$236+ 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STT
Sep 9 — Sep 161
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
Cheapest
Best
Last-minute
One-way
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 August 10, 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 August 10, 2026.
This FlightHub deal was found by Cheapflights users on 8/10. 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 9/266:00 am -
2 stops31h 01m
Sat 10/33:00 pm -
2 stops23h 45m
Deal found 8/10![JetBlue logo]()
$475
This FlightHub deal was found by Cheapflights users on 8/6. 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 9/96:00 am -
2 stops31h 01m
Wed 9/163:00 pm -
2 stops23h 45m
Deal found 8/6![JetBlue logo]()
$482
This FlightHub deal was found by Cheapflights users on 8/5. 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 9/106:00 am -
2 stops31h 01m
Tue 9/153:00 pm -
2 stops33h 08m
Deal found 8/5![JetBlue logo]()
$488
This FlightHub deal was found by Cheapflights users on 8/5. 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 10/302:35 pm -
2 stops24h 10m
Tue 11/35:40 pm -
2 stops32h 04m
Deal found 8/5![JetBlue logo]()
$490
This FlightHub deal was found by Cheapflights users on 8/9. 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 10/207:00 am -
2 stops31h 54m
Wed 10/284:40 pm -
2 stops21h 59m
Deal found 8/9![JetBlue logo]()
$493
This FlightHub deal was found by Cheapflights users on 8/9. 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 10/222:35 pm -
2 stops24h 19m
Thu 10/294:40 pm -
2 stops21h 59m
Deal found 8/9![JetBlue logo]()
$494
This FlightHub deal was found by Cheapflights users on 8/10. 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 9/53:20 pm -
2 stops22h 35m
Sat 9/123:00 pm -
2 stops23h 45m
Deal found 8/10![JetBlue logo]()
$499
This FlightHub deal was found by Cheapflights users on 8/7. 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.
Sun 9/133:00 pm -
2 stops22h 01m
Sat 9/193:00 pm -
2 stops23h 45m
Deal found 8/7![JetBlue logo]()
$504
This FlightHub deal was found by Cheapflights users on 8/6. 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 9/156:00 am -
2 stops31h 01m
Thu 9/173:00 pm -
2 stops23h 45m
Deal found 8/6![JetBlue logo]()
$508
This FlightHub deal was found by Cheapflights users on 8/10. 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 10/192:35 pm -
2 stops24h 19m
Mon 10/264:40 pm -
2 stops21h 59m
Deal found 8/10![JetBlue logo]()
$513
This FlightHub deal was found by Cheapflights users on 8/5. 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 9/116:00 am -
2 stops31h 01m
Mon 9/143:00 pm -
2 stops23h 45m
Deal found 8/5![JetBlue logo]()
$514
This FlightHub deal was found by Cheapflights users on 8/6. 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 11/253:20 pm -
2 stops22h 10m
Wed 12/23:26 pm -
2 stops24h 00m
Deal found 8/6![JetBlue logo]()
$527
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 August 10, 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 August 10, 2026.
This FlightHub deal was found by Cheapflights users on 8/5. 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 9/106:00 am -
2 stops31h 01m
Mon 9/143:00 pm -
2 stops23h 45m
Deal found 8/5![JetBlue logo]()
$519
This American Airlines deal was found by Cheapflights users on 8/8. 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.
Thu 10/85:00 am -
1 stop6h 39m
Fri 10/163:46 pm -
1 stop9h 52m
Deal found 8/8![American Airlines logo]()
$580
This CheapOair deal was found by Cheapflights users on 8/5. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:00 am -
2 stops31h 01m
Sat 1/301:46 pm -
2 stops11h 58m
Deal found 8/5![Multiple Airlines logo]()
$649
This Delta deal was found by Cheapflights users on 8/9. 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 10/175:27 am -
1 stop7h 10m
Thu 10/222:47 pm -
1 stop10h 05m
Deal found 8/9![Delta logo]()
$650
This United Airlines deal was found by Cheapflights users on 8/6. 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 11/39:30 pm -
2 stops14h 26m
Thu 11/51:07 pm -
1 stop7h 47m
Deal found 8/6![United Airlines logo]()
$662
This Southwest deal was found by Cheapflights users on 8/7. 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.
Sun 9/135:25 am -
1 stop7h 00m
Sat 9/192:05 pm -
1 stop7h 55m
Deal found 8/7![Southwest logo]()
$690
This Delta deal was found by Cheapflights users on 8/9. 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 11/156:00 am -
1 stop6h 40m
Sat 11/213:50 pm -
1 stop9h 06m
Deal found 8/9![Delta logo]()
$655
This American Airlines deal was found by Cheapflights users on 8/8. 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 11/86:50 am -
1 stop7h 03m
Fri 11/133:38 pm -
1 stop8h 52m
Deal found 8/8![American Airlines logo]()
$670
This United Airlines deal was found by Cheapflights users on 8/8. 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.
