$153 Cheap Flights from Weyers Cave (SHD) to Chicago (ORD)

View $153 flight on Mon, Nov 24, 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at $153 for one-way flights and $234 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, Feb 14 - Sun, Feb 15
SHD
Weyers Cave
ORD
Chicago
$234 Roundtrip, found 1 day ago
$234
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Feb 14 from Weyers Cave to Chicago, returning Sun, Feb 15, priced at $234 found 1 day ago
American Airlines
Tue, Mar 10 - Sat, Mar 14
SHD
Weyers Cave
ORD
Chicago
$264 Roundtrip, found 2 days ago
$264
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Mar 10 from Weyers Cave to Chicago, returning Sat, Mar 14, priced at $264 found 2 days ago
American Airlines
Sat, Feb 14 - Sun, Feb 15
SHD
Weyers Cave
ORD
Chicago
$277 Roundtrip, found 1 day ago
$277
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Feb 14 from Weyers Cave to Chicago, returning Sun, Feb 15, priced at $277 found 1 day ago
American Airlines
Tue, Apr 28 - Sat, May 9
SHD
Weyers Cave
ORD
Chicago
$284 Roundtrip, found 6 hours ago
$284
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Tue, Apr 28 from Weyers Cave to Chicago, returning Sat, May 9, priced at $284 found 6 hours ago
American Airlines
Fri, Feb 20 - Mon, Feb 23
SHD
Weyers Cave
ORD
Chicago
$291 Roundtrip, found 4 days ago
$291
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Feb 20 from Weyers Cave to Chicago, returning Mon, Feb 23, priced at $291 found 4 days ago
Contour Airlines
Wed, Dec 3 - Sat, Dec 6
SHD
Weyers Cave
ORD
Chicago
$298 Roundtrip, found 3 days ago
$298
Roundtrip
found 3 days ago
Select Contour Airlines flight, departing Wed, Dec 3 from Weyers Cave to Chicago, returning Sat, Dec 6, priced at $298 found 3 days ago
American Airlines
Sun, May 3 - Sat, May 9
SHD
Weyers Cave
ORD
Chicago
$304 Roundtrip, found 6 hours ago
$304
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Sun, May 3 from Weyers Cave to Chicago, returning Sat, May 9, priced at $304 found 6 hours ago
American Airlines
Mon, May 4 - Sat, May 9
SHD
Weyers Cave
ORD
Chicago
$309 Roundtrip, found 6 hours ago
$309
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Mon, May 4 from Weyers Cave to Chicago, returning Sat, May 9, priced at $309 found 6 hours ago
Contour Airlines
Sat, Dec 6 - Sun, Dec 7
SHD
Weyers Cave
ORD
Chicago
$310 Roundtrip, found 4 days ago
$310
Roundtrip
found 4 days ago
Select Contour Airlines flight, departing Sat, Dec 6 from Weyers Cave to Chicago, returning Sun, Dec 7, priced at $310 found 4 days ago
American Airlines
Thu, Feb 26 - Sat, Mar 14
SHD
Weyers Cave
ORD
Chicago
$314 Roundtrip, found 20 hours ago
$314
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Thu, Feb 26 from Weyers Cave to Chicago, returning Sat, Mar 14, priced at $314 found 20 hours ago

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 $438
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $438

Frequently asked questions

How much does a flight from Shenandoah Valley Regional Airport (SHD) to O'Hare Intl. Airport (ORD) cost?
Secure a cheap one-way flight from $153 or cheap return flight from $234 from Shenandoah Valley Regional Airport (SHD) to O'Hare Intl. Airport (ORD) 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 O'Hare Intl. Airport (ORD)?
February is the cheapest month to fly from SHD to ORD. Avoiding peak travel times is often the key to scoring lower fares.
Which airlines fly direct from Shenandoah Valley Regional Airport (SHD) to O'Hare Intl. Airport (ORD)?
There are no direct flights from Weyers Cave, VA (SHD-Shenandoah Valley Regional) to O'Hare Intl. Airport (ORD). However, you'll find other airports that have nonstop flights. Begin your journey at Charlottesville-Albemarle Airport (CHO) and head straight to Chicago without a layover.
What is the cheapest airline that flies from Shenandoah Valley Regional Airport (SHD) to O'Hare Intl. Airport (ORD)?
To find the cheapest airline that'll fly you from SHD to ORD, use Expedia's filter tool. Customize your search based on your travel needs, such as preferred carriers and cabin class. You can then sort your results by "Price (lowest to highest)" to discover the cheapest flight right away.
How many flights per day from Shenandoah Valley Regional Airport (SHD) to O'Hare Intl. Airport (ORD)?
You'll need to hop on a flight with a layover if you're traveling from Shenandoah Valley Regional Airport (SHD) to O'Hare Intl. Airport (ORD). Direct flights don't operate daily on this route. However, simply filter your search to include one or more stops to discover the best option for your trip.
What day of the week has the most flights from SHD to ORD?
You'll generally find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change from season to season and during public holidays or peak travel times.*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 O'Hare Intl. Airport (ORD)?
To avoid potential delays on the Shenandoah Valley Regional Airport (SHD) to O'Hare Intl. Airport (ORD) route, aim to travel 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.
Is it cheaper to buy a plane ticket from Shenandoah Valley Regional Airport (SHD) to O'Hare Intl. Airport (ORD) last-minute?
Last-minute fares from SHD to ORD are typically more expensive. For the lowest rates, start searching for flights as early as possible. That being said, if you're flexible with your travel dates, you may find a cheap fare just before your departure.
Is it cheaper to book a SHD to ORD flight and hotel package?
Compared with arranging flights and hotels separately, booking a SHD to ORD flight and hotel package with Expedia could result in significant savings. What's more, having everything in one place will take the stress out of travel planning. Simply pick your flights and select from our extensive range of stays, then personalize your trip with extras like tours, car rentals and activities.
Can I cancel or change the date of my flight from Shenandoah Valley Regional Airport (SHD) to O'Hare Intl. Airport (ORD)?
If you reserved your SHD to ORD flight within the last 24 hours, you may be able to cancel or modify it without fees. Depending on the airline and the type of fare you have, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal if you want more information.

Travel information

Origin airport
Shenandoah Valley Regional
Destination airport
O'Hare Intl.
Airlines serving
American Airlines
Roundtrip price
$233
Distance
540 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 February. 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 $153 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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Weyers Cave nearby Airports

Charlottesville

Charlottesville-Albemarle to Chicago
$208.96
*Available to One Key members.