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Cheap flights from Charleston, West Virginia to Chicago from $192

This is the cheapest one-way 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 6/16. 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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0 bags

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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
6:00 am - 10:09 am
CRW
-
MDW
5h 09m
1 stop
Delta Logo
6:00 am - 2:02 pm
MDW
-
CRW
7h 02m
1 stop
$333Delta
Tue, Jun 9 - Tue, Jun 23
Delta Logo
6:00 am - 1:19 pm
CRW
-
MDW
8h 19m
2 stops
Delta Logo
5:08 pm - 11:07 pm
MDW
-
CRW
4h 59m
1 stop
$404Delta
Thu, May 28 - Mon, Jun 1
Delta Logo
6:55 pm - 10:17 pm
CRW
-
MDW
4h 22m
1 stop
Delta Logo
11:05 am - 6:15 pm
MDW
-
CRW
6h 10m
1 stop
$408Delta
Thu, Jun 11 - Thu, Jun 18
Delta Logo
6:00 am - 1:19 pm
CRW
-
MDW
8h 19m
2 stops
Delta Logo
5:08 pm - 11:07 pm
MDW
-
CRW
4h 59m
1 stop
$434Delta
Thu, May 28 - Mon, Jun 1
Delta Logo
6:00 am - 12:46 pm
CRW
-
MDW
7h 46m
2 stops
Delta Logo
6:00 am - 2:02 pm
MDW
-
CRW
7h 02m
1 stop
$464Delta
Tue, Jun 9 - Tue, Jun 23
Delta Logo
6:00 am - 1:19 pm
CRW
-
MDW
8h 19m
2 stops
Delta Logo
10:59 am - 6:19 pm
MDW
-
CRW
6h 20m
1 stop
$484Delta
Thu, May 28 - Sun, May 31
Delta Logo
3:25 pm - 9:46 pm
CRW
-
MDW
7h 21m
1 stop
Delta Logo
5:25 pm - 10:42 pm
MDW
-
CRW
4h 17m
1 stop
$508Delta
Sat, Sep 19 - Wed, Sep 23
Delta Logo
3:25 pm - 9:46 pm
CRW
-
MDW
7h 21m
1 stop
Delta Logo
1:00 pm - 10:42 pm
MDW
-
CRW
8h 42m
2 stops
$514Delta
Sat, Sep 19 - Wed, Sep 23
Delta Logo
3:30 pm - 9:09 pm
CRW
-
MDW
6h 39m
1 stop
Delta Logo
5:08 pm - 11:07 pm
MDW
-
CRW
4h 59m
1 stop
$523Delta
Thu, May 28 - Mon, Jun 1
Delta Logo
6:00 am - 1:19 pm
CRW
-
MDW
8h 19m
2 stops
Delta Logo
5:08 pm - 11:07 pm
MDW
-
CRW
4h 59m
1 stop
$529Delta
Thu, May 28 - Mon, Jun 1

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
Jun 9
CRW6:00 amCharleston Yeager
5h 09m
1 stop
MDW10:09 amChicago Midway
Jun 23
MDW6:00 amChicago Midway
7h 02m
1 stop
CRW2:02 pmCharleston Yeager
$333
Delta
May 28
CRW6:00 amCharleston Yeager
8h 19m
2 stops
MDW1:19 pmChicago Midway
Jun 1
MDW5:08 pmChicago Midway
4h 59m
1 stop
CRW11:07 pmCharleston Yeager
$404
Delta
Jun 11
CRW6:55 pmCharleston Yeager
4h 22m
1 stop
MDW10:17 pmChicago Midway
Jun 18
MDW11:05 amChicago Midway
6h 10m
1 stop
CRW6:15 pmCharleston Yeager
$408

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 May 18, 2026.
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

Cheapest round-trip

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Tue 6/9

6:00 am-10:09 am

1 stop5h 09m

Chicago Midway

Tue 6/23

6:00 am-2:02 pm

1 stop7h 02m

$333

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Thu 5/28

6:00 am-1:19 pm

2 stops8h 19m

Chicago Midway

Mon 6/1

5:08 pm-11:07 pm

1 stop4h 59m

$404
Quickest round-trip

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Thu 6/11

6:55 pm-10:17 pm

1 stop4h 22m

Chicago Midway

Thu 6/18

11:05 am-6:15 pm

1 stop6h 10m

$408

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Thu 5/28

6:00 am-1:19 pm

2 stops8h 19m

Chicago Midway

Mon 6/1

5:08 pm-11:07 pm

1 stop4h 59m

$434

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Tue 6/9

6:00 am-12:46 pm

2 stops7h 46m

Chicago Midway

Tue 6/23

6:00 am-2:02 pm

1 stop7h 02m

$464

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Thu 5/28

6:00 am-1:19 pm

2 stops8h 19m

Chicago Midway

Sun 5/31

10:59 am-6:19 pm

1 stop6h 20m

$484

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Sat 9/19

3:25 pm-9:46 pm

1 stop7h 21m

Chicago Midway

Wed 9/23

5:25 pm-10:42 pm

1 stop4h 17m

$508

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Sat 9/19

3:25 pm-9:46 pm

1 stop7h 21m

Chicago Midway

Wed 9/23

1:00 pm-10:42 pm

2 stops8h 42m

$514

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Thu 5/28

3:30 pm-9:09 pm

1 stop6h 39m

Chicago Midway

Mon 6/1

5:08 pm-11:07 pm

1 stop4h 59m

$523

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Thu 5/28

6:00 am-1:19 pm

2 stops8h 19m

Chicago Midway

Mon 6/1

5:08 pm-11:07 pm

1 stop4h 59m

$529

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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

Fastest flight time

4h 19m

Direct flights

None
The fastest flight from Charleston, West Virginia to Chicago Midway Airport takes 4h 19m
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.
Search flight deals

Frequently asked questions about flying from Charleston, West Virginia to Chicago Midway Airport

  • 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 19m.

  • 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?

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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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