$223+ Cheap flights from Chicago (CHI) to the U.S. Virgin Islands
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STT
Nov 6 — Nov 131
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 October 7, 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 October 7, 2026.
This Southwest deal was found by Cheapflights users on 10/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:30 pm -
2 stops18h 30m
Wed 12/23:20 pm -
2 stops16h 20m
Deal found 10/5![Southwest logo]()
$554
This Kiwi.com deal was found by Cheapflights users on 10/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/158:15 am -
2 stops22h 50m
Fri 12/181:15 pm -
1 stop11h 13m
Deal found 10/3![Multiple Airlines logo]()
$564
This American Airlines deal was found by Cheapflights users on 10/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/318:25 am -
Nonstop4h 49m
Fri 1/84:20 pm -
1 stop9h 37m
Deal found 10/5![American Airlines logo]()
$576
This American Airlines deal was found by Cheapflights users on 10/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/309:06 pm -
1 stop14h 35m
Tue 12/82:02 pm -
1 stop11h 57m
Deal found 10/5![American Airlines logo]()
$580
This American Airlines deal was found by Cheapflights users on 10/4. 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 12/308:25 am -
Nonstop4h 49m
Wed 1/65:04 pm -
1 stop18h 26m
Deal found 10/4![American Airlines logo]()
$581
This CheapOair deal was found by Cheapflights users on 10/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/52:59 pm -
2 stops20h 44m
Sat 12/124:35 pm -
1 stop20h 11m
Deal found 10/7![Multiple Airlines logo]()
$584
This FlightHub deal was found by Cheapflights users on 10/2. 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 11/302:59 pm -
2 stops21h 30m
Tue 12/83:26 pm -
2 stops24h 04m
Deal found 10/2![JetBlue logo]()
$585
This American Airlines deal was found by Cheapflights users on 10/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/258:54 pm -
2 stops13h 21m
Wed 12/24:13 pm -
1 stop8h 17m
Deal found 10/5![American Airlines logo]()
$585
This Kiwi.com deal was found by Cheapflights users on 10/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/125:24 pm -
2 stops12h 26m
Wed 12/1610:35 am -
1 stop25h 13m
Deal found 10/3![Multiple Airlines logo]()
$588
This American Airlines deal was found by Cheapflights users on 10/2. 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 11/125:19 am -
1 stop6h 19m
Mon 11/164:53 pm -
1 stop17h 07m
Deal found 10/2![American Airlines logo]()
$590
This American Airlines deal was found by Cheapflights users on 10/6. 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.
Sat 11/289:06 pm -
1 stop14h 35m
Sun 12/203:54 pm -
Nonstop5h 49m
Deal found 10/6![American Airlines logo]()
$591
This American Airlines deal was found by Cheapflights users on 10/6. 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 11/158:57 pm -
2 stops13h 19m
Sat 11/215:30 pm -
1 stop18h 00m
Deal found 10/6![American Airlines logo]()
$595
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 October 7, 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 October 7, 2026.
This Southwest deal was found by Cheapflights users on 10/6. 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.
Mon 1/48:25 pm -
2 stops16h 10m
Tue 1/123:45 pm -
1 stop7h 35m
Deal found 10/6![Southwest logo]()
$540
This United Airlines deal was found by Cheapflights users on 10/3. 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 1/88:40 am -
1 stop7h 10m
Fri 1/153:00 pm -
Nonstop5h 45m
Deal found 10/3![United Airlines logo]()
$591
This Delta deal was found by Cheapflights users on 10/7. 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.
Sun 1/177:10 am -
1 stop7h 05m
Sun 1/244:15 pm -
1 stop9h 35m
Deal found 10/7![Delta logo]()
$615
This United deal was found by Cheapflights users on 10/5. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:16 pm -
1 stop21h 14m
Tue 11/33:14 pm -
1 stop22h 33m
Deal found 10/5![Multiple Airlines logo]()
$672
This Southwest deal was found by Cheapflights users on 10/3. 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 11/145:00 am -
1 stop8h 00m
Tue 11/173:20 pm -
2 stops9h 25m
Deal found 10/3![Southwest logo]()
$597
This Delta deal was found by Cheapflights users on 10/5. 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.
Sat 2/205:30 am -
1 stop7h 05m
Sat 2/273:35 pm -
1 stop8h 45m
Deal found 10/5![Delta logo]()
$616
This United Airlines deal was found by Cheapflights users on 10/5. 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.
