$244+ Cheap flights from Chicago (CHI) to the U.S. Virgin Islands
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STT
Jun 29 — Jul 61
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to U.S. Virgin Islands with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to U.S. Virgin Islands
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Cheapest flights from Chicago to U.S. Virgin IslandsExplore the most affordable flight options available from Chicago to U.S. Virgin Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 30, 2026.
Explore the most affordable flight options available from Chicago to U.S. Virgin Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 30, 2026.
This FlightHub deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/138:10 pm
ORD
- STT
1 stop16h 53m
JetBlue
Tue 7/212:53 pm
STT
- ORD
2 stops20h 13m
JetBlue
Deal found 5/30![JetBlue logo]()
$474
This FlightHub deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:20 pm
ORD
- STT
1 stop15h 39m
JetBlue
Sat 9/52:00 pm
STT
- ORD
2 stops20h 59m
JetBlue
Deal found 5/29![JetBlue logo]()
$487
This FlightHub deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/118:20 pm
ORD
- STT
1 stop17h 15m
JetBlue
Tue 6/232:58 pm
STT
- ORD
2 stops20h 08m
JetBlue
Deal found 5/25![JetBlue logo]()
$493
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/75:00 am
MDW
- STT
1 stop7h 50m
Southwest
Mon 9/142:35 pm
STT
- MDW
1 stop9h 05m
Southwest
Deal found 5/26![Southwest logo]()
$506
This FlightHub deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/128:20 pm
ORD
- STT
1 stop15h 40m
JetBlue
Fri 6/193:18 pm
STT
- ORD
2 stops22h 42m
JetBlue
Deal found 5/27![JetBlue logo]()
$506
This FlightHub deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/118:20 pm
ORD
- STT
1 stop17h 15m
JetBlue
Sat 6/202:00 pm
STT
- ORD
2 stops21h 01m
JetBlue
Deal found 5/29![JetBlue logo]()
$511
This FlightHub deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/218:20 pm
ORD
- STT
1 stop15h 39m
JetBlue
Fri 8/282:58 pm
STT
- ORD
2 stops23h 01m
JetBlue
Deal found 5/27![JetBlue logo]()
$512
This FlightHub deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/210:56 am
ORD
- STT
1 stop26h 27m
JetBlue
Fri 7/102:49 pm
STT
- ORD
2 stops22h 27m
JetBlue
Deal found 5/25![JetBlue logo]()
$519
This FlightHub deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/318:20 pm
ORD
- STT
1 stop16h 43m
JetBlue
Tue 9/153:40 pm
STT
- ORD
2 stops21h 07m
JetBlue
Deal found 5/26![JetBlue logo]()
$524
This FlightHub deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/199:39 am
ORD
- STX
2 stops28h 57m
JetBlue
Mon 8/244:34 pm
STX
- ORD
2 stops25h 46m
JetBlue
Deal found 5/27![JetBlue logo]()
$553
This FlightHub deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/202:35 pm
ORD
- STX
2 stops24h 01m
JetBlue
Mon 8/244:34 pm
STX
- ORD
2 stops25h 46m
JetBlue
Deal found 5/27![JetBlue logo]()
$557
This FlightHub deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/199:39 am
ORD
- STX
2 stops28h 57m
JetBlue
Sun 8/234:34 pm
STX
- ORD
2 stops22h 05m
JetBlue
Deal found 5/27![JetBlue logo]()
$563
Best flights from Chicago to U.S. Virgin IslandsDiscover carefully curated flight deals from Chicago to U.S. Virgin Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 30, 2026.
Discover carefully curated flight deals from Chicago to U.S. Virgin Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 30, 2026.
