$293+ 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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STX
Sep 28 — Oct 51
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Saint Croix 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.Cheap flight deals from Chicago to Saint Croix
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Best
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One-way
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 29, 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 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Tue 9/112:44 am -
1 stop30h 36m
Mon 11/234:55 pm -
1 stop16h 21m
Deal found 8/24![Multiple Airlines logo]()
$602
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Fri 8/2812:44 am -
1 stop14h 31m
Mon 11/234:55 pm -
1 stop16h 21m
Deal found 8/24![Multiple Airlines logo]()
$629
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Sun 8/3012:44 am -
1 stop10h 46m
Mon 11/234:55 pm -
1 stop16h 21m
Deal found 8/24![Multiple Airlines logo]()
$641
This American Airlines deal was found by Cheapflights users on 8/26. 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 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 10/155:08 pm -
1 stop15h 39m
Deal found 8/26![American Airlines logo]()
$656
This American Airlines deal was found by Cheapflights users on 8/27. 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.
Sun 10/115:05 am -
1 stop9h 57m
Sun 10/182:38 pm -
1 stop9h 55m
Deal found 8/27![American Airlines logo]()
$657
This American Airlines deal was found by Cheapflights users on 8/28. 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 10/127:29 pm -
1 stop17h 19m
Mon 10/192:38 pm -
1 stop9h 55m
Deal found 8/28![American Airlines logo]()
$658
This American Airlines deal was found by Cheapflights users on 8/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/75:00 am -
2 stops10h 02m
Wed 10/145:08 pm -
2 stops15h 19m
Deal found 8/24![American Airlines logo]()
$665
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Fri 8/2812:44 am -
1 stop14h 31m
Wed 11/254:55 pm -
1 stop16h 21m
Deal found 8/24![Multiple Airlines logo]()
$686
This American Airlines deal was found by Cheapflights users on 8/27. 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.
Sat 10/246:59 pm -
1 stop17h 49m
Sat 10/315:08 pm -
1 stop18h 21m
Deal found 8/27![American Airlines logo]()
$691
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 29, 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 29, 2026.
This Delta deal was found by Cheapflights users on 8/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/65:30 am -
1 stop7h 05m
Sat 2/273:35 pm -
1 stop10h 15m
Deal found 8/25![Delta logo]()
$656
This United Airlines deal was found by Cheapflights users on 8/28. 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 2/135:00 am -
1 stop7h 20m
Sat 2/203:25 pm -
1 stop10h 17m
Deal found 8/28![United Airlines logo]()
$746
This United deal was found by Cheapflights users on 8/26. 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.
Sat 9/195:00 am -
2 stops10h 15m
Sat 10/1010:25 am -
1 stop10h 40m
Deal found 8/26![Multiple Airlines logo]()
$781
This Delta deal was found by Cheapflights users on 8/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/206:00 am -
1 stop6h 35m
Sat 2/273:35 pm -
1 stop8h 35m
Deal found 8/25![Delta logo]()
$656
This Delta deal was found by Cheapflights users on 8/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/226:00 am -
1 stop6h 35m
Thu 2/253:35 pm -
1 stop8h 35m
Deal found 8/27![Delta logo]()
$656
This United Airlines deal was found by Cheapflights users on 8/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/95:00 am -
1 stop7h 20m
Sat 1/163:25 pm -
2 stops22h 00m
Deal found 8/24![United Airlines logo]()
$774
This United deal was found by Cheapflights users on 8/27. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/65:45 pm -
2 stops20h 30m
Sat 2/203:25 pm -
1 stop10h 17m
Deal found 8/27![Multiple Airlines logo]()
$804
This United deal was found by Cheapflights users on 8/28. 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.
