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

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

Frequently asked questions

How much does a flight from Stewart Intl. Airport (SWF) to Midway Intl. Airport (MDW) cost?
Lock in a cheap one-way flight or cheap return flight from Stewart Intl. Airport (SWF) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Stewart Intl. Airport (SWF) to Midway Intl. Airport (MDW)?
is the least expensive month to fly from SWF to MDW. Traveling outside of peak seasons is often the key to finding better deals on flights.
What is the cheapest airline that flies from Stewart Intl. Airport (SWF) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare airlines, flight times and baggage options all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest SWF to MDW flight.
How many flights per day from Stewart Intl. Airport (SWF) to Midway Intl. Airport (MDW)?
You'll need to catch a flight with a layover if you're traveling from Stewart Intl. Airport (SWF) to Midway Intl. Airport (MDW). There are no daily direct flights on this route. However, just filter your search to include one or two stops to find an option that works for you.
What day of the week has the most flights from SWF to MDW?
You'll typically find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary 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 Stewart Intl. Airport (SWF) to Midway Intl. Airport (MDW)?
To avoid potential delays on the Stewart Intl. Airport (SWF) to Midway Intl. Airport (MDW) route, aim to fly before 3 PM. Departures after this hour have a 22% higher chance of being 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 Midway Intl. Airport (MDW) last-minute?
Last-minute bookings from SWF to MDW are typically more expensive. For the best rates, start looking for flights as soon as possible. That being said, if you're flexible with your travel dates, it's possible to land a cheap ticket right before your trip.
Is it cheaper to book a SWF to MDW flight and hotel package?
Securing a SWF to MDW flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip all in one place. Select from our impressive range of accommodations and then add car rentals, flights and activities 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 Midway Intl. Airport (MDW)?
If you booked your SWF to MDW flight within the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the ticket type you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for further details.

Travel information

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

Book with confidence

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

Explore a world of travel with Expedia

*Available to One Key members.