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Saint Croix

$143+ 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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STX
Dec 5 — Dec 121
Fri 12/5
Fri 12/12
1 adult, Economy
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Cheap 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 November 5, 2025.

Round-trip from

$291
(Cheapflightsfares)

One-way from

$143
(Kiwi.com)

Good round-trip deal

$680 or less
From Chicago (CHI) to Saint Croix
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One-way flight from Chicago (CHI) to Saint Croix
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Price to beat on a round-trip flight from Chicago (CHI) to Saint Croix.
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Find 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 November 5, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/3. 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 11/183:26 pmORD - STX
1 stop23h 20mMultiple Airlines
Sat 11/224:36 pmSTX - ORD
1 stop28h 45mMultiple Airlines
Deal found 11/3$341
This Mytrip deal was found by Cheapflights users on 11/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/184:57 pmORD - STX
2 stops21h 49mSpirit Airlines
Sat 11/224:36 pmSTX - ORD
2 stops18h 25mSpirit Airlines
Deal found 11/3$342
This Mytrip deal was found by Cheapflights users on 11/5. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/195:10 amORD - STX
1 stop9h 36mSpirit Airlines
Sat 11/224:36 pmSTX - ORD
2 stops18h 25mSpirit Airlines
Deal found 11/5$380
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/195:10 amORD - STX
1 stop9h 36mMultiple Airlines
Sat 11/224:36 pmSTX - ORD
1 stop28h 45mMultiple Airlines
Deal found 11/5$389
This Delta deal was found by Cheapflights users on 11/3. 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.
Tue 12/306:00 amMDW - STX
1 stop6h 21mDelta
Wed 1/73:33 pmSTX - MDW
1 stop8h 36mDelta
Deal found 11/3$815
This Delta deal was found by Cheapflights users on 11/5. 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.
Wed 12/246:00 amMDW - STX
1 stop6h 21mDelta
Thu 1/83:33 pmSTX - MDW
1 stop8h 36mDelta
Deal found 11/5$1,089
This Delta deal was found by Cheapflights users on 11/4. 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 12/296:00 amMDW - STX
1 stop6h 21mDelta
Tue 12/303:22 pmSTX - MDW
1 stop9h 00mDelta
Deal found 11/4$1,109
This Delta deal was found by Cheapflights users on 11/4. 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 12/256:00 amMDW - STX
1 stop6h 21mDelta
Tue 12/303:22 pmSTX - MDW
1 stop9h 00mDelta
Deal found 11/4$1,277
This Delta deal was found by Cheapflights users on 11/4. 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.
Tue 12/236:00 amMDW - STX
1 stop6h 21mDelta
Thu 1/13:22 pmSTX - MDW
1 stop9h 00mDelta
Deal found 11/4$1,322
This Delta deal was found by Cheapflights users on 11/4. 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 12/276:00 amMDW - STX
1 stop6h 21mDelta
Tue 12/303:22 pmSTX - MDW
1 stop9h 00mDelta
Deal found 11/4$1,377
This Delta deal was found by Cheapflights users on 11/4. 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 12/286:00 amMDW - STX
1 stop6h 21mDelta
Wed 12/313:22 pmSTX - MDW
1 stop9h 00mDelta
Deal found 11/4$1,495
This Delta deal was found by Cheapflights users on 11/4. 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 12/256:00 amMDW - STX
1 stop6h 21mDelta
Thu 1/13:22 pmSTX - MDW
1 stop9h 00mDelta
Deal found 11/4$1,510

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 November 5, 2025.
Use the filters below to find and compare flights from Chicago to Saint Croix that are best for you.

