$218+ Cheap flights from Chicago (CHI) to Saint Thomas Island (STT)
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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STT
Sep 23 — Sep 301
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Saint Thomas Island 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.Cheapflights Tip: The best prices from Chicago to Saint Thomas Island Cyril E King are usually found in May or October, booked 65 days in advance, depart on a Tuesday or Thursday and return on a Friday
Cheap flight deals from Chicago to Saint Thomas Island
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Cheapest flights from Chicago to Saint Thomas IslandExplore the most affordable flight options available from Chicago to Saint Thomas Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 24, 2026.
Explore the most affordable flight options available from Chicago to Saint Thomas Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 24, 2026.
This FlightHub deal was found by Cheapflights users on 8/22. 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 12/32:50 pm -
2 stops20h 53m
Tue 12/82:35 pm -
2 stops24h 51m
Deal found 8/22![JetBlue logo]()
$482
This American Airlines deal was found by Cheapflights users on 8/19. 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 10/57:05 pm -
2 stops18h 50m
Wed 10/211:21 pm -
2 stops18h 38m
Deal found 8/19![American Airlines logo]()
$498
This American Airlines deal was found by Cheapflights users on 8/22. 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 10/2411:00 pm -
2 stops12h 41m
Wed 10/283:46 pm -
2 stops15h 13m
Deal found 8/22![American Airlines logo]()
$500
This American Airlines deal was found by Cheapflights users on 8/19. 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 10/67:05 pm -
2 stops16h 53m
Tue 10/201:07 pm -
2 stops18h 52m
Deal found 8/19![American Airlines logo]()
$503
This United Airlines deal was found by Cheapflights users on 8/21. 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 10/279:30 pm -
2 stops14h 26m
Sun 11/13:35 pm -
2 stops17h 01m
Deal found 8/21![United Airlines logo]()
$508
This FlightHub deal was found by Cheapflights users on 8/22. 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 12/12:50 pm -
2 stops20h 53m
Tue 12/82:35 pm -
2 stops24h 51m
Deal found 8/22![JetBlue logo]()
$509
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 8/2912:44 am -
1 stop13h 13m
Tue 9/15:40 pm -
1 stop30h 47m
Deal found 8/23![Multiple Airlines logo]()
$520
This CheapOair deal was found by Cheapflights users on 8/19. 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 12/52:50 pm -
2 stops20h 53m
Sat 12/124:35 pm -
1 stop20h 11m
Deal found 8/19![Multiple Airlines logo]()
$521
This American Airlines deal was found by Cheapflights users on 8/19. 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 10/57:05 pm -
2 stops18h 50m
Thu 10/221:21 pm -
2 stops18h 38m
Deal found 8/19![American Airlines logo]()
$523
This American Airlines deal was found by Cheapflights users on 8/19. 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 10/67:05 pm -
2 stops16h 53m
Thu 10/221:21 pm -
2 stops18h 38m
Deal found 8/19![American Airlines logo]()
$528
This FlightHub deal was found by Cheapflights users on 8/20. 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 11/303:20 pm -
2 stops20h 23m
Tue 12/82:35 pm -
2 stops24h 51m
Deal found 8/20![JetBlue logo]()
$532
This Southwest deal was found by Cheapflights users on 8/22. 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 9/276:10 am -
1 stop6h 15m
Mon 10/52:50 pm -
2 stops10h 05m
Deal found 8/22![Southwest logo]()
$560
Best flights from Chicago to Saint Thomas IslandDiscover carefully curated flight deals from Chicago to Saint Thomas Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 24, 2026.
Discover carefully curated flight deals from Chicago to Saint Thomas Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 24, 2026.
