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Cheap flights from the U.S. Virgin Islands to Chicago from $82

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 3/4. 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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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
5:40 pm - 11:47 pm
STT
-
ORD
8h 07m
1 stop
Spirit Airlines Logo
5:15 am - 4:34 pm
ORD
-
STT
9h 19m
1 stop
$168Spirit Airlines
Mon, Mar 2 - Wed, Mar 4
Spirit Airlines Logo
5:40 pm - 11:47 pm
STT
-
ORD
8h 07m
1 stop
Spirit Airlines Logo
4:43 pm - 2:31 pm
ORD
-
STT
19h 48m
2 stops
$172Spirit Airlines
Mon, Mar 2 - Wed, Mar 4
Spirit Airlines Logo
3:36 pm - 11:47 pm
STT
-
ORD
10h 11m
2 stops
Spirit Airlines Logo
4:43 pm - 2:31 pm
ORD
-
STT
19h 48m
2 stops
$193Spirit Airlines
Mon, Mar 2 - Wed, Mar 4
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
$226Spirit Airlines
Wed, Mar 25 - Mon, Mar 30
Multiple Airlines Logo
4:40 pm - 9:17 pm
STT
-
ORD
29h 37m
1 stop
Multiple Airlines Logo
1:27 pm - 3:34 pm
ORD
-
STT
25h 07m
1 stop
$230Multiple Airlines
Wed, May 6 - Mon, May 11
Spirit Airlines Logo
4:35 pm - 11:17 pm
STT
-
ORD
7h 42m
1 stop
Spirit Airlines Logo
7:17 am - 3:28 pm
ORD
-
STT
7h 11m
1 stop
$231Spirit Airlines
Wed, Mar 18 - Wed, Mar 25
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
$234Spirit Airlines
Wed, Mar 18 - Wed, Mar 25
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
$239Spirit Airlines
Wed, Mar 25 - Mon, Mar 30
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
$243Spirit Airlines
Wed, Mar 25 - Mon, Mar 30
American Airlines Logo
6:27 pm - 12:37 am
STX
-
ORD
8h 10m
1 stop
American Airlines Logo
8:07 am - 2:55 pm
ORD
-
STX
4h 48mnonstop
$676American Airlines
Tue, Feb 17 - Sat, Feb 21

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
Mar 25
STT4:35 pmSaint Thomas Island Cyril E King
7h 42m
1 stop
ORD11:17 pmChicago O'Hare Intl
Mar 30
ORD8:58 pmChicago O'Hare Intl
17h 30m
2 stops
STT3:28 pmSaint Thomas Island Cyril E King
$226
Spirit Airlines
Mar 18
STT4:35 pmSaint Thomas Island Cyril E King
7h 42m
1 stop
ORD11:17 pmChicago O'Hare Intl
Mar 25
ORD7:17 amChicago O'Hare Intl
7h 11m
1 stop
STT3:28 pmSaint Thomas Island Cyril E King
$231
Spirit Airlines
Mar 18
STT4:35 pmSaint Thomas Island Cyril E King
7h 42m
1 stop
ORD11:17 pmChicago O'Hare Intl
Mar 25
ORD6:10 pmChicago O'Hare Intl
20h 18m
1 stop
STT3:28 pmSaint Thomas Island Cyril E King
$234

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 25
STT1:13 pmSaint Thomas Island Cyril E King
5h 46m
ORD5:59 pmChicago O'Hare Intl
Mar 30
ORD8:18 amChicago O'Hare Intl
4h 45m
STT2:03 pmSaint Thomas Island Cyril E King
$521
American Airlines
Mar 25
STT5:25 pmSaint Thomas Island Cyril E King
16h 28m
1 stop
ORD8:53 amChicago O'Hare Intl
Mar 30
ORD8:18 amChicago O'Hare Intl
4h 45m
STT2:03 pmSaint Thomas Island Cyril E King
$526
American Airlines
Feb 17
STX6:27 pmChristiansted Henry Rohlsen
8h 10m
1 stop
ORD12:37 amChicago O'Hare Intl
Feb 21
ORD8:07 amChicago O'Hare Intl
4h 48m
STX2:55 pmChristiansted Henry Rohlsen
$676

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 February 6, 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

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Mon 3/2

5:40 pm-11:47 pm

1 stop8h 07m

Chicago O'Hare Intl

Wed 3/4

5:15 am-4:34 pm

1 stop9h 19m

$168

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Mon 3/2

5:40 pm-11:47 pm

1 stop8h 07m

Chicago O'Hare Intl

Wed 3/4

4:43 pm-2:31 pm

2 stops19h 48m

$172

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Mon 3/2

3:36 pm-11:47 pm

2 stops10h 11m

Chicago O'Hare Intl

Wed 3/4

4:43 pm-2:31 pm

2 stops19h 48m

$193

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

$226

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 5/6

4:40 pm-9:17 pm

1 stop29h 37m

Chicago O'Hare Intl

Mon 5/11

1:27 pm-3:34 pm

1 stop25h 07m

$230

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

Wed 3/25

7:17 am-3:28 pm

1 stop7h 11m

$231

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

Wed 3/25

6:10 pm-3:28 pm

1 stop20h 18m

$234

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

$239

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

6:10 pm-3:28 pm

1 stop20h 18m

$243

ChristianstedChicago

STX - ORD

STXORD

Christiansted Henry Rohlsen

Tue 2/17

6:27 pm-12:37 am

1 stop8h 10m

Chicago O'Hare Intl

Sat 2/21

8:07 am-2:55 pm

Nonstop4h 48m

$676

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 day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $540. 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 at noon. Flights from U.S. Virgin Islands to Chicago during this time can be as low as $540. 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 29% 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

Best Price Found

$471

Fastest flight time

5h 40m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from U.S. Virgin Islands in the past 72 hours is $471. The best round-trip flight deal from U.S. Virgin Islands to Chicago found on momondo in the last 72 hours is $346.
The fastest flight from U.S. Virgin Islands to Chicago takes 5h 40m
Direct flights go from U.S. Virgin Islands to Chicago every day.
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 $204Free CancellationRating
6.3
8,419 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $306Free CancellationRating
7.2
11,237 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
Munster
Crown Point
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