2 stops17h 30m

$249

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 2/25

5:40 pm-11:05 pm

1 stop31h 25m

Chicago O'Hare Intl

Sun 3/1

3:40 pm-4:34 pm

1 stop22h 54m

$250

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 3/18

4:35 pm-11:17 pm

1 stop7h 42m

Chicago O'Hare Intl

Tue 3/24

6:10 pm-1:26 pm

2 stops18h 16m

$256

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Thu 3/5

5:40 pm-11:47 pm

1 stop8h 07m

Chicago O'Hare Intl

Sun 3/8

5:15 am-3:34 pm

1 stop9h 19m

$259

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Thu 3/5

5:40 pm-11:47 pm

1 stop8h 07m

Chicago O'Hare Intl

Sun 3/8

5:15 am-3:34 pm

1 stop9h 19m

$269

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 3/25

4:35 pm-11:17 pm

1 stop7h 42m

Chicago O'Hare Intl

Mon 3/30

8:58 pm-3:28 pm

2 stops17h 30m

$270

ChristianstedChicago

STX - ORD

STXORD

Christiansted Henry Rohlsen

Fri 2/27

4:37 pm-11:24 pm

1 stop8h 47m

Chicago O'Hare Intl

Fri 3/6

4:44 pm-3:40 pm

2 stops20h 56m

$317

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 Tuesday when prices can be found for as low as $536. This is often the case because there is less demand to fly during this day of the week. On the other hand, Saturday 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 $813.

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 $540 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 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.

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

Best Price Found

$402

Fastest flight time

5h 40m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from U.S. Virgin Islands in the past 72 hours is $402. The best round-trip flight deal from U.S. Virgin Islands to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $346.
The fastest flight from U.S. Virgin Islands to Chicago O'Hare Intl Airport takes 5h 40m
Direct flights go from U.S. Virgin Islands to Chicago O'Hare Intl Airport every day.
Search flight deals

  • 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
8,451 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $306Free CancellationRating
7.2
11,277 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
Schaumburg
South Haven
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Merrillville
Gurnee
Naperville
Rosemont
New Buffalo
Kenosha
Oak Brook
Joliet
Orland Park
Racine
Hammond
Janesville
Tinley Park
Elgin
Aurora
South Holland

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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