This FlightHub deal was found by Cheapflights users on 8/23. 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 10/197:00 am -
2 stops31h 54m
Mon 10/264:40 pm -
2 stops22h 04m
Deal found 8/23![JetBlue logo]()
$556
This Delta deal was found by Cheapflights users on 8/19. 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 10/76:04 am -
1 stop6h 33m
Wed 10/212:47 pm -
1 stop8h 46m
Deal found 8/19![Delta logo]()
$580
This American Airlines deal was found by Cheapflights users on 8/23. 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 10/195:05 am -
1 stop6h 53m
Mon 10/263:46 pm -
1 stop9h 52m
Deal found 8/23![American Airlines logo]()
$580
This Southwest deal was found by Cheapflights users on 8/21. 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 10/195:00 am -
1 stop8h 00m
Mon 10/262:50 pm -
2 stops10h 05m
Deal found 8/21![Southwest logo]()
$582
This United Airlines deal was found by Cheapflights users on 8/22. 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 11/149:20 pm -
2 stops14h 36m
Tue 11/173:00 pm -
1 stop9h 18m
Deal found 8/22![United Airlines logo]()
$627
This Delta deal was found by Cheapflights users on 8/19. 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 10/56:05 am -
1 stop6h 37m
Wed 10/212:47 pm -
1 stop8h 46m
Deal found 8/19![Delta logo]()
$580
This American Airlines deal was found by Cheapflights users on 8/23. 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 11/159:06 pm -
2 stops13h 10m
Sat 11/214:37 pm -
1 stop18h 27m
Deal found 8/23![American Airlines logo]()
$585
This United Airlines deal was found by Cheapflights users on 8/21. 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 9/265:30 am -
1 stop9h 13m
Sat 10/32:10 pm -
1 stop10h 11m
Deal found 8/21![United Airlines logo]()
$630
This Delta deal was found by Cheapflights users on 8/19. 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 10/56:05 am -
1 stop6h 37m
Thu 10/222:47 pm -
1 stop8h 46m
Deal found 8/19![Delta logo]()
$580
This Southwest deal was found by Cheapflights users on 8/23. 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 2/25:45 am -
1 stop7h 10m
Tue 2/92:10 pm -
2 stops10h 50m
Deal found 8/23![Southwest logo]()
$690
This United Airlines deal was found by Cheapflights users on 8/22. 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 11/73:50 pm -
2 stops20h 06m
Tue 11/101:07 pm -
1 stop12h 54m
Deal found 8/22![United Airlines logo]()
$637
This Delta deal was found by Cheapflights users on 8/23. 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 2/26:00 am -
1 stop7h 05m
Tue 2/91:50 pm -
1 stop10h 20m
Deal found 8/23![Delta logo]()
$580
This Delta deal was found by Cheapflights users on 8/19. 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 10/75:27 am -
1 stop7h 10m
Wed 10/212:47 pm -
1 stop10h 10m
Deal found 8/19![Delta logo]()
$580
This United Airlines deal was found by Cheapflights users on 8/23. 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 stop11h 01m
Deal found 8/23![United Airlines logo]()
$676
This Delta deal was found by Cheapflights users on 8/19. 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 10/75:27 am -
1 stop7h 10m
Thu 10/222:47 pm -
1 stop10h 10m
Deal found 8/19![Delta logo]()
$580
This Southwest deal was found by Cheapflights users on 8/22. 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 11/125:05 am -
1 stop6h 45m
Mon 11/163:15 pm -
1 stop8h 00m
Deal found 8/22![Southwest logo]()
$800
This Delta deal was found by Cheapflights users on 8/19. 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
Tue 10/202:47 pm -
1 stop10h 10m
Deal found 8/19![Delta logo]()
$580
This Southwest deal was found by Cheapflights users on 8/19. 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 10/177:10 pm -
2 stops17h 50m
Sat 10/242:45 pm -
1 stop7h 30m
Deal found 8/19![Southwest logo]()
$800
This Delta deal was found by Cheapflights users on 8/19. 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 10/75:27 am -
1 stop7h 10m
Tue 10/202:47 pm -
1 stop10h 10m
Deal found 8/19![Delta logo]()
$580
This Delta deal was found by Cheapflights users on 8/21. 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 stop8h 15m
Tue 2/91:50 pm -
1 stop10h 20m
Deal found 8/21![Delta logo]()
$585
This Delta deal was found by Cheapflights users on 8/19. 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 10/45:30 am -
1 stop7h 12m
Thu 10/222:47 pm -
1 stop10h 10m
Deal found 8/19![Delta logo]()
$665
This Delta deal was found by Cheapflights users on 8/21. 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 11/133:50 pm -
1 stop9h 06m
Deal found 8/21![Delta logo]()
$847
Last-minute flights from Chicago to Saint Thomas IslandDiscover last-minute flight deals from Chicago to Saint Thomas Island. Data last updated August 24, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Saint Thomas Island. Data last updated August 24, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/20. 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.
