The cheapest times to fly from STX to ORD are

  • January 8th to February 25th (except the week of February 5th)
  • April 23rd to May 6th
  • August 6th to December 9th (except the week of November 26th)

based on data collected exclusively by Champion Traveler across tens of millions of flights. Among all the dates above, the very cheapest time to fly from STX to ORD is late October. Prices can be as high as $1132 for Sunday flights during early to mid March, or as low as $465 for Tuesday flights around late October.


When to Fly to Chicago

Flying from Christiansted, VI (STX) to Chicago, IL (ORD) will usually cost between $530 to $914 per person if booking more than four weeks in advance. On average the very cheapest time to fly is late October with an average ticket price of $553. Due to high demand the most expensive time to fly is early to mid March, with an average price of $883. Planning your trip to low-cost times can easily save you $331 on economy flights and even more on first-class flights. Generally, any price below $707 can be considered a good price for a round-trip STX to ORD flight.

See below for a graph of average weekly prices for the STX to ORD route. All prices are for round-trip tickets in USD.

STX to ORD Flight Prices

Compared to other flights, the STX to ORD flight is cheaper than the average and costs much less than the average flight leaving from Saint Croix. The average price per mile (for a direct flight) is $0.2, which is below average.


Flight Prices by Day of the Week

Tuesday is usually the cheapest day to depart and return on this flight. Sundays are the most expensive days to fly out or take a return trip. Selecting flights on the least expensive days could save you up to $115 (15%) on this flight.

Departing prices are for round-trip flights returning on the day of departure. For example, a flight departing on Tuesday and returning a week later will cost an average of $651. Return trip prices are from the ORD to STX flight, and often highlight the quality of our data in showing the same trend.

Departing Prices by Day

Departure Day Prices

Return Trip Prices by Day

Return Day Prices


Nonstop Flights and Layovers

Travelers looking to fly from STX to ORD can generally find a 1-layover flight. Because there is not usually a direct flight option the real-world direct flight time of 4 hour 52 minutes may not be realistic.


Flight Hacking STX to ORD

Flight hacking is when you book two tickets instead of a layover, sometimes with different airlines. You will need to either bring only a carry-on bag (highly recommended) or leave yourself plenty of time to go through security again. Flight hacking is completely allowed, but airlines don’t always tell you the cheapest way to get from STX to ORD — but Champion Traveler does!

Hack #1: San Juan, PR (STX > SJU > ORD)

  • Price for both tickets: $540
  • Average savings: $168 (23.69%)

See STX to SJU flights

Hack #2: Miami, FL (STX > MIA > ORD)

  • Price for both tickets: $617
  • Average savings: $90 (12.73%)

See STX to MIA flights

Hack #3: Charlotte Amalie, VI (STX > STT > ORD)

  • Price for both tickets: $621
  • Average savings: $86 (12.16%)

See STX to STT flights


Flight Questions Answered

Still have questions about flying from STX to ORD? We’ve got answers.

Which airlines fly this route?

You can find 8 major airlines flying this route most often: American, Cape Air, Delta, JetBlue, Seaborne Airlines, Silver Airways, Spirit, United, and potentially more during busy seasons.

How far away is it from Chicago O’Hare International Airport to Henry E. Rohlsen Airport?

The distance between the two airports is roughly 2160 miles or 3476 kilometers.

How long does it take to fly from STX to ORD?

The real-world flight time for a nonstop STX to ORD flight is about 4 hour 52 minutes.

How many flights go between Christiansted, VI and Chicago, IL?

It depends on the day of the week and the date, but a typical day might have around 18 available flights from STX to ORD.


Airport Location Info


Departing Airport

Origination codeSTX
Origination airport nameHenry E. Rohlsen Airport
CityChristiansted, VI
Countrythe United States

Return Airport

Destination codeORD
Destination airport nameChicago O’Hare International Airport
CityChicago, IL
Countrythe United States


Other Resources

Please note that while we’ve worked hard to analyzed tens of millions of flights to get you this data, we do not calculate current live prices or guarantee pricing. Please see our partners using the links above for current offers.