$274+ Cheap flights from Chicago (CHI) to Saint Croix
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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STX
Sep 14 — Sep 211
Round-trip
1 adult, Economy
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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 Chicago to Saint CroixExplore the most affordable flight options available from Chicago to Saint Croix. 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 Chicago to Saint Croix. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 15, 2026.
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/253:20 pm -
2 stops22h 10m
Tue 12/13:26 pm -
2 stops24h 00m
Deal found 8/11![JetBlue logo]()
$535
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.
Wed 9/167:00 pm -
1 stop19h 39m
Wed 9/234:40 pm -
1 stop17h 49m
Deal found 8/15![American Airlines logo]()
$575
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/53:20 pm -
2 stops23h 29m
Sat 9/129:10 am -
2 stops14h 58m
Deal found 8/10![Multiple Airlines logo]()
$577
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/42:50 pm -
2 stops21h 39m
Thu 12/103:26 pm -
2 stops24h 00m
Deal found 8/11![JetBlue logo]()
$578
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 9/285:29 pm -
1 stop21h 10m
Mon 10/52:38 pm -
1 stop21h 32m
Deal found 8/14![American Airlines logo]()
$579
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/263:20 pm -
2 stops22h 10m
Tue 12/13:26 pm -
2 stops24h 00m
Deal found 8/11![JetBlue logo]()
$592
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.
Sat 10/106:59 pm -
1 stop17h 49m
Thu 10/152:38 pm -
1 stop11h 00m
Deal found 8/14![American Airlines logo]()
$596
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2912:44 am -
1 stop10h 46m
Thu 9/34:55 pm -
1 stop7h 32m
Deal found 8/14![Multiple Airlines logo]()
$597
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.
Sat 10/37:00 pm -
1 stop19h 39m
Wed 10/72:38 pm -
1 stop11h 00m
Deal found 8/14![American Airlines logo]()
$609
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/22:35 pm -
2 stops24h 14m
Mon 9/74:42 pm -
2 stops21h 57m
Deal found 8/10![JetBlue logo]()
$610
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/266:00 am -
1 stop6h 25m
Sat 1/23:25 pm -
1 stop8h 45m
Deal found 8/12![Delta logo]()
$2,210
Best flights from Chicago to Saint CroixDiscover carefully curated flight deals from Chicago to Saint Croix 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 Chicago to Saint Croix 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 8/14. 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.
Sat 10/106:59 pm -
1 stop17h 49m
Thu 10/152:38 pm -
1 stop11h 00m
Deal found 8/14![American Airlines logo]()
$596
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/46:00 am -
1 stop6h 35m
Sat 1/93:35 pm -
1 stop8h 35m
Deal found 8/11![Delta logo]()
$656
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.
Wed 10/217:00 am -
1 stop8h 02m
Fri 10/302:38 pm -
1 stop9h 55m
Deal found 8/14![American Airlines logo]()
$661
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/66:00 am -
1 stop6h 35m
Sat 2/133:35 pm -
1 stop8h 35m
Deal found 8/13![Delta logo]()
$676
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 10/145:05 am -
1 stop9h 57m
Tue 10/202:38 pm -
1 stop7h 52m
Deal found 8/10![American Airlines logo]()
$661
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.
Wed 10/148:55 pm -
2 stops15h 53m
Wed 11/43:00 pm -
2 stops11h 01m
Deal found 8/11![American Airlines logo]()
$665
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.
Wed 10/287:00 am -
1 stop8h 02m
Wed 11/43:00 pm -
2 stops11h 01m
Deal found 8/14![American Airlines logo]()
$665
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 9/25:00 am -
1 stop9h 04m
Mon 9/73:54 pm -
1 stop16h 40m
Deal found 8/10![American Airlines logo]()
$681
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/266:00 am -
1 stop6h 25m
Sat 1/23:25 pm -
1 stop8h 45m
Deal found 8/12![Delta logo]()
$2,210
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/266:00 am -
1 stop6h 25m
Sun 1/33:25 pm -
1 stop8h 45m
Deal found 8/10![Delta logo]()
$2,742
Last-minute flights from Chicago to Saint CroixDiscover last-minute flight deals from Chicago to Saint Croix. Data last updated August 15, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Saint Croix. Data last updated August 15, 2026 and is based on user searches.
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/215:30 am -
2 stops13h 08m
Mon 8/2410:25 am -
2 stops12h 50m
Deal found 8/12![United Airlines logo]()
$2,201
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.
Sun 8/239:55 am -
1 stop9h 48m
Thu 9/33:54 pm -
1 stop7h 37m
Deal found 8/13![American Airlines logo]()
$786
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/237:00 am -
2 stops31h 47m
Thu 9/34:44 pm -
2 stops27h 42m
Deal found 8/12![JetBlue logo]()
$865
One-way flights from Chicago to Saint CroixSearch for one-way flight options from Chicago to Saint Croix. Find affordable one-way fares based on user searches. Data last updated August 15, 2026.
Search for one-way flight options from Chicago to Saint Croix. 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 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:50 am -
2 stops30h 25m
Deal found 8/12![Multiple Airlines logo]()
$274
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 9/65:00 am -
1 stop14h 43m
Deal found 8/12![American Airlines logo]()
$281
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:11 am -
2 stops48h 09m
Deal found 8/10![Multiple Airlines logo]()
$284
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 10/138:04 am -
2 stops34h 34m
Deal found 8/13![Multiple Airlines logo]()
$290
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 10/128:04 am -
2 stops47h 16m
Deal found 8/13![Multiple Airlines logo]()
$294
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:11 am -
2 stops48h 09m
Deal found 8/10![Multiple Airlines logo]()
$299
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.