Wed 8/2612:44 am -
1 stop17h 36m
Thu 9/33:00 pm -
1 stop9h 27m
Deal found 8/20![Multiple Airlines logo]()
$586
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 8/2912:44 am -
1 stop13h 13m
Tue 9/15:40 pm -
1 stop30h 47m
Deal found 8/23![Multiple Airlines logo]()
$520
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 8/2912:44 am -
1 stop8h 30m
Wed 9/25:45 pm -
1 stop30h 42m
Deal found 8/23![Multiple Airlines logo]()
$564
This Southwest deal was found by Cheapflights users on 8/21. 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 8/305:10 am -
1 stop7h 15m
Fri 9/42:35 pm -
1 stop9h 10m
Deal found 8/21![Southwest logo]()
$672
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
Mon 8/3112:44 am -
1 stop8h 30m
Fri 9/45:45 pm -
1 stop30h 42m
Deal found 8/19![Multiple Airlines logo]()
$601
This Southwest deal was found by Cheapflights users on 8/19. 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 8/315:00 am -
1 stop7h 50m
Sat 9/52:05 pm -
1 stop7h 55m
Deal found 8/19![Southwest logo]()
$661
This American Airlines deal was found by Cheapflights users on 8/19. 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 9/208:45 am -
2 stops27h 06m
Wed 9/231:41 pm -
2 stops18h 48m
Deal found 8/19![American Airlines logo]()
$599
This FlightHub deal was found by Cheapflights users on 8/21. 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 9/2210:59 am -
2 stops26h 02m
Tue 9/293:00 pm -
2 stops23h 45m
Deal found 8/21![JetBlue logo]()
$569
This FlightHub deal was found by Cheapflights users on 8/22. 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 9/2210:59 am -
2 stops26h 02m
Sun 9/273:00 pm -
2 stops23h 45m
Deal found 8/22![JetBlue logo]()
$570
This FlightHub deal was found by Cheapflights users on 8/19. 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 10/31:40 pm -
2 stops20h 08m
Deal found 8/19![JetBlue logo]()
$559
This FlightHub deal was found by Cheapflights users on 8/19. 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 9/263:00 pm -
2 stops22h 01m
Sun 10/43:00 pm -
2 stops33h 10m
Deal found 8/19![JetBlue logo]()
$590
This Southwest deal was found by Cheapflights users on 8/22. 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 9/276:10 am -
1 stop6h 15m
Mon 10/52:50 pm -
2 stops10h 05m
Deal found 8/22![Southwest logo]()
$560
One-way flights from Chicago to Saint Thomas IslandSearch for one-way flight options from Chicago to Saint Thomas Island. Find affordable one-way fares based on user searches. Data last updated August 24, 2026.
Search for one-way flight options from Chicago to Saint Thomas Island. Find affordable one-way fares based on user searches. Data last updated August 24, 2026.
