$115 Cheap Flights from Christiansted (STX) to Chicago (ORD)

View $115 flight on Sat, Nov 8, 2025Opens in a new window

Popular airlines from Henry E. Rohlsen Airport (STX) to Chicago O'Hare Intl. Airport (ORD)

Cheap Flights from Christiansted to Chicago (STX-ORD)

Prices were available within the past 7 days and start at $115 for one-way flights and $250 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Wed, Nov 5 - Wed, Nov 12
STX
St. Croix Island
ORD
Chicago
$250 Roundtrip, found 3 days ago
$250
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Wed, Nov 5 from St. Croix Island to Chicago, returning Wed, Nov 12, priced at $250 found 3 days ago
Spirit Airlines
Fri, Nov 7 - Mon, Nov 10
STX
St. Croix Island
ORD
Chicago
$277 Roundtrip, found 4 days ago
$277
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Fri, Nov 7 from St. Croix Island to Chicago, returning Mon, Nov 10, priced at $277 found 4 days ago
Spirit Airlines
Wed, Nov 12 - Wed, Nov 19
STX
St. Croix Island
ORD
Chicago
$283 Roundtrip, found 3 days ago
$283
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Wed, Nov 12 from St. Croix Island to Chicago, returning Wed, Nov 19, priced at $283 found 3 days ago
Spirit Airlines
Fri, Oct 31 - Fri, Nov 7
STX
St. Croix Island
ORD
Chicago
$321 Roundtrip, found 5 days ago
$321
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Fri, Oct 31 from St. Croix Island to Chicago, returning Fri, Nov 7, priced at $321 found 5 days ago
Spirit Airlines
Wed, Oct 29 - Fri, Oct 31
STX
St. Croix Island
ORD
Chicago
$322 Roundtrip, found 5 days ago
$322
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Wed, Oct 29 from St. Croix Island to Chicago, returning Fri, Oct 31, priced at $322 found 5 days ago
Spirit Airlines
Wed, Nov 12 - Sat, Nov 15
STX
St. Croix Island
ORD
Chicago
$326 Roundtrip, found 3 days ago
$326
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Wed, Nov 12 from St. Croix Island to Chicago, returning Sat, Nov 15, priced at $326 found 3 days ago
American Airlines
Wed, Nov 12 - Wed, Nov 19
STX
St. Croix Island
ORD
Chicago
$427 Roundtrip, found 3 days ago
$427
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Nov 12 from St. Croix Island to Chicago, returning Wed, Nov 19, priced at $427 found 3 days ago
JetBlue Airways
Fri, Nov 7 - Mon, Nov 10
STX
St. Croix Island
ORD
Chicago
$492 Roundtrip, found 4 days ago
$492
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Fri, Nov 7 from St. Croix Island to Chicago, returning Mon, Nov 10, priced at $492 found 4 days ago
Delta
Thu, Jan 22 - Sun, Jan 25
STX
St. Croix Island
ORD
Chicago
$495 Roundtrip, found 5 days ago
$495
Roundtrip
found 5 days ago
Select Delta flight, departing Thu, Jan 22 from St. Croix Island to Chicago, returning Sun, Jan 25, priced at $495 found 5 days ago
United
Wed, Jan 21 - Sat, Jan 24
STX
St. Croix Island
ORD
Chicago
$1,561 Roundtrip, found 5 days ago
$1,561
Roundtrip
found 5 days ago
Select United flight, departing Wed, Jan 21 from St. Croix Island to Chicago, returning Sat, Jan 24, priced at $1,561 found 5 days ago

Find the cheapest month to fly from Estate Mannings Bay (STX) to Chicago (ORD)

May is typically the cheapest month to fly

From $277 - $757 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $769
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $769
Flights from Christiansted (STX) to Chicago (ORD)
Origin airport
Henry E. Rohlsen
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, JetBlue Airways, Spirit Airlines, United
Roundtrip price
$250
Distance
2160 mi

Christiansted to Chicago Flights

The cheapest times to fly from Christiansted to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Christiansted to Chicago are during the month of November. You can find some of the cheapest flights from Christiansted to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Christiansted to Chicago

Sunday is one of the best days to book for cheap flights from Christiansted to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Christiansted to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Christiansted to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $115 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Christiansted to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Christiansted to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Henry E. Rohlsen Airport (STX) to O'Hare Intl. Airport (ORD) cost?
Lock in a cheap one-way flight from $115 or cheap return flight from $250 from Henry E. Rohlsen Airport (STX) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Henry E. Rohlsen Airport (STX) to O'Hare Intl. Airport (ORD)?
Planning your getaway for November may help you find better deals, as it's the cheapest month for flights between STX and ORD. You'll typically find the lowest prices during the off-season.
Which airlines fly direct from Henry E. Rohlsen Airport (STX) to O'Hare Intl. Airport (ORD)?
You can't take a direct flight from Christiansted (STX-Henry E. Rohlsen) to O'Hare Intl. Airport (ORD). However, you can seamlessly travel to Chicago without any layovers by taking off from Cyril E. King Airport (STT).
What is the cheapest airline that flies from Henry E. Rohlsen Airport (STX) to O'Hare Intl. Airport (ORD)?
Use the filter tool on Expedia to compare different airlines and find the cheapest carrier that'll take you from STX to ORD. Then, sort your results by "Price (lowest to highest)" to score a good deal.
How many flights per day from Henry E. Rohlsen Airport (STX) to O'Hare Intl. Airport (ORD)?
There are no daily nonstop flights available from Henry E. Rohlsen Airport (STX) to O'Hare Intl. Airport (ORD). But you can choose flights with layovers. Filter your search on Expedia to include one or more stops, and you'll be cruising above the clouds in no time.
What day of the week has the most flights from STX to ORD?
Friday is usually the busiest day for flights, while Tuesday is often the quietest.* Just remember that flight schedules can change depending on a range of factors, including the airline and season.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Henry E. Rohlsen Airport (STX) to O'Hare Intl. Airport (ORD)?
To reach O'Hare Intl. Airport (ORD) on schedule, choose a flight that leaves from Henry E. Rohlsen Airport (STX) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Henry E. Rohlsen Airport (STX) to O'Hare Intl. Airport (ORD) last-minute?
Last-minute fares from STX to ORD are generally more expensive. To lock in the lowest prices, start searching for flights well ahead of time. That being said, if you're flexible with your travel dates, it's possible to find a cheap ticket just before your departure.
Is it cheaper to book a STX to ORD flight and hotel package?
Compared with arranging flights and hotels separately, booking a STX to ORD flight and hotel package with Expedia could lead to significant savings. What's more, having it all in one place will take the stress out of travel planning. Simply secure your flights and choose from our extensive range of hotels, then customize your trip with extras like tours and car rentals.
Can I cancel or change the date of my flight from Henry E. Rohlsen Airport (STX) to O'Hare Intl. Airport (ORD)?
If you booked your STX to ORD flight in the last 24 hours, you may be able to cancel or modify it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal for further details.

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*Available to One Key members.