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

Popular airlines from Stewart Intl. Airport (SWF) to Chicago O'Hare Intl. Airport (ORD)

Frequently asked questions

How much does a flight from Stewart Intl. Airport (SWF) to O'Hare Intl. Airport (ORD) cost?
Secure a cheap one-way flight or cheap return flight from Stewart Intl. Airport (SWF) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Stewart Intl. Airport (SWF) to O'Hare Intl. Airport (ORD)?
Flying in can help you save, as it's the cheapest month for flights between SWF and ORD. You'll usually find the lowest prices during the off-season.
Which airlines fly direct from Stewart Intl. Airport (SWF) to O'Hare Intl. Airport (ORD)?
You can't catch a direct flight to O'Hare Intl. Airport (ORD) from Newburgh, NY (SWF-Stewart Intl.). However, you can easily journey to Chicago without any layovers by taking off from John F. Kennedy Intl. Airport (JFK).
What is the cheapest airline that flies from Stewart Intl. Airport (SWF) to O'Hare Intl. Airport (ORD)?
Expedia's filter tool lets you easily compare airlines, flight times and baggage options all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest SWF to ORD flight.
How many flights per day from Stewart Intl. Airport (SWF) to O'Hare Intl. Airport (ORD)?
There are no daily nonstop flights available from Stewart Intl. Airport (SWF) to O'Hare Intl. Airport (ORD). But you can opt for flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be on your way in no time.
What day of the week has the most flights from SWF to ORD?
Friday is generally the busiest day for flights, while Tuesday is often the quietest.* Keep in mind that flight schedules can vary depending on various 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 Stewart Intl. Airport (SWF) to O'Hare Intl. Airport (ORD)?
Choose a flight from Stewart Intl. Airport (SWF) to O'Hare Intl. Airport (ORD) that leaves before 3 PM to reduce the risk of delays and cancellations. Later departures are on average 22% more likely to be canceled.**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 Stewart Intl. Airport (SWF) to O'Hare Intl. Airport (ORD) last-minute?
Booking your plane ticket from SWF to ORD just before your getaway is typically more expensive. However, if you're flexible with your departure dates and times, you could score a cheap last-minute fare.
Is it cheaper to book a SWF to ORD flight and hotel package?
Opting for a SWF to ORD flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels in one place. Choose from our wide range of accommodations and then add activities, flights and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Stewart Intl. Airport (SWF) to O'Hare Intl. Airport (ORD)?
Typically, it's possible to cancel or reschedule your SWF to ORD flight. However, if it's been more than 24 hours since booking, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find more details on our Customer Service portal.

Travel information

Origin airport
Stewart Intl.
Destination airport
O'Hare Intl.
Distance
712 mi

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Newburgh to Chicago Flights

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

 

The best time to book a flight from Newburgh to Chicago

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

 

Newburgh to Chicago Flights

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*Available to One Key members.