$282+ 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 8/10. Fares are subject to change and may not be available on all flights or dates of travel.
STX — CHI
Jun 15 — Jun 221
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 May 16, 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 May 16, 2026.
This American Airlines deal was found by Cheapflights users on 5/13. 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.
Fri 5/299:00 am
STX
- ORD
1 stop13h 29m
American Airlines
Tue 6/27:00 am
ORD
- STX
1 stop12h 45m
American Airlines
Deal found 5/13![American Airlines logo]()
$706
This American Airlines deal was found by Cheapflights users on 5/14. 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.
Sun 5/319:00 am
STX
- ORD
1 stop14h 33m
American Airlines
Wed 6/105:00 am
ORD
- STX
1 stop14h 44m
American Airlines
Deal found 5/14![American Airlines logo]()
$793
This Kiwi.com deal was found by Cheapflights users on 5/13. 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.
Wed 5/275:23 pm
STX
- ORD
1 stop30h 23m
Multiple Airlines
Fri 5/2912:33 am
ORD
- STX
1 stop14h 50m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$802
This American Airlines deal was found by Cheapflights users on 5/11. 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.
Mon 5/253:48 pm
STX
- ORD
1 stop18h 22m
American Airlines
Thu 5/286:08 am
ORD
- STX
1 stop13h 37m
American Airlines
Deal found 5/11![American Airlines logo]()
$828
This American Airlines deal was found by Cheapflights users on 5/13. 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.
Wed 5/279:00 am
STX
- ORD
2 stops12h 21m
American Airlines
Sat 5/308:00 am
ORD
- STX
2 stops11h 45m
American Airlines
Deal found 5/13![American Airlines logo]()
$867
This American Airlines deal was found by Cheapflights users on 5/12. 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 5/279:00 am
STX
- ORD
2 stops10h 53m
American Airlines
Sun 5/318:48 am
ORD
- STX
2 stops10h 57m
American Airlines
Deal found 5/12![American Airlines logo]()
$1,004
This United Airlines deal was found by Cheapflights users on 5/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2710:20 am
STX
- ORD
3 stops15h 24m
United Airlines
Sat 5/305:30 am
ORD
- STX
2 stops10h 40m
United Airlines
Deal found 5/13![United Airlines logo]()
$1,582
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 May 16, 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 May 16, 2026.
This American Airlines deal was found by Cheapflights users on 5/13. 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.
Fri 5/299:00 am
STX
- ORD
1 stop13h 29m
American Airlines
Tue 6/27:00 am
ORD
- STX
1 stop12h 45m
American Airlines
Deal found 5/13![American Airlines logo]()
$706
This United Airlines deal was found by Cheapflights users on 5/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2710:20 am
STX
- ORD
3 stops15h 24m
United Airlines
Sat 5/305:30 am
ORD
- STX
2 stops10h 40m
United Airlines
Deal found 5/13![United Airlines logo]()
$1,582
This American Airlines deal was found by Cheapflights users on 5/12. 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 5/279:00 am
STX
- ORD
1 stop16h 24m
American Airlines
Sun 5/316:08 am
ORD
- STX
1 stop13h 37m
American Airlines
Deal found 5/12![American Airlines logo]()
$828
This American Airlines deal was found by Cheapflights users on 5/13. 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.
Wed 5/279:00 am
STX
- ORD
1 stop11h 57m
American Airlines
Sat 5/308:48 am
ORD
- STX
2 stops10h 57m
American Airlines
Deal found 5/13![American Airlines logo]()
$867
This United Airlines deal was found by Cheapflights users on 5/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:59 am
STX
- ORD
3 stops15h 45m
United Airlines
Tue 6/25:30 am
ORD
- STX
2 stops10h 40m
United Airlines
Deal found 5/13![United Airlines logo]()
$2,065
This United Airlines deal was found by Cheapflights users on 5/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/319:59 am
STX
- ORD
3 stops15h 45m
United Airlines
Wed 6/105:30 am
ORD
- STX
2 stops10h 40m
United Airlines
Deal found 5/14![United Airlines logo]()
$2,201
This United Airlines deal was found by Cheapflights users on 5/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2710:20 am
STX
- ORD
3 stops15h 24m
United Airlines
Sun 5/315:30 am
ORD
- STX
2 stops13h 08m
United Airlines
Deal found 5/12![United Airlines logo]()
$2,370
Last-minute flights from Saint Croix to ChicagoDiscover last-minute flight deals from Saint Croix to Chicago. Data last updated May 16, 2026 and is based on user searches.
