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Saint Croix

$273+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STX
Jun 26 — Jul 31
Fri 6/26
Fri 7/3
1 adult, Economy
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Cheap flight deals from Chicago to Saint Croix

Cheapest flights from Chicago to Saint Croix
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 May 27, 2026.

This FlightHub deal was found by Cheapflights users on 5/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/202:35 pm
ORD
-
STX
2 stops24h 01m
JetBlue
Fri 8/284:34 pm
STX
-
ORD
2 stops17h 34m
JetBlue
Deal found 5/24$577
This FlightHub deal was found by Cheapflights users on 5/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:00 am
ORD
-
STX
2 stops31h 36m
JetBlue
Fri 8/284:34 pm
STX
-
ORD
2 stops17h 34m
JetBlue
Deal found 5/24$591
This FlightHub deal was found by Cheapflights users on 5/23. 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 8/57:00 am
ORD
-
STX
2 stops31h 36m
JetBlue
Tue 8/114:34 pm
STX
-
ORD
2 stops17h 14m
JetBlue
Deal found 5/23$593
This FlightHub deal was found by Cheapflights users on 5/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:00 am
ORD
-
STX
2 stops31h 36m
JetBlue
Sun 8/304:34 pm
STX
-
ORD
2 stops22h 05m
JetBlue
Deal found 5/24$600
This FlightHub deal was found by Cheapflights users on 5/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/222:35 pm
ORD
-
STX
2 stops24h 01m
JetBlue
Sun 8/304:34 pm
STX
-
ORD
2 stops22h 05m
JetBlue
Deal found 5/24$613
This American Airlines deal was found by Cheapflights users on 5/27. 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 8/169:55 am
ORD
-
STX
1 stop9h 48m
American Airlines
Sun 8/308:04 am
STX
-
ORD
1 stop8h 01m
American Airlines
Deal found 5/27$656
This FlightHub deal was found by Cheapflights users on 5/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/167:00 am
ORD
-
STX
2 stops31h 47m
JetBlue
Tue 7/214:44 pm
STX
-
ORD
2 stops27h 31m
JetBlue
Deal found 5/25$659
This American Airlines deal was found by Cheapflights users on 5/27. 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.
Wed 11/48:10 am
ORD
-
STX
1 stop7h 42m
American Airlines
Tue 11/106:42 pm
STX
-
ORD
1 stop18h 20m
American Airlines
Deal found 5/27$661
This American Airlines deal was found by Cheapflights users on 5/23. 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 6/176:10 am
ORD
-
STX
1 stop13h 34m
American Airlines
Tue 6/239:01 am
STX
-
ORD
1 stop16h 18m
American Airlines
Deal found 5/23$681
This Delta deal was found by Cheapflights users on 5/27. 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 8/226:05 am
MDW
-
STX
1 stop6h 58m
Delta
Sat 8/293:05 pm
STX
-
MDW
1 stop8h 31m
Delta
Deal found 5/27$726
This Delta deal was found by Cheapflights users on 5/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/276:00 am
MDW
-
STX
1 stop6h 25m
Delta
Mon 1/43:35 pm
STX
-
MDW
1 stop8h 10m
Delta
Deal found 5/26$2,283
This Delta deal was found by Cheapflights users on 5/25. 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 12/266:00 am
MDW
-
STX
1 stop6h 25m
Delta
Sat 1/23:25 pm
STX
-
MDW
1 stop8h 20m
Delta
Deal found 5/25$2,358

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 May 27, 2026.

Round-trip from

$577
(FlightHub)

One-way from

$273
(FlightHub)

Good round-trip deal

$596 or less
From Chicago (CHI) to Saint Croix
Search Deals
One-way flight from Chicago (CHI) to Saint Croix
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Saint Croix.
Search Deals

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 May 27, 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

