Cheap flights from Chicago to the U.S. Virgin Islands from $240

1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Chicago to the U.S. Virgin Islands

Cheap round-trip flights

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Southwest Logo
3:50 pm - 1:20 pmMDW  Chicago Midway-STT Saint Thomas Island Cyril E King
19h 30m2 stops Nashville Intl Baltimore/Washington
Southwest Logo
3:45 pm - 11:00 pmSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
9h 15m1 stop Baltimore/Washington
$498Southwest
Sun, Jan 31 - Sun, Feb 7
Southwest Logo
5:05 am - 2:55 pmMDW  Chicago Midway-STT Saint Thomas Island Cyril E King
7h 50m1 stop Orlando
Southwest Logo
3:45 pm - 11:00 pmSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
9h 15m1 stop Baltimore/Washington
$498Southwest
Sun, Jan 31 - Sun, Feb 7
Multiple Airlines Logo
8:59 am - 10:05 amORD  Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King
23h 06m2 stops Fort Lauderdale Tampa
Multiple Airlines Logo
5:28 pm - 9:01 pmSTT  Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl
29h 33m1 stop San Juan Luis Munoz Marin Intl
$525Multiple Airlines
Fri, Jan 1 - Sun, Jan 10
American Airlines Logo
8:30 am - 3:19 pmORD  Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King
4h 49mnonstop
American Airlines Logo
4:20 pm - 8:16 pmSTT  Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl
5h 56mnonstop
$611American Airlines
Thu, Feb 11 - Thu, Feb 18
American Airlines Logo
8:30 am - 3:19 pmORD  Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King
4h 49mnonstop
American Airlines Logo
4:20 pm - 8:16 pmSTT  Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl
5h 56mnonstop
$611American Airlines
Thu, Feb 18 - Thu, Feb 25
United Airlines Logo
7:40 am - 2:31 pmORD  Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King
4h 51mnonstop
United Airlines Logo
3:00 pm - 6:45 pmSTT  Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl
5h 45mnonstop
$611United Airlines
Sun, Dec 6 - Fri, Dec 18
United Airlines Logo
9:25 am - 4:20 pmORD  Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King
4h 55mnonstop
United Airlines Logo
3:00 pm - 6:45 pmSTT  Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl
5h 45mnonstop
$611United Airlines
Mon, Feb 22 - Mon, Mar 1
American Airlines Logo
8:30 am - 3:19 pmORD  Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King
4h 49mnonstop
American Airlines Logo
4:20 pm - 8:16 pmSTT  Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl
5h 56mnonstop
$611American Airlines
Mon, Feb 15 - Mon, Feb 22
Delta Logo
5:30 am - 2:53 pmORD  Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King
7h 23m1 stop Atlanta Hartsfield-Jackson
Delta Logo
4:03 pm - 10:20 pmSTT  Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl
8h 17m1 stop Atlanta Hartsfield-Jackson
$620Delta
Wed, Jan 20 - Wed, Feb 3
Delta Logo
5:30 am - 3:05 pmORD  Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King
7h 35m1 stop Atlanta Hartsfield-Jackson
Delta Logo
4:15 pm - 10:23 pmSTT  Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl
8h 08m1 stop Atlanta Hartsfield-Jackson
$620Delta
Mon, Feb 22 - Tue, Mar 2

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Southwest flights from Chicago to U.S. Virgin Islands

Our best Southwest deals on Chicago to U.S. Virgin Islands flight tickets
Southwest
Jan 31
MDW3:50 pmChicago Midway
19h 30m
2 stops
STT1:20 pmSaint Thomas Island Cyril E King
Feb 7
STT3:45 pmSaint Thomas Island Cyril E King
9h 15m
1 stop
MDW11:00 pmChicago Midway
$498
Southwest
Feb 1
MDW5:25 amChicago Midway
7h 30m
1 stop
STT2:55 pmSaint Thomas Island Cyril E King
Feb 7
STT3:45 pmSaint Thomas Island Cyril E King
9h 15m
1 stop
MDW11:00 pmChicago Midway
$536
Southwest
Feb 22
MDW8:50 pmChicago Midway
16h 05m
2 stops
STT2:55 pmSaint Thomas Island Cyril E King
Mar 2
STT2:10 pmSaint Thomas Island Cyril E King
8h 50m
1 stop
MDW9:00 pmChicago Midway
$538

