$260+ Cheap flights from Chicago (CHI) to Saint Thomas Island (STT)
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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STT
Nov 29 — Dec 61
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 January, booked 65 days in advance, depart on a Tuesday or Thursday and return on a Tuesday
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 October 30, 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 October 30, 2026.
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/315:20 am -
1 stop7h 10m
Fri 1/82:10 pm -
1 stop10h 40m
Deal found 10/30![Southwest logo]()
$522
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/115:05 am -
1 stop6h 45m
Thu 12/172:40 pm -
2 stops11h 30m
Deal found 10/26![Southwest logo]()
$547
This CheapOair deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 10/28![Multiple Airlines logo]()
$562
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/135:05 am -
1 stop6h 45m
Sun 12/202:40 pm -
2 stops10h 35m
Deal found 10/27![Southwest logo]()
$579
This FlightHub deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/42:59 pm -
2 stops20h 44m
Mon 12/72:35 pm -
2 stops24h 55m
Deal found 10/29![JetBlue logo]()
$603
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/115:05 am -
1 stop6h 45m
Sun 12/202:40 pm -
1 stop10h 35m
Deal found 10/25![Southwest logo]()
$613
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/154:00 pm -
2 stops16h 05m
Sat 12/2611:05 am -
1 stop13h 44m
Deal found 10/27![Multiple Airlines logo]()
$613
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/195:30 pm -
2 stops18h 20m
Thu 12/243:20 pm -
2 stops16h 20m
Deal found 10/28![Southwest logo]()
$614
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/135:00 am -
1 stop7h 19m
Mon 12/213:54 pm -
Nonstop5h 49m
Deal found 10/28![American Airlines logo]()
$614
This American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/318:25 am -
Nonstop4h 49m
Fri 1/84:21 pm -
1 stop8h 25m
Deal found 10/30![American Airlines logo]()
$616
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/156:00 am -
1 stop6h 52m
Tue 12/223:20 pm -
1 stop9h 02m
Deal found 10/26![Delta logo]()
$620
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/305:19 am -
1 stop6h 22m
Tue 12/83:13 pm -
2 stops10h 31m
Deal found 10/27![American Airlines logo]()
$620
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 October 30, 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 October 30, 2026.
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/115:05 am -
1 stop6h 45m
Thu 12/172:40 pm -
2 stops11h 30m
Deal found 10/26![Southwest logo]()
$547
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/156:00 am -
1 stop6h 52m
Tue 12/223:20 pm -
1 stop9h 02m
Deal found 10/29![Delta logo]()
$620
This United Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/168:40 am -
1 stop7h 10m
Wed 1/273:00 pm -
Nonstop5h 45m
Deal found 10/29![United Airlines logo]()
$641
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/15:20 am -
1 stop7h 10m
Wed 1/62:10 pm -
1 stop8h 50m
Deal found 10/29![Southwest logo]()
$630
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/316:00 am -
1 stop7h 05m
Fri 1/84:03 pm -
1 stop8h 14m
Deal found 10/26![Delta logo]()
$645
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/287:40 am -
Nonstop4h 51m
Sat 12/53:35 pm -
1 stop9h 21m
Deal found 10/28![United Airlines logo]()
$666
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/145:25 am -
1 stop7h 30m
Mon 1/182:10 pm -
2 stops11h 45m
Deal found 10/29![Southwest logo]()
$637
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/57:10 am -
1 stop6h 39m
Thu 2/253:10 pm -
1 stop10h 40m
Deal found 10/26![Delta logo]()
$645
This United Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/149:25 am -
Nonstop4h 55m
Mon 1/183:00 pm -
Nonstop5h 45m
Deal found 10/29![United Airlines logo]()
$711
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/286:00 am -
1 stop6h 43m
Thu 12/34:02 pm -
1 stop8h 52m
Deal found 10/28![Delta logo]()
$655
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/39:25 am -
Nonstop4h 55m
Fri 2/265:25 pm -
1 stop8h 00m
Deal found 10/26![United Airlines logo]()
$716
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/309:05 pm -
2 stops15h 25m
Sat 12/52:40 pm -
1 stop9h 00m
Deal found 10/29![Southwest logo]()
$730
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/166:00 am -
1 stop6h 53m
Sat 1/303:11 pm -
1 stop10h 44m
Deal found 10/28![Delta logo]()
$715
This United Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/137:40 am -
Nonstop4h 51m
Sun 12/203:00 pm -
Nonstop5h 45m
Deal found 10/29![United Airlines logo]()
$736
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/309:05 pm -
2 stops15h 25m
Fri 12/43:20 pm -
1 stop8h 00m
Deal found 10/29![Southwest logo]()
$760
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:00 am -
1 stop6h 43m
Wed 12/24:02 pm -
1 stop8h 52m
Deal found 10/28![Delta logo]()
$722
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/259:25 am -
Nonstop4h 55m
Sun 1/311:07 pm -
1 stop10h 53m
Deal found 10/28![United Airlines logo]()
$751
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/315:30 am -
1 stop8h 19m
Fri 2/261:50 pm -
1 stop9h 20m
Deal found 10/26![Delta logo]()
$735
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/67:40 am -
Nonstop4h 51m
Sat 2/133:35 pm -
1 stop11h 10m
Deal found 10/28![United Airlines logo]()
$766
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/236:00 am -
1 stop6h 53m
Sat 1/303:11 pm -
1 stop10h 44m
Deal found 10/26![Delta logo]()
$760
Last-minute flights from Chicago to Saint Thomas IslandDiscover last-minute flight deals from Chicago to Saint Thomas Island. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Saint Thomas Island. Data last updated October 30, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/74:00 pm -
2 stops14h 43m
Tue 11/105:28 pm -
2 stops25h 39m
Deal found 10/26![Multiple Airlines logo]()
$683
This Mytrip deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/94:42 pm -
2 stops20h 25m
Fri 11/138:00 am -
2 stops16h 43m
Deal found 10/25![Multiple Airlines logo]()
$681
This FlightHub deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/132:59 pm -
2 stops24h 09m
Tue 11/175:59 pm -
2 stops21h 43m
Deal found 10/27![JetBlue logo]()
$691
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:30 am -
1 stop7h 13m
Thu 12/34:02 pm -
1 stop9h 54m
Deal found 10/28![Delta logo]()
$645
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:00 am -
1 stop6h 43m
Thu 12/34:02 pm -
1 stop8h 52m
Deal found 10/28![Delta logo]()
$645
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/264:50 pm -
