HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$209+ 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
SHD — CHI
mar. 6 — mar. 131
fre. 3/6
fre. 3/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Staunton to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 februar 4, 2026.

This American Airlines deal was found by Cheapflights users on 2/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tor. 3/512:54 pm
SHD
-
ORD
Nonstop2h 07m
American Airlines
tor. 3/126:14 pm
ORD
-
SHD
Nonstop1h 55m
American Airlines
Deal found 2/3$234
This American Airlines deal was found by Cheapflights users on 2/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tor. 11/1212:45 pm
SHD
-
ORD
Nonstop2h 00m
American Airlines
søn. 11/155:50 pm
ORD
-
SHD
Nonstop2h 00m
American Airlines
Deal found 2/3$254
This American Airlines deal was found by Cheapflights users on 2/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tir. 3/312:54 pm
SHD
-
ORD
Nonstop2h 07m
American Airlines
lør. 3/76:42 pm
ORD
-
SHD
Nonstop1h 55m
American Airlines
Deal found 2/3$309
This American Airlines deal was found by Cheapflights users on 2/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
fre. 2/612:45 pm
SHD
-
ORD
Nonstop2h 00m
American Airlines
ons. 2/115:50 pm
ORD
-
SHD
Nonstop2h 00m
American Airlines
Deal found 2/2$334
This American Airlines deal was found by Cheapflights users on 2/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
søn. 3/2212:56 pm
SHD
-
ORD
Nonstop2h 07m
American Airlines
ons. 3/256:14 pm
ORD
-
SHD
Nonstop1h 55m
American Airlines
Deal found 2/3$413
This American Airlines deal was found by Cheapflights users on 2/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lør. 2/2812:54 pm
SHD
-
ORD
Nonstop2h 07m
American Airlines
tir. 3/36:44 pm
ORD
-
SHD
1 stop40h 40m
American Airlines
Deal found 2/3$520
This American Airlines deal was found by Cheapflights users on 2/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tir. 2/1712:54 pm
SHD
-
ORD
Nonstop2h 07m
American Airlines
fre. 2/208:10 am
ORD
-
SHD
1 stop27h 14m
American Airlines
Deal found 2/3$571

Find 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 februar 4, 2026.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$234
(American Airlines)

One-way from

$209
(American Airlines)

Good round-trip deal

$546 or less
Provider with most accurate pricing for Staunton Shenandoah Valley-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Staunton Shenandoah Valley-Chicago (CHI) flights.
Search Deals
From Staunton Shenandoah Valley to Chicago (CHI)
Search Deals
One-way flight from Staunton Shenandoah Valley to Chicago (CHI)
Search Deals
Price to beat on a round-trip flight from Staunton Shenandoah Valley to Chicago (CHI).
Search Deals

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 februar 4, 2026.
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

tor. 3/5

12:54 pm-2:01 pm

Nonstop2h 07m

Chicago O'Hare Intl

tor. 3/12

6:14 pm-9:09 pm

Nonstop1h 55m

$234

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

tir. 3/3

12:54 pm-2:01 pm

Nonstop2h 07m

Chicago O'Hare Intl

lør. 3/7

6:42 pm-9:37 pm

Nonstop1h 55m

$309

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

tir. 2/17

12:54 pm-2:01 pm

Nonstop2h 07m

Chicago O'Hare Intl

lør. 2/21

6:42 pm-9:37 pm

Nonstop1h 55m

$334

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

ons. 2/18

12:54 pm-2:01 pm

Nonstop2h 07m

Chicago O'Hare Intl

søn. 2/22

6:14 pm-9:09 pm

Nonstop1h 55m

$334

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

søn. 3/22

12:56 pm-2:03 pm

Nonstop2h 07m

Chicago O'Hare Intl

ons. 3/25

6:14 pm-9:09 pm

Nonstop1h 55m

$413

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

tir. 2/17

12:54 pm-2:01 pm

Nonstop2h 07m

Chicago O'Hare Intl

fre. 2/20

5:29 pm-8:24 pm

Nonstop1h 55m

$413

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

ons. 3/4

12:54 pm-2:01 pm

Nonstop2h 07m

$209

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

tor. 7/30

1:02 pm-2:14 pm

Nonstop2h 12m

$209

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

lør. 8/1

1:02 pm-2:14 pm

Nonstop2h 12m

$209

StauntonChicago

SHD - ORD

SHDORD

Staunton Shenandoah Valley

fre. 5/1

12:55 pm-2:08 pm

Nonstop2h 13m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/4

Showing 1-10 of 15 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% 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, February is the cheapest month in which you can book a flight from Staunton to Chicago (average of $191). Flying from Staunton to Chicago in March is currently the most expensive (average of $280). 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.

Weekly flight availability from Staunton to Chicago

Explore weekly flight availability from Staunton to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated februar 4, 2026.

The most flights from SHD to CHI are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

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 1 outbound flight 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 2h 07m. Your travel time will be generally consistent. The distance between Staunton and Chicago is about 540 mi. All flights are typically nonstop.

  • What are the cheapest flights from Staunton to Chicago?

    While on average a flight from Staunton to Chicago is generally $701, our data shows the cheapest flight currently is $233. When looking at the most popular route, (Staunton Shenandoah Valley - Chicago O'Hare Intl), you can expect to pay $234 for that flight.

  • 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, February is the cheapest month in which you can book a flight from Staunton to Chicago (average of $191). Flying from Staunton to Chicago in March is currently the most expensive (average of $280). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Staunton to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Dulles Intl to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Dulles Intl to Midway flights
Raleigh to O'Hare Intl flights
Greensboro to O'Hare Intl flights
Reagan-National to Midway flights
Raleigh to Midway flights
Dulles Intl to St. Louis flights
Richmond to O'Hare Intl flights
Reagan-National to St. Louis flights
Norfolk to O'Hare Intl flights
Charlottesville to O'Hare Intl flights
Raleigh to St. Louis flights
Richmond to Midway flights
Norfolk to Midway flights
Greensboro to Midway flights
Richmond to St. Louis flights
Roanoke to O'Hare Intl flights
Greensboro to St. Louis flights
Charlottesville to Midway flights
Norfolk to St. Louis flights
Roanoke to Midway flights
Roanoke to St. Louis flights
Norfolk to Moline flights
Reagan-National to Peoria flights
Dulles Intl to Peoria flights
Reagan-National to Champaign flights
Lynchburg to O'Hare Intl flights
Blountville to O'Hare Intl flights
Blountville to St. Louis flights
Raleigh to Peoria flights
Dulles Intl to Moline flights
Raleigh to Moline flights
Dulles Intl to Evansville flights
Newport News to O'Hare Intl flights
Richmond to Bloomington flights
Charlottesville to St. Louis flights
Raleigh to Evansville flights
Reagan-National to Evansville flights
Dulles Intl to Champaign flights
Richmond to Peoria flights
Raleigh to Bloomington flights
Raleigh to Dubuque flights
Richmond to Moline flights
Roanoke to Peoria flights
Staunton to O'Hare Intl flights
Greensboro to Peoria flights
Richmond to Champaign flights
Reagan-National to Moline flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.