Wed 2/109:25 am -
Nonstop4h 55m
Sun 2/145:25 pm -
1 stop7h 50m
Deal found 10/5![United Airlines logo]()
$677
This United deal was found by Cheapflights users on 10/2. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/39:25 am -
2 stops20h 55m
Tue 3/93:14 pm -
2 stops19h 15m
Deal found 10/2![Multiple Airlines logo]()
$697
This Delta deal was found by Cheapflights users on 10/5. 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.
Mon 2/16:00 am -
1 stop7h 05m
Mon 2/84:15 pm -
1 stop7h 55m
Deal found 10/5![Delta logo]()
$649
This Southwest deal was found by Cheapflights users on 10/6. 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.
Mon 1/115:45 am -
1 stop7h 10m
Sun 1/172:10 pm -
2 stops10h 50m
Deal found 10/6![Southwest logo]()
$684
This United Airlines deal was found by Cheapflights users on 10/5. 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.
Fri 1/229:25 am -
Nonstop4h 55m
Tue 2/21:07 pm -
1 stop7h 33m
Deal found 10/5![United Airlines logo]()
$691
This Delta deal was found by Cheapflights users on 10/6. 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.
Tue 1/56:00 am -
1 stop7h 05m
Tue 1/124:15 pm -
1 stop7h 55m
Deal found 10/6![Delta logo]()
$675
This Southwest deal was found by Cheapflights users on 10/3. 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 11/135:10 am -
1 stop7h 50m
Sun 11/153:45 pm -
1 stop9h 25m
Deal found 10/3![Southwest logo]()
$720
This Delta deal was found by Cheapflights users on 10/5. 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 1/226:00 am -
1 stop7h 05m
Thu 1/281:50 pm -
1 stop10h 20m
Deal found 10/5![Delta logo]()
$694
This United Airlines deal was found by Cheapflights users on 10/2. 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 1/236:50 am -
2 stops9h 00m
Sat 1/301:07 pm -
1 stop7h 33m
Deal found 10/2![United Airlines logo]()
$771
This United deal was found by Cheapflights users on 10/5. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/208:55 am -
1 stop22h 25m
Sun 10/259:10 am -
1 stop27h 37m
Deal found 10/5![Multiple Airlines logo]()
$874
This Southwest deal was found by Cheapflights users on 10/2. 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 11/259:05 pm -
2 stops14h 55m
Mon 11/303:45 pm -
1 stop9h 30m
Deal found 10/2![Southwest logo]()
$763
This United Airlines deal was found by Cheapflights users on 10/2. 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 11/295:30 am -
1 stop8h 50m
Fri 12/43:00 pm -
1 stop9h 27m
Deal found 10/2![United Airlines logo]()
$780
This Delta deal was found by Cheapflights users on 10/2. 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 11/266:00 am -
1 stop6h 43m
Sat 12/52:26 pm -
1 stop8h 27m
Deal found 10/2![Delta logo]()
$718
This United deal was found by Cheapflights users on 10/3. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/295:30 am -
2 stops23h 55m
Sat 12/53:25 pm -
1 stop9h 02m
Deal found 10/3![Multiple Airlines logo]()
$929
This United Airlines deal was found by Cheapflights users on 10/3. 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 11/157:40 am -
Nonstop4h 51m
Sat 11/213:00 pm -
Nonstop5h 45m
Deal found 10/3![United Airlines logo]()
$796
This Delta deal was found by Cheapflights users on 10/7. 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.
Sun 1/105:30 am -
1 stop7h 05m
Sun 1/173:35 pm -
1 stop10h 15m
Deal found 10/7![Delta logo]()
$740
This United Airlines deal was found by Cheapflights users on 10/5. 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 3/205:00 am -
1 stop7h 20m
Sat 3/272:25 pm -
1 stop9h 33m
Deal found 10/5![United Airlines logo]()
$849
This Delta deal was found by Cheapflights users on 10/2. 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 1/236:00 am -
1 stop8h 15m
Sat 1/304:15 pm -
1 stop7h 55m
Deal found 10/2![Delta logo]()
$834
This United Airlines deal was found by Cheapflights users on 10/3. 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.
Mon 10/265:38 pm -
1 stop16h 27m
Thu 10/292:00 pm -
2 stops19h 00m
Deal found 10/3![United Airlines logo]()
$854
This Delta deal was found by Cheapflights users on 10/6. 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.
