Cheap flights from Chicago to the U.S. Virgin Islands from $186

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to the U.S. Virgin Islands departing on 8/31. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

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

Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
8:10 pm - 1:59 pm
ORD
-
STT
16h 49m
1 stop
JetBlue Logo
2:53 pm - 8:50 am
STT
-
ORD
18h 57m
3 stops
$470JetBlue
Thu, Jul 16 - Tue, Jul 21
JetBlue Logo
5:27 pm - 2:03 pm
ORD
-
STT
19h 36m
2 stops
JetBlue Logo
2:53 pm - 8:50 am
STT
-
ORD
18h 57m
3 stops
$484JetBlue
Mon, Jul 13 - Tue, Jul 21
JetBlue Logo
8:10 pm - 1:59 pm
ORD
-
STT
16h 49m
1 stop
JetBlue Logo
2:53 pm - 10:06 am
STT
-
ORD
20h 13m
2 stops
$489JetBlue
Thu, Jul 16 - Tue, Jul 21
JetBlue Logo
8:10 pm - 12:59 pm
ORD
-
STT
15h 49m
1 stop
JetBlue Logo
2:53 pm - 8:50 am
STT
-
ORD
18h 57m
3 stops
$490JetBlue
Fri, Jul 10 - Tue, Jul 14
JetBlue Logo
8:20 pm - 2:03 pm
ORD
-
STT
16h 43m
1 stop
JetBlue Logo
2:58 pm - 12:59 pm
STT
-
ORD
23h 01m
2 stops
$491JetBlue
Mon, Aug 24 - Fri, Aug 28
Southwest Logo
5:10 am - 1:25 pm
MDW
-
STT
7h 15m
1 stop
Southwest Logo
2:10 pm - 11:30 pm
STT
-
MDW
10h 20m
1 stop
$518Southwest
Sun, Aug 23 - Sun, Aug 30
Southwest Logo
5:00 am - 1:50 pm
MDW
-
STT
7h 50m
1 stop
Southwest Logo
2:05 pm - 8:55 pm
STT
-
MDW
7h 50m
1 stop
$543Southwest
Mon, Sep 21 - Sat, Sep 26
Delta Logo
6:05 am - 1:44 pm
MDW
-
STT
6h 39m
1 stop
Delta Logo
2:54 pm - 10:25 pm
STT
-
MDW
8h 31m
1 stop
$580Delta
Tue, Sep 22 - Tue, Sep 29
Delta Logo
6:05 am - 1:34 pm
MDW
-
STT
6h 29m
1 stop
Delta Logo
4:13 pm - 10:36 pm
STT
-
MDW
7h 23m
1 stop
$585Delta
Sun, Aug 16 - Sat, Aug 29
Multiple Airlines Logo
12:29 am - 4:23 pm
ORD
-
STX
14h 54m
1 stop
Multiple Airlines Logo
9:10 am - 10:26 pm
STX
-
ORD
14h 16m
1 stop
$613Multiple Airlines
Fri, Aug 21 - Sun, Aug 30

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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
Aug 23
MDW5:10 amChicago Midway
7h 15m
1 stop
STT1:25 pmSaint Thomas Island Cyril E King
Aug 30
STT2:10 pmSaint Thomas Island Cyril E King
10h 20m
1 stop
MDW11:30 pmChicago Midway
$518
Southwest
Aug 29
MDW6:00 pmChicago Midway
18h 25m
2 stops
STT1:25 pmSaint Thomas Island Cyril E King
Sep 6
STT2:10 pmSaint Thomas Island Cyril E King
8h 40m
1 stop
MDW9:50 pmChicago Midway
$572
Southwest
Aug 23
MDW5:10 amChicago Midway
7h 15m
1 stop
STT1:25 pmSaint Thomas Island Cyril E King
Aug 30
STT2:10 pmSaint Thomas Island Cyril E King
16h 30m
2 stops
MDW5:40 amChicago Midway
$578