Fly from

Chicago

Fly to

Saint Croix

Route

Depart

Return

Price

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Tue 11/18

3:26 pm-4:46 pm

1 stop23h 20m

Christiansted Henry Rohlsen

Sat 11/22

4:36 pm-7:21 pm

1 stop28h 45m

$341

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Sun 2/1

11:42 am-3:35 pm

1 stop25h 53m

Christiansted Henry Rohlsen

Sat 2/7

4:32 pm-7:29 pm

1 stop28h 57m

$342

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Sun 2/1

11:42 am-3:35 pm

1 stop25h 53m

Christiansted Henry Rohlsen

Fri 2/6

4:32 pm-12:18 am

1 stop9h 46m

$346

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Tue 11/18

2:31 pm-4:46 pm

3 stops24h 15m

Christiansted Henry Rohlsen

Sat 11/22

4:36 pm-5:11 pm

3 stops26h 35m

$412

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Sun 12/14

3:20 pm-3:58 pm

1 stop22h 38m

Christiansted Henry Rohlsen

Sat 12/20

10:41 am-9:02 am

2 stops24h 21m

$477

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Mon 11/17

5:10 am-4:46 pm

1 stop9h 36m

Christiansted Henry Rohlsen

Fri 11/21

4:36 pm-5:39 pm

2 stops27h 03m

$482

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Fri 1/30

5:15 am-3:35 pm

1 stop8h 20m

Christiansted Henry Rohlsen

Sat 2/7

4:32 pm-12:18 am

1 stop9h 46m

$506

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Sat 11/15

5:10 am-4:46 pm

1 stop9h 36m

Christiansted Henry Rohlsen

Mon 11/24

4:36 pm-11:13 pm

1 stop8h 37m

$506

ChicagoChristiansted

ORD - STX

ORDSTX

Chicago O'Hare Intl

Sat 1/31

5:05 am-8:55 am

2 stops25h 50m

Christiansted Henry Rohlsen

Sat 2/7

4:32 pm-12:18 am

1 stop9h 46m

$526

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

Sun 1/25

6:00 am-2:33 pm

1 stop6h 33m

Christiansted Henry Rohlsen

Thu 1/29

3:33 pm-10:26 pm

1 stop8h 53m

$615

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

Showing 1-10 of 31 results
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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, January is the cheapest month in which you can book a flight from Chicago to Saint Croix (average of $276). Flying from Chicago to Saint Croix in June is currently the most expensive (average of $766). 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 November 5, 2025.
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
7.2
Good
11,042 reviews

Crew

8.0

Overall

7.2

Entertainment

6.9

Boarding

7.5

Comfort

7.2

Food

6.4

Reviews

1 / 20
8.0
Excellent

Monica,Nov 2025

JAC - DFW

At least there was an option of entertainment on this flight.
American Airlines
7.2
Good
11,042 reviews
American Airlines
7.2
Good
11,042 reviews

Crew

8.0

Overall

7.2

Entertainment

6.9

Boarding

7.5

Comfort

7.2

Food

6.4

Reviews

1 / 20
8.0
Excellent

Monica,Nov 2025

JAC - DFW

At least there was an option of entertainment on this flight.
Spirit Airlines
6.3
Okay
8,115 reviews
American Airlines
7.2
Good
11,042 reviews

Crew

8.0

Overall

7.2

Entertainment

6.9

Boarding

7.5

Comfort

7.2

Food

6.4

Reviews

1 / 20
8.0
Excellent

Monica,Nov 2025

JAC - DFW

At least there was an option of entertainment on this flight.

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?

    Delta can get you from Chicago to Saint Croix in just under 6h 33m. Your travel time can differ by up to . Chicago and Saint Croix are separated by a distance of 2144 mi.

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

    The cheapest flight price from Chicago to Saint Croix is $635. On average you can expect to pay $977. The most popular route, (Chicago O'Hare Intl - Christiansted Henry Rohlsen), can usually be booked for $291.

  • 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, January is the cheapest month in which you can book a flight from Chicago to Saint Croix (average of $276). Flying from Chicago to Saint Croix in June is currently the most expensive (average of $766). 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

Browse thousands of different options on Cheapflights for your next trip

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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 November 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$270Average$365FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$454Average$604FlexibilityNo cancel feeOn-time71%

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