Discover last-minute flight deals from Saint Croix to Chicago. Data last updated May 16, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 5/11. 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.
Mon 5/253:48 pm
STX
- ORD
1 stop18h 22m
American Airlines
Thu 5/286:08 am
ORD
- STX
1 stop13h 37m
American Airlines
Deal found 5/11![American Airlines logo]()
$828
This Kiwi.com deal was found by Cheapflights users on 5/13. 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.
Wed 5/275:23 pm
STX
- ORD
1 stop30h 23m
Multiple Airlines
Fri 5/2912:33 am
ORD
- STX
1 stop14h 50m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$802
This American Airlines deal was found by Cheapflights users on 5/13. 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.
Wed 5/279:00 am
STX
- ORD
2 stops12h 21m
American Airlines
Sat 5/308:00 am
ORD
- STX
2 stops11h 45m
American Airlines
Deal found 5/13![American Airlines logo]()
$867
This American Airlines deal was found by Cheapflights users on 5/12. 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 5/279:00 am
STX
- ORD
2 stops10h 53m
American Airlines
Sun 5/318:48 am
ORD
- STX
2 stops10h 57m
American Airlines
Deal found 5/12![American Airlines logo]()
$1,004
This United Airlines deal was found by Cheapflights users on 5/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2710:20 am
STX
- ORD
3 stops15h 24m
United Airlines
Sat 5/305:30 am
ORD
- STX
2 stops10h 40m
United Airlines
Deal found 5/13![United Airlines logo]()
$1,582
This American Airlines deal was found by Cheapflights users on 5/13. 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.
Fri 5/299:00 am
STX
- ORD
1 stop13h 29m
American Airlines
Tue 6/27:00 am
ORD
- STX
1 stop12h 45m
American Airlines
Deal found 5/13![American Airlines logo]()
$706
This American Airlines deal was found by Cheapflights users on 5/14. 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.
Sun 5/319:00 am
STX
- ORD
1 stop14h 33m
American Airlines
Wed 6/105:00 am
ORD
- STX
1 stop14h 44m
American Airlines
Deal found 5/14![American Airlines logo]()
$793
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 May 16, 2026.
Search for one-way flight options from Saint Croix to Chicago. Find affordable one-way fares based on user searches. Data last updated May 16, 2026.
This FlightHub deal was found by Cheapflights users on 5/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/104:34 pm
STX
- ORD
2 stops25h 46m
JetBlue
Deal found 5/14![JetBlue logo]()
$282
This FlightHub deal was found by Cheapflights users on 5/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/74:34 pm
STX
- ORD
2 stops29h 53m
JetBlue
Deal found 5/12![JetBlue logo]()
$292
This FlightHub deal was found by Cheapflights users on 5/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/93:45 pm
STX
- ORD
2 stops32h 13m
JetBlue
Deal found 5/13![JetBlue logo]()
$293
This American Airlines deal was found by Cheapflights users on 5/14. 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.
Wed 6/109:01 am
STX
- ORD
1 stop16h 18m
American Airlines
Deal found 5/14![American Airlines logo]()
$298
This FlightHub deal was found by Cheapflights users on 5/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/53:45 pm
STX
- ORD
2 stops19h 09m
JetBlue
Deal found 5/11![JetBlue logo]()
$307
This American Airlines deal was found by Cheapflights users on 5/13. 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.