Sun 11/87:40 am -
Nonstop4h 51m
Fri 11/133:00 pm -
1 stop8h 18m
Deal found 8/8![United Airlines logo]()
$676
This FlightHub deal was found by Cheapflights users on 8/5. 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 9/48:20 pm -
1 stop15h 44m
Mon 9/73:45 pm -
2 stops22h 54m
Deal found 8/5![JetBlue logo]()
$679
This Delta deal was found by Cheapflights users on 8/7. 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 2/65:30 am -
1 stop7h 05m
Sat 2/133:35 pm -
1 stop10h 15m
Deal found 8/7![Delta logo]()
$656
This Southwest deal was found by Cheapflights users on 8/7. 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 9/215:00 am -
1 stop7h 50m
Fri 9/252:35 pm -
2 stops18h 00m
Deal found 8/7![Southwest logo]()
$746
This American Airlines deal was found by Cheapflights users on 8/10. 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 2/68:15 am -
Nonstop4h 40m
Sat 2/133:55 pm -
Nonstop5h 40m
Deal found 8/10![American Airlines logo]()
$717
This United Airlines deal was found by Cheapflights users on 8/8. 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 10/245:07 pm -
1 stop16h 58m
Sat 10/312:00 pm -
Nonstop5h 45m
Deal found 8/8![United Airlines logo]()
$719
This Delta deal was found by Cheapflights users on 8/10. 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 2/66:00 am -
1 stop6h 35m
Sat 2/133:35 pm -
1 stop8h 35m
Deal found 8/10![Delta logo]()
$656
This Southwest deal was found by Cheapflights users on 8/7. 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.
Wed 1/275:45 am -
1 stop7h 10m
Wed 2/32:10 pm -
1 stop10h 40m
Deal found 8/7![Southwest logo]()
$783
This Delta deal was found by Cheapflights users on 8/7. 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 12/126:00 am -
1 stop6h 25m
Mon 12/213:25 pm -
1 stop8h 45m
Deal found 8/7![Delta logo]()
$656
This United Airlines deal was found by Cheapflights users on 8/10. 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 10/24:00 pm -
1 stop18h 07m
Sat 10/1012:09 pm -
1 stop10h 33m
Deal found 8/10![United Airlines logo]()
$723
This American Airlines deal was found by Cheapflights users on 8/10. 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 12/156:59 am -
1 stop13h 18m
Mon 12/217:10 am -
1 stop12h 49m
Deal found 8/10![American Airlines logo]()
$756
This Southwest deal was found by Cheapflights users on 8/9. 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 10/107:10 pm -
2 stops17h 50m
Fri 10/162:50 pm -
2 stops9h 20m
Deal found 8/9![Southwest logo]()
$813
This United Airlines deal was found by Cheapflights users on 8/5. 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 1/305:00 am -
1 stop7h 20m
Sat 2/63:25 pm -
1 stop10h 17m
Deal found 8/5![United Airlines logo]()
$746
This Delta deal was found by Cheapflights users on 8/10. 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 10/55:30 am -
1 stop7h 12m
Mon 10/122:47 pm -
1 stop7h 05m
Deal found 8/10![Delta logo]()
$685
This Southwest deal was found by Cheapflights users on 8/7. 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.
Wed 9/28:20 pm -
2 stops16h 30m
Sat 9/52:05 pm -
1 stop7h 55m
Deal found 8/7![Southwest logo]()
$839
This Delta deal was found by Cheapflights users on 8/7. 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 1/306:00 am -
1 stop8h 15m
Sat 2/63:10 pm -
1 stop9h 00m
Deal found 8/7![Delta logo]()
$720
This United Airlines deal was found by Cheapflights users on 8/10. 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 2/65:00 am -
1 stop7h 20m
Sat 2/133:25 pm -
2 stops18h 26m
Deal found 8/10![United Airlines logo]()
$806
This Southwest deal was found by Cheapflights users on 8/6. 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 11/286:35 am -
1 stop6h 25m
Sat 12/52:40 pm -
1 stop9h 00m
Deal found 8/6![Southwest logo]()
$840
This Delta deal was found by Cheapflights users on 8/5. 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 9/46:05 am -
1 stop6h 29m
Sun 9/62:49 pm -
1 stop8h 47m
Deal found 8/5![Delta logo]()
$720
This United Airlines deal was found by Cheapflights users on 8/9. 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 1/305:00 am -
1 stop7h 20m
Sat 2/133:25 pm -
2 stops18h 26m
Deal found 8/9![United Airlines logo]()
$806
This Delta deal was found by Cheapflights users on 8/6. 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 2/46:00 am -
1 stop6h 35m
Mon 2/83:35 pm -
1 stop8h 35m
Deal found 8/6![Delta logo]()
$726
This Delta deal was found by Cheapflights users on 8/9. 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 1/76:00 am -
1 stop6h 35m
Sun 1/103:35 pm -
1 stop8h 35m
Deal found 8/9![Delta logo]()
$766
