$133 Cheap Flights from Charleston (CRW) to Chicago (ORD)

View $133 flight on Thu, Nov 13, 2025Opens in a new window

Popular airlines from Charleston, WV (CRW-Yeager) to Chicago O'Hare Intl. Airport (ORD)

Cheap Flights from Charleston to Chicago (CRW-ORD)

Prices were available within the past 7 days and start at $133 for one-way flights and $179 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Sat, Nov 8 - Tue, Nov 11
CRW
Charleston
ORD
Chicago
$179 Roundtrip, found 1 hour ago
$179
Roundtrip
found 1 hour ago
Select United flight, departing Sat, Nov 8 from Charleston to Chicago, returning Tue, Nov 11, priced at $179 found 1 hour ago
United
Mon, Dec 8 - Thu, Dec 25
CRW
Charleston
ORD
Chicago
$184 Roundtrip, found 5 hours ago
$184
Roundtrip
found 5 hours ago
Select United flight, departing Mon, Dec 8 from Charleston to Chicago, returning Thu, Dec 25, priced at $184 found 5 hours ago
United
Thu, Oct 23 - Thu, Oct 30
CRW
Charleston
ORD
Chicago
$189 Roundtrip, found 6 days ago
$189
Roundtrip
found 6 days ago
Select United flight, departing Thu, Oct 23 from Charleston to Chicago, returning Thu, Oct 30, priced at $189 found 6 days ago
United
Fri, Nov 7 - Sun, Nov 9
CRW
Charleston
ORD
Chicago
$197 Roundtrip, found 10 hours ago
$197
Roundtrip
found 10 hours ago
Select United flight, departing Fri, Nov 7 from Charleston to Chicago, returning Sun, Nov 9, priced at $197 found 10 hours ago
United
Sat, Nov 8 - Mon, Nov 10
CRW
Charleston
ORD
Chicago
$198 Roundtrip, found 4 days ago
$198
Roundtrip
found 4 days ago
Select United flight, departing Sat, Nov 8 from Charleston to Chicago, returning Mon, Nov 10, priced at $198 found 4 days ago
American Airlines
Thu, Nov 13 - Mon, Nov 17
CRW
Charleston
ORD
Chicago
$198 Roundtrip, found 1 hour ago
$198
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Thu, Nov 13 from Charleston to Chicago, returning Mon, Nov 17, priced at $198 found 1 hour ago
Delta
Wed, Dec 3 - Mon, Dec 15
CRW
Charleston
ORD
Chicago
$198 Roundtrip, found 5 hours ago
$198
Roundtrip
found 5 hours ago
Select Delta flight, departing Wed, Dec 3 from Charleston to Chicago, returning Mon, Dec 15, priced at $198 found 5 hours ago
American Airlines
Sat, Dec 6 - Sat, Dec 13
CRW
Charleston
ORD
Chicago
$203 Roundtrip, found 14 hours ago
$203
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Sat, Dec 6 from Charleston to Chicago, returning Sat, Dec 13, priced at $203 found 14 hours ago
United
Sat, Apr 4 - Sun, Apr 5
CRW
Charleston
ORD
Chicago
$208 Roundtrip, found 8 hours ago
$208
Roundtrip
found 8 hours ago
Select United flight, departing Sat, Apr 4 from Charleston to Chicago, returning Sun, Apr 5, priced at $208 found 8 hours ago
American Airlines
Thu, Oct 30 - Sun, Nov 2
CRW
Charleston
ORD
Chicago
$208 Roundtrip, found 4 hours ago
$208
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Thu, Oct 30 from Charleston to Chicago, returning Sun, Nov 2, priced at $208 found 4 hours ago

Find the cheapest month to fly from Charleston (CRW) to Chicago (ORD)

August is typically the cheapest month to fly

From $178 - $477 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $448
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $448
0
Flights from Charleston (CRW) to Chicago (ORD)
Origin airport
Yeager
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Roundtrip price
$179
Distance
415 mi

