$270+ Cheap flights from Saint Croix to Chicago (CHI)
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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
STX — CHI
Sep 14 — Sep 211
Round-trip
1 adult, Economy
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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
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Cheapest flights from Saint Croix to ChicagoExplore the most affordable flight options available from Saint Croix to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 15, 2026.
Explore the most affordable flight options available from Saint Croix to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 15, 2026.
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/28:30 am -
1 stop12h 33m
Sun 9/66:00 am -
1 stop13h 43m
Deal found 8/10![American Airlines logo]()
$587
This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 8/284:55 pm -
1 stop7h 32m
Mon 8/3112:44 am -
1 stop17h 54m
Deal found 8/13![Multiple Airlines logo]()
$596
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/184:40 pm -
1 stop16h 08m
Sat 10/106:40 pm -
2 stops18h 08m
Deal found 8/12![American Airlines logo]()
$612
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/204:40 pm -
2 stops16h 49m
Sat 10/106:40 pm -
2 stops18h 08m
Deal found 8/12![American Airlines logo]()
$660
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/184:40 pm -
1 stop17h 49m
Thu 10/86:40 pm -
2 stops18h 08m
Deal found 8/12![American Airlines logo]()
$666
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/214:40 pm -
2 stops15h 49m
Sat 10/106:40 pm -
2 stops18h 08m
Deal found 8/12![American Airlines logo]()
$673
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/164:40 pm -
1 stop16h 08m
Thu 10/86:40 pm -
2 stops18h 08m
Deal found 8/12![American Airlines logo]()
$676
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/184:40 pm -
1 stop16h 08m
Tue 10/1310:01 am -
1 stop29h 01m
Deal found 8/12![American Airlines logo]()
$679
Best flights from Saint Croix to ChicagoDiscover carefully curated flight deals from Saint Croix to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 15, 2026.
Discover carefully curated flight deals from Saint Croix to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 15, 2026.
This American Airlines deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 9/194:40 pm -
1 stop17h 49m
Sat 10/106:59 pm -
1 stop17h 49m
Deal found 8/15![American Airlines logo]()
$691
This American Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 9/194:40 pm -
1 stop17h 49m
Sat 10/39:15 pm -
2 stops17h 24m
Deal found 8/13![American Airlines logo]()
$695
Last-minute flights from Saint Croix to ChicagoDiscover last-minute flight deals from Saint Croix to Chicago. Data last updated August 15, 2026 and is based on user searches.
Discover last-minute flight deals from Saint Croix to Chicago. Data last updated August 15, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 8/284:55 pm -
1 stop7h 32m
Mon 8/3112:44 am -
1 stop17h 54m
Deal found 8/13![Multiple Airlines logo]()
$596
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/28:30 am -
1 stop12h 33m
Sun 9/66:00 am -
1 stop13h 43m
Deal found 8/10![American Airlines logo]()
$587
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/164:40 pm -
1 stop16h 08m
Thu 10/86:40 pm -
2 stops18h 08m
Deal found 8/12![American Airlines logo]()
$676
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/184:40 pm -
1 stop16h 08m
Sat 10/106:40 pm -
2 stops18h 08m
Deal found 8/12![American Airlines logo]()
$612
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/184:40 pm -
1 stop17h 49m
Thu 10/86:40 pm -
2 stops18h 08m
Deal found 8/12![American Airlines logo]()
$666
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/184:40 pm -
1 stop16h 08m
Tue 10/1310:01 am -
1 stop29h 01m
Deal found 8/12![American Airlines logo]()
$679
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/204:40 pm -
2 stops16h 49m
Sat 10/106:40 pm -
2 stops18h 08m
Deal found 8/12![American Airlines logo]()
$660
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/214:40 pm -
2 stops15h 49m
Sat 10/106:40 pm -
2 stops18h 08m
Deal found 8/12![American Airlines logo]()
$673
One-way flights from Saint Croix to ChicagoSearch for one-way flight options from Saint Croix to Chicago. Find affordable one-way fares based on user searches. Data last updated August 15, 2026.
