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Cheap flights from the U.S. Virgin Islands to Chicago from $141

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 4/28. 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
$281Spirit Airlines
Wed, Apr 8 - Mon, Apr 13
Spirit Airlines Logo
4:35 pm - 7:51 pm
STT
-
ORD
28h 16m
1 stop
Spirit Airlines Logo
5:05 am - 3:28 pm
ORD
-
STT
9h 23m
1 stop
$288Spirit Airlines
Wed, Apr 8 - Sun, Apr 12
Spirit Airlines Logo
4:35 pm - 7:51 pm
STT
-
ORD
28h 16m
1 stop
Spirit Airlines Logo
5:05 am - 3:28 pm
ORD
-
STT
9h 23m
1 stop
$289Spirit Airlines
Wed, Apr 8 - Mon, Apr 13
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
$304Spirit Airlines
Tue, Apr 7 - Sat, Apr 11
Multiple Airlines Logo
4:35 pm - 4:00 pm
STT
-
ORD
24h 25m
1 stop
Multiple Airlines Logo
5:05 am - 3:28 pm
ORD
-
STT
9h 23m
1 stop
$308Multiple Airlines
Thu, Apr 9 - Mon, Apr 13
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
$314Spirit Airlines
Wed, Apr 8 - Mon, Apr 13
Spirit Airlines Logo
5:10 pm - 12:27 am
STT
-
ORD
8h 17m
1 stop
Spirit Airlines Logo
7:45 pm - 1:09 pm
ORD
-
STT
16h 24m
1 stop
$317Spirit Airlines
Sat, May 9 - Fri, May 15
Spirit Airlines Logo
2:36 pm - 7:51 pm
STT
-
ORD
30h 15m
2 stops
Spirit Airlines Logo
7:17 am - 3:28 pm
ORD
-
STT
7h 11m
1 stop
$322Spirit Airlines
Wed, Apr 8 - Mon, Apr 13
Multiple Airlines Logo
4:35 pm - 4:00 pm
STT
-
ORD
24h 25m
1 stop
Multiple Airlines Logo
6:10 pm - 1:26 pm
ORD
-
STT
18h 16m
2 stops
$323Multiple Airlines
Thu, Apr 9 - Mon, Apr 13
Spirit Airlines Logo
4:35 pm - 11:50 am
STT
-
ORD
20h 15m
2 stops
Spirit Airlines Logo
7:17 am - 3:28 pm
ORD
-
STT
7h 11m
1 stop
$335Spirit Airlines
Tue, Apr 7 - Sat, Apr 11

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
Apr 8
STT4:35 pmSaint Thomas Island Cyril E King
7h 42m
1 stop
ORD11:17 pmChicago O'Hare Intl
Apr 13
ORD5:05 amChicago O'Hare Intl
9h 23m
1 stop
STT3:28 pmSaint Thomas Island Cyril E King
$281
Spirit Airlines
Apr 8
STT4:35 pmSaint Thomas Island Cyril E King
28h 16m
1 stop
ORD7:51 pmChicago O'Hare Intl
Apr 12
ORD5:05 amChicago O'Hare Intl
9h 23m
1 stop
STT3:28 pmSaint Thomas Island Cyril E King
$288
Spirit Airlines
Apr 8
STT4:35 pmSaint Thomas Island Cyril E King
28h 16m
1 stop
ORD7:51 pmChicago O'Hare Intl
Apr 13
ORD5:05 amChicago O'Hare Intl
9h 23m
1 stop
STT3:28 pmSaint Thomas Island Cyril E King
$289

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 9
STT2:10 pmSaint Thomas Island Cyril E King
5h 34m
ORD6:44 pmChicago O'Hare Intl
May 15
ORD5:00 amChicago O'Hare Intl
7h 08m
1 stop
STT1:08 pmSaint Thomas Island Cyril E King
$614
United Airlines
Apr 7
STT1:22 pmSaint Thomas Island Cyril E King
9h 11m
1 stop
ORD9:33 pmChicago O'Hare Intl
Apr 11
ORD10:59 amChicago O'Hare Intl
5h 01m
STT5:00 pmSaint Thomas Island Cyril E King
$797
United Airlines
Apr 8
STT4:45 pmSaint Thomas Island Cyril E King
7h 58m
1 stop
ORD11:43 pmChicago O'Hare Intl
Apr 13
ORD9:30 amChicago O'Hare Intl
5h 01m
STT3:31 pmSaint Thomas Island Cyril E King
$835

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 March 28, 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
Quickest round-trip

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 4/8

4:35 pm-11:17 pm

1 stop7h 42m

Chicago O'Hare Intl

Mon 4/13

5:05 am-3:28 pm

1 stop9h 23m

$281

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 4/8

4:35 pm-7:51 pm

1 stop28h 16m

Chicago O'Hare Intl

Sun 4/12

5:05 am-3:28 pm

1 stop9h 23m

$288

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 4/8

4:35 pm-7:51 pm

1 stop28h 16m

Chicago O'Hare Intl

Mon 4/13

5:05 am-3:28 pm

1 stop9h 23m

$289

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Tue 4/7

4:35 pm-11:17 pm

1 stop7h 42m

Chicago O'Hare Intl

Sat 4/11

5:05 am-3:28 pm

1 stop9h 23m

$304

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Thu 4/9

4:35 pm-4:00 pm

1 stop24h 25m

Chicago O'Hare Intl

Mon 4/13

5:05 am-3:28 pm

1 stop9h 23m

$308

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 4/8

4:35 pm-11:17 pm

1 stop7h 42m

Chicago O'Hare Intl

Mon 4/13

6:10 pm-1:26 pm

2 stops18h 16m

$314

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Sat 5/9

5:10 pm-12:27 am

1 stop8h 17m

Chicago O'Hare Intl

Fri 5/15

7:45 pm-1:09 pm

1 stop16h 24m

$317

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 4/8

2:36 pm-7:51 pm

2 stops30h 15m

Chicago O'Hare Intl

Mon 4/13

7:17 am-3:28 pm

1 stop7h 11m

$322

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Thu 4/9

4:35 pm-4:00 pm

1 stop24h 25m

Chicago O'Hare Intl

Mon 4/13

6:10 pm-1:26 pm

2 stops18h 16m

$323

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Tue 4/7

4:35 pm-11:50 am

2 stops20h 15m

Chicago O'Hare Intl

Sat 4/11

7:17 am-3:28 pm

1 stop7h 11m

$335

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 $516. 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 $540. 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

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 46% 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

$186

Fastest flight time

5h 34m

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 $186. The best round-trip flight deal from U.S. Virgin Islands to Chicago found on momondo in the last 72 hours is $387.
The fastest flight from U.S. Virgin Islands to Chicago takes 5h 34m
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
8,552 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $306Free CancellationRating
7.1
11,520 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
Schererville
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