ORD - STX

$283 Find Cheap Flights from Chicago to Christiansted - Compare and Save

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 Christiansted departing on 9/3. 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 Christiansted

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Christiansted, 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 Christiansted, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$566
Typical prices: $1,034-$494
JetBlue
Tue 8/4Sun 8/9
ORD - STX • 2 stops
Cheapest one-way
$283
Typical prices: $363-$371
Multiple Airlines
Thu 9/3
ORD - STX • 1 stop
Top airlines
Cheapest • from $566 (round-trip)
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Chicago and Christiansted. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $569 (round-trip)
Shortest trip • 6h 39m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 29% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Christiansted!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Christiansted (ORD-STX)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Christiansted 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 Christiansted

Tue, Aug 4 - Sun, Aug 9
JetBlue Logo
9:40 am - 3:49 pm
ORD
-
STX
29h 09m
2 stops
JetBlue Logo
4:34 pm - 1:39 pm
STX
-
ORD
22h 05m
2 stops
$566JetBlue
Tue, Aug 4 - Fri, Aug 7
JetBlue Logo
9:40 am - 3:49 pm
ORD
-
STX
29h 09m
2 stops
JetBlue Logo
4:34 pm - 9:55 pm
STX
-
ORD
30h 21m
2 stops
$587JetBlue
Sun, Aug 16 - Sun, Aug 30
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
$594JetBlue
Mon, Aug 10 - 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
$600JetBlue
Mon, Aug 3 - Sun, Aug 9
JetBlue Logo
7:00 am - 3:47 pm
ORD
-
STX
31h 47m
2 stops
JetBlue Logo
4:34 pm - 1:39 pm
STX
-
ORD
22h 05m
2 stops
$610JetBlue
Sun, Aug 16 - Sun, Aug 30
JetBlue Logo
6:00 am - 3:36 pm
ORD
-
STX
32h 36m
2 stops
JetBlue Logo
4:34 pm - 1:39 pm
STX
-
ORD
22h 05m
2 stops
$618JetBlue
Mon, Aug 3 - Fri, Aug 7
JetBlue Logo
7:00 am - 3:47 pm
ORD
-
STX
31h 47m
2 stops
JetBlue Logo
4:34 pm - 9:55 pm
STX
-
ORD
30h 21m
2 stops
$632JetBlue
Wed, Sep 2 - Mon, Sep 7
JetBlue Logo
8:20 pm - 3:36 pm
ORD
-
STX
18h 16m
2 stops
JetBlue Logo
4:34 pm - 10:06 am
STX
-
ORD
18h 32m
2 stops
$651JetBlue
Sun, Aug 16 - Sun, Aug 30
American Airlines Logo
5:00 am - 3:04 pm
ORD
-
STX
9h 04m
1 stop
American Airlines Logo
3:54 pm - 10:31 pm
STX
-
ORD
7h 37m
1 stop
$656American Airlines
Sun, Aug 16 - Sun, Aug 30
American Airlines Logo
6:49 am - 8:43 pm
ORD
-
STX
12h 54m
2 stops
American Airlines Logo
8:04 am - 3:05 pm
STX
-
ORD
8h 01m
1 stop
$660American Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Christiansted flights

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

How much is a round-trip flight from Chicago O'Hare Intl Airport to Christiansted?

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 O'Hare Intl Airport to Christiansted departing in August.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Christiansted?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Christiansted, 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 O'Hare Intl Airport to Christiansted is January, where tickets cost $482 (return) on average. On the other hand, the most expensive months are June and November, where the average cost of round-trip tickets is $1,195 and $924 respectively.

Good to know

Low seasonSeptember
Cheapest flight$283
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 30% lower on average.
Flight from Chicago to Christiansted

When to book flights from Chicago to Christiansted

Are your dates flexible? Find out the best times to travel from Chicago to Christiansted based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Christiansted flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Christiansted?

    In the last 5 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Christiansted was $283 for a one-way ticket and $566 for a round-trip.

  • Do I need a passport to fly between Chicago and Christiansted?

    Yes, you'll most likely have to show a valid passport before boarding the plane in Chicago and on arrival in Christiansted.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Christiansted?

    American Airlines, and JetBlue offer inflight Wi-Fi service on the Chicago to Christiansted flight route.

  • Which aircraft models fly most regularly from Chicago to Christiansted?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago to Christiansted flight route.

  • Which airline alliances offer flights from Chicago to Christiansted?

    oneworld is the only airline alliance operating flights between Chicago and Christiansted.

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

    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 Christiansted.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Christiansted from Chicago 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 Christiansted?

    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 to Christiansted with an airline and back to Chicago with another airline. Booking your flights between Chicago and STX can sometimes prove cheaper using this method.

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

    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 to Christiansted from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago O'Hare Intl Airport to Christiansted

  • Looking for a cheap flight? 25% of our users found flights on this route for $596 or less round-trip.

Reviews of the top airline flying from Chicago to Christiansted

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Christiansted. 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 Christiansted? 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 11635 reviews
6.4Food
6.9Entertainment
7.2Comfort
7.5Boarding
7.9Crew
Airline reviews

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

8.0 ExcellentLuis, Jun 2026
ORD - IND
Read more American Airlines reviews

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

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Everything you need to know for your flight from Chicago to Christiansted

Information on your arrival and departure airports