Search for one-way flight options from Saint Croix to Chicago. Find affordable one-way fares based on user searches. Data last updated August 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 11/113:14 pm -
2 stops26h 10m
Deal found 8/11![Multiple Airlines logo]()
$270
This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 9/154:55 pm -
2 stops46h 50m
Deal found 8/13![Multiple Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/104:40 pm -
1 stop17h 49m
Deal found 8/11![American Airlines logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/84:55 pm -
2 stops46h 50m
Deal found 8/11![Multiple Airlines logo]()
$284
This American Airlines deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” 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 10/122:38 pm -
1 stop18h 09m
Deal found 8/14![American Airlines logo]()
$298
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/114:40 pm -
1 stop17h 49m
Deal found 8/11![American Airlines logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 10/134:55 pm -
3 stops50h 36m
Deal found 8/13![Multiple Airlines logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 11/164:55 pm -
3 stops45h 07m
Deal found 8/13![Multiple Airlines logo]()
$308
Find flight deals from Saint Croix to Chicago
Keep the following information in mind while searching for Saint Croix to Chicago flight deals. Data was last updated August 15, 2026.
Round-trip from | $587 (American Airlines) |
|---|---|
One-way from | $270 (Kiwi.com) |
Cheapflights Fare Finder
Customize your flight search to find flights from Saint Croix to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 15, 2026.
Use the filters below to find and compare flights from Saint Croix to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChristianstedChicago
STX Christiansted Henry Rohlsen - ORD Chicago O'Hare Intl
STXORD
Christiansted Henry Rohlsen
Sat 9/19
4:40 pm-9:29 am
1 stop17h 49m
Chicago O'Hare Intl
Sat 10/10
6:59 pm-1:48 pm
1 stop17h 49m
$691
Quickest round-trip
ChristianstedChicago
STX Christiansted Henry Rohlsen - ORD Chicago O'Hare Intl
STXORD
Christiansted Henry Rohlsen
Sat 9/19
4:40 pm-9:29 am
1 stop17h 49m
Chicago O'Hare Intl
Sat 10/3
9:15 pm-3:39 pm
2 stops17h 24m
$695
Cheapest one-way
ChristianstedChicago
STX Christiansted Henry Rohlsen - ORD Chicago O'Hare Intl
STXORD
Christiansted Henry Rohlsen
Sun 9/13
4:40 pm-7:48 am
1 stop16h 08m
$281
ChristianstedChicago
STX Christiansted Henry Rohlsen - ORD Chicago O'Hare Intl
STXORD
Christiansted Henry Rohlsen
Thu 9/10
4:40 pm-9:29 am
1 stop17h 49m
$281
ChristianstedChicago
STX Christiansted Henry Rohlsen - ORD Chicago O'Hare Intl
STXORD
Christiansted Henry Rohlsen
Sun 9/13
3:14 pm-11:51 am
3 stops45h 37m
$335
ChristianstedChicago
STX Christiansted Henry Rohlsen - ORD Chicago O'Hare Intl
STXORD
Christiansted Henry Rohlsen
Wed 2/10
8:30 am-7:56 pm
1 stop13h 26m
$338
Quickest one-way
ChristianstedChicago
STX Christiansted Henry Rohlsen - ORD Chicago O'Hare Intl
STXORD
Christiansted Henry Rohlsen
Wed 10/14
2:38 pm-12:38 am
1 stop11h 00m
$338
ChristianstedChicago
STX Christiansted Henry Rohlsen - ORD Chicago O'Hare Intl
STXORD
Christiansted Henry Rohlsen
Tue 11/10
7:00 am-7:49 pm
1 stop14h 49m
$338
ChristianstedChicago
STX Christiansted Henry Rohlsen - ORD Chicago O'Hare Intl
STXORD
Christiansted Henry Rohlsen
Tue 10/13
5:08 pm-7:47 am
1 stop15h 39m
$338
ChristianstedChicago
STX Christiansted Henry Rohlsen - ORD Chicago O'Hare Intl
STXORD
Christiansted Henry Rohlsen
Fri 11/13
9:10 am-12:02 pm
3 stops28h 52m
$339
Showing 1-10 of 13 resultsSorted by cheapest first
Best time to book a flight from Saint Croix to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Saint Croix with our price prediction graph.
STX-ORD
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 Saint Croix to Chicago
VISC-CHI
STX-ORD
No data available for this route at this time. Please check back soon.
Related info for your journey
Find useful and relevant information for your journey from Saint Croix to Chicago. 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 Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Complete your trip
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Saint Croix and Chicago flights
Browse other Saint Croix and Chicago flight options. Last updated on August 15, 2026.
Popular flight searches
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Top airline flying from Saint Croix to Chicago
Discover the top airline that operate flights from Saint Croix to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$572 | Average$649 | FlexibilityNo cancel fee | On-time71% |