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Cheap flights from Chicago to Staunton from $185

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Staunton departing on 10/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

Contour Logo
2:10 pm - 6:55 pmORD-SHD
27h 45m2 stops
Contour Logo
6:30 am - 6:45 pmSHD-ORD
13h 15m2 stops
$304Contour
Find Deal
Fri, Sep 5 - Sun, Sep 7
Contour Logo
2:10 pm - 6:55 pmORD-SHD
27h 45m2 stops
Contour Logo
6:30 am - 6:45 pmSHD-ORD
13h 15m2 stops
$310Contour
Find Deal
Fri, Sep 5 - Sun, Sep 7
Contour Logo
2:10 pm - 12:30 pmORD-SHD
45h 20m2 stops
Contour Logo
6:30 am - 6:45 pmSHD-ORD
13h 15m2 stops
$346Contour
Find Deal
Wed, Sep 24 - Mon, Sep 29
Logo
8:12 pm - 6:55 pmORD-SHD
21h 43m2 stops
Logo
1:00 pm - 11:59 pmSHD-ORD
11h 59m2 stops
$400
Find Deal
Wed, Aug 13 - Sun, Aug 17
Logo
2:10 pm - 6:55 pmORD-SHD
27h 45m2 stops
Logo
6:30 am - 10:22 pmSHD-ORD
16h 52m2 stops
$478
Find Deal
Fri, Aug 15 - Tue, Aug 19
Contour Logo
2:10 pm - 6:55 pmORD-SHD
27h 45m2 stops
Contour Logo
1:00 pm - 6:45 pmSHD-ORD
30h 45m2 stops
$500Contour
Find Deal
Wed, Aug 13 - Sun, Aug 17
Logo
2:10 pm - 6:55 pmORD-SHD
27h 45m2 stops
Logo
6:30 am - 4:10 pmSHD-ORD
34h 40m3 stops
$509
Find Deal
Wed, Aug 13 - Sun, Aug 17
Logo
2:10 pm - 6:55 pmORD-SHD
27h 45m2 stops
Logo
6:30 am - 11:59 pmSHD-ORD
18h 29m3 stops
$542
Find Deal
Fri, Aug 15 - Tue, Aug 19

Contour flights from Chicago to Staunton

Our best Contour deals on Chicago to Staunton flight tickets
Contour
Sep 5
ORD2:10 pmChicago O'Hare Intl
27h 45m
2 stops
SHD6:55 pmStaunton Shenandoah Valley
Sep 7
SHD6:30 amStaunton Shenandoah Valley
13h 15m
2 stops
ORD6:45 pmChicago O'Hare Intl
$304
Find similar
Contour
Sep 5
ORD2:10 pmChicago O'Hare Intl
27h 45m
2 stops
SHD6:55 pmStaunton Shenandoah Valley
Sep 7
SHD6:30 amStaunton Shenandoah Valley
13h 15m
2 stops
ORD6:45 pmChicago O'Hare Intl
$310
Find similar
Contour
Sep 24
ORD2:10 pmChicago O'Hare Intl
45h 20m
2 stops
SHD12:30 pmStaunton Shenandoah Valley
Sep 29
SHD6:30 amStaunton Shenandoah Valley
13h 15m
2 stops
ORD6:45 pmChicago O'Hare Intl
$346
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Staunton that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated July 31, 2025.
Use the filters below to find and compare flights from Chicago to Staunton that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoStaunton

