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

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Flight from Newburgh to Chicago route information
Origin airport
Stewart Intl.
Destination airport
Midway Intl.
Distance
1127 km

Compare flights from Newburgh to Chicago easily and book with confidence

For travelling on business or for pleasure, Expedia makes it easy to book your flights from Newburgh to Chicago. Operating between them flights per day, airlines cover the route. And fly direct, getting you to Midway Intl. in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from Stewart Intl. to Midway Intl..  

To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights. 

Grab a great deal on your flight from Stewart Intl. (SWF) to Midway Intl. (MDW) 

The easiest way to view the best deals on flights from Newburgh to Chicago today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from Stewart Intl. to Midway Intl. start at just and range up to .  

To find an even better deal, try  

  • being flexible on your dates – midweek flights can be cheaper
  • looking for other airports near Newburgh and Chicago
  • booking your flight during , the cheapest month on this route
  • varying your flight times – early morning and late at night are sometimes cheaper 

Why you should book your Newburgh to Chicago flight with Expedia!

We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from Stewart Intl. to Midway Intl. for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.  

Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.  

Frequently asked questions

How much is a flight from Stewart Intl. Airport to Midway Airport?
Start packing your suitcase, because round-trip flights between Stewart Intl. Airport (SWF) and Midway Airport start from . That’s based on fares advertised within the last 7 days on Expedia for flights departing within the next year. Prices can rise quickly, so book now to nab the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Stewart Intl. Airport to Midway Intl. Airport (MDW)?
Each airline has its own set of terms and conditions. If you decide to cancel your trip, visit our Customer Service Portal.
How do I find cheap flights from SWF to MDW that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you’re searching for SWF to Chicago Airport flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from SWF to Midway Intl. Airport (MDW)?
With a flight distance of 1,150 kilometres, it’s just a hop from SWF to MDW. It might be a quick journey, but it’s still worth bringing something to read.
Which airlines fly direct from SWF to Chicago Airport?
Unfortunately, there are no airlines that directly fly between Stewart Intl. Airport (SWF) and MDW. You’ll need to book a flight with at least one stop.
Are Stewart Intl. Airport (SWF) to MDW flight tickets cheaper when they're purchased at the last minute?
Booking your trip from SWF to Midway Intl. Airport (MDW) last minute could save you some cash. However, it could end up costing a good deal more! If you’d prefer not to take any chances, book well ahead of your departure date. In fact, Expedia has some of the best bargains up to a year in advance. If your preferred carrier hasn’t released tickets yet, check back regularly as deals are updated on Expedia all the time.
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