This American Airlines deal was found by Cheapflights users on 8/19. 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 11/169:02 pm -
2 stops15h 32m
Deal found 8/19![American Airlines logo]()
$218
This FlightHub deal was found by Cheapflights users on 8/21. 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 10/197:00 am -
2 stops31h 54m
Deal found 8/21![JetBlue logo]()
$241
This United Airlines deal was found by Cheapflights users on 8/23. 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 11/103:45 pm -
2 stops20h 11m
Deal found 8/23![United Airlines logo]()
$246
This United Airlines deal was found by Cheapflights users on 8/23. 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 11/119:35 pm -
2 stops14h 21m
Deal found 8/23![United Airlines logo]()
$252
This FlightHub deal was found by Cheapflights users on 8/19. 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 11/172:35 pm -
2 stops24h 09m
Deal found 8/19![JetBlue logo]()
$263
This FlightHub deal was found by Cheapflights users on 8/22. 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
Deal found 8/22![JetBlue logo]()
$264
This Southwest deal was found by Cheapflights users on 8/22. 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 11/295:45 pm -
2 stops18h 05m
Deal found 8/22![Southwest logo]()
$268
This American Airlines deal was found by Cheapflights users on 8/21. 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 10/176:40 pm -
2 stops19h 15m
Deal found 8/21![American Airlines logo]()
$270
This FlightHub deal was found by Cheapflights users on 8/19. 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 11/182:35 pm -
2 stops21h 03m
Deal found 8/19![JetBlue logo]()
$275
This United Airlines deal was found by Cheapflights users on 8/20. 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 11/79:30 pm -
2 stops14h 26m
Deal found 8/20![United Airlines logo]()
$276
This FlightHub deal was found by Cheapflights users on 8/18. 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 10/172:35 pm -
2 stops24h 19m
Deal found 8/18![JetBlue logo]()
$280
This FlightHub deal was found by Cheapflights users on 8/19. 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 9/193:00 pm -
2 stops22h 01m
Deal found 8/19![JetBlue logo]()
$287
Find flight deals from Chicago to Saint Thomas Island
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Saint Thomas Island (STT). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $482 (FlightHub) |
One-way from | $218 (American Airlines) |
Popular in | December |
Cheapest in | May |
Average price | $772 |
Good round-trip deal | $732 or less |
Good one-way deal | $324 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Saint Thomas Island 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 August 24, 2026.
Use the filters below to find and compare flights from Chicago to Saint Thomas Island 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
Mon 10/19
7:00 am-3:54 pm
2 stops31h 54m
Saint Thomas Island Cyril E King
Mon 10/26
4:40 pm-1:44 pm
2 stops22h 04m
$556
ChicagoSaint Thomas Island
MDW Chicago Midway - STT Saint Thomas Island Cyril E King
MDWSTT
Chicago Midway
Wed 10/7
6:04 am-1:37 pm
1 stop6h 33m
Saint Thomas Island Cyril E King
Wed 10/21
2:47 pm-10:33 pm
1 stop8h 46m
$580
ChicagoSaint Thomas Island
ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King
ORDSTT
Chicago O'Hare Intl
Mon 10/19
5:05 am-12:58 pm
1 stop6h 53m
Saint Thomas Island Cyril E King
Mon 10/26
3:46 pm-12:38 am
1 stop9h 52m
$580
ChicagoSaint Thomas Island
MDW Chicago Midway - STT Saint Thomas Island Cyril E King
MDWSTT
Chicago Midway
Mon 10/5
6:05 am-1:42 pm
1 stop6h 37m
Saint Thomas Island Cyril E King
Wed 10/21
2:47 pm-10:33 pm
1 stop8h 46m
$580
ChicagoSaint Thomas Island
MDW Chicago Midway - STT Saint Thomas Island Cyril E King
MDWSTT
Chicago Midway
Mon 10/5
6:05 am-1:42 pm
1 stop6h 37m
Saint Thomas Island Cyril E King
Thu 10/22
2:47 pm-10:33 pm
1 stop8h 46m
$580
ChicagoSaint Thomas Island
MDW Chicago Midway - STT Saint Thomas Island Cyril E King
MDWSTT
Chicago Midway
Tue 2/2
6:00 am-3:05 pm
1 stop7h 05m
Saint Thomas Island Cyril E King
Tue 2/9
1:50 pm-10:10 pm
1 stop10h 20m
$580
ChicagoSaint Thomas Island
ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King
ORDSTT
Chicago O'Hare Intl
Wed 10/7
5:27 am-1:37 pm
1 stop7h 10m
Saint Thomas Island Cyril E King
Wed 10/21
2:47 pm-11:57 pm
1 stop10h 10m
$580
ChicagoSaint Thomas Island
ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King
ORDSTT
Chicago O'Hare Intl
Wed 10/7
5:27 am-1:37 pm
1 stop7h 10m
Saint Thomas Island Cyril E King
Thu 10/22
2:47 pm-11:57 pm
1 stop10h 10m
$580
ChicagoSaint Thomas Island
ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King
ORDSTT
Chicago O'Hare Intl
Mon 10/5
5:30 am-1:42 pm
1 stop7h 12m
Saint Thomas Island Cyril E King
