$184 Cheap flight deals from Chicago (CHI) to Staunton (CHO)

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Airfares from $184 One Way, $239 Round Trip from Chicago to Staunton

Prices starting at $239 for return flights and $184 for one-way flights to Staunton were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Aug 13 - Sun, Aug 16
ORD
Chicago
SHD
Weyers Cave
$239 Roundtrip, found 6 hours ago
$239
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Thu, Aug 13 from Chicago to Weyers Cave, returning Sun, Aug 16, priced at $239 found 6 hours ago
Thu, Aug 13 - Sun, Aug 16
RFD
Rockford
SHD
Weyers Cave
$288 Roundtrip, found 6 hours ago
$288
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Thu, Aug 13 from Rockford to Weyers Cave, returning Sun, Aug 16, priced at $288 found 6 hours ago
Sat, Oct 17 - Fri, Oct 23
ORD
Chicago
CHO
Charlottesville
$289 Roundtrip, found 1 day ago
$289
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Oct 17 from Chicago to Charlottesville, returning Fri, Oct 23, priced at $289 found 1 day ago
Thu, Aug 13 - Sun, Aug 16
ORD
Chicago
SHD
Weyers Cave
$290 Roundtrip, found 6 hours ago
$290
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Thu, Aug 13 from Chicago to Weyers Cave, returning Sun, Aug 16, priced at $290 found 6 hours ago
Sat, Oct 17 - Fri, Oct 23
ORD
Chicago
CHO
Charlottesville
$328 Roundtrip, found 1 day ago
$328
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Oct 17 from Chicago to Charlottesville, returning Fri, Oct 23, priced at $328 found 1 day ago

Staunton economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel 24 South
3.0-star property

Hotel 24 South

9.6/10 Exceptional! (1,159 reviews)

Aug 13 - Aug 16

3 night stay

Chicago (CHI) to Weyers Cave (SHD)

American Airlines • Roundtrip • Coach
Price was $502, price is now $439 per person
$439
per person
found 6 hours ago
Hotel was good. We enjoyed our stay.

Reviewed on May 26, 2026

The Blackburn Inn and Conference Center
3.5-star property

The Blackburn Inn and Conference Center

9.2/10 Wonderful! (1,004 reviews)

Aug 13 - Aug 16

3 night stay

Chicago (CHI) to Weyers Cave (SHD)

American Airlines • Roundtrip • Coach
Price was $529, price is now $448 per person
$448
per person
found 6 hours ago
Nice, quaint property. Hardwood floors and nice view. Only concern is that there are some rooms on the 4th floor which isn't accessible via the elevator.

Reviewed on Jun 13, 2025

Massanutten Resort
2.5-star property

Massanutten Resort

8/10 Very Good! (1,373 reviews)

Aug 13 - Aug 16

3 night stay

Chicago (CHI) to Weyers Cave (SHD)

American Airlines • Roundtrip • Coach
Price was $503, price is now $445 per person
$445
per person
found 6 hours ago
Loved it! Great for families. Comfortable accommodations. Friendly staff.

Reviewed on Apr 19, 2026

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More About Flying To Staunton from Chicago

Route Information for Flights from Chicago to Staunton

Origin Airport IATA Code
CHI
Destination Airport IATA Code
CHO
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Staunton

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Frequently asked questions

Are there non-stop flights from Chicago to Staunton?
United Airlines will fly you nonstop from ORD to Charlottesville, VA (CHO-Charlottesville-Albemarle), so you won't have to worry about annoying stopovers or missing your next flight.
What is the shortest flight from Chicago to Staunton?
The trip from Chicago to Staunton can be as fast as 2 hours and 32 minutes. With a short and sweet flight time like this, why not round up some friends and take off on an impromptu getaway?
What airlines fly from Chicago to Staunton most frequently?
United Airlines is the most frequent airline operating on the Chicago to Staunton route. You can select from 43 flights each month with this carrier.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

More Destinations

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.