$89 Cheap Flights from Charleston (CRW) to Chicago (MDW)

View $89 flight on Tue, Oct 7, 2025Opens in a new window

Popular airlines from Charleston, WV (CRW-Yeager) to Chicago Midway Airport (MDW)

Cheap Flights from Charleston to Chicago (CRW-MDW)

Prices were available within the past 7 days and start at $89 for one-way flights and $198 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Nov 25 - Wed, Dec 17
CRW
Charleston
MDW
Chicago
$198 Roundtrip, just found
$198
Roundtrip
just found
Select Delta flight, departing Tue, Nov 25 from Charleston to Chicago, returning Wed, Dec 17, priced at $198 just found
Delta
Sat, Oct 25 - Wed, Nov 12
CRW
Charleston
MDW
Chicago
$203 Roundtrip, found 9 hours ago
$203
Roundtrip
found 9 hours ago
Select Delta flight, departing Sat, Oct 25 from Charleston to Chicago, returning Wed, Nov 12, priced at $203 found 9 hours ago
Delta
Sat, Oct 4 - Tue, Oct 7
CRW
Charleston
MDW
Chicago
$208 Roundtrip, found 18 hours ago
$208
Roundtrip
found 18 hours ago
Select Delta flight, departing Sat, Oct 4 from Charleston to Chicago, returning Tue, Oct 7, priced at $208 found 18 hours ago
Delta
Mon, Nov 24 - Thu, Nov 27
CRW
Charleston
MDW
Chicago
$218 Roundtrip, found 1 day ago
$218
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Nov 24 from Charleston to Chicago, returning Thu, Nov 27, priced at $218 found 1 day ago
Delta
Mon, Dec 8 - Wed, Dec 24
CRW
Charleston
MDW
Chicago
$228 Roundtrip, found 5 hours ago
$228
Roundtrip
found 5 hours ago
Select Delta flight, departing Mon, Dec 8 from Charleston to Chicago, returning Wed, Dec 24, priced at $228 found 5 hours ago
Delta
Sat, Oct 25 - Mon, Nov 10
CRW
Charleston
MDW
Chicago
$233 Roundtrip, found 9 hours ago
$233
Roundtrip
found 9 hours ago
Select Delta flight, departing Sat, Oct 25 from Charleston to Chicago, returning Mon, Nov 10, priced at $233 found 9 hours ago
Delta
Fri, Oct 24 - Tue, Nov 11
CRW
Charleston
MDW
Chicago
$257 Roundtrip, found 9 hours ago
$257
Roundtrip
found 9 hours ago
Select Delta flight, departing Fri, Oct 24 from Charleston to Chicago, returning Tue, Nov 11, priced at $257 found 9 hours ago
Delta
Wed, Oct 22 - Mon, Nov 10
CRW
Charleston
MDW
Chicago
$258 Roundtrip, found 9 hours ago
$258
Roundtrip
found 9 hours ago
Select Delta flight, departing Wed, Oct 22 from Charleston to Chicago, returning Mon, Nov 10, priced at $258 found 9 hours ago
Delta
Sat, Oct 25 - Tue, Nov 11
CRW
Charleston
MDW
Chicago
$262 Roundtrip, found 9 hours ago
$262
Roundtrip
found 9 hours ago
Select Delta flight, departing Sat, Oct 25 from Charleston to Chicago, returning Tue, Nov 11, priced at $262 found 9 hours ago
Delta
Tue, Nov 25 - Sun, Dec 7
CRW
Charleston
MDW
Chicago
$262 Roundtrip, just found
$262
Roundtrip
just found
Select Delta flight, departing Tue, Nov 25 from Charleston to Chicago, returning Sun, Dec 7, priced at $262 just found

Frequently asked questions

How much does a flight from Yeager Airport (CRW) to Midway Intl. Airport (MDW) cost?
Get a cheap one-way flight from $89 or cheap return flight from $198 from Yeager Airport (CRW) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Yeager Airport (CRW) to Midway Intl. Airport (MDW)?
November is the least expensive month to fly from CRW to MDW. Traveling during an off-peak travel window is often the key to finding a great deal.
What is the cheapest airline that flies from Yeager Airport (CRW) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare different airlines, flight durations and fares all in one place. Customize the search to your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest CRW to MDW flight.
How many flights per day from Yeager Airport (CRW) to Midway Intl. Airport (MDW)?
Nonstop flights from Yeager Airport (CRW) to Midway Intl. Airport (MDW) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel details and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from CRW to MDW?
Friday is usually the busiest day for flights, while Tuesday is often the quietest.* Remember that flight schedules can vary based on various factors, such as the carrier and season.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Yeager Airport (CRW) to Midway Intl. Airport (MDW)?
Choose a flight from Yeager Airport (CRW) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the risk of cancellations and delays. Departures after this hour are on average 22% more likely to be 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 taking a direct flight from Yeager Airport (CRW) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Yeager Airport (CRW) to Midway Intl. Airport (MDW) last-minute?
Booking your ticket from CRW to MDW right before your journey is usually more expensive. However, if you're flexible with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a CRW to MDW flight and hotel package?
Opting for a CRW to MDW flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip all in one place. Choose from our extensive range of stays and then add car rentals, flights and activities to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Yeager Airport (CRW) to Midway Intl. Airport (MDW)?
In most instances, you can cancel or modify your CRW to MDW flight. However, additional fees may apply, especially if your booking was made more than 24 hours ago. Check your itinerary for the airline's rules and fees on flight changes, or if you want more details, head to our Customer Service portal.

Travel information

Travel information

Origin airport
Yeager
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$198
Distance
401 mi

Book with confidence

Book with confidence

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 $89 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.

 

Charleston to Chicago Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.