Cheap Flights from Chicago (MDW) to Winston-Salem (INT)

Popular airlines from Chicago Midway Airport (MDW) to Winston-Salem, NC (INT-Smith Reynolds)

Alternative airports near Winston-Salem

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Piedmont Triad Intl. GSO. Cheapest option available. Flights from $849
GSO
Piedmont Triad Intl.
Cheapest
Flights from $849

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Winston-Salem, NC (INT-Smith Reynolds) cost?
Grab a cheap one-way flight or cheap return flight from Midway Intl. Airport (MDW) to Winston-Salem, NC (INT-Smith Reynolds) 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 Winston-Salem, NC (INT-Smith Reynolds)?
Traveling in is a good way to save, as it's the cheapest month for flights between MDW and INT. You'll often find the lowest prices during off-peak months.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Winston-Salem, NC (INT-Smith Reynolds)?
To find the cheapest airline flying from MDW to INT, use Expedia's filter tool. Customize your search based on your travel needs, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to list the most affordable options first.
How many flights per day from Midway Intl. Airport (MDW) to Winston-Salem, NC (INT-Smith Reynolds)?
You'll have to book a flight with a layover if you're traveling from Midway Intl. Airport (MDW) to Winston-Salem, NC (INT-Smith Reynolds). There are no daily direct flights on this route. However, just filter your search to include one or two stops to find the best option for your trip.
What day of the week has the most flights from MDW to INT?
You'll typically find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can vary from season to season and during public holidays or peak travel times.*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 Winston-Salem, NC (INT-Smith Reynolds)?
To avoid possible delays on the Midway Intl. Airport (MDW) to Winston-Salem, NC (INT-Smith Reynolds) route, travel before 3 PM. Flights after this time are 22% more likely to be 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 Midway Intl. Airport (MDW) to Winston-Salem, NC (INT-Smith Reynolds) last-minute?
Last-minute fares from MDW to INT are typically more expensive. For the lowest rates, start looking for flights early. That being said, if you're flexible with your travel dates, you may score a cheap ticket right before your trip.
Is it cheaper to book a MDW to INT flight and hotel package?
Compared with arranging hotels and flights separately, booking a MDW to INT flight and hotel package with Expedia could result in significant savings. What's more, having everything in one convenient place will take the hassle out of travel planning. Just secure your flights and choose from our extensive range of stays, then personalize your trip with extras like tours and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Winston-Salem, NC (INT-Smith Reynolds)?
If you booked your MDW to INT flight within the last 24 hours, you may be able to cancel or modify it without any fees. Depending on the airline and the fare type you purchased, additional charges may apply for changes after 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

Travel information

Origin airport
Midway Intl.
Destination airport
Smith Reynolds
Distance
561 mi

Book with confidence

Book with confidence

Chicago to Winston-Salem Flights

The cheapest times to fly from Chicago to Winston-Salem

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 Winston-Salem are during the month of . You can find some of the cheapest flights from Chicago to Winston-Salem with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Winston-Salem

Sunday is one of the best days to book for cheap flights from Chicago to Winston-Salem: 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 Winston-Salem

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 Winston-Salem 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 Winston-Salem 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 Winston-Salem 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 Winston-Salem Flights

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Explore a world of travel with Expedia

*Available to One Key members.