Last-minute flights from Chicago to U.S. Virgin IslandsDiscover last-minute flight deals from Chicago to U.S. Virgin Islands. Data last updated August 10, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to U.S. Virgin Islands. Data last updated August 10, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 8/8. 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 8/287:00 am -
2 stops30h 57m
Tue 9/11:53 pm -
2 stops21h 18m
Deal found 8/8![JetBlue logo]()
$522
This FlightHub deal was found by Cheapflights users on 8/5. 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 8/297:00 am -
2 stops30h 55m
Wed 9/23:45 pm -
2 stops22h 54m
Deal found 8/5![JetBlue logo]()
$527
This FlightHub deal was found by Cheapflights users on 8/10. 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 9/53:20 pm -
2 stops22h 35m
Sat 9/123:00 pm -
2 stops23h 45m
Deal found 8/10![JetBlue logo]()
$499
This FlightHub deal was found by Cheapflights users on 8/6. 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 9/96:00 am -
2 stops31h 01m
Wed 9/163:00 pm -
2 stops23h 45m
Deal found 8/6![JetBlue logo]()
$482
This FlightHub deal was found by Cheapflights users on 8/5. 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 9/106:00 am -
2 stops31h 01m
Tue 9/153:00 pm -
2 stops33h 08m
Deal found 8/5![JetBlue logo]()
$488
This FlightHub deal was found by Cheapflights users on 8/5. 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 9/106:00 am -
2 stops31h 01m
Mon 9/143:00 pm -
2 stops23h 45m
Deal found 8/5![JetBlue logo]()
$519
This FlightHub deal was found by Cheapflights users on 8/5. 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 9/116:00 am -
2 stops31h 01m
Mon 9/143:00 pm -
2 stops23h 45m
Deal found 8/5![JetBlue logo]()
$514
This Southwest deal was found by Cheapflights users on 8/9. 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.
Fri 9/115:00 am -
1 stop7h 50m
Sat 9/192:05 pm -
1 stop7h 55m
Deal found 8/9![Southwest logo]()
$533
This FlightHub deal was found by Cheapflights users on 8/7. 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.
Sun 9/133:00 pm -
2 stops22h 01m
Sat 9/193:00 pm -
2 stops23h 45m
Deal found 8/7![JetBlue logo]()
$504
This FlightHub deal was found by Cheapflights users on 8/6. 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 9/156:00 am -
2 stops31h 01m
Thu 9/173:00 pm -
2 stops23h 45m
Deal found 8/6![JetBlue logo]()
$508
This FlightHub deal was found by Cheapflights users on 8/10. 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 9/266:00 am -
2 stops31h 01m
Sat 10/33:00 pm -
2 stops23h 45m
Deal found 8/10![JetBlue logo]()
$475
This Southwest deal was found by Cheapflights users on 8/9. 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 9/285:00 am -
1 stop7h 50m
Mon 10/52:50 pm -
1 stop10h 30m
Deal found 8/9![Southwest logo]()
$531
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 August 10, 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 August 10, 2026.
This FlightHub deal was found by Cheapflights users on 8/6. 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 9/53:20 pm -
2 stops23h 29m
Deal found 8/6![JetBlue logo]()
$236
This FlightHub deal was found by Cheapflights users on 8/7. 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 9/57:00 am -
2 stops30h 55m
Deal found 8/7![JetBlue logo]()
$236
This FlightHub deal was found by Cheapflights users on 8/6. 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 10/307:00 am -
2 stops31h 45m
Deal found 8/6![JetBlue logo]()
$247
This FlightHub deal was found by Cheapflights users on 8/6. 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 9/47:00 am -
2 stops30h 57m
Deal found 8/6![JetBlue logo]()
$252
This United Airlines deal was found by Cheapflights users on 8/9. 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 9/114:29 pm -
2 stops19h 29m
Deal found 8/9![United Airlines logo]()
$266
This FlightHub deal was found by Cheapflights users on 8/7. 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 10/63:00 pm -
2 stops47h 54m
Deal found 8/7![JetBlue logo]()
$276
This American Airlines deal was found by Cheapflights users on 8/6. 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 9/65:00 am -
1 stop14h 43m
Deal found 8/6![American Airlines logo]()
$280
This Southwest deal was found by Cheapflights users on 8/9. 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 10/265:00 am -
1 stop8h 00m
Deal found 8/9![Southwest logo]()
$288
This FlightHub deal was found by Cheapflights users on 8/9. 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 9/93:00 pm -
2 stops22h 01m
Deal found 8/9![JetBlue logo]()
$289
This American Airlines deal was found by Cheapflights users on 8/6. 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.
