$278 Cheap Flights from Chicago (MDW) to Christiansted (STX)

View $278 flight on Tue, Feb 24, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Henry E. Rohlsen Airport (STX)

Cheap Flights from Chicago to Christiansted (MDW-STX)

Prices were available within the past 7 days and start at $278 for one-way flights and $495 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Jan 20 - Thu, Feb 5
MDW
Chicago
STX
St. Croix Island
$495 Roundtrip, found 3 hours ago
$495
Roundtrip
found 3 hours ago
Select Delta flight, departing Tue, Jan 20 from Chicago to St. Croix Island, returning Thu, Feb 5, priced at $495 found 3 hours ago
Delta
Fri, Jan 16 - Fri, Jan 23
MDW
Chicago
STX
St. Croix Island
$520 Roundtrip, found 5 days ago
$520
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Jan 16 from Chicago to St. Croix Island, returning Fri, Jan 23, priced at $520 found 5 days ago
Delta
Wed, Jan 21 - Thu, Jan 22
MDW
Chicago
STX
St. Croix Island
$535 Roundtrip, found 3 hours ago
$535
Roundtrip
found 3 hours ago
Select Delta flight, departing Wed, Jan 21 from Chicago to St. Croix Island, returning Thu, Jan 22, priced at $535 found 3 hours ago
Delta
Sat, Nov 8 - Sat, Nov 15
MDW
Chicago
STX
St. Croix Island
$545 Roundtrip, found 2 hours ago
$545
Roundtrip
found 2 hours ago
Select Delta flight, departing Sat, Nov 8 from Chicago to St. Croix Island, returning Sat, Nov 15, priced at $545 found 2 hours ago
Delta
Thu, Jan 22 - Fri, Jan 23
MDW
Chicago
STX
St. Croix Island
$560 Roundtrip, found 3 hours ago
$560
Roundtrip
found 3 hours ago
Select Delta flight, departing Thu, Jan 22 from Chicago to St. Croix Island, returning Fri, Jan 23, priced at $560 found 3 hours ago
Delta
Fri, Jan 23 - Sat, Jan 24
MDW
Chicago
STX
St. Croix Island
$585 Roundtrip, found 3 hours ago
$585
Roundtrip
found 3 hours ago
Select Delta flight, departing Fri, Jan 23 from Chicago to St. Croix Island, returning Sat, Jan 24, priced at $585 found 3 hours ago
Delta
Tue, Jan 20 - Thu, Jan 29
MDW
Chicago
STX
St. Croix Island
$595 Roundtrip, found 3 hours ago
$595
Roundtrip
found 3 hours ago
Select Delta flight, departing Tue, Jan 20 from Chicago to St. Croix Island, returning Thu, Jan 29, priced at $595 found 3 hours ago
Delta
Sat, Jan 17 - Fri, Jan 23
MDW
Chicago
STX
St. Croix Island
$620 Roundtrip, found 6 days ago
$620
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Jan 17 from Chicago to St. Croix Island, returning Fri, Jan 23, priced at $620 found 6 days ago
Delta
Fri, Jan 16 - Fri, Jan 23
MDW
Chicago
STX
St. Croix Island
$640 Roundtrip, found 5 days ago
$640
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Jan 16 from Chicago to St. Croix Island, returning Fri, Jan 23, priced at $640 found 5 days ago
Delta
Sat, Jan 17 - Sat, Jan 24
MDW
Chicago
STX
St. Croix Island
$645 Roundtrip, found 4 days ago
$645
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Jan 17 from Chicago to St. Croix Island, returning Sat, Jan 24, priced at $645 found 4 days ago

Alternative airports near Estate Mannings Bay

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

Select flight to Henry E. Rohlsen STX. Cheapest option available. Flights from $2,239
STX
Henry E. Rohlsen
Cheapest
Flights from $2,239

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Henry E. Rohlsen Airport (STX) cost?
Snag a cheap one-way flight from $278 or cheap return flight from $495 from Midway Intl. Airport (MDW) to Henry E. Rohlsen Airport (STX) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Henry E. Rohlsen Airport (STX)?
Flying in January is a great way to save, as it's the cheapest month for flights between MDW and STX. You'll typically find the lowest prices during the off-season.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Henry E. Rohlsen Airport (STX)?
To find the cheapest airline flying from MDW to STX, use Expedia's filter tool. Customize your search based on your travel style, such as preferred carriers and seat class. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
How many flights per day from Midway Intl. Airport (MDW) to Henry E. Rohlsen Airport (STX)?
Nonstop flights from Midway Intl. Airport (MDW) to Henry E. Rohlsen Airport (STX) aren't available daily, so you'll have to take a flight with a layover. Explore your options with our filter tool. Enter your travel dates and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to STX?
You'll usually find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can vary from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Henry E. Rohlsen Airport (STX)?
To reach Henry E. Rohlsen Airport (STX) on time, pick a flight that leaves Midway Intl. Airport (MDW) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**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 Midway Intl. Airport (MDW) to Henry E. Rohlsen Airport (STX) last-minute?
Booking your ticket from MDW to STX just before your journey is generally more expensive. However, if there's some wiggle room with your travel times and dates, you could land a cheap last-minute fare.
Is it cheaper to book a MDW to STX flight and hotel package?
Booking a MDW to STX flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip in one place. Pick from our impressive range of accommodations and then add flights, activities and car rentals to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Henry E. Rohlsen Airport (STX)?
Generally, it's possible to reschedule or cancel your MDW to STX flight. However, if it's been more than 24 hours since booking, additional fees may apply. Check your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find more details on our Customer Service portal.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Henry E. Rohlsen
Airlines serving
Delta
Roundtrip price
$494
Distance
2145 mi

Book with confidence

Book with confidence

Chicago to Christiansted Flights

The cheapest times to fly from Chicago to Christiansted

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 Chicago to Christiansted are during the month of January. You can find some of the cheapest flights from Chicago to Christiansted with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Christiansted

Sunday is one of the best days to book for cheap flights from Chicago to Christiansted: 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 Chicago to Christiansted

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 Chicago to Christiansted in 2025. You can also book with separate airlines for your outbound and return journeys, from $278 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 Chicago to Christiansted 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 Chicago to Christiansted 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.

 

Chicago to Christiansted Flights
*Available to One Key members.