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Cheap flights from Charleston, West Virginia to Chicago from $198

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Charleston, West Virginia to Chicago departing on 2/21. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Charleston, West Virginia to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
11:03 am - 3:23 pmCRW-MDW
5h 20m1 stop
Delta Logo
12:46 pm - 5:54 pmMDW-CRW
4h 08m1 stop
$198Delta
Find Deal
Sat, Feb 21 - Wed, Feb 25
Delta Logo
6:34 pm - 10:44 pmCRW-MDW
5h 10m1 stop
Delta Logo
4:13 pm - 9:34 pmMDW-CRW
4h 21m1 stop
$243Delta
Find Deal
Wed, Mar 4 - Sat, Mar 7
Delta Logo
6:15 am - 6:37 pmCRW-MDW
13h 22m2 stops
Delta Logo
4:13 pm - 9:34 pmMDW-CRW
4h 21m1 stop
$336Delta
Find Deal
Wed, Mar 4 - Sat, Mar 7
Delta Logo
6:15 am - 6:37 pmCRW-MDW
13h 22m2 stops
Delta Logo
4:13 pm - 9:34 pmMDW-CRW
4h 21m1 stop
$351Delta
Find Deal
Wed, Mar 4 - Sat, Mar 7
Delta Logo
11:03 am - 9:08 amCRW-MDW
23h 05m2 stops
Delta Logo
12:46 pm - 5:54 pmMDW-CRW
4h 08m1 stop
$356Delta
Find Deal
Sat, Feb 21 - Wed, Feb 25
Delta Logo
6:24 am - 9:51 amCRW-MDW
4h 27m1 stop
Delta Logo
10:35 am - 5:55 pmMDW-CRW
6h 20m1 stop
$368Delta
Find Deal
Thu, Apr 16 - Sun, Apr 19
Delta Logo
6:24 am - 9:51 amCRW-MDW
4h 27m1 stop
Delta Logo
10:35 am - 5:55 pmMDW-CRW
6h 20m1 stop
$398Delta
Find Deal
Fri, Apr 17 - Sun, Apr 19
Multiple Airlines Logo
2:43 pm - 9:17 amCRW-MDW
43h 34m2 stops
Multiple Airlines Logo
7:44 am - 2:03 pmMDW-CRW
5h 19m1 stop
$440Multiple Airlines
Find Deal
Sun, Nov 30 - Thu, Dec 4
Delta Logo
11:18 am - 3:44 pmCRW-MDW
5h 26m1 stop
Delta Logo
10:49 am - 6:09 pmMDW-CRW
6h 20m1 stop
$448Delta
Find Deal
Sat, Dec 13 - Sun, Dec 14
Multiple Airlines Logo
2:43 pm - 4:52 pmCRW-MDW
27h 09m1 stop
Multiple Airlines Logo
7:44 am - 2:03 pmMDW-CRW
5h 19m1 stop
$496Multiple Airlines
Find Deal
Sun, Nov 30 - Thu, Dec 4

Delta flights from Charleston, West Virginia to Chicago Midway Airport

Our best Delta deals on Charleston, West Virginia to Chicago Midway Airport flight tickets
Delta
Feb 21
CRW11:03 amCharleston Yeager
5h 20m
1 stop
MDW3:23 pmChicago Midway
Feb 25
MDW12:46 pmChicago Midway
4h 08m
1 stop
CRW5:54 pmCharleston Yeager
$198
Find similar
Delta
Mar 4
CRW6:34 pmCharleston Yeager
5h 10m
1 stop
MDW10:44 pmChicago Midway
Mar 7
MDW4:13 pmChicago Midway
4h 21m
1 stop
CRW9:34 pmCharleston Yeager
$243
Find similar
Delta
Mar 4
CRW6:15 amCharleston Yeager
13h 22m
2 stops
MDW6:37 pmChicago Midway
Mar 7
MDW4:13 pmChicago Midway
4h 21m
1 stop
CRW9:34 pmCharleston Yeager
$336
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Charleston, West Virginia to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated November 17, 2025.
Use the filters below to find and compare flights from Charleston, West Virginia to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Sat 2/21