Delta flights from Chicago to U.S. Virgin Islands

Our best Delta deals on Chicago to U.S. Virgin Islands flight tickets
Delta
Jan 7
MDW6:00 amChicago Midway
7h 49m
1 stop
STT3:49 pmSaint Thomas Island Cyril E King
Jan 15
STT4:03 pmSaint Thomas Island Cyril E King
8h 14m
1 stop
MDW10:17 pmChicago Midway
$645
Delta
Jan 9
MDW6:00 amChicago Midway
6h 53m
1 stop
STT2:53 pmSaint Thomas Island Cyril E King
Jan 15
STT4:03 pmSaint Thomas Island Cyril E King
8h 14m
1 stop
MDW10:17 pmChicago Midway
$655
Delta
Jan 7
ORD5:30 amChicago O'Hare Intl
6h 55m
1 stop
STX2:25 pmChristiansted Henry Rohlsen
Jan 16
STX3:30 pmChristiansted Henry Rohlsen
8h 50m
1 stop
ORD10:20 pmChicago O'Hare Intl
$656

momondo Fare Finder

 
Use the filters below to find and compare flights from Chicago to the U.S. Virgin Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSaint Thomas Island

MDW Chicago Midway - STT Saint Thomas Island Cyril E King

MDWSTT

Chicago Midway

Sun 1/31

3:50 pm-1:20 pm

2 stops19h 30m

Saint Thomas Island Cyril E King

Sun 2/7

3:45 pm-11:00 pm

1 stop9h 15m

$498

ChicagoSaint Thomas Island

MDW Chicago Midway - STT Saint Thomas Island Cyril E King

MDWSTT

Chicago Midway

Sun 1/31

5:05 am-2:55 pm

1 stop7h 50m

Saint Thomas Island Cyril E King

Sun 2/7

3:45 pm-11:00 pm

1 stop9h 15m

$498

ChicagoSaint Thomas Island

ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King

ORDSTT

Chicago O'Hare Intl

Fri 1/1

8:59 am-10:05 am

2 stops23h 06m

Saint Thomas Island Cyril E King

Sun 1/10

5:28 pm-9:01 pm

1 stop29h 33m

$525

ChicagoSaint Thomas Island

ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King

ORDSTT

Chicago O'Hare Intl

Thu 2/11

8:30 am-3:19 pm

Nonstop4h 49m

Saint Thomas Island Cyril E King

Thu 2/18

4:20 pm-8:16 pm

Nonstop5h 56m

$611

ChicagoSaint Thomas Island

ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King

ORDSTT

Chicago O'Hare Intl

Thu 2/18

8:30 am-3:19 pm

Nonstop4h 49m

Saint Thomas Island Cyril E King

Thu 2/25

4:20 pm-8:16 pm

Nonstop5h 56m

$611
Quickest round-trip

ChicagoSaint Thomas Island

ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King

ORDSTT

Chicago O'Hare Intl

Sun 12/6

7:40 am-2:31 pm

Nonstop4h 51m

Saint Thomas Island Cyril E King

Fri 12/18

3:00 pm-6:45 pm

Nonstop5h 45m

$611

ChicagoSaint Thomas Island

ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King

ORDSTT

Chicago O'Hare Intl

Mon 2/22

9:25 am-4:20 pm

Nonstop4h 55m

Saint Thomas Island Cyril E King

Mon 3/1

3:00 pm-6:45 pm

Nonstop5h 45m

$611

ChicagoSaint Thomas Island

ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King

ORDSTT

Chicago O'Hare Intl

Mon 2/15

8:30 am-3:19 pm

Nonstop4h 49m

Saint Thomas Island Cyril E King

Mon 2/22

4:20 pm-8:16 pm

Nonstop5h 56m

$611

ChicagoSaint Thomas Island

ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King

ORDSTT

Chicago O'Hare Intl

Wed 1/20

5:30 am-2:53 pm

1 stop7h 23m

Saint Thomas Island Cyril E King

Wed 2/3

4:03 pm-10:20 pm

1 stop8h 17m

$620

ChicagoSaint Thomas Island

ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King

ORDSTT

Chicago O'Hare Intl

Mon 2/22

5:30 am-3:05 pm

1 stop7h 35m

Saint Thomas Island Cyril E King

Tue 3/2

4:15 pm-10:23 pm

1 stop8h 08m

$620

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 the U.S. Virgin Islands from

How to get the cheapest flight ticket from Chicago to U.S. Virgin Islands

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 U.S. Virgin Islands?

