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

Popular airlines from Winston-Salem, NC (INT-Smith Reynolds) to Chicago O'Hare Intl. Airport (ORD)

Frequently asked questions

How much does a flight from Winston-Salem, NC (INT-Smith Reynolds) to O'Hare Intl. Airport (ORD) cost?
Snag a cheap one-way flight or cheap return flight from Winston-Salem, NC (INT-Smith Reynolds) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Winston-Salem, NC (INT-Smith Reynolds) to O'Hare Intl. Airport (ORD)?
is the cheapest month to fly from INT to ORD. Traveling during an off-peak travel window is often the key to finding a great deal.
Which airlines fly direct from Winston-Salem, NC (INT-Smith Reynolds) to O'Hare Intl. Airport (ORD)?
You can't catch a direct flight to O'Hare Intl. Airport (ORD) from Winston-Salem, NC (INT-Smith Reynolds). However, you can easily journey to Chicago without any layovers by leaving from Piedmont Triad Intl. Airport (GSO).
What is the cheapest airline that flies from Winston-Salem, NC (INT-Smith Reynolds) to O'Hare Intl. Airport (ORD)?
Use the filters on Expedia to compare airlines and find the most affordable carrier that'll fly you from INT to ORD. Then, sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Winston-Salem, NC (INT-Smith Reynolds) to O'Hare Intl. Airport (ORD)?
Nonstop flights from Winston-Salem, NC (INT-Smith Reynolds) to O'Hare Intl. Airport (ORD) 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 details and pick either "1 Stop" or "2+ Stops."
What day of the week has the most flights from INT to ORD?
Friday is typically the busiest day for flights, while Tuesday tends to be the quietest.* Remember that flight schedules can change based on various factors, such as the time of year and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Winston-Salem, NC (INT-Smith Reynolds) to O'Hare Intl. Airport (ORD)?
Book a flight from Winston-Salem, NC (INT-Smith Reynolds) to O'Hare Intl. Airport (ORD) 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.
Is it cheaper to buy a plane ticket from Winston-Salem, NC (INT-Smith Reynolds) to O'Hare Intl. Airport (ORD) last-minute?
Holding off until just before your departure to book a ticket from INT to ORD often results in higher prices. Although you may find some last-minute offers, there's no guarantee. Be flexible with your travel plans for the best chance of landing a bargain.
Is it cheaper to book an INT to ORD flight and hotel package?
Booking an INT to ORD flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip in one place. Select from our impressive range of accommodations and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Winston-Salem, NC (INT-Smith Reynolds) to O'Hare Intl. Airport (ORD)?
Typically, you can modify or cancel your INT to ORD flight. However, additional charges may apply, especially if you made your booking over 24 hours ago. Check your itinerary for the airline's fees and policies on flight changes, or if you want further details, go to our Customer Service portal.

Travel information

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

Book with confidence

Winston-Salem to Chicago Flights

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

 

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

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

 

Winston-Salem to Chicago Flights

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*Available to One Key members.