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

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

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Find available prices by choosing your travel dates.
Flights from Newburgh (SWF) to Chicago (MDW)
Origin airport
Stewart Intl.
Destination airport
Midway Intl.
Distance
704 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

How much does a flight from Stewart Intl. Airport (SWF) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from SWF to MDW 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 SWF to MDW?
The cheapest flights from SWF to MDW 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 SWF to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from SWF to MDW. Sort your results by “Price (lowest to highest)” to snap up a great deal.
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.

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*Available to One Key members.