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

Popular airlines from Chicago O'Hare Intl. Airport (ORD) 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 $249
GSO
Piedmont Triad Intl.
Cheapest
Flights from $249

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Winston-Salem, NC (INT-Smith Reynolds) cost?
Lock in a cheap one-way flight or cheap return flight from O'Hare Intl. Airport (ORD) to Winston-Salem, NC (INT-Smith Reynolds) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Winston-Salem, NC (INT-Smith Reynolds)?
The cheapest month to fly from ORD to INT is , when there's less demand. Off-peak months are often when you'll find lower airfares between these airports.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Winston-Salem, NC (INT-Smith Reynolds)?
Expedia's filter tool lets you easily compare airlines, flight times and baggage options all in one place. Select your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest ORD to INT flight.
How many flights per day from O'Hare Intl. Airport (ORD) to Winston-Salem, NC (INT-Smith Reynolds)?
You'll need to hop on a flight with a layover when traveling from O'Hare Intl. Airport (ORD) to Winston-Salem, NC (INT-Smith Reynolds). Direct flights don't operate daily on this route. However, just filter your search to include one or more stops to discover an option that works for you.
What day of the week has the most flights from ORD to INT?
You'll usually find Tuesday the quietest day for flights, while Fridays tend to be 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 O'Hare Intl. Airport (ORD) to Winston-Salem, NC (INT-Smith Reynolds)?
Select a flight from O'Hare Intl. Airport (ORD) to Winston-Salem, NC (INT-Smith Reynolds) that takes off before 3 PM to reduce the risk of cancellations and delays. Later departures 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 Winston - Salem from O'Hare Intl. Airport (ORD)?
If you're flying on a direct flight from O'Hare Intl. Airport (ORD) to Winston - Salem, Piedmont Triad Intl. Airport (GSO) is the only airport you can land at.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Winston-Salem, NC (INT-Smith Reynolds) last-minute?
Last-minute bookings from ORD to INT are usually more expensive. To secure the lowest prices, start searching for flights ahead of time. That said, if you're flexible with your travel plans, it's possible to land a cheap fare just before your departure.
Is it cheaper to book an ORD to INT flight and hotel package?
Compared with arranging hotels and flights separately, booking an ORD to INT flight and hotel package with Expedia could result in significant savings. What's more, having everything in one easy place takes the hassle out of planning your trip. Just secure your flights and choose from our extensive range of hotels, then customize your trip with extras like tours, activities and car rentals.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Winston-Salem, NC (INT-Smith Reynolds)?
If you booked your ORD to INT flight in the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the fare type you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Smith Reynolds
Distance
576 mi

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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*Available to One Key members.