Find Deals on Flights from Chicago to U.S. Virgin Islands

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
The price shown for each flight will be the average for all passengers including any infants.
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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Chicago to U.S. Virgin Islands

(Round-trip)
Depart: Tue Aug 22 2017 Return: Wed Aug 30 2017 Trip spans 9 days
Spirit Airlines
Spirit Airlines
ORD
STT
7h 03m
1 stop
STT
ORD
8h 44m
1 stop
Depart: Mon Aug 14 2017 Return: Thu Aug 24 2017 Trip spans 11 days
Major Airline
Major Airline
ORD
STT
9h 13m
1 stop
STT
ORD
8h 44m
1 stop
Depart: Wed May 10 2017 Return: Wed May 17 2017 Trip spans 8 days
Delta
Delta
MDW
STT
7h 42m
1 stop
STT
MDW
7h 24m
1 stop
Depart: Thu Aug 31 2017 Return: Fri Sep 8 2017 Trip spans 9 days
JetBlue
JetBlue
ORD
STT
7h 46m
2 stops
STT
ORD
8h 35m
2 stops
Depart: Sat Apr 1 2017 Return: Wed Apr 5 2017 Trip spans 5 days
American Airlines
American Airlines
ORD
STT
29h 42m
2 stops
STT
ORD
8h 21m
1 stop
Depart: Wed Mar 29 2017 Return: Wed Apr 5 2017 Trip spans 8 days
United
United
ORD
STT
16h 41m
1 stop
STT
ORD
9h 51m
1 stop
Depart: Tue Mar 21 2017 Return: Wed Mar 29 2017 Trip spans 9 days
Spirit Airlines
Spirit Airlines
ORD
STT
9h 14m
1 stop
STT
ORD
7h 40m
1 stop
Depart: Tue Apr 11 2017 Return: Tue Apr 18 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
STT
9h 14m
1 stop
STT
ORD
7h 38m
1 stop
Depart: Tue Aug 1 2017 Return: Tue Aug 8 2017 Trip spans 8 days
Delta
Delta
MDW
STT
7h 42m
1 stop
STT
MDW
8h 03m
1 stop
Depart: Thu May 4 2017 Return: Tue May 16 2017 Trip spans 13 days
Spirit Airlines
Spirit Airlines
ORD
STT
7h 02m
1 stop
STT
ORD
8h 40m
1 stop
Depart: Tue Mar 14 2017 Return: Tue Mar 21 2017 Trip spans 8 days
Delta
Delta
MDW
STT
6h 20m
1 stop
STT
MDW
9h 35m
1 stop
Depart: Thu Jun 8 2017 Return: Wed Jun 14 2017 Trip spans 7 days
Major Airline
Major Airline
ORD
STT
9h 08m
1 stop
STT
ORD
8h 38m
1 stop
Depart: Sat Jul 15 2017 Return: Tue Jul 25 2017 Trip spans 11 days
American Airlines
American Airlines
ORD
STT
16h 25m
1 stop
STT
ORD
8h 07m
1 stop
Depart: Sat Aug 12 2017 Return: Sat Aug 19 2017 Trip spans 8 days
Delta
Delta
MDW
STX
6h 36m
1 stop
STX
MDW
8h 15m
1 stop
Depart: Sat Aug 12 2017 Return: Sat Aug 19 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
STX
20h 40m
2 stops
STX
ORD
13h 52m
2 stops
Depart: Tue Mar 14 2017 Return: Tue Mar 21 2017 Trip spans 8 days
Delta
Delta
MDW
STT
7h 35m
1 stop
STT
MDW
9h 35m
1 stop
Depart: Sat May 20 2017 Return: Mon May 29 2017 Trip spans 10 days
American Airlines
American Airlines
ORD
STT
13h 18m
1 stop
STT
ORD
17h 20m
1 stop
Depart: Mon Jun 5 2017 Return: Tue Jun 13 2017 Trip spans 9 days
Major Airline
Major Airline
ORD
STX
9h 36m
2 stops
STX
ORD
11h 13m
2 stops
Depart: Mon Jun 12 2017 Return: Fri Jun 16 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
STT
9h 08m
1 stop
STT
ORD
8h 44m
1 stop
Depart: Wed Mar 22 2017 Return: Wed Mar 29 2017 Trip spans 8 days
American Airlines
American Airlines
ORD
STX
9h 46m
2 stops
STX
ORD
8h 01m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Chicago
only $331
only $348
Destination

Saint Thomas Island
$331
Christiansted
$415