The cheapest times to fly from SWF to ORD are

  • January 1st to March 11th
  • April 16th to June 10th (except the weeks of May 7th and May 14th)
  • July 2nd to July 22nd
  • August 27th to September 9th

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 SWF to ORD is late January and early February. Prices can be as high as $725 for Sunday flights during early August, or as low as $164 for Tuesday flights around late January and early February.


When to Fly to Chicago

Flying from Newburgh/Poughkeepsie, NY (SWF) to Chicago, IL (ORD) will usually cost between $171 to $476 per person if booking more than four weeks in advance. On average the very cheapest time to fly is late January and early February with an average ticket price of $190. Due to high demand the most expensive time to fly is early August, with an average price of $498. Planning your trip to low-cost times can easily save you $309 on economy flights and even more on first-class flights. Generally, any price below $294 can be considered a good price for a round-trip SWF to ORD flight.

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

SWF to ORD Flight Prices

Compared to other flights, the SWF to ORD flight is much cheaper than the average and costs much less than the average flight leaving from Newburgh. The average price per mile (for a direct flight) is $0.26, 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 $132 (35%) 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 $240. Return trip prices are from the ORD to SWF 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 SWF 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 2 hour 16 minutes may not be realistic.


Flight Questions Answered

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

Which airlines fly this route?

You can find 4 major airlines flying this route most often: American, Delta, JetBlue, United, and potentially more during busy seasons.

How far away is it from Chicago O’Hare International Airport to Stewart International Airport?

The distance between the two airports is roughly 711 miles or 1144 kilometers.

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

The real-world flight time for a nonstop SWF to ORD flight is about 2 hour 16 minutes.

How many flights go between Newburgh/Poughkeepsie, NY and Chicago, IL?

It depends on the day of the week and the date, but a typical day might have around 82 available flights from SWF to ORD.


Airport Location Info


Departing Airport

Origination code SWF
Origination airport name Stewart International Airport
City Newburgh/Poughkeepsie, NY
Country the United States
Latitude 41.5
Longitude -74.1

Return Airport

Destination code ORD
Destination airport name Chicago O’Hare International Airport
City Chicago, IL
Country the United States
Latitude 42
Longitude -87.9


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.