Cheap Flights from Chicago (ORD) to Newburgh (SWF)

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Find available prices by choosing your travel dates.
Flights from Chicago (ORD) to Newburgh (SWF)
Origin airport
O'Hare Intl.
Destination airport
Stewart Intl.
Distance
712 mi

Chicago to Newburgh Flights

The cheapest times to fly from Chicago to Newburgh

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

The best time to book a flight from Chicago to Newburgh

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

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 Newburgh in 2025. You can also book with separate airlines for your outbound and return journeys, from 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 Newburgh 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 Newburgh 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 O'Hare Intl. Airport (ORD) to Stewart Intl. Airport (SWF) cost?
Discover the latest flight deals from ORD to SWF by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from ORD to SWF?
The cheapest flights from ORD to SWF are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from ORD to SWF?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from ORD to SWF. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from O'Hare Intl. Airport (ORD) to Stewart Intl. Airport (SWF)?
You’ll need to catch a flight with a layover when traveling from O’Hare Intl. Airport (ORD) to Stewart Intl. Airport (SWF). There are no daily direct flights on this route. However, just filter your search to include one or more stops to find an option that works for you.
What day of the week has the most flights from ORD to SWF?
Typically you’ll have the most choice when it comes to flights on a Friday. Tuesdays are often the quietest.* However, this can vary depending on the season, airline and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Stewart Intl. Airport (SWF)?
To reach Stewart Intl. Airport (SWF) without delays, opt for a flight that leaves O’Hare Intl. Airport (ORD) before 3 PM. The chance 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.
What airports do you fly into for New York from O'Hare Intl. Airport (ORD)?
O’Hare Intl. Airport (ORD) has direct flights to New York. Here are a few of the airports you can fly to without stops:

  • LaGuardia Airport (LGA)
  • Liberty Intl. Airport (EWR)
  • John F. Kennedy Intl. Airport (JFK)

Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Stewart Intl. Airport (SWF) last-minute?
Holding off until just before your trip to book a ticket from ORD to SWF generally means paying more. While you might find some last-minute offers, they aren’t always guaranteed. Keep your travel schedule open to maximize your chances of snagging a bargain.
Is it cheaper to book an ORD to SWF flight and hotel package?
Securing an ORD to SWF flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels in one place. Pick from our extensive range of hotels and then add activities, car rentals and flights 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 O'Hare Intl. Airport (ORD) to Stewart Intl. Airport (SWF)?
If you reserved your ORD to SWF flight within 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 purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal for more details.

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*Available to One Key members.