11:03 am-3:23 pm

1 stop5h 20m

Chicago Midway

Wed 2/25

12:46 pm-5:54 pm

1 stop4h 08m

$198

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Wed 3/4

6:34 pm-10:44 pm

1 stop5h 10m

Chicago Midway

Sat 3/7

4:13 pm-9:34 pm

1 stop4h 21m

$243

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Wed 3/4

6:15 am-6:37 pm

2 stops13h 22m

Chicago Midway

Sat 3/7

4:13 pm-9:34 pm

1 stop4h 21m

$336

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Wed 3/4

6:15 am-6:37 pm

2 stops13h 22m

Chicago Midway

Sat 3/7

4:13 pm-9:34 pm

1 stop4h 21m

$351

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Sat 2/21

11:03 am-9:08 am

2 stops23h 05m

Chicago Midway

Wed 2/25

12:46 pm-5:54 pm

1 stop4h 08m

$356

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Thu 4/16

6:24 am-9:51 am

1 stop4h 27m

Chicago Midway

Sun 4/19

10:35 am-5:55 pm

1 stop6h 20m

$368

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Fri 4/17

6:24 am-9:51 am

1 stop4h 27m

Chicago Midway

Sun 4/19

10:35 am-5:55 pm

1 stop6h 20m

$398

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Sun 11/30

2:43 pm-9:17 am

2 stops43h 34m

Chicago Midway

Thu 12/4

7:44 am-2:03 pm

1 stop5h 19m

$440

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Sat 12/13

11:18 am-3:44 pm

1 stop5h 26m

Chicago Midway

Sun 12/14

10:49 am-6:09 pm

1 stop6h 20m

$448

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Sun 11/30

2:43 pm-4:52 pm

1 stop27h 09m

Chicago Midway

Thu 12/4

7:44 am-2:03 pm

1 stop5h 19m

$496

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

When to book flights from Charleston, West Virginia to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Charleston, West Virginia to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Charleston, West Virginia to Chicago Midway Airport (CRW to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Charleston, West Virginia to Chicago Midway Airport

Direct flights

None
There are no direct flights from Charleston, West Virginia to Chicago Midway Airport. There are no popular flight routes from Charleston, West Virginia to Chicago Midway Airport.
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  • How far is Charleston Yeager to Chicago Midway by plane?

    The straight-line distance from Charleston Yeager to Chicago Midway is 400.6 mi. A reasonable flight in good conditions will take 4h 27m.

  • When did momondo last update prices for flights from Charleston Yeager Airport to Chicago Midway Airport?

    Prices for flights from Charleston Yeager Airport to Chicago Midway Airport refresh daily.

  • How old do you have to be to fly from Charleston Yeager Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Charleston Yeager Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • How do I get Price Alerts for flights from Charleston, West Virginia to Chicago Midway Airport?

    Search flight deals from Charleston, West Virginia to Chicago Midway Airport. While viewing offers you’ll have the option to create a Price Alert.

  • How can I save money on flights from Charleston, West Virginia to Chicago Midway Airport with momondo?

    Plan your trips smart with the “Price Forecast” feature, which uses flight data to help you pick the best days to fly for the lowest fares. Our “Price Calendar” helps you get the most for your money by showing you when it’s most advantageous to fly. Curate your own travel experiences for less with “Explore”. Expert travel hacks to fuel your next adventure are a click away with “Discover” by momondo. Set up our “Price Alerts” to track fare changes and book when prices are at their lowest point.

  • How does momondo find its flight prices?

    We aggregate our prices from over 700+ competitors from airlines to OTAs. We operate in over 30 markets worldwide to show you a wide range of travel options.

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Why use momondo?

Why should I use momondo to find a flight deal from Charleston to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Charleston to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Charleston to Chicago with flexible booking policies on momondo?

Flights from Charleston to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Charleston to Chicago?

Once all potential Charleston to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Charleston to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Charleston to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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