This FlightHub deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/287:00 am
ORD
- STT
2 stops30h 48m
JetBlue
Tue 8/42:58 pm
STT
- ORD
2 stops20h 08m
JetBlue
Deal found 5/29![JetBlue logo]()
$569
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:05 am
MDW
- STT
1 stop6h 29m
Delta
Sat 8/224:13 pm
STT
- MDW
1 stop7h 23m
Delta
Deal found 5/29![Delta logo]()
$585
This United Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/225:30 am
ORD
- STT
1 stop9h 13m
United Airlines
Sat 8/14:00 pm
STT
- ORD
1 stop9h 45m
United Airlines
Deal found 5/29![United Airlines logo]()
$620
This American Airlines deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/266:10 am
ORD
- STX
1 stop13h 40m
American Airlines
Fri 7/319:00 am
STX
- ORD
1 stop15h 30m
American Airlines
Deal found 5/27![American Airlines logo]()
$656
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/185:00 am
MDW
- STT
1 stop6h 55m
Southwest
Sat 7/251:40 pm
STT
- MDW
1 stop11h 05m
Southwest
Deal found 5/26![Southwest logo]()
$764
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:47 pm
ORD
- STT
1 stop15h 16m
American Airlines
Tue 8/44:50 pm
STT
- ORD
1 stop17h 51m
American Airlines
Deal found 5/29![American Airlines logo]()
$665
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:28 am
ORD
- STT
1 stop7h 06m
Delta
Tue 8/182:49 pm
STT
- ORD
1 stop7h 01m
Delta
Deal found 5/27![Delta logo]()
$665
This United Airlines deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/175:30 am
ORD
- STT
1 stop9h 13m
United Airlines
Sun 7/194:45 pm
STT
- ORD
1 stop7h 46m
United Airlines
Deal found 5/27![United Airlines logo]()
$706
This FlightHub deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/33:27 pm
ORD
- STX
2 stops22h 19m
JetBlue
Wed 6/103:45 pm
STX
- ORD
2 stops28h 40m
JetBlue
Deal found 5/27![JetBlue logo]()
$733
This Delta deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/176:35 am
ORD
- STT
1 stop6h 48m
Delta
Wed 7/223:33 pm
STT
- ORD
1 stop9h 20m
Delta
Deal found 5/24![Delta logo]()
$670
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/88:54 pm
ORD
- STT
1 stop15h 54m
American Airlines
Tue 7/144:50 pm
STT
- ORD
1 stop8h 36m
American Airlines
Deal found 5/29![American Airlines logo]()
$670
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/306:30 am
MDW
- STT
1 stop6h 20m
Southwest
Mon 8/32:45 pm
STT
- MDW
1 stop11h 00m
Southwest
Deal found 5/26![Southwest logo]()
$783
This FlightHub deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/182:35 pm
ORD
- STX
2 stops24h 01m
JetBlue
Tue 8/253:14 pm
STX
- ORD
2 stops9h 30m
JetBlue
Deal found 5/29![JetBlue logo]()
$734
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/266:00 am
MDW
- STT
1 stop7h 23m
Delta
Sat 8/11:21 pm
STT
- MDW
1 stop9h 54m
Delta
Deal found 5/27![Delta logo]()
$690
This American Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/185:00 am
ORD
- STX
1 stop14h 50m
American Airlines
Wed 7/229:00 am
STX
- ORD
1 stop15h 30m
American Airlines
Deal found 5/26![American Airlines logo]()
$691
This American Airlines deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/218:00 am
ORD
- STX
2 stops11h 43m
American Airlines
Sat 8/298:04 am
STX
- ORD
1 stop10h 14m
American Airlines
Deal found 5/25![American Airlines logo]()
$695
This Delta deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:35 am
ORD
- STT
1 stop6h 48m
Delta
Sat 7/185:47 pm
STT
- ORD
1 stop7h 06m
Delta
Deal found 5/24![Delta logo]()
$710
This FlightHub deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:15 am
ORD
- STX
2 stops31h 31m
JetBlue
Thu 6/114:34 pm
STX
- ORD
2 stops17h 11m
JetBlue
Deal found 5/27![JetBlue logo]()
$807
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/119:00 am
ORD
- STT
1 stop6h 37m
Delta
Sat 7/185:47 pm
STT
- ORD
1 stop7h 06m
Delta
Deal found 5/27![Delta logo]()
$711
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/55:28 am
ORD
- STT
1 stop8h 52m
Delta
Wed 8/122:49 pm
STT
- ORD
1 stop7h 01m
Delta
Deal found 5/28![Delta logo]()
$720
This American Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/196:37 am
ORD
- STX
2 stops13h 13m
American Airlines
Sun 7/269:00 am
STX
- ORD
2 stops14h 00m
American Airlines
Deal found 5/26![American Airlines logo]()
$830
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:28 am
ORD
- STX
1 stop7h 35m
Delta
Sat 8/293:05 pm
STX
- ORD
1 stop9h 57m
Delta
Deal found 5/27![Delta logo]()