Sat 10/106:40 pm -
2 stops20h 22m
Deal found 8/11![American Airlines logo]()
$308
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.
Thu 11/127:50 am -
2 stops30h 25m
Deal found 8/13![Multiple Airlines logo]()
$309
Find flight deals from Chicago to Saint Croix
Keep the following information in mind while searching for Chicago to Saint Croix flight deals. Data was last updated August 15, 2026.
Round-trip from | $535 (FlightHub) |
|---|---|
One-way from | $274 (Kiwi.com) |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Saint Croix 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 Chicago to Saint Croix that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoChristiansted
ORD Chicago O'Hare Intl - STX Christiansted Henry Rohlsen
ORDSTX
Chicago O'Hare Intl
Sat 10/10
6:59 pm-1:48 pm
1 stop17h 49m
Christiansted Henry Rohlsen
Thu 10/15
2:38 pm-12:38 am
1 stop11h 00m
$596
Quickest round-trip
ChicagoChristiansted
MDW Chicago Midway - STX Christiansted Henry Rohlsen
MDWSTX
Chicago Midway
Mon 1/4
6:00 am-2:35 pm
1 stop6h 35m
Christiansted Henry Rohlsen
Sat 1/9
3:35 pm-10:10 pm
1 stop8h 35m
$656
ChicagoChristiansted
ORD Chicago O'Hare Intl - STX Christiansted Henry Rohlsen
ORDSTX
Chicago O'Hare Intl
Wed 10/21
7:00 am-4:02 pm
1 stop8h 02m
Christiansted Henry Rohlsen
Fri 10/30
2:38 pm-11:33 pm
1 stop9h 55m
$661
ChicagoChristiansted
ORD Chicago O'Hare Intl - STX Christiansted Henry Rohlsen
ORDSTX
Chicago O'Hare Intl
Wed 10/14
5:05 am-4:02 pm
1 stop9h 57m
Christiansted Henry Rohlsen
Tue 10/20
2:38 pm-9:30 pm
1 stop7h 52m
$661
ChicagoChristiansted
ORD Chicago O'Hare Intl - STX Christiansted Henry Rohlsen
ORDSTX
Chicago O'Hare Intl
Wed 10/14
8:55 pm-1:48 pm
2 stops15h 53m
Christiansted Henry Rohlsen
Wed 11/4
3:00 pm-12:01 am
2 stops11h 01m
$665
ChicagoChristiansted
ORD Chicago O'Hare Intl - STX Christiansted Henry Rohlsen
ORDSTX
Chicago O'Hare Intl
Wed 10/28
7:00 am-4:02 pm
1 stop8h 02m
Christiansted Henry Rohlsen
Wed 11/4
3:00 pm-12:01 am
2 stops11h 01m
$665
ChicagoChristiansted
MDW Chicago Midway - STX Christiansted Henry Rohlsen
MDWSTX
Chicago Midway
Sat 2/6
6:00 am-2:35 pm
1 stop6h 35m
Christiansted Henry Rohlsen
Sat 2/13
3:35 pm-10:10 pm
1 stop8h 35m
$676
ChicagoChristiansted
ORD Chicago O'Hare Intl - STX Christiansted Henry Rohlsen
ORDSTX
Chicago O'Hare Intl
Wed 9/2
5:00 am-3:04 pm
1 stop9h 04m
Christiansted Henry Rohlsen
Mon 9/7
3:54 pm-7:34 am
1 stop16h 40m
$681
ChicagoChristiansted
MDW Chicago Midway - STX Christiansted Henry Rohlsen
MDWSTX
Chicago Midway
Sat 12/26
6:00 am-2:25 pm
1 stop6h 25m
Christiansted Henry Rohlsen
Sat 1/2
3:25 pm-10:10 pm
1 stop8h 45m
$2,210
ChicagoChristiansted
MDW Chicago Midway - STX Christiansted Henry Rohlsen
MDWSTX
Chicago Midway
Sat 12/26
6:00 am-2:25 pm
1 stop6h 25m
Christiansted Henry Rohlsen
Sun 1/3
3:25 pm-10:10 pm
1 stop8h 45m
$2,742
Showing 1-10 of 19 resultsSorted by cheapest first
Best time to book a flight from Chicago to Saint Croix
Have a flexible travel schedule? Discover the best time to fly to Saint Croix from Chicago with our price prediction graph.
ORD-STX
MDW-STX
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 Croix
CHI-VISC
ORD-STX
MDW-STX
What is the cheapest month to book a flight from Chicago to Saint Croix?
Currently, January is the cheapest month in which you can book a flight from Chicago to Saint Croix (average of $481). Flying from Chicago to Saint Croix in June is currently the most expensive (average of $1,094). 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.
Reviews of airlines servicing Saint Croix
Get insights into the airlines that provide service to Saint Croix. 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 Croix. Reviews last updated August 15, 2026.
Get a feel of what it's like to fly with American Airlines from Chicago to Saint Croix by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
6.8
Comfort
7.2
Crew
7.9
Food
6.4
Overall
7.1
Boarding
7.5
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Entertainment
6.8
Comfort
7.2
Crew
7.9
Food
6.4
Overall
7.1
Boarding
7.5
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Related info for your journey
Find useful and relevant information for your journey from Chicago to Saint Croix. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Complete your trip
Complete your trip to Saint Croix by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Chicago to Saint Croix, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Saint Croix flights
Browse other Chicago and Saint Croix flight options. Last updated on August 15, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Chicago to Saint Croix
Discover the top airline that operate flights from Chicago to Saint Croix. 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$482 | Average$716 | FlexibilityNo cancel fee | On-time71% |