Sat 1/236:00 am -
1 stop8h 15m
Sun 1/314:15 pm -
1 stop7h 55m
Deal found 10/6![Delta logo]()
$834
This United Airlines deal was found by Cheapflights users on 10/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/179:25 am -
Nonstop4h 55m
Fri 1/221:07 pm -
1 stop7h 33m
Deal found 10/7![United Airlines logo]()
$855
This Delta deal was found by Cheapflights users on 10/7. 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 1/95:30 am -
1 stop7h 05m
Sun 1/173:35 pm -
1 stop10h 15m
Deal found 10/7![Delta logo]()
$844
This Delta deal was found by Cheapflights users on 10/4. 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 11/86:04 am -
1 stop6h 33m
Fri 11/133:53 pm -
1 stop9h 01m
Deal found 10/4![Delta logo]()
$950
This United Airlines deal was found by Cheapflights users on 10/6. 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.
Sat 2/65:30 am -
2 stops12h 08m
Sat 2/133:25 pm -
2 stops22h 05m
Deal found 10/6![United Airlines logo]()
$1,076
Last-minute flights from Chicago to U.S. Virgin IslandsDiscover last-minute flight deals from Chicago to U.S. Virgin Islands. Data last updated October 7, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to U.S. Virgin Islands. Data last updated October 7, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/2. 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 11/125:19 am -
1 stop6h 19m
Mon 11/164:53 pm -
1 stop17h 07m
Deal found 10/2![American Airlines logo]()
$590
This American Airlines deal was found by Cheapflights users on 10/4. 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 11/135:19 am -
1 stop6h 19m
Tue 11/173:15 pm -
2 stops10h 15m
Deal found 10/4![American Airlines logo]()
$615
This Southwest deal was found by Cheapflights users on 10/3. 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 11/145:00 am -
1 stop8h 00m
Tue 11/173:20 pm -
1 stop8h 00m
Deal found 10/3![Southwest logo]()
$597
This American Airlines deal was found by Cheapflights users on 10/6. 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 11/158:57 pm -
2 stops13h 19m
Sat 11/215:30 pm -
1 stop18h 00m
Deal found 10/6![American Airlines logo]()
$595
This Southwest deal was found by Cheapflights users on 10/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:30 pm -
2 stops18h 30m
Wed 12/23:20 pm -
2 stops16h 20m
Deal found 10/5![Southwest logo]()
$554
This American Airlines deal was found by Cheapflights users on 10/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/258:54 pm -
2 stops13h 21m
Wed 12/24:13 pm -
1 stop8h 17m
Deal found 10/5![American Airlines logo]()
$585
This American Airlines deal was found by Cheapflights users on 10/6. 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.
Sat 11/289:06 pm -
1 stop14h 35m
Sun 12/203:54 pm -
Nonstop5h 49m
Deal found 10/6![American Airlines logo]()
$591
This American Airlines deal was found by Cheapflights users on 10/6. 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.
Sat 11/288:11 am -
Nonstop4h 48m
Sat 12/125:34 pm -
1 stop18h 08m
Deal found 10/6![American Airlines logo]()
$606
This American Airlines deal was found by Cheapflights users on 10/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/309:06 pm -
1 stop14h 35m
Tue 12/82:02 pm -
1 stop11h 57m
Deal found 10/5![American Airlines logo]()
$580
This FlightHub deal was found by Cheapflights users on 10/2. 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 11/302:59 pm -
2 stops21h 30m
Tue 12/83:26 pm -
2 stops24h 04m
Deal found 10/2![JetBlue logo]()
$585
This American Airlines deal was found by Cheapflights users on 10/4. 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 11/309:06 pm -
2 stops13h 09m
Mon 12/73:15 pm -
2 stops10h 44m
Deal found 10/4![American Airlines logo]()
$605
This FlightHub deal was found by Cheapflights users on 10/2. 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 11/302:59 pm -
2 stops21h 30m
Mon 12/73:26 pm -
2 stops24h 04m
Deal found 10/2![JetBlue logo]()
$608
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 October 7, 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 October 7, 2026.
This FlightHub deal was found by Cheapflights users on 10/7. 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.