$726
This American Airlines deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:00 am
ORD
- STX
1 stop12h 45m
American Airlines
Thu 6/119:01 am
STX
- ORD
1 stop15h 29m
American Airlines
Deal found 5/27![American Airlines logo]()
$831
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:05 am
MDW
- STX
1 stop6h 58m
Delta
Sat 8/293:05 pm
STX
- MDW
1 stop8h 31m
Delta
Deal found 5/27![Delta logo]()
$726
This American Airlines deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/35:00 am
ORD
- STX
1 stop14h 45m
American Airlines
Wed 6/103:46 pm
STX
- ORD
1 stop9h 33m
American Airlines
Deal found 5/25![American Airlines logo]()
$831
This Delta deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:05 am
MDW
- STT
1 stop8h 15m
Delta
Wed 8/122:49 pm
STT
- MDW
1 stop8h 47m
Delta
Deal found 5/25![Delta logo]()
$750
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:00 am
MDW
- STT
1 stop7h 23m
Delta
Tue 7/141:21 pm
STT
- MDW
1 stop9h 54m
Delta
Deal found 5/28![Delta logo]()
$763
This Delta deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/26:00 am
MDW
- STT
1 stop8h 21m
Delta
Fri 7/101:21 pm
STT
- MDW
1 stop9h 54m
Delta
Deal found 5/25![Delta logo]()
$800
This Delta deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:00 am
MDW
- STT
1 stop8h 20m
Delta
Mon 7/203:33 pm
STT
- MDW
1 stop7h 42m
Delta
Deal found 5/24![Delta logo]()
$810
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/176:00 am
MDW
- STT
1 stop8h 21m
Delta
Wed 6/243:29 pm
STT
- MDW
1 stop7h 48m
Delta
Deal found 5/26![Delta logo]()
$820
Last-minute flights from Chicago to U.S. Virgin IslandsDiscover last-minute flight deals from Chicago to U.S. Virgin Islands. Data last updated May 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to U.S. Virgin Islands. Data last updated May 30, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:30 pm
ORD
- STT
1 stop15h 13m
JetBlue
Fri 6/123:30 pm
STT
- ORD
2 stops22h 30m
JetBlue
Deal found 5/28![JetBlue logo]()
$569
This FlightHub deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/93:27 pm
ORD
- STX
2 stops22h 19m
JetBlue
Tue 6/164:26 pm
STX
- ORD
2 stops18h 40m
JetBlue
Deal found 5/25![JetBlue logo]()
$713
This FlightHub deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/118:20 pm
ORD
- STT
1 stop17h 15m
JetBlue
Sat 6/202:00 pm
STT
- ORD
2 stops21h 01m
JetBlue
Deal found 5/28![JetBlue logo]()
$487
This FlightHub deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/118:20 pm
ORD
- STT
1 stop17h 15m
JetBlue
Tue 6/232:58 pm
STT
- ORD
2 stops20h 08m
JetBlue
Deal found 5/25![JetBlue logo]()
$493
This FlightHub deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/128:20 pm
ORD
- STT
1 stop15h 40m
JetBlue
Fri 6/193:18 pm
STT
- ORD
2 stops22h 42m
JetBlue
Deal found 5/27![JetBlue logo]()
$506
This FlightHub deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/128:20 pm
ORD
- STT
1 stop15h 40m
JetBlue
Sat 6/202:00 pm
STT
- ORD
2 stops21h 01m
JetBlue
Deal found 5/25![JetBlue logo]()
$636
This FlightHub deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/158:20 pm
ORD
- STT
1 stop16h 43m
JetBlue
Fri 6/193:18 pm
STT
- ORD
2 stops22h 42m
JetBlue
Deal found 5/27![JetBlue logo]()
$566
This FlightHub deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/1510:56 am
ORD
- STT
1 stop26h 07m
JetBlue
Tue 6/232:58 pm
STT
- ORD
2 stops20h 08m
JetBlue
Deal found 5/26![JetBlue logo]()
$622
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/166:00 am
MDW
- STT
1 stop8h 21m
Delta
Wed 6/241:20 pm
STT
- MDW
1 stop9h 57m
Delta
Deal found 5/26![Delta logo]()
$820
This FlightHub deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/228:20 pm
ORD
- STT
1 stop16h 43m
JetBlue
Fri 6/263:18 pm
STT
- ORD
2 stops22h 42m
JetBlue
Deal found 5/27![JetBlue logo]()
$626
This Delta deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/296:00 am
MDW
- STT
1 stop8h 21m
Delta
Mon 7/133:33 pm
STT
- MDW
1 stop7h 42m
Delta
Deal found 5/25![Delta logo]()
$810
This Delta deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:00 am
MDW
- STT
1 stop8h 21m
Delta
Fri 7/101:21 pm
STT
- MDW
1 stop9h 54m
Delta
Deal found 5/25![Delta logo]()
$775
One-way flights from Chicago to U.S. Virgin IslandsSearch for one-way flight options from Chicago to U.S. Virgin Islands. Find affordable one-way fares based on user searches. Data last updated May 30, 2026.