Charleston to Chicago Flights

The cheapest times to fly from Charleston to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Charleston to Chicago are during the month of November. You can find some of the cheapest flights from Charleston to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Charleston to Chicago

Sunday is one of the best days to book for cheap flights from Charleston to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Charleston to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Charleston to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $133 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Charleston to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Charleston to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Yeager Airport (CRW) to O'Hare Intl. Airport (ORD) cost?
Secure a cheap one-way flight from $133 or cheap return flight from $179 from Yeager Airport (CRW) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Yeager Airport (CRW) to O'Hare Intl. Airport (ORD)?
The cheapest month to fly from CRW to ORD is November, when there's less demand. Off-peak season is often when you'll find lower airfares between these airports.
Which airlines fly direct from Yeager Airport (CRW) to O'Hare Intl. Airport (ORD)?
If you're departing from Yeager Airport (CRW), you can board a nonstop flight to O'Hare Intl. Airport (ORD) with United Airlines.
What is the cheapest airline that flies from Yeager Airport (CRW) to O'Hare Intl. Airport (ORD)?
Use the filter tool on Expedia to compare airlines and find the most affordable carrier that'll fly you from CRW to ORD. Then, sort your results by "Price (lowest to highest)" to pick up a great deal.
How many flights per day from Yeager Airport (CRW) to O'Hare Intl. Airport (ORD)?
When flying out of Yeager Airport (CRW), you can take your pick from an average of 2 daily direct flights to O'Hare Intl. Airport (ORD).
What are the most popular departure times for flights from Yeager Airport (CRW) to O'Hare Intl. Airport (ORD)?
More passengers fly between CRW and ORD at 7 AM than at any other point in the day. Looking for a quieter experience? Travel outside of rush hours and there's a chance you'll save on your fare as well.
What day of the week has the most flights from CRW to ORD?
If you fly on a Friday, you'll get the greatest range of options for flights from Yeager Airport (CRW) to O'Hare Intl. Airport (ORD).
What is the earliest flight from Yeager Airport (CRW) to O'Hare Intl. Airport (ORD)?
The earliest flight out of Yeager Airport (CRW) is at around 7:00AM UTC-5. Board this plane and you'll reach O'Hare Intl. Airport (ORD) at approximately 8:00AM UTC-6. The total time in the air is 2h.
How long does it take to fly from Yeager Airport (CRW) to O'Hare Intl. Airport (ORD)?
The average flight time from CRW to ORD is 2 hours, covering a total distance of 420 mi.
What airline has the least delays from CRW to ORD?
With 80% of journeys usually arriving as scheduled, American Airlines has the best on-time performance for direct flights from Yeager Airport (CRW) to O'Hare Intl. Airport (ORD). To monitor your flight status and get notified about any changes, use the Expedia App.
What is the best time to fly from Yeager Airport (CRW) to O'Hare Intl. Airport (ORD)?
To avoid potential delays on the Yeager Airport (CRW) to O'Hare Intl. Airport (ORD) route, fly before 3 PM. Later departures have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Yeager Airport (CRW)?
If you're flying on a direct flight from Yeager Airport (CRW) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can land at.
Is it cheaper to buy a plane ticket from Yeager Airport (CRW) to O'Hare Intl. Airport (ORD) last-minute?
Holding off until right before your break to book your flight from CRW to ORD often results in higher prices. While it's possible to find some last-minute deals, there's no guarantee. Be flexible with your travel plans for the best chance of landing a bargain.
Is it cheaper to book a CRW to ORD flight and hotel package?
You can save money by booking a CRW to ORD flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one convenient place. Once you've chosen your preferred flights and accommodations, consider other add-ons like car rentals, activities and tours.
Can I cancel or change the date of my flight from Yeager Airport (CRW) to O'Hare Intl. Airport (ORD)?
It's generally possible to reschedule or cancel your CRW to ORD flight. However, for bookings made more than 24 hours ago, additional charges may apply. Check your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find further details on our Customer Service portal.

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*Available to One Key members.