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

Popular airlines from Chicago Midway Airport (MDW) to Stewart Intl. Airport (SWF)

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Stewart Intl. Airport (SWF) cost?
Snag a cheap one-way flight or cheap return flight from Midway Intl. Airport (MDW) to Stewart Intl. Airport (SWF) 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 Midway Intl. Airport (MDW) to Stewart Intl. Airport (SWF)?
is the least expensive month to fly from MDW to SWF. Planning your trip for the off-season is often the key to finding a great deal.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Stewart Intl. Airport (SWF)?
Use the filters on Expedia to compare airlines and find the cheapest carrier that'll take you from MDW to SWF. Then, sort your results by "Price (lowest to highest)" to snag a great deal.
How many flights per day from Midway Intl. Airport (MDW) to Stewart Intl. Airport (SWF)?
Nonstop flights from Midway Intl. Airport (MDW) to Stewart Intl. Airport (SWF) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filters. Enter your travel dates and pick either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to SWF?
You'll typically find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Stewart Intl. Airport (SWF)?
Book a flight from Midway Intl. Airport (MDW) to Stewart Intl. Airport (SWF) that leaves before 3 PM to reduce the risk of cancellations and delays. Departures after this hour have a 22% higher chance of being canceled, on average.**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 Midway Intl. Airport (MDW)?
LaGuardia Airport (LGA) is the only airport in New York with direct flights from Midway Intl. Airport (MDW). Compare the available options and discover cheap fares on Expedia.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Stewart Intl. Airport (SWF) last-minute?
Last-minute bookings from MDW to SWF are typically more expensive. For the best prices, start looking for flights well ahead of time. That being said, if your travel plans are flexible, you may land a cheap ticket right before your journey.
Is it cheaper to book a MDW to SWF flight and hotel package?
You can save money by securing a MDW to SWF flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. After selecting your preferred flights and accommodations, consider adding extras such as car rentals, activities and tours.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Stewart Intl. Airport (SWF)?
In most cases, you can reschedule or cancel your MDW to SWF flight. However, there may be additional fees, especially if you booked more than 24 hours ago. Check your itinerary for the airline's fees and policies on flight changes, or if you want more details, head to our Customer Service portal.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Stewart Intl.
Distance
704 mi

Book with confidence

Book with confidence

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.

 

Chicago to Newburgh Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.