$272 Find Cheap Flights from Chicago to Saint Croix

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Saint Croix departing on 9/7. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Saint Croix

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Saint Croix, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Saint Croix, as well as popular online travel agencies
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Flight Deals

Book Cheap Chicago to Saint Croix Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Saint Croix that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Saint Croix

Thu, Aug 13 - Sun, Aug 16
JetBlue Logo
2:35 pm - 3:36 pm
ORD
-
STX
24h 01m
2 stops
JetBlue Logo
4:34 pm - 1:39 pm
STX
-
ORD
22h 05m
2 stops
$585JetBlue
Fri, Aug 14 - Sun, Aug 23
JetBlue Logo
7:00 am - 3:36 pm
ORD
-
STX
31h 36m
2 stops
JetBlue Logo
4:34 pm - 1:39 pm
STX
-
ORD
22h 05m
2 stops
$586JetBlue
Sat, Aug 8 - Sun, Aug 16
JetBlue Logo
2:35 pm - 3:36 pm
ORD
-
STX
24h 01m
2 stops
JetBlue Logo
4:34 pm - 1:39 pm
STX
-
ORD
22h 05m
2 stops
$596JetBlue
Sun, Aug 16 - Sun, Aug 30
JetBlue Logo
7:00 am - 3:36 pm
ORD
-
STX
31h 36m
2 stops
JetBlue Logo
4:34 pm - 1:39 pm
STX
-
ORD
22h 05m
2 stops
$600JetBlue
Fri, Aug 21 - Sun, Aug 30
Multiple Airlines Logo
12:29 am - 4:23 pm
ORD
-
STX
14h 54m
1 stop
Multiple Airlines Logo
9:10 am - 10:26 pm
STX
-
ORD
14h 16m
1 stop
$613Multiple Airlines
Thu, Aug 6 - Mon, Aug 17
JetBlue Logo
7:00 am - 3:36 pm
ORD
-
STX
31h 36m
2 stops
JetBlue Logo
4:34 pm - 11:44 pm
STX
-
ORD
32h 10m
2 stops
$622JetBlue
Sat, Aug 29 - Sun, Sep 6
JetBlue Logo
2:35 pm - 3:36 pm
ORD
-
STX
24h 01m
2 stops
JetBlue Logo
4:34 pm - 8:48 am
STX
-
ORD
17h 14m
2 stops
$629JetBlue
Sat, Aug 8 - Sat, Aug 15
Delta Logo
6:05 am - 2:03 pm
MDW
-
STX
6h 58m
1 stop
Delta Logo
3:08 pm - 10:36 pm
STX
-
MDW
8h 28m
1 stop
$726Delta
Fri, Aug 14 - Sat, Aug 22
Delta Logo
5:10 pm - 2:03 pm
MDW
-
STX
19h 53m
1 stop
Delta Logo
3:08 pm - 10:36 pm
STX
-
MDW
8h 28m
1 stop
$2,442Delta
Sat, Aug 8 - Sat, Aug 15
Delta Logo
6:05 am - 2:03 pm
MDW
-
STX
6h 58m
1 stop
Delta Logo
3:08 pm - 12:39 pm
STX
-
MDW
22h 31m
2 stops
$3,511Delta
Booking Insights

KAYAK's insights & trends for Chicago to Saint Croix flights

Get data-powered insights and trends into flights from Chicago to Saint Croix to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago to Saint Croix?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Saint Croix departing in August.

What is the cheapest Chicago to Saint Croix flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Saint Croix from Chicago found in the last 5 days was to Christiansted, at $1,951 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Christiansted (STX), and the cheapest round-trip airline ticket found on this route in the last 5 days was $1,951.

What is the cheapest month to fly from Chicago to Saint Croix?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Saint Croix, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Saint Croix is February, when tickets cost $252 (return) on average. On the other hand, the most expensive months are June and March, when the average cost of round-trip tickets is $605 and $495 respectively.

Good to know

Cheapest flight$272
Flight from Chicago to Christiansted

FAQs - booking Saint Croix flights

  • How does KAYAK find such low prices on flights from Chicago to Saint Croix?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Saint Croix.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Saint Croix?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Saint Croix is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Saint Croix?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago to Saint Croix with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Saint Croix?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago to Saint Croix up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Chicago to Saint Croix

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Saint Croix. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Saint Croix? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
American AirlinesOverall score based on 11668 reviews
6.8Entertainment
6.4Food
7.5Boarding
7.2Comfort
7.9Crew
Airline reviews

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

2.0 MediocreGirish, Jun 2026
ORD - DFW
Read more American Airlines reviews

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

My pillow had a shoe print on it, when I asked if I can have another pillow, I was told “I’m sorry but it is one pillow per guest, do YOU want to turn it inside out” to which I responded , no thanks I will go without. This is generally not ok, but For the price tag I paid flying business this is absolutely unacceptable. Hopefully American Airlines can update their accommodations to bedding that is not tossed on the ground and stepped on, or at least have a couple of extra pillows in hand, incase someone had decided to step on the pillows for what ever reason

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Our flight was cancelled while we are on our way to the airport. So, no notice. We were rescheduled to another airline with a 2 hour later takeoff and so arrived at our destination on time. We pre-paid American Airlines $190 to upgrade our seats. No refund. So no use for AA or Kayak.

Terrible, horrible, disappointing- without telling us they changed planes and moved and separated our seats to opposite sides - said they changed seats putting us together - got to airport to find no, they did not - we sat opposing sides of plane - food overly salty to inedible, never saw stewardess but once - it was terrible

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Everything you need to know for your flight from Chicago to Saint Croix

Cabin class types available on flights to Saint Croix

Cabin classes available on flights to Saint Croix. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.