Tue 10/20
2:47 pm-11:57 pm
1 stop10h 10m
$580
ChicagoSaint Thomas Island
ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King
ORDSTT
Chicago O'Hare Intl
Wed 10/7
5:27 am-1:37 pm
1 stop7h 10m
Saint Thomas Island Cyril E King
Tue 10/20
2:47 pm-11:57 pm
1 stop10h 10m
$580
Showing 1-10 of 42 resultsSorted by cheapest first
Compare providers for flights from Chicago to Saint Thomas Island
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Saint Thomas Island in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Chicago-Saint Thomas Island flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Saint Thomas Island flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Saint Thomas Island flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Saint Thomas Island flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Saint Thomas Island flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to Saint Thomas Island
Have a flexible travel schedule? Discover the best time to fly to Saint Thomas Island from Chicago with our price prediction graph.
CHI-STT
ORD-STT
MDW-STT
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 Saint Thomas Island
CHI-STT
ORD-STT
MDW-STT
What is the cheapest month to book a flight from Chicago to Saint Thomas Island?
Currently, May is the cheapest month in which you can book a flight from Chicago to Saint Thomas Island (average of $439). Flying from Chicago to Saint Thomas Island in December is currently the most expensive (average of $930). 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 much does it cost to fly round-trip from Chicago to Saint Thomas Island?
Airfare is below average for this route at the moment.
Chicago to Saint Thomas Island flights typically cost between $608 and $804 in December.The cheapest round-trip price found within the last 5 days was $482 on JetBlue (Dec 3-Dec 8).
What’s the top layover airport for flights from Chicago to Saint Thomas Island?
Share of 1-stop round-trip flights from Chicago to Saint Thomas Island chosen by Cheapflights users in the past 12 months, using the same layover each way.
Orlando (MCO) – chosen by Cheapflights users on 60% of 1-stop itineraries from Chicago to Saint Thomas Island on Cheapflights.
What’s the cheapest layover airport for flights from Chicago to Saint Thomas Island?
Average round-trip fare for 1-stop flights from Chicago to Saint Thomas Island, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Orlando (MCO) is the most affordable 1-stop option, with an average round-trip price of $520.
What’s the fastest layover option from Chicago to Saint Thomas Island?
Shortest average travel time for 1-stop one-way flights from Chicago to Saint Thomas Island, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Orlando (MCO) have the shortest average one-way travel time for 1-stop routes: 6h 20m.
Which airport typically offers the quickest layover for flights from Chicago to Saint Thomas Island?
Average layover duration for 1-stop one-way flights from Chicago to Saint Thomas Island, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Washington, D.C. (IAD) offer the fastest connection on this route, with an average layover time of 1h 10m.
How often are flights from Chicago to Saint Thomas Island delayed?
About 26% of weekly flights between Chicago and Saint Thomas Island 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 Saint Thomas Island 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 Saint Thomas Island 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 Saint Thomas Island?
Booking 20 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Saint Thomas Island. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Reviews of airlines servicing Saint Thomas Island
Get insights into the airlines that provide service to Saint Thomas Island. 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 Saint Thomas Island. Reviews last updated August 24, 2026.
Read through reviews of airlines operating flights from Chicago to Saint Thomas Island, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
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 Saint Thomas Island. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Saint Thomas Island?
Book flights to Saint Thomas Island if you plan to visit one of these locationsSt. John
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Chicago and Saint Thomas Island flights
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Top 3 airlines flying from Chicago to Saint Thomas Island
Discover the top 3 airlines that operate flights from Chicago to Saint Thomas Island. 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 August 24, 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$500 | Average$692 | FlexibilityNo cancel fee | On-time71% |