2 stops18h 51m
Thu 12/33:15 pm -
1 stop10h 41m
Deal found 10/28![American Airlines logo]()
$650
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/276:00 am -
1 stop6h 43m
Thu 12/34:02 pm -
1 stop8h 52m
Deal found 10/28![Delta logo]()
$655
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/276:00 am -
1 stop6h 43m
Thu 12/34:02 pm -
1 stop9h 54m
Deal found 10/28![Delta logo]()
$655
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/287:40 am -
Nonstop4h 51m
Sat 12/53:35 pm -
1 stop9h 21m
Deal found 10/28![United Airlines logo]()
$666
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/305:19 am -
1 stop6h 22m
Tue 12/83:13 pm -
2 stops10h 31m
Deal found 10/27![American Airlines logo]()
$620
This FlightHub deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/307:00 am -
2 stops28h 43m
Tue 12/82:35 pm -
2 stops24h 55m
Deal found 10/29![JetBlue logo]()
$649
This American Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/309:06 pm -
2 stops13h 09m
Sat 12/54:36 pm -
1 stop18h 24m
Deal found 10/29![American Airlines logo]()
$675
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 October 30, 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 October 30, 2026.
This FlightHub deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/182:59 pm -
2 stops20h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![JetBlue logo]()
$260
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/115:05 am -
1 stop6h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Southwest logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/49:07 am -
2 stops51h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Multiple Airlines logo]()
$273
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/275:10 am -
1 stop7h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Southwest logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/96:00 am -
2 stops30h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Multiple Airlines logo]()
$285
This Sun Country Air deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1111:48 am -
1 stop25h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Sun Country Air logo]()
$289
This FlightHub deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/77:00 am -
2 stops28h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![JetBlue logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/41:11 pm -
2 stops47h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Multiple Airlines logo]()
$300
This FlightHub deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/247:50 pm -
2 stops15h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![JetBlue logo]()
$304
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Southwest logo]()
$305
This FlightHub deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/87:00 am -
2 stops28h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![JetBlue logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/261:16 pm -
2 stops18h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Multiple Airlines logo]()
$329
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 October 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $484 (Southwest) |
One-way from | $260 (FlightHub) |
Popular in | December |
Cheapest in | May |
Average price | $780 |
Good round-trip deal | $671 or less |
Good one-way deal | $500 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 October 30, 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 1/4
9:07 am-2:50 pm
2 stops51h 43m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$275
ChicagoSaint Thomas Island
MDW Chicago Midway - STT Saint Thomas Island Cyril E King
MDWSTT
Chicago Midway
Fri 11/27
5:10 am-3:00 pm
1 stop7h 50m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$281
ChicagoSaint Thomas Island
ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King
ORDSTT
Chicago O'Hare Intl
Sun 1/10
7:50 pm-1:41 pm
2 stops15h 51m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$298
ChicagoSaint Thomas Island
MDW Chicago Midway - STT Saint Thomas Island Cyril E King
MDWSTT
Chicago Midway
Mon 1/4
1:11 pm-2:50 pm
2 stops47h 39m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$300
ChicagoSaint Thomas Island
ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King
ORDSTT
Chicago O'Hare Intl
Mon 1/4
7:04 am-5:50 pm
1 stop8h 46m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$339
ChicagoSaint Thomas Island
ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King
ORDSTT
Chicago O'Hare Intl
Mon 2/8
2:16 pm-8:43 am
1 stop16h 27m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$352
ChicagoSaint Thomas Island
MDW Chicago Midway - STT Saint Thomas Island Cyril E King
MDWSTT
Chicago Midway
Sun 12/13
8:25 pm-2:30 pm
2 stops16h 05m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$354
Quickest round-trip
ChicagoSaint Thomas Island
ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King
ORDSTT
Chicago O'Hare Intl
Sun 12/13
7:40 am-2:31 pm
Nonstop4h 51m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$354
ChicagoSaint Thomas Island
ORD Chicago O'Hare Intl - STT Saint Thomas Island Cyril E King
ORDSTT
Chicago O'Hare Intl
Sun 1/10
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
$354
ChicagoSaint Thomas Island
MDW Chicago Midway - STT Saint Thomas Island Cyril E King
MDWSTT
Chicago Midway
Mon 12/7
6:00 am-2:52 pm
1 stop6h 52m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$358
Showing 1-10 of 37 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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | 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 $477). Flying from Chicago to Saint Thomas Island in December is currently the most expensive (average of $937). 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 $617 and $847 in February.The cheapest round-trip price found within the last 5 days was $484 on Southwest (Feb 1-Feb 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 67% 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 Orlando (MCO) offer the fastest connection on this route, with an average layover time of 0h 59m.
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 63 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 October 30, 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.
Entertainment
7.4
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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 October 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$414 | Average$743 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$521 | Average$695 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$545 | Average$685 | FlexibilityNo cancel fee | On-timeN/A |