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Cheap flights from the U.S. Virgin Islands to Chicago from $249

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 8/4. 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

Enter your travel dates to find the best prices.
American Airlines Logo
4:50 pm - 9:08 am
STT
-
ORD
17h 18m
1 stop
American Airlines Logo
5:07 am - 4:00 pm
ORD
-
STT
9h 53m
2 stops
$580American Airlines
Wed, Jul 22 - Mon, Jul 27
American Airlines Logo
11:52 am - 9:37 pm
STT
-
ORD
10h 45m
1 stop
American Airlines Logo
6:47 pm - 11:03 am
ORD
-
STT
15h 16m
1 stop
$625American Airlines
Tue, Jun 2 - Tue, Jun 16
American Airlines Logo
4:42 pm - 7:25 am
STT
-
ORD
15h 43m
1 stop
American Airlines Logo
9:10 pm - 11:03 am
ORD
-
STT
12h 53m
2 stops
$656American Airlines
Mon, Jun 1 - Mon, Jun 8
American Airlines Logo
2:41 pm - 9:37 pm
STT
-
ORD
7h 56m
1 stop
American Airlines Logo
5:10 am - 3:57 pm
ORD
-
STT
9h 47m
2 stops
$660American Airlines
Tue, Jun 2 - Tue, Jun 16
American Airlines Logo
1:49 pm - 11:30 pm
STT
-
ORD
10h 41m
2 stops
American Airlines Logo
5:07 am - 4:00 pm
ORD
-
STT
9h 53m
2 stops
$665American Airlines
Wed, Jul 22 - Mon, Jul 27
American Airlines Logo
11:52 am - 9:21 pm
STT
-
ORD
10h 29m
2 stops
American Airlines Logo
5:10 am - 3:57 pm
ORD
-
STT
9h 47m
2 stops
$700American Airlines
Tue, Jun 2 - Tue, Jun 16
American Airlines Logo
1:35 pm - 12:19 am
STT
-
ORD
11h 44m
1 stop
American Airlines Logo
4:33 pm - 11:12 am
ORD
-
STT
17h 39m
1 stop
$720American Airlines
Thu, Jun 4 - Thu, Jun 11
American Airlines Logo
11:52 am - 7:45 pm
STT
-
ORD
8h 53m
1 stop
American Airlines Logo
10:00 pm - 11:03 am
ORD
-
STT
12h 03m
2 stops
$737American Airlines
Tue, Jun 30 - Tue, Jun 30
Multiple Airlines Logo
12:49 pm - 7:59 am
STT
-
ORD
20h 10m
2 stops
Multiple Airlines Logo
8:20 pm - 2:35 pm
ORD
-
STT
17h 15m
1 stop
$745Multiple Airlines
Thu, Jun 4 - Thu, Jun 11
American Airlines Logo
4:48 pm - 12:24 am
STT
-
ORD
8h 36m
1 stop
American Airlines Logo
6:47 pm - 11:03 am
ORD
-
STT
15h 16m
1 stop
$760American Airlines
Fri, May 22 - Mon, May 25

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
Jul 22
STT4:50 pmSaint Thomas Island Cyril E King
17h 18m
1 stop
ORD9:08 amChicago O'Hare Intl
Jul 27
ORD5:07 amChicago O'Hare Intl
9h 53m
2 stops
STT4:00 pmSaint Thomas Island Cyril E King
$580
American Airlines
Jun 2
STT11:52 amSaint Thomas Island Cyril E King
10h 45m
1 stop
ORD9:37 pmChicago O'Hare Intl
Jun 16
ORD6:47 pmChicago O'Hare Intl
15h 16m
1 stop
STT11:03 amSaint Thomas Island Cyril E King
$625
American Airlines
Jun 1
STT4:42 pmSaint Thomas Island Cyril E King
15h 43m
1 stop
ORD7:25 amChicago O'Hare Intl
Jun 8
ORD9:10 pmChicago O'Hare Intl
12h 53m
2 stops
STT11:03 amSaint Thomas Island Cyril E King
$656

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
May 15
STT2:10 pmSaint Thomas Island Cyril E King
10h 27m
1 stop
ORD11:37 pmChicago O'Hare Intl
May 18
ORD5:00 amChicago O'Hare Intl
7h 08m
1 stop
STT1:08 pmSaint Thomas Island Cyril E King
$761
United Airlines
Jun 6
STT4:45 pmSaint Thomas Island Cyril E King
7h 41m
1 stop
ORD11:26 pmChicago O'Hare Intl
Jun 13
ORD8:53 amChicago O'Hare Intl
5h 01m
STT2:54 pmSaint Thomas Island Cyril E King
$814
United Airlines
Jun 6
STT4:45 pmSaint Thomas Island Cyril E King
7h 41m
1 stop
ORD11:26 pmChicago O'Hare Intl
Jun 13
ORD5:30 amChicago O'Hare Intl
9h 13m
1 stop
STT3:43 pmSaint Thomas Island Cyril E King
$818

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 May 12, 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

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 7/22

4:50 pm-9:08 am

1 stop17h 18m

Chicago O'Hare Intl

Mon 7/27

5:07 am-4:00 pm

2 stops9h 53m

$580

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Tue 6/2

11:52 am-9:37 pm

1 stop10h 45m

Chicago O'Hare Intl

Tue 6/16

6:47 pm-11:03 am

1 stop15h 16m

$625

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Mon 6/1

4:42 pm-7:25 am

1 stop15h 43m

Chicago O'Hare Intl

Mon 6/8

9:10 pm-11:03 am

2 stops12h 53m

$656
Quickest round-trip

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Tue 6/2

2:41 pm-9:37 pm

1 stop7h 56m

Chicago O'Hare Intl

Tue 6/16

5:10 am-3:57 pm

2 stops9h 47m

$660

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 7/22

1:49 pm-11:30 pm

2 stops10h 41m

Chicago O'Hare Intl

Mon 7/27

5:07 am-4:00 pm

2 stops9h 53m

$665

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Tue 6/2

11:52 am-9:21 pm

2 stops10h 29m

Chicago O'Hare Intl

Tue 6/16

5:10 am-3:57 pm

2 stops9h 47m

$700

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Thu 6/4

1:35 pm-12:19 am

1 stop11h 44m

Chicago O'Hare Intl

Thu 6/11

4:33 pm-11:12 am

1 stop17h 39m

$720

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Tue 6/30

11:52 am-7:45 pm

1 stop8h 53m

Chicago O'Hare Intl

Tue 6/30

10:00 pm-11:03 am

2 stops12h 03m

$737

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Thu 6/4

12:49 pm-7:59 am

2 stops20h 10m

Chicago O'Hare Intl

Thu 6/11

8:20 pm-2:35 pm

1 stop17h 15m

$745

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Fri 5/22

4:48 pm-12:24 am

1 stop8h 36m

Chicago O'Hare Intl

Mon 5/25

6:47 pm-11:03 am

1 stop15h 16m

$760

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

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 month to fly to Chicago?

The month of July is, on average, the cheapest month to fly to Chicago from U.S. Virgin Islands, with most prices found around $0. If you’re not able to fly to Chicago in July, then March is your next best option. Flight prices from U.S. Virgin Islands to Chicago during March average around $212.

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 $536. 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 Saint Thomas Island Cyril E King to Chicago O'Hare Intl for the best U.S. Virgin Islands - Chicago flight prices

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

11h 43m

Direct flights

Mon and Sun

Airports in Chicago

3 airports
The fastest flight from U.S. Virgin Islands to Chicago takes 11h 43m
Direct flights go from U.S. Virgin Islands to Chicago on Monday 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
11,661 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
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