Sat 1/162:25 pm -
2 stops27h 13m
Sat 1/233:25 pm -
1 stop8h 50m
Deal found 8/28![Multiple Airlines logo]()
$809
This Delta deal was found by Cheapflights users on 8/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/256:00 am -
1 stop6h 35m
Mon 3/13:35 pm -
1 stop8h 35m
Deal found 8/25![Delta logo]()
$762
This United Airlines deal was found by Cheapflights users on 8/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/205:00 am -
1 stop7h 20m
Sat 2/273:25 pm -
2 stops28h 56m
Deal found 8/24![United Airlines logo]()
$959
This United Airlines deal was found by Cheapflights users on 8/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/165:00 am -
1 stop7h 20m
Wed 1/209:59 am -
2 stops13h 06m
Deal found 8/24![United Airlines logo]()
$964
This Delta deal was found by Cheapflights users on 8/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/136:00 am -
1 stop6h 35m
Sat 2/203:35 pm -
1 stop8h 35m
Deal found 8/25![Delta logo]()
$1,100
This Delta deal was found by Cheapflights users on 8/27. 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 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 2/203:35 pm -
1 stop8h 35m
Deal found 8/27![Delta logo]()
$1,102
Last-minute flights from Chicago to Saint CroixDiscover last-minute flight deals from Chicago to Saint Croix. Data last updated August 29, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Saint Croix. Data last updated August 29, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Fri 8/2812:44 am -
1 stop14h 31m
Mon 11/234:55 pm -
1 stop16h 21m
Deal found 8/24![Multiple Airlines logo]()
$629
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Fri 8/2812:44 am -
1 stop14h 31m
Wed 11/254:55 pm -
1 stop16h 21m
Deal found 8/24![Multiple Airlines logo]()
$686
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 8/2912:44 am -
2 stops9h 50m
Mon 11/234:55 pm -
1 stop16h 21m
Deal found 8/24![Multiple Airlines logo]()
$705
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Sun 8/3012:44 am -
1 stop10h 46m
Mon 11/234:55 pm -
1 stop16h 21m
Deal found 8/24![Multiple Airlines logo]()
$641
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Sun 8/3012:44 am -
1 stop10h 46m
Wed 11/254:55 pm -
1 stop16h 21m
Deal found 8/24![Multiple Airlines logo]()
$699
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Tue 9/112:44 am -
1 stop30h 36m
Mon 11/234:55 pm -
1 stop16h 21m
Deal found 8/24![Multiple Airlines logo]()
$602
This American Airlines deal was found by Cheapflights users on 8/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/229:16 pm -
2 stops17h 23m
Fri 10/92:38 pm -
2 stops17h 21m
Deal found 8/26![American Airlines logo]()
$707
This American Airlines deal was found by Cheapflights users on 8/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/229:16 pm -
2 stops17h 23m
Tue 10/135:08 pm -
2 stops13h 41m
Deal found 8/26![American Airlines logo]()
$708
This American Airlines deal was found by Cheapflights users on 8/28. 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 9/279:01 pm -
2 stops17h 38m
Sun 10/44:40 pm -
2 stops16h 09m
Deal found 8/28![American Airlines logo]()
$660
This American Airlines deal was found by Cheapflights users on 8/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:00 am -
1 stop8h 39m
Sat 10/102:38 pm -
1 stop9h 55m
Deal found 8/25![American Airlines logo]()
$696
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 29, 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 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:04 am -
2 stops47h 16m
Deal found 8/26![Multiple Airlines logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 8/27. 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.
Wed 9/237:11 am -
2 stops48h 09m
Deal found 8/27![Multiple Airlines logo]()
$297
This FlightHub deal was found by Cheapflights users on 8/27. 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.
Sun 12/132:50 pm -
2 stops21h 39m
Deal found 8/27![JetBlue logo]()
$304
This FlightHub deal was found by Cheapflights users on 8/27. 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.
Wed 11/182:35 pm -
2 stops22h 55m
Deal found 8/27![JetBlue logo]()
$310
This Kiwi.com deal was found by Cheapflights users on 8/25. 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.
Thu 10/226:00 am -
2 stops25h 20m
Deal found 8/25![Multiple Airlines logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 8/29. 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.
Thu 10/17:11 am -
2 stops32h 04m
Deal found 8/29![Multiple Airlines logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 8/25. 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.
