Chicago

$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
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Cheap flight deals from Saint Croix to Chicago

Cheapest flights from Saint Croix to Chicago
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$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$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$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$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$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$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$1,582

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)
From Saint Croix to Chicago (CHI)
One-way flight from Saint Croix to Chicago (CHI)

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

Price

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

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/13

Showing 1-10 of 12 resultsSorted by cheapest first
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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.
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
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.
  • How long is the flight from Saint Croix to Chicago?

    American Airlines and United Airlines can get you from Saint Croix to Chicago in just under 15h 24m. Your travel time can differ by up to 1h 51m. The distance from Saint Croix to Chicago is about 2159 mi. This flight may include one or multiple stops.

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

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

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

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

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

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

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Alternative routes for Saint Croix to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

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.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$494Average$649FlexibilityNo cancel feeOn-time71%

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