$302+ Cheap flights from Saint Croix to Chicago (CHI)
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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
STX — CHI
Oct 29 — Nov 51
Round-trip
1 adult, Economy
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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 September 29, 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 September 29, 2026.
This American Airlines deal was found by Cheapflights users on 9/29. 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.
Thu 11/199:00 am -
1 stop16h 59m
Sat 11/286:00 am -
1 stop14h 07m
Deal found 9/29![American Airlines logo]()
$676
This United deal was found by Cheapflights users on 9/26. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:25 am -
1 stop12h 01m
Sat 11/285:00 am -
1 stop7h 20m
Deal found 9/26![Multiple Airlines logo]()
$704
This United deal was found by Cheapflights users on 9/28. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/194:55 pm -
2 stops17h 05m
Sat 10/245:30 am -
2 stops13h 08m
Deal found 9/28![Multiple Airlines logo]()
$723
This Mytrip deal was found by Cheapflights users on 9/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/63:14 pm -
2 stops32h 45m
Tue 10/136:00 am -
2 stops12h 38m
Deal found 9/29![Multiple Airlines logo]()
$799
This American Airlines deal was found by Cheapflights users on 9/28. 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.
Mon 10/192:38 pm -
2 stops16h 11m
Mon 10/265:29 pm -
2 stops21h 33m
Deal found 9/28![American Airlines logo]()
$810
This American Airlines deal was found by Cheapflights users on 9/28. 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 10/182:38 pm -
2 stops16h 48m
Mon 10/269:00 pm -
2 stops18h 02m
Deal found 9/28![American Airlines logo]()
$830
This American Airlines deal was found by Cheapflights users on 9/28. 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.
Tue 10/202:38 pm -
2 stops17h 33m
Mon 10/269:29 pm -
2 stops17h 33m
Deal found 9/28![American Airlines logo]()
$831
This American Airlines deal was found by Cheapflights users on 9/29. 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.
Tue 10/65:08 pm -
1 stop8h 30m
Tue 10/135:05 am -
1 stop7h 43m
Deal found 9/29![American Airlines logo]()
$858
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 September 29, 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 September 29, 2026.
This American Airlines deal was found by Cheapflights users on 9/29. 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.
Thu 11/199:00 am -
1 stop16h 59m
Sat 11/286:00 am -
1 stop14h 07m
Deal found 9/29![American Airlines logo]()
$676
This United deal was found by Cheapflights users on 9/26. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:25 am -
1 stop12h 01m
Sat 11/285:00 am -
1 stop7h 20m
Deal found 9/26![Multiple Airlines logo]()
$704
This United deal was found by Cheapflights users on 9/28. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/194:55 pm -
2 stops17h 05m
Sat 10/245:30 am -
2 stops13h 08m
Deal found 9/28![Multiple Airlines logo]()
$723
This United Airlines deal was found by Cheapflights users on 9/26. 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.
Thu 11/199:59 am -
3 stops14h 19m
Sat 11/285:30 am -
2 stops12h 08m
Deal found 9/26![United Airlines logo]()
$1,532
This KAYAK deal was found by Cheapflights users on 9/28. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/252:38 pm -
2 stops18h 50m
Fri 10/306:14 am -
1 stop8h 48m
Deal found 9/28![American Airlines logo]()
$926
This American Airlines deal was found by Cheapflights users on 9/28. 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.
Mon 10/192:38 pm -
1 stop7h 52m
Fri 10/236:14 am -
1 stop8h 48m
Deal found 9/28![American Airlines logo]()
$1,154
This American Airlines deal was found by Cheapflights users on 9/28. 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 10/182:38 pm -
1 stop7h 52m
Thu 10/225:05 am -
1 stop7h 43m
Deal found 9/28![American Airlines logo]()
$1,154
Last-minute flights from Saint Croix to ChicagoDiscover last-minute flight deals from Saint Croix to Chicago. Data last updated September 29, 2026 and is based on user searches.
Discover last-minute flight deals from Saint Croix to Chicago. Data last updated September 29, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 9/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/63:14 pm -
2 stops32h 45m
Tue 10/136:00 am -
2 stops12h 38m
Deal found 9/29![Multiple Airlines logo]()
$799
This American Airlines deal was found by Cheapflights users on 9/29. 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.
Tue 10/65:08 pm -
1 stop8h 30m
Tue 10/135:05 am -
1 stop7h 43m
Deal found 9/29![American Airlines logo]()
$858
This American Airlines deal was found by Cheapflights users on 9/28. 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.
