Cheap flights from Staunton to Chicago from $337

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Staunton to Chicago departing on 10/2. 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

Multiple Airlines Logo
6:30 am - 1:12 pmSHD-ORD
7h 42m1 stop
Multiple Airlines Logo
7:40 am - 6:55 pmORD-SHD
10h 15m1 stop
$337Multiple Airlines
Find Deal
Thu, Oct 2 - Mon, Oct 6
Multiple Airlines Logo
1:00 pm - 7:44 pmSHD-ORD
31h 44m2 stops
Multiple Airlines Logo
7:40 am - 6:55 pmORD-SHD
10h 15m1 stop
$338Multiple Airlines
Find Deal
Thu, Oct 2 - Mon, Oct 6
Contour Logo
6:30 am - 6:45 pmSHD-ORD
13h 15m2 stops
Contour Logo
2:10 pm - 10:55 amORD-SHD
43h 45m2 stops
$406Contour
Find Deal
Sat, Oct 18 - Sat, Oct 25
Contour Logo
6:30 am - 6:45 pmSHD-ORD
13h 15m2 stops
Contour Logo
2:10 pm - 10:55 amORD-SHD
43h 45m2 stops
$440Contour
Find Deal
Fri, Oct 3 - Tue, Oct 7
Contour Logo
1:00 pm - 6:45 pmSHD-ORD
30h 45m2 stops
Contour Logo
2:10 pm - 6:55 pmORD-SHD
27h 45m2 stops
$470Contour
Find Deal
Thu, Oct 2 - Mon, Oct 6
Contour Logo
1:00 pm - 6:45 pmSHD-ORD
30h 45m2 stops
Contour Logo
2:10 pm - 10:55 amORD-SHD
43h 45m2 stops
$504Contour
Find Deal
Thu, Oct 9 - Sun, Oct 12

Contour flights from Staunton to Chicago

Our best Contour deals on Staunton to Chicago flight tickets
Contour
Oct 18
SHD6:30 amStaunton Shenandoah Valley
13h 15m
2 stops
ORD6:45 pmChicago O'Hare Intl
Oct 25
ORD2:10 pmChicago O'Hare Intl
43h 45m
2 stops
SHD10:55 amStaunton Shenandoah Valley
Contour
Oct 3
SHD6:30 amStaunton Shenandoah Valley
13h 15m
2 stops
ORD6:45 pmChicago O'Hare Intl
Oct 7
ORD2:10 pmChicago O'Hare Intl
43h 45m
2 stops
SHD10:55 amStaunton Shenandoah Valley
Contour
Oct 2
SHD1:00 pmStaunton Shenandoah Valley
30h 45m
2 stops
ORD6:45 pmChicago O'Hare Intl
Oct 6
ORD2:10 pmChicago O'Hare Intl
27h 45m
2 stops
SHD6:55 pmStaunton Shenandoah Valley

momondo Fare Finder

 
Customize your flight search to find flights from Staunton to Chicago 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 September 18, 2025.
Use the filters below to find and compare flights from Staunton to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

Thu 10/2

6:30 am-1:12 pm

1 stop7h 42m

Chicago O'Hare Intl

Mon 10/6

7:40 am-6:55 pm

1 stop10h 15m

$337

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

Thu 10/2

1:00 pm-7:44 pm

2 stops31h 44m

Chicago O'Hare Intl

Mon 10/6

7:40 am-6:55 pm

1 stop10h 15m

$338

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

Sat 10/18

6:30 am-6:45 pm

2 stops13h 15m

Chicago O'Hare Intl

Sat 10/25

2:10 pm-10:55 am

2 stops43h 45m

$406

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

Fri 10/3

6:30 am-6:45 pm

2 stops13h 15m

Chicago O'Hare Intl

Tue 10/7

2:10 pm-10:55 am

2 stops43h 45m

$440

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

Thu 10/2

1:00 pm-6:45 pm

2 stops30h 45m

Chicago O'Hare Intl

Mon 10/6

2:10 pm-6:55 pm

2 stops27h 45m

$470

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

Thu 10/9

1:00 pm-6:45 pm

2 stops30h 45m

Chicago O'Hare Intl

Sun 10/12

2:10 pm-10:55 am

2 stops43h 45m

$504

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to Chicago from

How to get the cheapest flight ticket from Staunton to Chicago

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 airlines fly to Chicago?

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Chicago from Staunton according to our data. United Airlines is the first choice among our users, with 83% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

When to book flights from Staunton to Chicago

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

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

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

Direct flights

None
There are no direct flights from Staunton to Chicago. There are no popular flight routes from Staunton to Chicago.
  • How far is Staunton Shenandoah Valley to Chicago by plane?

    There are 520.0 mi between Staunton Shenandoah Valley and Chicago. 7h 42m is a normal flight duration for this route.

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

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

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

    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 Staunton Shenandoah Valley Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

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

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

momondo does allow users to show only those flights to Chicago from Staunton which offer a flexible booking policy as well as other useful filters and features.

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

Once all potential Staunton to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Yes momondo offers price alerts on flights to Chicago from Staunton. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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1 adult
Sat 10/18
Sat 10/25

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago