Cheap Flights from Chicago (MDW) to Winchester (WGO)

Popular airlines from Chicago Midway Airport (MDW) to Winchester, VA (WGO-Winchester Regional)

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Winchester, VA (WGO-Winchester Regional) cost?
Secure a cheap one-way flight or cheap return flight from Midway Intl. Airport (MDW) to Winchester, VA (WGO-Winchester Regional) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Winchester, VA (WGO-Winchester Regional)?
The cheapest month to fly from MDW to WGO is , when there's less demand. Off-peak months are typically when better flight deals are available between these airports.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Winchester, VA (WGO-Winchester Regional)?
Expedia's filter tool lets you easily compare different airlines, flight durations and fares all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest MDW to WGO flight.
How many flights per day from Midway Intl. Airport (MDW) to Winchester, VA (WGO-Winchester Regional)?
You'll need to hop on a flight with a layover when traveling from Midway Intl. Airport (MDW) to Winchester, VA (WGO-Winchester Regional). Direct flights don't operate daily on this route. However, simply 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 WGO?
Friday is typically the busiest day for flights, while Tuesday tends to be the quietest.* Keep in mind that flight schedules can vary based on various factors, including the airline and season.*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 Winchester, VA (WGO-Winchester Regional)?
Book a flight from Midway Intl. Airport (MDW) to Winchester, VA (WGO-Winchester Regional) that leaves before 3 PM to reduce the risk of cancellations and delays. Departures after this time are on average 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 Winchester, VA (WGO-Winchester Regional) last-minute?
Last-minute bookings from MDW to WGO are typically more expensive. To secure the best rates, start looking for flights ahead of time. That said, if you can play around with your travel dates, you may score a cheap ticket right before you leave.
Is it cheaper to book a MDW to WGO flight and hotel package?
Booking a MDW to WGO flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip all in one place. Pick from our impressive range of hotels and then add car rentals, flights and activities to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Winchester, VA (WGO-Winchester Regional)?
In most instances, you can cancel or reschedule your MDW to WGO flight. However, there may be additional fees, especially if you made your booking more than 24 hours ago. Check your itinerary for the airline's policies and fees on flight changes, or if you want more details, head to our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Winchester Regional
Distance
535 mi

Book with confidence

Chicago to Winchester Flights

The cheapest times to fly from Chicago to Winchester

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

 

The best time to book a flight from Chicago to Winchester

Sunday is one of the best days to book for cheap flights from Chicago to Winchester: 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 Winchester

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 Winchester 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 Winchester 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 Winchester 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 Winchester Flights

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*Available to One Key members.