In general, May is the cheapest month to fly from Chicago to U.S. Virgin Islands. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $559. If you aren’t able to travel to U.S. Virgin Islands during the month of May, then flying in January is also cheap. Prices for this month can be found on momondo for an average of $623.

What is the cheapest day to depart on your flight to U.S. Virgin Islands?

According to our data, Tuesday is the cheapest day to fly to U.S. Virgin Islands from Chicago. The lowest ticket price found for a Tuesday departure recently was $571. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Saturday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $809.

What is the cheapest Chicago to U.S. Virgin Islands flight route?

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

How far in advance should I book a flight from Chicago to the U.S. Virgin Islands?

You are more likely to see cheaper flights to U.S. Virgin Islands from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to U.S. Virgin Islands for around $726 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to U.S. Virgin Islands from Chicago for as low as $629 on momondo.

What cabin class options are available on Chicago to U.S. Virgin Islands flights?

There are 4 cabin classes available to choose from on Chicago to U.S. Virgin Islands 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 Chicago to U.S. Virgin Islands flights?

You could potentially save up to 50% on your flight if you consider stops on a Chicago to U.S. Virgin Islands flight.

Cheap Chicago to U.S. Virgin Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to U.S. Virgin Islands

Best Price Found

$240

Fastest flight time

4h 49m

Direct flights

Mon, Wed, Thu, Fri, Sat and Sun

Airports in U.S. Virgin Islands

6 airports
The best one-way flight to U.S. Virgin Islands from Chicago in the past 72 hours is $240. The best round-trip flight deal from Chicago to U.S. Virgin Islands found on momondo in the last 72 hours is $498.
The fastest flight from Chicago to U.S. Virgin Islands takes 4h 49m
Direct flights go from Chicago to U.S. Virgin Islands on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There are 6 airports in U.S. Virgin Islands. From Chicago there are direct flights to Saint Thomas Island Cyril E King (STT), Christiansted Henry Rohlsen (STX).

Frequently asked questions about flying from Chicago to the U.S. Virgin Islands

  • When did momondo last update prices for flights from Chicago to U.S. Virgin Islands?

    Prices for flights from Chicago to U.S. Virgin Islands were last updated today.

  • How many operators does momondo search for flights from Chicago to U.S. Virgin Islands?

  • How old do you have to be to fly from Chicago to U.S. Virgin Islands?

    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 Chicago to U.S. Virgin Islands.

  • What documentation or ID do you need to fly to U.S. Virgin Islands?

    The travel and health documents required for your trip to U.S. Virgin Islands 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 U.S. Virgin Islands. 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 Chicago to U.S. Virgin Islands?

Best airlines flying from Chicago to U.S. Virgin Islands

Compare and see reviews for airlines that fly from Chicago to U.S. Virgin Islands with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $472Free CancellationRating
7.3
10,461 reviews
Search United Airlines flights
American AirlinesPriceFrom $482Free CancellationRating
7.0
12,230 reviews
Search American Airlines flights
DeltaPriceFrom $545Free CancellationRating
7.8
8,697 reviews
Search Delta flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to U.S. Virgin Islands?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to U.S. Virgin Islands for you.

Can I find flights from Chicago to U.S. Virgin Islands with flexible booking policies on momondo?

momondo does allow users to show only those flights to U.S. Virgin Islands from Chicago which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Chicago to U.S. Virgin Islands?

Once all potential Chicago to U.S. Virgin Islands flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to U.S. Virgin Islands right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to U.S. Virgin Islands from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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