Cheap Flights from Weyers Cave (SHD) to Chicago (PWK)

Popular airlines from Weyers Cave, VA (SHD-Shenandoah Valley Regional) to Chicago, IL (PWK-Chicago Executive)

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $536
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $536

Frequently asked questions

How much does a flight from Shenandoah Valley Regional Airport (SHD) to Chicago Executive Airport (PWK) cost?
Get a cheap one-way flight or cheap return flight from Shenandoah Valley Regional Airport (SHD) to Chicago Executive Airport (PWK) 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 Shenandoah Valley Regional Airport (SHD) to Chicago Executive Airport (PWK)?
Planning your getaway for is a good way to save, as it's the cheapest month for flights between SHD and PWK. You'll usually find the lowest fares during off-peak months.
What is the cheapest airline that flies from Shenandoah Valley Regional Airport (SHD) to Chicago Executive Airport (PWK)?
Expedia's filter tool lets you easily compare travel time, airlines and fares all in one place. Select your preferences, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest SHD to PWK flight.
How many flights per day from Shenandoah Valley Regional Airport (SHD) to Chicago Executive Airport (PWK)?
There are no daily direct flights from Shenandoah Valley Regional Airport (SHD) to Chicago Executive Airport (PWK). But you can choose flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be soaring above the clouds in no time at all.
What day of the week has the most flights from SHD to PWK?
Friday is typically the busiest day for flights, while Tuesday is often the quietest.* Remember that flight schedules can vary based on a number of 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 Shenandoah Valley Regional Airport (SHD) to Chicago Executive Airport (PWK)?
To avoid possible delays on the Shenandoah Valley Regional Airport (SHD) to Chicago Executive Airport (PWK) route, travel before 3 PM. Later flights have a 22% higher chance of being 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 Shenandoah Valley Regional Airport (SHD) to Chicago Executive Airport (PWK) last-minute?
Booking your plane ticket from SHD to PWK just before your trip is typically more expensive. However, if you're flexible with your itinerary, you could land a cheap last-minute fare.
Is it cheaper to book a SHD to PWK flight and hotel package?
You'll typically save money by securing a SHD to PWK flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one place. After selecting your ideal accommodations and flights, consider adding extras including car rentals, tours and activities.
Can I cancel or change the date of my flight from Shenandoah Valley Regional Airport (SHD) to Chicago Executive Airport (PWK)?
If you booked your SHD to PWK flight within the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the type of fare you have, 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
Shenandoah Valley Regional
Destination airport
Chicago Executive
Distance
544 mi

Book with confidence

Weyers Cave to Chicago Flights

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

 

The best time to book a flight from Weyers Cave to Chicago

Sunday is one of the best days to book for cheap flights from Weyers Cave 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 Weyers Cave 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 Weyers Cave 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 Weyers Cave 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 Weyers Cave 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.

 

Weyers Cave to Chicago Flights

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*Available to One Key members.