Wed 10/216:00 am -
3 stops25h 20m
Deal found 8/25![Multiple Airlines logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 8/29. 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 10/268:36 am -
2 stops30h 39m
Deal found 8/29![Multiple Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Thu 9/247:11 am -
2 stops35h 27m
Deal found 8/24![Multiple Airlines logo]()
$335
This Delta deal was found by Cheapflights users on 8/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/176:00 am -
1 stop6h 35m
Deal found 8/24![Delta logo]()
$358
This Delta deal was found by Cheapflights users on 8/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/156:00 am -
1 stop6h 35m
Deal found 8/24![Delta logo]()
$434
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 9/411:50 am -
3 stops47h 40m
Deal found 8/27![Multiple Airlines logo]()
$458
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 29, 2026.
Round-trip from | $656 (Delta) |
|---|---|
One-way from | $293 (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 7,457,451 searches. Data last updated August 29, 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 2/6
5:30 am-2:35 pm
1 stop7h 05m
Christiansted Henry Rohlsen
Sat 2/27
3:35 pm-11:50 pm
1 stop10h 15m
$656
Quickest round-trip
ChicagoChristiansted
MDW Chicago Midway - STX Christiansted Henry Rohlsen
MDWSTX
Chicago Midway
Sat 2/20
6:00 am-2:35 pm
1 stop6h 35m
Christiansted Henry Rohlsen
Sat 2/27
3:35 pm-10:10 pm
1 stop8h 35m
$656
ChicagoChristiansted
MDW Chicago Midway - STX Christiansted Henry Rohlsen
MDWSTX
Chicago Midway
Mon 2/22
6:00 am-2:35 pm
1 stop6h 35m
Christiansted Henry Rohlsen
Thu 2/25
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
Sat 2/13
5:00 am-2:20 pm
1 stop7h 20m
Christiansted Henry Rohlsen
Sat 2/20
3:25 pm-11:42 pm
1 stop10h 17m
$746
ChicagoChristiansted
MDW Chicago Midway - STX Christiansted Henry Rohlsen
MDWSTX
Chicago Midway
Thu 2/25
6:00 am-2:35 pm
1 stop6h 35m
Christiansted Henry Rohlsen
Mon 3/1
3:35 pm-10:10 pm
1 stop8h 35m
$762
ChicagoChristiansted
ORD Chicago O'Hare Intl - STX Christiansted Henry Rohlsen
ORDSTX
Chicago O'Hare Intl
Sat 1/9
5:00 am-2:20 pm
1 stop7h 20m
Christiansted Henry Rohlsen
Sat 1/16
3:25 pm-11:25 am
2 stops22h 00m
$774
ChicagoChristiansted
ORD Chicago O'Hare Intl - STX Christiansted Henry Rohlsen
ORDSTX
Chicago O'Hare Intl
Sat 9/19
5:00 am-4:15 pm
2 stops10h 15m
Christiansted Henry Rohlsen
Sat 10/10
10:25 am-8:05 pm
1 stop10h 40m
$781
ChicagoChristiansted
ORD Chicago O'Hare Intl - STX Christiansted Henry Rohlsen
ORDSTX
Chicago O'Hare Intl
Sat 2/6
5:45 pm-4:15 pm
2 stops20h 30m
Christiansted Henry Rohlsen
Sat 2/20
3:25 pm-11:42 pm
1 stop10h 17m
$804
ChicagoChristiansted
ORD Chicago O'Hare Intl - STX Christiansted Henry Rohlsen
ORDSTX
Chicago O'Hare Intl
Sat 1/16
2:25 pm-7:38 pm
2 stops27h 13m
Christiansted Henry Rohlsen
Sat 1/23
3:25 pm-10:15 pm
1 stop8h 50m
$809
ChicagoChristiansted
ORD Chicago O'Hare Intl - STX Christiansted Henry Rohlsen
ORDSTX
Chicago O'Hare Intl
Sat 2/20
5:00 am-2:20 pm
1 stop7h 20m
Christiansted Henry Rohlsen
Sat 2/27
3:25 pm-6:21 pm
2 stops28h 56m
$959
Showing 1-10 of 29 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 29, 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.
Comfort
7.2
Food
6.4
Entertainment
6.8
Overall
7.1
Boarding
7.5
Crew
7.9
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Comfort
7.2
Food
6.4
Entertainment
6.8
Overall
7.1
Boarding
7.5
Crew
7.9
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 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 29, 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 7,457,451 searches. Data last updated August 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$482 | Average$706 | FlexibilityNo cancel fee | On-time71% |