Sun 11/86:42 pm
STX
- ORD
2 stops16h 23m
American Airlines
Deal found 5/13![American Airlines logo]()
$308
This FlightHub deal was found by Cheapflights users on 5/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/74:34 pm
STX
- ORD
2 stops24h 41m
JetBlue
Deal found 5/13![JetBlue logo]()
$311
This FlightHub deal was found by Cheapflights users on 5/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/83:45 pm
STX
- ORD
2 stops28h 49m
JetBlue
Deal found 5/13![JetBlue logo]()
$317
This Orbitz deal was found by Cheapflights users on 5/14. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/264:34 pm
STX
- ORD
2 stops17h 11m
JetBlue
Deal found 5/14![JetBlue logo]()
$319
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 May 16, 2026.
Round-trip from | $706 (American Airlines) |
|---|---|
One-way from | $282 (FlightHub) |
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 May 16, 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 - ORD
STXORD
Christiansted Henry Rohlsen
Fri 5/29
9:00 am-9:29 pm
1 stop13h 29m
Chicago O'Hare Intl
Tue 6/2
7:00 am-8:45 pm
1 stop12h 45m
$706
ChristianstedChicago
STX - ORD
STXORD
Christiansted Henry Rohlsen
Wed 5/27
9:00 am-12:24 am
1 stop16h 24m
Chicago O'Hare Intl
Sun 5/31
6:08 am-8:45 pm
1 stop13h 37m
$828
Quickest round-trip
ChristianstedChicago
STX - ORD
STXORD
Christiansted Henry Rohlsen
Wed 5/27
9:00 am-7:57 pm
1 stop11h 57m
Chicago O'Hare Intl
Sat 5/30
8:48 am-8:45 pm
2 stops10h 57m
$867
ChristianstedChicago
STX - ORD
STXORD
Christiansted Henry Rohlsen
Wed 5/27
10:20 am-12:44 am
3 stops15h 24m
Chicago O'Hare Intl
Sat 5/30
5:30 am-5:10 pm
2 stops10h 40m
$1,582
ChristianstedChicago
STX - ORD
STXORD
Christiansted Henry Rohlsen
Fri 5/29
9:59 am-12:44 am
3 stops15h 45m
Chicago O'Hare Intl
Tue 6/2
5:30 am-5:10 pm
2 stops10h 40m
$2,065
ChristianstedChicago
STX - ORD
STXORD
Christiansted Henry Rohlsen
Sun 5/31
9:59 am-12:44 am
3 stops15h 45m
Chicago O'Hare Intl
Wed 6/10
5:30 am-5:10 pm
2 stops10h 40m
$2,201
ChristianstedChicago
STX - ORD
STXORD
Christiansted Henry Rohlsen
Wed 5/27
10:20 am-12:44 am
3 stops15h 24m
Chicago O'Hare Intl
Sun 5/31
5:30 am-7:38 pm
2 stops13h 08m
$2,370
Cheapest one-way
Quickest one-way
ChristianstedChicago
STX - ORD
STXORD
Christiansted Henry Rohlsen
Sat 6/6
2:55 pm-9:53 pm
1 stop7h 58m
$333
ChristianstedChicago
STX - ORD
STXORD
Christiansted Henry Rohlsen
Sat 8/8
3:05 pm-11:58 pm
1 stop9h 53m
$333
ChristianstedChicago
STX - ORD
STXORD
Christiansted Henry Rohlsen
Sat 6/13
3:05 pm-12:04 am
1 stop9h 59m
$333
Showing 1-10 of 12 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
Hammond
Porter
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 16, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Saint Croix to Chicago by cabin class
Find flights from Saint Croix to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Saint Croix and Chicago flights
Browse other Saint Croix and Chicago flight options. Last updated on May 16, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 May 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$494 | Average$649 | FlexibilityNo cancel fee | On-time71% |