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

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

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 30% on select hotels after you book a flight*
  • one key icon
    Earn twice
    Earn your airline miles on top of our OneKeyCash
    Learn about One Key
Find available prices by choosing your travel dates.
Flights from Newburgh (SWF) to Chicago (ORD)
Origin airport
Stewart Intl.
Destination airport
O'Hare Intl.
Distance
712 mi

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.

Frequently asked questions

Is it cheaper to buy a plane ticket from Stewart Intl. Airport (SWF) to O'Hare Airport last minute?
Being a spontaneous soul is a fantastic way to travel around, but it’s not necessarily the smartest way to get your hands on a cheap fare. It’s better to book your Stewart Intl. Airport to ORD trip well in advance instead of leaving it till the last minute. Based on flight pricing and demand studies in 2022, we have found that the best time to book domestic flights is between 28 – 35 days ahead of the departure date, and international flights three to four months in advance. You can unleash your spontaneous side when you’re discovering ORD!
What airports do you fly into for Chicago from New York?
O’Hare Intl. Airport (ORD), Midway Intl. Airport (MDW) and Lewis University Airport (LOT) are your options when connecting from New York to Chicago. About 16 mi northwest of downtown Chicago, O’Hare Intl. Airport (ORD) is the city’s main entry point. Think about factors such as flight arrival and departure times and the distance to your hotel before deciding where you fly into. Wrigley Field and Millennium Park are two terrific attractions to put on your must-see list when you arrive.
Can I change the date of my flight from SWF to O'Hare Intl. Airport (ORD)?
It’s a piece of cake to make changes to your Stewart Intl. Airport to O’Hare Airport trip yourself. Simply go to the Expedia Trips portal and choose “change flight.” Look for new flights and choose the one that better suits your plans. You’ll see an estimate of any flight change costs. You can also find your way to our Customer Service portal to chat to our Virtual Agent and get answers to your questions.

Explore a world of travel with Expedia

*Available to One Key members.