Search for one-way flight options from Chicago to U.S. Virgin Islands. Find affordable one-way fares based on user searches. Data last updated May 30, 2026.
This Priceline deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/238:10 pm
ORD
- STT
1 stop16h 49m
JetBlue
Deal found 5/27![JetBlue logo]()
$244
This United Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/143:46 pm
ORD
- STT
2 stops19h 34m
United Airlines
Deal found 5/28![United Airlines logo]()
$256
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/254:48 pm
ORD
- STT
1 stop17h 11m
American Airlines
Deal found 5/29![American Airlines logo]()
$259
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/244:30 pm
ORD
- STT
1 stop17h 29m
American Airlines
Deal found 5/29![American Airlines logo]()
$263
This American Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/144:30 pm
ORD
- STT
1 stop17h 29m
American Airlines
Deal found 5/30![American Airlines logo]()
$264
This American Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/249:15 pm
ORD
- STT
2 stops14h 38m
American Airlines
Deal found 5/28![American Airlines logo]()
$265
This American Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/215:55 pm
ORD
- STT
2 stops16h 08m
American Airlines
Deal found 5/28![American Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/2412:52 pm
ORD
- STT
1 stop21h 20m
American Airlines
Deal found 5/29![American Airlines logo]()
$277
This United Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/249:30 pm
ORD
- STT
1 stop12h 37m
United Airlines
Deal found 5/28![United Airlines logo]()
$278
This United Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/259:41 pm
ORD
- STT
2 stops14h 27m
United Airlines
Deal found 5/29![United Airlines logo]()
$279
This United Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/219:40 pm
ORD
- STT
2 stops14h 18m
United Airlines
Deal found 5/28![United Airlines logo]()
$282
This FlightHub deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/222:35 pm
ORD
- STX
2 stops24h 01m
JetBlue
Deal found 5/27![JetBlue logo]()
$283
Find flight deals from Chicago to U.S. Virgin Islands
Keep the following information in mind while searching for Chicago to U.S. Virgin Islands flight deals. Data was last updated May 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $474 (FlightHub) |
One-way from | $244 (Priceline) |
Popular in | December |
Cheapest in | May |
Average price | $370 |
Good round-trip deal | $596 or less |
Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated May 30, 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
Cheapest round-trip
ChicagoSaint Thomas Island
ORD - STT
ORDSTT
Chicago O'Hare Intl
Tue 7/28
7:00 am-2:48 pm
2 stops30h 48m
Saint Thomas Island Cyril E King
Tue 8/4
2:58 pm-10:06 am
2 stops20h 08m
$569
ChicagoSaint Thomas Island
MDW - STT
MDWSTT
Chicago Midway
Tue 8/11
6:05 am-1:34 pm
1 stop6h 29m
Saint Thomas Island Cyril E King
Sat 8/22
4:13 pm-10:36 pm
1 stop7h 23m
$585
ChicagoSaint Thomas Island
ORD - STT
ORDSTT
Chicago O'Hare Intl
Wed 7/22
5:30 am-3:43 pm
1 stop9h 13m
Saint Thomas Island Cyril E King
Sat 8/1
4:00 pm-12:45 am
1 stop9h 45m
$620
ChicagoChristiansted
ORD - STX
ORDSTX
Chicago O'Hare Intl
Sun 7/26
6:10 am-8:50 pm
1 stop13h 40m
Christiansted Henry Rohlsen
Fri 7/31
9:00 am-11:30 pm
1 stop15h 30m
$656
ChicagoSaint Thomas Island
ORD - STT
ORDSTT
Chicago O'Hare Intl
Tue 7/28
6:47 pm-11:03 am
1 stop15h 16m
Saint Thomas Island Cyril E King
Tue 8/4
4:50 pm-9:41 am
1 stop17h 51m
$665
ChicagoSaint Thomas Island
ORD - STT
ORDSTT
Chicago O'Hare Intl
Wed 8/12
5:28 am-1:34 pm
1 stop7h 06m
Saint Thomas Island Cyril E King
Tue 8/18
2:49 pm-8:50 pm
1 stop7h 01m
$665
ChicagoSaint Thomas Island
ORD - STT
ORDSTT
Chicago O'Hare Intl
Fri 7/17
6:35 am-2:23 pm
1 stop6h 48m
Saint Thomas Island Cyril E King
Wed 7/22
3:33 pm-11:53 pm
1 stop9h 20m
$670
ChicagoSaint Thomas Island
ORD - STT
ORDSTT
Chicago O'Hare Intl
Wed 7/8
8:54 pm-1:48 pm
1 stop15h 54m
Saint Thomas Island Cyril E King
Tue 7/14
4:50 pm-12:26 am
1 stop8h 36m
$670
ChicagoSaint Thomas Island
MDW - STT
MDWSTT
Chicago Midway
Sun 7/26