Thu 9/35:00 am -
1 stop14h 43m
Deal found 8/6![American Airlines logo]()
$290
This United Airlines deal was found by Cheapflights users on 8/6. 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 11/39:30 pm -
2 stops14h 26m
Deal found 8/6![United Airlines logo]()
$291
This FlightHub deal was found by Cheapflights users on 8/10. 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.
Sun 10/43:00 pm -
2 stops22h 01m
Deal found 8/10![JetBlue logo]()
$293
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 August 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $475 (FlightHub) |
One-way from | $236 (FlightHub) |
Popular in | December |
Cheapest in | October |
Average price | $772 |
Good round-trip deal | $665 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 August 10, 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 Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King
ORDSTT
Chicago O'Hare Intl
Thu 9/10
6:00 am-2:01 pm
2 stops31h 01m
Saint Thomas Island Cyril E King
Mon 9/14
3:00 pm-1:45 pm
2 stops23h 45m
$519
ChicagoSaint Thomas Island
ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King
ORDSTT
Chicago O'Hare Intl
Thu 10/8
5:00 am-12:39 pm
1 stop6h 39m
Saint Thomas Island Cyril E King
Fri 10/16
3:46 pm-12:38 am
1 stop9h 52m
$580
ChicagoSaint Thomas Island
ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King
ORDSTT
Chicago O'Hare Intl
Wed 9/9
6:00 am-2:01 pm
2 stops31h 01m
Saint Thomas Island Cyril E King
Sat 1/30
1:46 pm-11:44 pm
2 stops11h 58m
$649
ChicagoSaint Thomas Island
ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King
ORDSTT
Chicago O'Hare Intl
Sat 10/17
5:27 am-1:37 pm
1 stop7h 10m
Saint Thomas Island Cyril E King
Thu 10/22
2:47 pm-11:52 pm
1 stop10h 05m
$650
ChicagoSaint Thomas Island
MDW Chicago Midway - STT Saint Thomas Island Cyril E King
MDWSTT
Chicago Midway
Sun 11/15
6:00 am-2:40 pm
1 stop6h 40m
Saint Thomas Island Cyril E King
Sat 11/21
3:50 pm-10:56 pm
1 stop9h 06m
$655
ChicagoChristiansted
ORD Chicago O'Hare Intl - STX Christiansted Henry Rohlsen
ORDSTX
Chicago O'Hare Intl
Sat 2/6
5:30 am-2:35 pm
1 stop7h 05m
Christiansted Henry Rohlsen
Sat 2/13
3:35 pm-11:50 pm
1 stop10h 15m
$656
ChicagoChristiansted
MDW Chicago Midway - STX Christiansted Henry Rohlsen
MDWSTX
Chicago Midway
Sat 2/6
6:00 am-2:35 pm
1 stop6h 35m
Christiansted Henry Rohlsen
Sat 2/13
3:35 pm-10:10 pm
1 stop8h 35m
$656
ChicagoChristiansted
MDW Chicago Midway - STX Christiansted Henry Rohlsen
MDWSTX
Chicago Midway
Sat 12/12
6:00 am-2:25 pm
1 stop6h 25m
Christiansted Henry Rohlsen
Mon 12/21
3:25 pm-10:10 pm
1 stop8h 45m
$656
ChicagoSaint Thomas Island
ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King
ORDSTT
Chicago O'Hare Intl
Tue 11/3
9:30 pm-1:56 pm
2 stops14h 26m
Saint Thomas Island Cyril E King
Thu 11/5
1:07 pm-6:54 pm
1 stop7h 47m
$662
ChicagoSaint Thomas Island
ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King
ORDSTT
Chicago O'Hare Intl
Sun 11/8
6:50 am-3:53 pm
1 stop7h 03m
Saint Thomas Island Cyril E King
Fri 11/13
3:38 pm-10:30 pm
1 stop8h 52m
$670
Showing 1-10 of 52 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
MDW-STT
ORD-STX
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
MDW-STT
ORD-STX
MDW-STX
What is the cheapest month to book a flight from Chicago to U.S. Virgin Islands?
Currently, October is the cheapest month in which you can book a flight from Chicago to U.S. Virgin Islands (average of $477). Flying from Chicago to U.S. Virgin Islands in December is currently the most expensive (average of $901). 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 August 10, 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 26% 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 24% 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 21 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 August 10, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited 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.
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top regions
Alternative routes for Chicago to U.S. Virgin Islands
See prices for flight routes from nearby airports that may be better suited for you.
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 August 10, 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 3 airlines flying from Chicago to U.S. Virgin Islands
Discover the top 3 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 August 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$376 | Average$710 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$410 | Average$685 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$482 | Average$707 | FlexibilityNo cancel fee | On-time71% |