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

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

  • 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
Flights from Chicago (MDW) to Newburgh (SWF)
Origin airport
Midway Intl.
Destination airport
Stewart Intl.
Distance
704 mi

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.

 

Frequently asked questions

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

Explore a world of travel with Expedia

*Available to One Key members.