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$185+ Cheap flights from Staunton (SHD) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/17. Fares are subject to change and may not be available on all flights or dates of travel.
SHD — CHI
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Find flight deals from Staunton to Chicago

Cheapest flights from Staunton to Chicago
Explore the most affordable flight options available from Staunton to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/111:35 pmSHD - ORD
2 stops25h 56mMultiple Airlines
Sat 11/1511:51 amORD - SHD
1 stop22h 14mMultiple Airlines
Deal found 10/27$281
This Mytrip deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/96:30 amSHD - ORD
2 stops18h 39mMultiple Airlines
Sat 12/133:26 pmORD - SHD
2 stops18h 39mMultiple Airlines
Deal found 10/27$303
This Kiwi.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/126:30 amSHD - ORD
2 stops33h 01mMultiple Airlines
Sun 11/1611:43 amORD - SHD
1 stop22h 22mMultiple Airlines
Deal found 10/28$305
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/76:30 amSHD - ORD
1 stop11h 45mMultiple Airlines
Fri 11/79:47 pmORD - SHD
2 stops19h 18mMultiple Airlines
Deal found 10/27$374

Cheap flight deals from Staunton to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Staunton (SHD) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 29, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$234
(American Airlines)

One-way from

$185
(American Airlines)
Provider with most accurate pricing for Staunton Shenandoah Valley-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Staunton Shenandoah Valley-Chicago (CHI) flights.
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From Staunton Shenandoah Valley to Chicago (CHI)
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One-way flight from Staunton Shenandoah Valley to Chicago (CHI)
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Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated October 29, 2025.
Use the filters below to find and compare flights from Staunton to Chicago that are best for you.

Fly from

Staunton

Fly to

Chicago

Route

Depart

Return

Price

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

Fri 2/13

1:00 pm-1:24 pm

Nonstop1h 24m

Chicago O'Hare Intl

Wed 2/18

5:50 pm-8:45 pm

Nonstop1h 55m

$234

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

Sun 3/1

1:00 pm-1:24 pm

Nonstop1h 24m

Chicago O'Hare Intl

Sat 3/7

5:50 pm-8:45 pm

Nonstop1h 55m

$234

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

Wed 2/18

1:00 pm-1:24 pm

Nonstop1h 24m

Chicago O'Hare Intl

Sat 3/7

5:50 pm-8:45 pm

Nonstop1h 55m

$284

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

Tue 3/3

1:00 pm-1:24 pm

Nonstop1h 24m

Chicago O'Hare Intl

Sat 3/7

5:50 pm-8:45 pm

Nonstop1h 55m

$284

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

Sat 2/21

1:00 pm-1:24 pm

Nonstop1h 24m

Chicago O'Hare Intl

Mon 3/2

5:50 pm-8:45 pm

Nonstop1h 55m

$284

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

Wed 11/12

6:30 am-2:31 pm

2 stops33h 01m

Chicago O'Hare Intl

Sun 11/16

11:43 am-11:05 am

1 stop22h 22m

$305

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

Fri 2/13

1:00 pm-1:24 pm

Nonstop1h 24m

Chicago O'Hare Intl

Sun 2/15

5:50 pm-8:45 pm

Nonstop1h 55m

$309

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

Sat 2/28

1:00 pm-1:24 pm

Nonstop1h 24m

Chicago O'Hare Intl

Sun 3/8

5:50 pm-8:50 pm

Nonstop2h 00m

$314

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

Sat 2/21

1:00 pm-1:24 pm

Nonstop1h 24m

Chicago O'Hare Intl

Sun 3/8

5:50 pm-8:50 pm

Nonstop2h 00m

$314

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

Sun 3/1

1:00 pm-1:24 pm

Nonstop1h 24m

Chicago O'Hare Intl

Sun 3/8

5:50 pm-8:50 pm

Nonstop2h 00m

$314

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 13 results
1
2
  • Most accurate provider: When it comes to deals on Staunton-Chicago flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Staunton-Chicago flight deals on Cheapflights vs. Expedia 90-95% of the time. Price accuracy is based on data collected from Staunton-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Staunton-Chicago flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Staunton-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Staunton to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Staunton with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Staunton to Chicago

What is the cheapest month to book a flight from Staunton to Chicago?

Currently, October is the cheapest month in which you can book a flight from Staunton to Chicago (average of $207). Flying from Staunton to Chicago in June is currently the most expensive (average of $284). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Staunton to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Staunton to Chicago?

    Most people fly from Staunton Shenandoah Valley (SHD) if they book a flight from Staunton to Chicago. On average, Shenandoah Valley has 0 outbound flights to Chicago per day from 0 airlines. Staunton Shenandoah Valley is conveniently located just 12.1 mi from Staunton’s city center.

  • How long is the flight from Staunton to Chicago?

    American Airlines can get you from Staunton to Chicago in just under 1h 24m. Your travel time will be generally consistent. The distance between Staunton and Chicago is about 540 mi. All flights are typically nonstop.

  • Can I find deals for flights from Staunton to Chicago that include hotel bookings?

    Yes. In addition to deals on Staunton to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Staunton to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Staunton to Chicago.

  • Can I find deals for business class flights from Staunton to Chicago?

    Yes. Cheapflights offers flight deals from Staunton to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Staunton to Chicago?

    Currently, October is the cheapest month in which you can book a flight from Staunton to Chicago (average of $207). Flying from Staunton to Chicago in June is currently the most expensive (average of $284). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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