6:00 am-2:23 pm
1 stop7h 23m
Saint Thomas Island Cyril E King
Sat 8/1
1:21 pm-10:15 pm
1 stop9h 54m
$690
ChicagoChristiansted
ORD - STX
ORDSTX
Chicago O'Hare Intl
Sat 7/18
5:00 am-8:50 pm
1 stop14h 50m
Christiansted Henry Rohlsen
Wed 7/22
9:00 am-11:30 pm
1 stop15h 30m
$691
Showing 1-10 of 49 resultsSorted by cheapest first
Best time to book a flight from Chicago to U.S. Virgin Islands
Have a flexible travel schedule? Discover the best time to fly to U.S. Virgin Islands from Chicago with our price prediction graph.
ORD-STT
ORD-STX
MDW-STT
MDW-STX
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to the U.S. Virgin Islands
CHI-VI0
ORD-STT
ORD-STX
MDW-STT
MDW-STX
What is the cheapest month to book a flight from Chicago to U.S. Virgin Islands?
Currently, April is the cheapest month in which you can book a flight from Chicago to U.S. Virgin Islands (average of $80). Flying from Chicago to U.S. Virgin Islands in June is currently the most expensive (average of $287). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to VI?
Find hourly flight availability from Chicago to U.S. Virgin Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 30, 2026.
When flying from Chicago to U.S. Virgin Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How often are flights from Chicago to the U.S. Virgin Islands delayed?
About 25% of weekly flights between Chicago and U.S. Virgin Islands have experienced delays in the past year, with the average delay time being 135 minutes.
What is the most punctual flight time for Chicago to the U.S. Virgin Islands flights?
Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Wednesday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to the U.S. Virgin Islands flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 23% of flights being delayed.
How far ahead should I book a flight from Chicago to U.S. Virgin Islands?
The best time to book flights from Chicago to U.S. Virgin Islands is 22 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Reviews of airlines servicing U.S. Virgin Islands
Get insights into the airlines that provide service to U.S. Virgin Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to U.S. Virgin Islands. Reviews last updated May 30, 2026.
Read reviews from past customers who have flown Delta,United Airlines, andAmerican Airlines from Chicago to the U.S. Virgin Islands. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Crew
8.5
Overall
7.9
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Crew
8.5
Overall
7.9
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Crew
8.5
Overall
7.9
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Crew
8.5
Overall
7.9
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Spirit Airlines
Comfort
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Crew
8.5
Overall
7.9
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Related info for your journey
Find useful and relevant information for your journey from Chicago to U.S. Virgin Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to U.S. Virgin Islands
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Complete your trip
Complete your trip to U.S. Virgin Islands by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to U.S. Virgin Islands by cabin class
Find flights from Chicago to U.S. Virgin Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and U.S. Virgin Islands flights
Browse other Chicago and U.S. Virgin Islands flight options. Last updated on May 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to U.S. Virgin Islands regions
Consider these flights traveling to U.S. Virgin Islands regions.
Top 4 airlines flying from Chicago to U.S. Virgin Islands
Discover the top 4 airlines that operate flights from Chicago to U.S. Virgin Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$219 | Average$359 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$359 | Average$670 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$376 | Average$706 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$482 | Average$668 | FlexibilityNo cancel fee | On-time71% |