Delta flights from Chicago to U.S. Virgin Islands

Our best Delta deals on Chicago to U.S. Virgin Islands flight tickets
Delta
Aug 16
MDW6:05 amChicago Midway
6h 29m
1 stop
STT1:34 pmSaint Thomas Island Cyril E King
Aug 29
STT4:13 pmSaint Thomas Island Cyril E King
7h 23m
1 stop
MDW10:36 pmChicago Midway
$585
Delta
Aug 28
ORD5:30 amChicago O'Hare Intl
7h 04m
1 stop
STT1:34 pmSaint Thomas Island Cyril E King
Sep 5
STT2:49 pmSaint Thomas Island Cyril E King
7h 06m
1 stop
ORD8:55 pmChicago O'Hare Intl
$590
Delta
Aug 15
ORD5:30 amChicago O'Hare Intl
7h 33m
1 stop
STX2:03 pmChristiansted Henry Rohlsen
Aug 22
STX3:08 pmChristiansted Henry Rohlsen
9h 49m
1 stop
ORD11:57 pmChicago O'Hare Intl
$726

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to U.S. Virgin Islands 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 June 18, 2026.
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

ORD - STT

ORDSTT

Chicago O'Hare Intl

Thu 7/16

8:10 pm-1:59 pm

1 stop16h 49m

Saint Thomas Island Cyril E King

Tue 7/21

2:53 pm-8:50 am

3 stops18h 57m

$470

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Mon 7/13

5:27 pm-2:03 pm

2 stops19h 36m

Saint Thomas Island Cyril E King

Tue 7/21

2:53 pm-8:50 am

3 stops18h 57m

$484

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Thu 7/16

8:10 pm-1:59 pm

1 stop16h 49m

Saint Thomas Island Cyril E King

Tue 7/21

2:53 pm-10:06 am

2 stops20h 13m

$489

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Fri 7/10

8:10 pm-12:59 pm

1 stop15h 49m

Saint Thomas Island Cyril E King

Tue 7/14

2:53 pm-8:50 am

3 stops18h 57m

$490

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Mon 8/24

8:20 pm-2:03 pm

1 stop16h 43m

Saint Thomas Island Cyril E King

Fri 8/28

2:58 pm-12:59 pm

2 stops23h 01m

$491

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 8/23

5:10 am-1:25 pm

1 stop7h 15m

Saint Thomas Island Cyril E King

Sun 8/30

2:10 pm-11:30 pm

1 stop10h 20m

$518

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 9/21

5:00 am-1:50 pm

1 stop7h 50m

Saint Thomas Island Cyril E King

Sat 9/26

2:05 pm-8:55 pm

1 stop7h 50m

$543

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 9/22

6:05 am-1:44 pm

1 stop6h 39m

Saint Thomas Island Cyril E King

Tue 9/29

2:54 pm-10:25 pm

1 stop8h 31m

$580
Quickest round-trip

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 8/16

6:05 am-1:34 pm

1 stop6h 29m

Saint Thomas Island Cyril E King

Sat 8/29

4:13 pm-10:36 pm

1 stop7h 23m

$585

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Fri 8/21

12:29 am-4:23 pm

1 stop14h 54m

Christiansted Henry Rohlsen

Sun 8/30

9:10 am-10:26 pm

1 stop14h 16m

$613

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, April 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 $80. If you aren’t able to travel to U.S. Virgin Islands during the month of April, then flying in March is also cheap. Prices for this month can be found on momondo for an average of $147.

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

According to our data, Thursday is the cheapest day to fly to U.S. Virgin Islands from Chicago. The lowest ticket price found for a Thursday departure recently was $610. 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 $770.

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

Fly from Chicago O'Hare Intl to Christiansted Henry Rohlsen 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 $644 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 $604 on momondo.

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

There are 2 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 40% 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

$671

Fastest flight time

4h 40m

Direct flights

Mon and Sun

Airports in U.S. Virgin Islands

6 airports
The best flight deal from Chicago to U.S. Virgin Islands found on momondo in the last 72 hours is $671
The fastest flight from Chicago to U.S. Virgin Islands takes 4h 40m
Direct flights go from Chicago to U.S. Virgin Islands on Monday 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
DeltaPriceFrom $359Free CancellationRating
7.8
8,410 reviews
Search Delta flights
United AirlinesPriceFrom $376Free CancellationRating
7.4
9,859 reviews
Search United Airlines flights
American AirlinesPriceFrom $482Free CancellationRating
7.1
11,686 reviews
Search American Airlines 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.

An easier way to manage your U.S. Virgin Islands trip

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1 adult
Sat 7/18
Sat 7/25

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Popular flights according to clicks in the last 7 days on momondo