$154 Cheap Flights from Weyers Cave (SHD) to Chicago (ORD)

View $154 flight on Tue, Oct 7, 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 $154 for one-way flights and $298 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Contour Airlines
Wed, Oct 8 - Sat, Oct 11
SHD
Weyers Cave
ORD
Chicago
$298 Roundtrip, found 5 days ago
$298
Roundtrip
found 5 days ago
Select Contour Airlines flight, departing Wed, Oct 8 from Weyers Cave to Chicago, returning Sat, Oct 11, priced at $298 found 5 days ago
Contour Airlines
Tue, Oct 14 - Tue, Oct 21
SHD
Weyers Cave
ORD
Chicago
$308 Roundtrip, found 2 days ago
$308
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Tue, Oct 14 from Weyers Cave to Chicago, returning Tue, Oct 21, priced at $308 found 2 days ago
Contour Airlines
Tue, Oct 28 - Fri, Oct 31
SHD
Weyers Cave
ORD
Chicago
$310 Roundtrip, found 7 hours ago
$310
Roundtrip
found 7 hours ago
Select Contour Airlines flight, departing Tue, Oct 28 from Weyers Cave to Chicago, returning Fri, Oct 31, priced at $310 found 7 hours ago
Contour Airlines
Fri, Oct 10 - Tue, Oct 21
SHD
Weyers Cave
ORD
Chicago
$318 Roundtrip, found 2 days ago
$318
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Fri, Oct 10 from Weyers Cave to Chicago, returning Tue, Oct 21, priced at $318 found 2 days ago
Contour Airlines
Wed, Oct 8 - Sat, Oct 11
SHD
Weyers Cave
ORD
Chicago
$322 Roundtrip, found 5 days ago
$322
Roundtrip
found 5 days ago
Select Contour Airlines flight, departing Wed, Oct 8 from Weyers Cave to Chicago, returning Sat, Oct 11, priced at $322 found 5 days ago
Contour Airlines
Tue, Oct 28 - Fri, Oct 31
SHD
Weyers Cave
ORD
Chicago
$325 Roundtrip, found 7 hours ago
$325
Roundtrip
found 7 hours ago
Select Contour Airlines flight, departing Tue, Oct 28 from Weyers Cave to Chicago, returning Fri, Oct 31, priced at $325 found 7 hours ago
Contour Airlines
Tue, Oct 14 - Sun, Oct 19
SHD
Weyers Cave
ORD
Chicago
$327 Roundtrip, found 2 days ago
$327
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Tue, Oct 14 from Weyers Cave to Chicago, returning Sun, Oct 19, priced at $327 found 2 days ago
Contour Airlines
Fri, Oct 10 - Wed, Oct 15
SHD
Weyers Cave
ORD
Chicago
$328 Roundtrip, found 2 days ago
$328
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Fri, Oct 10 from Weyers Cave to Chicago, returning Wed, Oct 15, priced at $328 found 2 days ago
Contour Airlines
Tue, Oct 28 - Fri, Oct 31
SHD
Weyers Cave
ORD
Chicago
$329 Roundtrip, found 7 hours ago
$329
Roundtrip
found 7 hours ago
Select Contour Airlines flight, departing Tue, Oct 28 from Weyers Cave to Chicago, returning Fri, Oct 31, priced at $329 found 7 hours ago
Contour Airlines
Fri, Oct 10 - Sun, Oct 19
SHD
Weyers Cave
ORD
Chicago
$337 Roundtrip, found 2 days ago
$337
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Fri, Oct 10 from Weyers Cave to Chicago, returning Sun, Oct 19, priced at $337 found 2 days 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 $406
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $406
Flights from Weyers Cave (SHD) to Chicago (ORD)
Origin airport
Shenandoah Valley Regional
Destination airport
O'Hare Intl.
Airlines serving
Contour Airlines
Roundtrip price
$298
Distance
540 mi

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 October. 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 $154 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.

 

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 $154 or cheap return flight from $298 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)?
October 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.

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*Available to One Key members.