$219 Cheap Flights from Chicago (ORD) to Weyers Cave (SHD)

View $219 flight on Tue, Oct 14, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Weyers Cave, VA (SHD-Shenandoah Valley Regional)

Cheap Flights from Chicago to Weyers Cave (ORD-SHD)

Prices were available within the past 7 days and start at $219 for one-way flights and $322 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Thu, Oct 30 - Mon, Nov 3
ORD
Chicago
SHD
Weyers Cave
$322 Roundtrip, found 4 days ago
$322
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Oct 30 from Chicago to Weyers Cave, returning Mon, Nov 3, priced at $322 found 4 days ago
American Airlines
Wed, Nov 5 - Sun, Nov 9
ORD
Chicago
SHD
Weyers Cave
$337 Roundtrip, found 1 day ago
$337
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Nov 5 from Chicago to Weyers Cave, returning Sun, Nov 9, priced at $337 found 1 day ago
Contour Airlines
Tue, Oct 28 - Fri, Oct 31
ORD
Chicago
SHD
Weyers Cave
$340 Roundtrip, found 3 days ago
$340
Roundtrip
found 3 days ago
Select Contour Airlines flight, departing Tue, Oct 28 from Chicago to Weyers Cave, returning Fri, Oct 31, priced at $340 found 3 days ago
American Airlines
Fri, Nov 7 - Sun, Nov 9
ORD
Chicago
SHD
Weyers Cave
$349 Roundtrip, found 1 day ago
$349
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Nov 7 from Chicago to Weyers Cave, returning Sun, Nov 9, priced at $349 found 1 day ago
American Airlines
Fri, Oct 24 - Mon, Oct 27
ORD
Chicago
SHD
Weyers Cave
$354 Roundtrip, found 22 hours ago
$354
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Fri, Oct 24 from Chicago to Weyers Cave, returning Mon, Oct 27, priced at $354 found 22 hours ago
Contour Airlines
Wed, Oct 22 - Fri, Oct 24
ORD
Chicago
SHD
Weyers Cave
$356 Roundtrip, found 22 hours ago
$356
Roundtrip
found 22 hours ago
Select Contour Airlines flight, departing Wed, Oct 22 from Chicago to Weyers Cave, returning Fri, Oct 24, priced at $356 found 22 hours ago
Contour Airlines
Mon, Oct 27 - Fri, Oct 31
ORD
Chicago
SHD
Weyers Cave
$359 Roundtrip, found 3 days ago
$359
Roundtrip
found 3 days ago
Select Contour Airlines flight, departing Mon, Oct 27 from Chicago to Weyers Cave, returning Fri, Oct 31, priced at $359 found 3 days ago
American Airlines
Wed, Nov 5 - Sun, Nov 9
ORD
Chicago
SHD
Weyers Cave
$362 Roundtrip, found 1 day ago
$362
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Nov 5 from Chicago to Weyers Cave, returning Sun, Nov 9, priced at $362 found 1 day ago
American Airlines
Fri, Oct 24 - Mon, Oct 27
ORD
Chicago
SHD
Weyers Cave
$364 Roundtrip, found 22 hours ago
$364
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Fri, Oct 24 from Chicago to Weyers Cave, returning Mon, Oct 27, priced at $364 found 22 hours ago
United
Tue, Dec 16 - Tue, Dec 30
ORD
Chicago
SHD
Weyers Cave
$373 Roundtrip, found 2 days ago
$373
Roundtrip
found 2 days ago
Select United flight, departing Tue, Dec 16 from Chicago to Weyers Cave, returning Tue, Dec 30, priced at $373 found 2 days ago

Alternative airports near Weyers Cave

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

Select flight to Charlottesville-Albemarle CHO. Average driving time to city center is 1 hour 3 minutes. Flights from $551
CHO
Charlottesville-Albemarle
Average driving time to city center1 h 3 min
Flights from $551

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Shenandoah Valley Regional Airport (SHD) cost?
Snag a cheap one-way flight from $219 or cheap return flight from $322 from O'Hare Intl. Airport (ORD) to Shenandoah Valley Regional Airport (SHD) 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 O'Hare Intl. Airport (ORD) to Shenandoah Valley Regional Airport (SHD)?
Traveling in October may help you find better deals, as it's the cheapest month for flights between ORD and SHD. You'll often find the lowest prices during the off-season.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Shenandoah Valley Regional Airport (SHD)?
To find the cheapest airline flying from ORD to SHD, use Expedia's filter tool. Tailor your search based on what matters most to you, such as preferred carriers and number of stops. You can then sort your results by "Price (lowest to highest)" to see the cheapest flights first.
How many flights per day from O'Hare Intl. Airport (ORD) to Shenandoah Valley Regional Airport (SHD)?
There aren't any daily direct flights from O'Hare Intl. Airport (ORD) to Shenandoah Valley Regional Airport (SHD). 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 ORD to SHD?
Friday is generally the busiest day for flights, while Tuesday is often the quietest.* Keep in mind that flight schedules can change depending on a number of factors, such as the time of year and carrier.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What airline has the least delays from ORD to SHD?
United Airlines has the best performance for on-time direct flights from O'Hare Intl. Airport (ORD) to Shenandoah Valley Regional Airport (SHD), with an on-time score of 81%. Use the Expedia App to look up your flight status before you jet off and get real-time updates about any changes.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Shenandoah Valley Regional Airport (SHD)?
To avoid potential delays on the O'Hare Intl. Airport (ORD) to Shenandoah Valley Regional Airport (SHD) route, fly before 3 PM. Later departures 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.
What airports do you fly into for Staunton from O'Hare Intl. Airport (ORD)?
Charlottesville-Albemarle Airport (CHO) is the only airport in Staunton with direct flights from O'Hare Intl. Airport (ORD). Browse the options and find cheap fares on Expedia.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Shenandoah Valley Regional Airport (SHD) last-minute?
Booking your flight from ORD to SHD shortly before your getaway is generally more expensive. But if you're flexible with your itinerary, you could snag a cheap last-minute fare.
Is it cheaper to book an ORD to SHD flight and hotel package?
Securing an ORD to SHD flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip in one place. Select from our extensive range of accommodations and then add activities, flights 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 O'Hare Intl. Airport (ORD) to Shenandoah Valley Regional Airport (SHD)?
In most cases, you can reschedule or cancel your ORD to SHD flight. However, there may be additional fees, especially if you booked more than 24 hours ago. Check your itinerary for the airline's guidelines and fees on flight changes, or if you want further information, head to our Customer Service portal.

Travel information

Travel information

Origin airport
O'Hare Intl.
Destination airport
Shenandoah Valley Regional
Airlines serving
Contour Airlines
Roundtrip price
$322
Distance
540 mi

Book with confidence

Book with confidence

Chicago to Weyers Cave Flights

The cheapest times to fly from Chicago to Weyers Cave

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

 

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

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

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 Weyers Cave in 2025. You can also book with separate airlines for your outbound and return journeys, from $219 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 Weyers Cave 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 Weyers Cave 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 Weyers Cave Flights

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*Available to One Key members.