Thu 1/77:45 pm -
2 stops16h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![JetBlue logo]()
$223
This FlightHub deal was found by Cheapflights users on 10/6. 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 12/52:59 pm -
2 stops20h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![JetBlue logo]()
$223
This FlightHub deal was found by Cheapflights users on 10/7. 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 1/57:45 pm -
2 stops16h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![JetBlue logo]()
$246
This FlightHub deal was found by Cheapflights users on 10/7. 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 1/57:45 pm -
2 stops15h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![JetBlue logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 10/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/510:18 am -
1 stop25h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$248
This FlightHub deal was found by Cheapflights users on 10/5. 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 12/42:59 pm -
2 stops21h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![JetBlue logo]()
$256
This FlightHub deal was found by Cheapflights users on 10/6. 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.
Mon 1/42:32 pm -
2 stops21h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![JetBlue logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 10/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/810:18 am -
1 stop25h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$272
This FlightHub deal was found by Cheapflights users on 10/7. 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.
Mon 12/77:00 am -
2 stops28h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![JetBlue logo]()
$273
This Southwest deal was found by Cheapflights users on 10/4. 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 12/74:10 pm -
2 stops20h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Southwest logo]()
$274
This American Airlines deal was found by Cheapflights users on 10/6. 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.
Sat 11/79:00 pm -
2 stops14h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![American Airlines logo]()
$276
This FlightHub deal was found by Cheapflights users on 10/4. 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 12/42:59 pm -
2 stops20h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![JetBlue logo]()
$279
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 October 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $511 (FlightHub) |
One-way from | $223 (FlightHub) |
Popular in | December |
Cheapest in | May |
Average price | $746 |
Good round-trip deal | $646 or less |
Good one-way deal | $368 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 7,457,451 searches. Data last updated October 7, 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
MDW Chicago Midway - STT Saint Thomas Island Cyril E King
MDWSTT
Chicago Midway
Mon 12/7
5:20 am-2:35 pm
1 stop7h 15m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$318
ChicagoSaint Thomas Island
MDW Chicago Midway - STT Saint Thomas Island Cyril E King
MDWSTT
Chicago Midway
Fri 1/8
5:45 am-2:55 pm
1 stop7h 10m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$318
ChicagoSaint Thomas Island
ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King
ORDSTT
Chicago O'Hare Intl
Thu 1/14
9:25 am-4:20 pm
Nonstop4h 55m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$334
ChicagoSaint Thomas Island
ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King
ORDSTT
Chicago O'Hare Intl
Mon 4/5
5:30 am-2:45 pm
1 stop8h 15m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$338
ChicagoChristiansted
ORD Chicago O'Hare Intl - STX Christiansted Henry Rohlsen
ORDSTX
Chicago O'Hare Intl
Mon 4/5
5:00 am-4:15 pm
2 stops10h 15m
Christiansted Henry Rohlsen
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$344
ChicagoSaint Thomas Island
MDW Chicago Midway - STT Saint Thomas Island Cyril E King
MDWSTT
Chicago Midway
Mon 3/15
8:35 pm-2:20 pm
2 stops16h 45m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$344
ChicagoSaint Thomas Island
ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King
ORDSTT
Chicago O'Hare Intl
Sun 1/3
5:25 am-4:24 pm
1 stop8h 59m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$348
ChicagoSaint Thomas Island
ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King
ORDSTT
Chicago O'Hare Intl
Mon 1/4
5:30 am-3:05 pm
1 stop7h 35m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$348
ChicagoSaint Thomas Island
MDW Chicago Midway - STT Saint Thomas Island Cyril E King
MDWSTT
Chicago Midway
Sun 10/18
6:24 am-10:14 am
2 stops26h 50m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$353
ChicagoChristiansted
ORD Chicago O'Hare Intl - STX Christiansted Henry Rohlsen
ORDSTX
Chicago O'Hare Intl
Sun 4/4
5:30 am-1:20 pm
1 stop6h 50m
Christiansted Henry Rohlsen
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$362
Showing 1-10 of 58 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.
MDW-STT
ORD-STT
ORD-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
MDW-STT
ORD-STT
ORD-STX
What is the cheapest month to book a flight from Chicago to U.S. Virgin Islands?
Currently, May is the cheapest month in which you can book a flight from Chicago to U.S. Virgin Islands (average of $542). Flying from Chicago to U.S. Virgin Islands in December is currently the most expensive (average of $920). 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.
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 133 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 63 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 October 7, 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
Food
7.0
Boarding
8.1
Crew
8.6
Overall
7.9
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Overall
7.9
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Overall
7.9
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Overall
7.9
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Overall
7.9
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
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
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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 October 7, 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 7,457,451 searches. Data last updated October 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$376 | Average$736 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$482 | Average$691 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$545 | Average$685 | FlexibilityNo cancel fee | On-timeN/A |