Sat 10/172:38 pm -
1 stop7h 52m
Mon 10/267:00 am -
1 stop8h 02m
Deal found 9/28![American Airlines logo]()
$901
This American Airlines deal was found by Cheapflights users on 9/28. 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 10/182:38 pm -
2 stops16h 48m
Mon 10/267:29 pm -
1 stop17h 19m
Deal found 9/28![American Airlines logo]()
$830
This American Airlines deal was found by Cheapflights users on 9/28. 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 10/182:38 pm -
2 stops16h 48m
Sat 10/2411:00 pm -
2 stops13h 48m
Deal found 9/28![American Airlines logo]()
$920
This United deal was found by Cheapflights users on 9/28. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/194:55 pm -
2 stops17h 05m
Sat 10/245:30 am -
2 stops13h 08m
Deal found 9/28![Multiple Airlines logo]()
$723
This American Airlines deal was found by Cheapflights users on 9/28. 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.
Mon 10/195:08 pm -
2 stops13h 41m
Mon 10/267:00 am -
1 stop8h 02m
Deal found 9/28![American Airlines logo]()
$810
This American Airlines deal was found by Cheapflights users on 9/28. 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.
Tue 10/202:38 pm -
2 stops17h 33m
Mon 10/269:29 pm -
2 stops17h 33m
Deal found 9/28![American Airlines logo]()
$831
This American Airlines deal was found by Cheapflights users on 9/28. 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.
Tue 10/202:38 pm -
2 stops17h 33m
Sat 10/2411:00 pm -
2 stops13h 48m
Deal found 9/28![American Airlines logo]()
$921
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 September 29, 2026.
Search for one-way flight options from Saint Croix to Chicago. Find affordable one-way fares based on user searches. Data last updated September 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 10/274:55 pm -
2 stops25h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Multiple Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 10/244:48 pm -
2 stops15h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Multiple Airlines logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 9/28. 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 12/244:55 pm -
1 stop31h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Multiple Airlines logo]()
$307
This FlightHub deal was found by Cheapflights users on 9/26. 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.
Tue 11/244:20 pm -
2 stops33h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![JetBlue logo]()
$310
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:54 pm -
2 stops24h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Multiple Airlines logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 9/27. 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.
Fri 10/234:55 pm -
2 stops30h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Multiple Airlines logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/224:55 pm -
2 stops27h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Multiple Airlines logo]()
$328
This Kiwi.com deal was found by Cheapflights users on 9/29. 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.
Fri 10/304:55 pm -
2 stops41h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Multiple Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 9/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/263:25 pm -
1 stop8h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![United Airlines logo]()
$336
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 September 29, 2026.
Round-trip from | $676 (American Airlines) |
|---|---|
One-way from | $302 (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 7,457,451 searches. Data last updated September 29, 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 12/26
3:25 pm-10:15 pm
1 stop8h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$336
ChristianstedChicago
STX Christiansted Henry Rohlsen - ORD Chicago O'Hare Intl
STXORD
Christiansted Henry Rohlsen
Tue 3/23
2:25 pm-10:20 pm
1 stop8h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$366
ChristianstedChicago
STX Christiansted Henry Rohlsen - ORD Chicago O'Hare Intl
STXORD
Christiansted Henry Rohlsen
Mon 12/28
3:38 pm-11:59 pm
1 stop10h 21m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$366
Quickest round-trip
ChristianstedChicago
STX Christiansted Henry Rohlsen - ORD Chicago O'Hare Intl
STXORD
Christiansted Henry Rohlsen
Mon 3/22
2:25 pm-9:10 pm
1 stop7h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$366
ChristianstedChicago
STX Christiansted Henry Rohlsen - ORD Chicago O'Hare Intl
STXORD
Christiansted Henry Rohlsen
Wed 12/30
3:38 pm-11:59 pm
1 stop10h 21m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$366
ChristianstedChicago
STX Christiansted Henry Rohlsen - ORD Chicago O'Hare Intl
STXORD
Christiansted Henry Rohlsen
Fri 12/25
3:38 pm-11:03 pm
1 stop9h 25m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$366
ChristianstedChicago
STX Christiansted Henry Rohlsen - ORD Chicago O'Hare Intl
STXORD
Christiansted Henry Rohlsen
Sun 12/27
3:38 pm-11:59 pm
1 stop10h 21m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$398
ChristianstedChicago
STX Christiansted Henry Rohlsen - ORD Chicago O'Hare Intl
STXORD
Christiansted Henry Rohlsen
Wed 3/24
2:25 pm-10:20 pm
1 stop8h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$398
ChristianstedChicago
STX Christiansted Henry Rohlsen - ORD Chicago O'Hare Intl
STXORD
Christiansted Henry Rohlsen
Tue 12/29
3:38 pm-11:59 pm
1 stop10h 21m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$398
ChristianstedChicago
STX Christiansted Henry Rohlsen - ORD Chicago O'Hare Intl
STXORD
Christiansted Henry Rohlsen
Thu 11/19
9:00 am-11:59 pm
1 stop16h 59m
Chicago O'Hare Intl
Sat 11/28
6:00 am-10:07 pm
1 stop14h 07m
$676
Showing 1-10 of 16 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
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