$104 Cheap Flights from Charleston (CRW) to Chicago (MDW)

View $104 flight on Sat, Sep 13, 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 $104 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 18 - Wed, Dec 3
CRW
Charleston
MDW
Chicago
$198 Roundtrip, found 4 days ago
$198
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Nov 18 from Charleston to Chicago, returning Wed, Dec 3, priced at $198 found 4 days ago
Delta
Sat, Oct 4 - Tue, Oct 21
CRW
Charleston
MDW
Chicago
$218 Roundtrip, found 1 day ago
$218
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Oct 4 from Charleston to Chicago, returning Tue, Oct 21, priced at $218 found 1 day ago
Delta
Mon, Nov 24 - Thu, Nov 27
CRW
Charleston
MDW
Chicago
$222 Roundtrip, found 2 days ago
$222
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Nov 24 from Charleston to Chicago, returning Thu, Nov 27, priced at $222 found 2 days ago
Delta
Tue, Nov 18 - Sat, Dec 6
CRW
Charleston
MDW
Chicago
$228 Roundtrip, found 4 days ago
$228
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Nov 18 from Charleston to Chicago, returning Sat, Dec 6, priced at $228 found 4 days ago
Delta
Sat, Oct 4 - Wed, Oct 22
CRW
Charleston
MDW
Chicago
$234 Roundtrip, found 6 days ago
$234
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Oct 4 from Charleston to Chicago, returning Wed, Oct 22, priced at $234 found 6 days ago
Delta
Sat, Oct 18 - Mon, Oct 27
CRW
Charleston
MDW
Chicago
$248 Roundtrip, found 1 day ago
$248
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Oct 18 from Charleston to Chicago, returning Mon, Oct 27, priced at $248 found 1 day ago
Delta
Tue, Nov 25 - Fri, Dec 12
CRW
Charleston
MDW
Chicago
$258 Roundtrip, found 4 days ago
$258
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Nov 25 from Charleston to Chicago, returning Fri, Dec 12, priced at $258 found 4 days ago
Delta
Mon, Nov 24 - Mon, Dec 1
CRW
Charleston
MDW
Chicago
$263 Roundtrip, found 2 days ago
$263
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Nov 24 from Charleston to Chicago, returning Mon, Dec 1, priced at $263 found 2 days ago
Delta
Wed, Dec 31 - Tue, Jan 13
CRW
Charleston
MDW
Chicago
$277 Roundtrip, found 4 days ago
$277
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Dec 31 from Charleston to Chicago, returning Tue, Jan 13, priced at $277 found 4 days ago
Delta
Wed, Sep 3 - Tue, Sep 23
CRW
Charleston
MDW
Chicago
$283 Roundtrip, found 2 days ago
$283
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Sep 3 from Charleston to Chicago, returning Tue, Sep 23, priced at $283 found 2 days ago

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $244
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $244
Flights from Charleston (CRW) to Chicago (MDW)
Origin airport
Yeager
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$198
Distance
401 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 $104 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 Midway Intl. Airport (MDW) cost?
Get a cheap one-way flight from $104 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.

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*Available to One Key members.