Chicago

$165+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
SHD — CHI
Aug 3 — Aug 101
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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 July 29, 2025.

Round-trip from

$356
(Contour)

One-way from

$165
(Contour)
From Staunton Shenandoah Valley to Chicago (CHI)
One-way flight from Staunton Shenandoah Valley to Chicago (CHI)

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 July 29, 2025.

This Contour deal was found by Cheapflights users on 7/27. 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 Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/306:30 amSHD - ORD
2 stops13h 15mContour
Tue 9/22:10 pmORD - SHD
2 stops43h 45mContour
Deal found 7/27$356
This Mytrip deal was found by Cheapflights users on 7/27. 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.
Mon 8/116:30 amSHD - ORD
2 stops16h 00mMultiple Airlines
Fri 8/155:21 pmORD - SHD
3 stops24h 34mMultiple Airlines
Deal found 7/27$374

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 July 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

Sat 8/30

6:30 am-6:45 pm

2 stops13h 15m

Chicago O'Hare Intl

Tue 9/2

2:10 pm-10:55 am

2 stops43h 45m

$356

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

Mon 8/11

6:30 am-9:30 pm

2 stops16h 00m

Chicago O'Hare Intl

Fri 8/15

5:21 pm-6:55 pm

3 stops24h 34m

$374

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

Sat 8/30

6:30 am-6:45 pm

2 stops13h 15m

$165

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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, August is the cheapest month in which you can book a flight from Staunton to Chicago (average of $245). Flying from Staunton to Chicago in March is currently the most expensive (average of $321). 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.

  • 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, August is the cheapest month in which you can book a flight from Staunton to Chicago (average of $245). Flying from Staunton to Chicago in March is currently the most expensive (average of $321). 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
Benton Harbor
Porter
Valparaiso
Chesterton

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