Price

Cheapest round-trip

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Sun 7/19

5:00 am-8:50 pm

1 stop14h 50m

Christiansted Henry Rohlsen

Fri 7/24

9:00 am-11:30 pm

1 stop15h 30m

$656

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Thu 7/16

8:30 am-8:50 pm

1 stop11h 20m

Christiansted Henry Rohlsen

Mon 7/20

9:00 am-11:30 pm

1 stop15h 30m

$656

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Sun 7/26

6:30 am-8:50 pm

2 stops13h 20m

Christiansted Henry Rohlsen

Fri 7/31

9:00 am-11:30 pm

1 stop15h 30m

$660

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Sat 7/18

5:00 am-8:50 pm

1 stop14h 50m

Christiansted Henry Rohlsen

Wed 7/22

9:00 am-11:30 pm

1 stop15h 30m

$691

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Fri 8/21

8:00 am-8:43 pm

2 stops11h 43m

Christiansted Henry Rohlsen

Sat 8/29

8:04 am-5:18 pm

1 stop10h 14m

$695

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Sun 7/26

7:00 am-3:47 pm

2 stops31h 47m

Christiansted Henry Rohlsen

Sun 8/2

4:44 pm-4:16 pm

2 stops24h 32m

$725
Quickest round-trip

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

Sat 8/22

6:05 am-2:03 pm

1 stop6h 58m

Christiansted Henry Rohlsen

Sat 8/29

3:05 pm-10:36 pm

1 stop8h 31m

$726

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Thu 7/16

2:35 pm-3:47 pm

2 stops24h 12m

Christiansted Henry Rohlsen

Mon 7/20

4:44 pm-8:50 am

2 stops17h 06m

$729

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Fri 8/21

6:00 am-3:04 pm

1 stop8h 04m

Christiansted Henry Rohlsen

Mon 8/31

3:54 pm-10:31 pm

1 stop7h 37m

$776

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Wed 6/3

5:00 am-8:45 pm

1 stop14h 45m

Christiansted Henry Rohlsen

Wed 6/10

3:46 pm-12:19 am

1 stop9h 33m

$831

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/23

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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.
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

What is the cheapest month to book a flight from Chicago to Saint Croix?

Currently, February is the cheapest month in which you can book a flight from Chicago to Saint Croix (average of $252). Flying from Chicago to Saint Croix in June is currently the most expensive (average of $595). 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.

How much does it cost to fly round-trip from Chicago to Saint Croix?

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 May 27, 2026.
Get a feel of what it's like to fly with American Airlines and Spirit 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.
American Airlines
7.1
Good
11,639 reviews

Boarding

7.5

Crew

7.9

Comfort

7.2

Food

6.4

Entertainment

6.9

Overall

7.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Apr 2026

DFW - BDL

They keep changing the gate, delaying the hours and then finally canceled it. No accomodation, no food, nothing!
American Airlines
7.1
Good
11,639 reviews
American Airlines
7.1
Good
11,639 reviews

Boarding

7.5

Crew

7.9

Comfort

7.2

Food

6.4

Entertainment

6.9

Overall

7.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Apr 2026

DFW - BDL

They keep changing the gate, delaying the hours and then finally canceled it. No accomodation, no food, nothing!
Spirit Airlines
6.2
Okay
American Airlines
7.1
Good
11,639 reviews

Boarding

7.5

Crew

7.9

Comfort

7.2

Food

6.4

Entertainment

6.9

Overall

7.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Apr 2026

DFW - BDL

They keep changing the gate, delaying the hours and then finally canceled it. No accomodation, no food, nothing!

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.

  • How long is the flight from Chicago to Saint Croix?

    American Airlines and Delta can get you from Chicago to Saint Croix in just under 6h 58m. Your travel time can differ by up to 7h 52m. Chicago and Saint Croix are separated by a distance of 2144 mi. This flight may include one or multiple stops.

  • What are the cheapest flights from Chicago to Saint Croix?

    The cheapest flight price from Chicago to Saint Croix is $596. On average you can expect to pay $908. The most popular route, (Chicago O'Hare Intl - Christiansted Henry Rohlsen), can usually be booked for $659.

  • Can I find deals for flights from Chicago to Saint Croix that include hotel bookings?

    Yes. In addition to deals on Chicago to Saint Croix flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Saint Croix?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Saint Croix.

  • Can I find deals for business class flights from Chicago to Saint Croix?

    Yes. Cheapflights offers flight deals from Chicago to Saint Croix by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Saint Croix?

    Currently, February is the cheapest month in which you can book a flight from Chicago to Saint Croix (average of $252). Flying from Chicago to Saint Croix in June is currently the most expensive (average of $595). 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.

See more FAQs

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Alternative routes for Chicago to Saint Croix

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Saint Thomas Island flights
St. Louis to Saint Thomas Island flights
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Moline to Saint Thomas Island flights

Top 2 airlines flying from Chicago to Saint Croix

Discover the top 2 airlines 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 May 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$295Average$362FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$482Average$658FlexibilityNo cancel feeOn-time71%

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