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Cheap flights from Charleston, West Virginia to Chicago from $293

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 9/30. 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

Delta Logo
3:25 pm - 9:36 pmCRW-MDW
7h 11m1 stop
Delta Logo
4:25 pm - 10:40 pmMDW-CRW
5h 15m1 stop
$293Delta
Find Deal
Tue, Sep 30 - Sat, Oct 4
Delta Logo
4:05 pm - 9:10 pmCRW-MDW
6h 05m1 stop
Delta Logo
10:35 am - 6:08 pmMDW-CRW
6h 33m1 stop
$298Delta
Find Deal
Sat, Sep 27 - Tue, Sep 30
Multiple Airlines Logo
7:36 pm - 1:38 pmCRW-MDW
19h 02m2 stops
Multiple Airlines Logo
9:45 am - 6:56 pmMDW-CRW
8h 11m1 stop
$325Multiple Airlines
Find Deal
Mon, Oct 20 - Fri, Oct 24
Delta Logo
6:25 am - 9:45 amCRW-MDW
4h 20m1 stop
Delta Logo
4:23 pm - 10:50 pmMDW-CRW
5h 27m1 stop
$348Delta
Find Deal
Sat, Nov 1 - Sat, Nov 8
Delta Logo
6:24 am - 9:56 amCRW-MDW
4h 32m1 stop
Delta Logo
6:00 am - 11:29 amMDW-CRW
4h 29m1 stop
$368Delta
Find Deal
Wed, Mar 4 - Sat, Mar 7
Delta Logo
3:25 pm - 9:46 pmCRW-MDW
7h 21m1 stop
Delta Logo
6:00 am - 11:29 amMDW-CRW
4h 29m1 stop
$408Delta
Find Deal
Wed, Mar 4 - Sat, Mar 7
Delta Logo
3:25 pm - 9:46 pmCRW-MDW
7h 21m1 stop
Delta Logo
6:00 am - 11:29 amMDW-CRW
4h 29m1 stop
$448Delta
Find Deal
Wed, Mar 4 - Sat, Mar 7
Delta Logo
6:25 am - 9:40 amCRW-MDW
4h 15m1 stop
Delta Logo
4:23 pm - 10:50 pmMDW-CRW
5h 27m1 stop
$462Delta
Find Deal
Sat, Nov 8 - Sat, Nov 8
Delta Logo
6:24 am - 6:34 pmCRW-MDW
13h 10m2 stops
Delta Logo
6:00 am - 11:29 amMDW-CRW
4h 29m1 stop
$467Delta
Find Deal
Wed, Mar 4 - Sat, Mar 7
Multiple Airlines Logo
7:36 pm - 2:40 pmCRW-MDW
20h 04m2 stops
Multiple Airlines Logo
6:20 am - 2:03 pmMDW-CRW
6h 43m1 stop
$1,081Multiple Airlines
Find Deal
Fri, Nov 28 - Sun, Nov 30

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
Sep 30
CRW3:25 pmCharleston Yeager
7h 11m
1 stop
MDW9:36 pmChicago Midway
Oct 4
MDW4:25 pmChicago Midway
5h 15m
1 stop
CRW10:40 pmCharleston Yeager
$293
Find similar
Delta
Sep 27
CRW4:05 pmCharleston Yeager
6h 05m
1 stop
MDW9:10 pmChicago Midway
Sep 30
MDW10:35 amChicago Midway
6h 33m
1 stop
CRW6:08 pmCharleston Yeager
$298
Find similar
Delta
Nov 1
CRW6:25 amCharleston Yeager
4h 20m
1 stop
MDW9:45 amChicago Midway
Nov 8
MDW4:23 pmChicago Midway
5h 27m
1 stop
CRW10:50 pmCharleston Yeager
$348
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 September 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

Tue 9/30

3:25 pm-9:36 pm

1 stop7h 11m

Chicago Midway

Sat 10/4

4:25 pm-10:40 pm

1 stop5h 15m

$293

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Sat 9/27

4:05 pm-9:10 pm

1 stop6h 05m

Chicago Midway

Tue 9/30

10:35 am-6:08 pm

1 stop6h 33m

$298

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Mon 10/20

7:36 pm-1:38 pm

2 stops19h 02m

Chicago Midway

Fri 10/24

9:45 am-6:56 pm

1 stop8h 11m

$325

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Sat 11/1

6:25 am-9:45 am

1 stop4h 20m

Chicago Midway

Sat 11/8

4:23 pm-10:50 pm

1 stop5h 27m

$348

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Wed 3/4

6:24 am-9:56 am

1 stop4h 32m

Chicago Midway

Sat 3/7

6:00 am-11:29 am

1 stop4h 29m

$368

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Wed 3/4

3:25 pm-9:46 pm

1 stop7h 21m

Chicago Midway

Sat 3/7

6:00 am-11:29 am

1 stop4h 29m

$408

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Wed 3/4

3:25 pm-9:46 pm

1 stop7h 21m

Chicago Midway

Sat 3/7

6:00 am-11:29 am

1 stop4h 29m

$448

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Sat 11/8

6:25 am-9:40 am

1 stop4h 15m

Chicago Midway

Sat 11/8

4:23 pm-10:50 pm

1 stop5h 27m

$462

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Wed 3/4

6:24 am-6:34 pm

2 stops13h 10m

Chicago Midway

Sat 3/7

6:00 am-11:29 am

1 stop4h 29m

$467

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Fri 11/28

7:36 pm-2:40 pm

2 stops20h 04m

Chicago Midway

Sun 11/30

6:20 am-2:03 pm

1 stop6h 43m

$1,081

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 11 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Charleston, West Virginia to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Charleston Yeager to Chicago Midway?

Delta is the most popular carrier operating from Charleston Yeager to Chicago Midway

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 15m.

  • 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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Portage
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Valparaiso
Crown Point
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Saint John

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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