ORD - SHD

ORDSHD

Chicago O'Hare Intl

Fri 9/5

2:10 pm-6:55 pm

2 stops27h 45m

Staunton Shenandoah Valley

Sun 9/7

6:30 am-6:45 pm

2 stops13h 15m

$304

ChicagoStaunton

ORD - SHD

ORDSHD

Chicago O'Hare Intl

Fri 9/5

2:10 pm-6:55 pm

2 stops27h 45m

Staunton Shenandoah Valley

Sun 9/7

6:30 am-6:45 pm

2 stops13h 15m

$310

ChicagoStaunton

ORD - SHD

ORDSHD

Chicago O'Hare Intl

Wed 9/24

2:10 pm-12:30 pm

2 stops45h 20m

Staunton Shenandoah Valley

Mon 9/29

6:30 am-6:45 pm

2 stops13h 15m

$346

ChicagoStaunton

ORD - SHD

ORDSHD

Chicago O'Hare Intl

Wed 8/13

8:12 pm-6:55 pm

2 stops21h 43m

Staunton Shenandoah Valley

Sun 8/17

1:00 pm-11:59 pm

2 stops11h 59m

$400

ChicagoStaunton

ORD - SHD

ORDSHD

Chicago O'Hare Intl

Fri 8/15

2:10 pm-6:55 pm

2 stops27h 45m

Staunton Shenandoah Valley

Tue 8/19

6:30 am-10:22 pm

2 stops16h 52m

$478

ChicagoStaunton

ORD - SHD

ORDSHD

Chicago O'Hare Intl

Wed 8/13

2:10 pm-6:55 pm

2 stops27h 45m

Staunton Shenandoah Valley

Sun 8/17

1:00 pm-6:45 pm

2 stops30h 45m

$500

ChicagoStaunton

ORD - SHD

ORDSHD

Chicago O'Hare Intl

Wed 8/13

2:10 pm-6:55 pm

2 stops27h 45m

Staunton Shenandoah Valley

Sun 8/17

6:30 am-4:10 pm

3 stops34h 40m

$509

ChicagoStaunton

ORD - SHD

ORDSHD

Chicago O'Hare Intl

Fri 8/15

2:10 pm-6:55 pm

2 stops27h 45m

Staunton Shenandoah Valley

Tue 8/19

6:30 am-11:59 pm

3 stops18h 29m

$542

ChicagoStaunton

ORD - SHD

ORDSHD

Chicago O'Hare Intl

Mon 10/20

2:10 pm-6:55 pm

2 stops27h 45m

$185

ChicagoStaunton

ORD - SHD

ORDSHD

Chicago O'Hare Intl

Sun 8/17

8:12 pm-6:55 pm

2 stops21h 43m

$206

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 resultsSorted by cheapest first
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See travel insights to Staunton from

How to get the cheapest flight ticket from Chicago to Staunton

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Chicago to Staunton Shenandoah Valley?

Contour is the most popular carrier operating from Chicago to Staunton Shenandoah Valley

When to book flights from Chicago to Staunton

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Staunton according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Staunton (CHI to SHD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Staunton

Best Price Found

$185

Fastest flight time

21h 43m

Direct flights

None

Airports in Staunton

1 airport
The best one-way flight to Staunton from Chicago in the past 72 hours is $185. The best round-trip flight deal from Chicago to Staunton found on momondo in the last 72 hours is $304.
The fastest flight from Chicago to Staunton takes 21h 43m
There are no direct flights from Chicago to Staunton. Popular non-direct route for this connection is Chicago O'Hare Intl Airport - Staunton Shenandoah Valley Airport.
There is 1 airport near Staunton: Staunton Shenandoah Valley (SHD)
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  • How far is Chicago to Staunton Shenandoah Valley by plane?

    Chicago and Staunton Shenandoah Valley are 520.0 mi apart from one another. Flights usually cover this in 21h 43m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago to Staunton Shenandoah Valley Airport?

    Prices for flights from Chicago to Staunton Shenandoah Valley Airport refresh daily.

  • How old do you have to be to fly from Chicago to Staunton Shenandoah Valley Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Staunton Shenandoah Valley Airport.

  • What documentation or ID do you need to fly to Staunton Shenandoah Valley Airport?

    The travel and health documents required for your trip to Staunton Shenandoah Valley Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Staunton Shenandoah Valley Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near Staunton?

Book flights to Staunton if you plan to visit one of these locations
Harrisonburg
Waynesboro

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Staunton?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Staunton. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Staunton with flexible booking policies on momondo?

All flight searches from Chicago to Staunton on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Staunton?

Once you have performed a search for Chicago to Staunton flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to Staunton right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Staunton flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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