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Cheap flights from Chicago Midway Airport to Charleston from $394

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Charleston departing on 8/27. 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 Chicago Midway Airport to Charleston (MDW-CRW)

Cheap round-trip flights

Delta Logo
1:08 pm - 10:50 pmMDW-CRW
8h 42m2 stops
Delta Logo
6:24 am - 9:51 amCRW-MDW
4h 27m1 stop
$514Delta
Find Deal
Wed, Nov 5 - Sun, Nov 9
Delta Logo
10:35 am - 5:55 pmMDW-CRW
6h 20m1 stop
Delta Logo
3:25 pm - 9:44 pmCRW-MDW
7h 19m1 stop
$548Delta
Find Deal
Fri, Nov 14 - Mon, Nov 17
Delta Logo
5:09 pm - 10:50 pmMDW-CRW
4h 41m1 stop
Delta Logo
6:24 am - 11:55 amCRW-MDW
6h 31m1 stop
$598Delta
Find Deal
Wed, Nov 5 - Sun, Nov 9
Delta Logo
9:30 am - 5:55 pmMDW-CRW
7h 25m2 stops
Delta Logo
3:25 pm - 9:44 pmCRW-MDW
7h 19m1 stop
$604Delta
Find Deal
Fri, Nov 14 - Mon, Nov 17
Delta Logo
1:08 pm - 10:43 pmMDW-CRW
8h 35m2 stops
Delta Logo
3:25 pm - 9:26 pmCRW-MDW
7h 01m1 stop
$674Delta
Find Deal
Fri, Sep 5 - Sun, Sep 7
Delta Logo
4:25 pm - 10:43 pmMDW-CRW
5h 18m1 stop
Delta Logo
4:05 pm - 9:12 pmCRW-MDW
6h 07m1 stop
$682Delta
Find Deal
Wed, Aug 27 - Sun, Aug 31
Delta Logo
4:25 pm - 10:43 pmMDW-CRW
5h 18m1 stop
Delta Logo
3:25 pm - 9:26 pmCRW-MDW
7h 01m1 stop
$708Delta
Find Deal
Fri, Sep 5 - Sun, Sep 7
Delta Logo
4:25 pm - 10:43 pmMDW-CRW
5h 18m1 stop
Delta Logo
6:40 am - 12:28 pmCRW-MDW
6h 48m2 stops
$734Delta
Find Deal
Wed, Aug 27 - Sun, Aug 31
Delta Logo
1:08 pm - 10:43 pmMDW-CRW
8h 35m2 stops
Delta Logo
11:15 am - 6:37 pmCRW-MDW
8h 22m2 stops
$759Delta
Find Deal
Fri, Sep 5 - Sun, Sep 7
Delta Logo
1:08 pm - 10:40 pmMDW-CRW
8h 32m2 stops
Delta Logo
6:30 am - 11:48 amCRW-MDW
6h 18m1 stop
$844Delta
Find Deal
Thu, Sep 18 - Sun, Sep 21

Delta flights from Chicago Midway Airport to Charleston, West Virginia

Our best Delta deals on Chicago Midway Airport to Charleston, West Virginia flight tickets
Delta
Aug 19
MDW10:31 amChicago Midway
6h 43m
1 stop
CRW6:14 pmCharleston Yeager
Aug 26
CRW6:40 amCharleston Yeager
6h 48m
2 stops
MDW12:28 pmChicago Midway
$264
Find similar
Delta
Aug 19
MDW1:08 pmChicago Midway
8h 35m
2 stops
CRW10:43 pmCharleston Yeager
Aug 26
CRW6:40 amCharleston Yeager
6h 48m
2 stops
MDW12:28 pmChicago Midway
$269
Find similar
Delta
Aug 19
MDW12:43 pmChicago Midway
4h 31m
1 stop
CRW6:14 pmCharleston Yeager
Aug 26
CRW3:25 pmCharleston Yeager
7h 19m
1 stop
MDW9:44 pmChicago Midway
$447
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Charleston, West Virginia 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 August 14, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Charleston, West Virginia that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoCharleston

MDW - CRW

MDWCRW

Chicago Midway

Wed 11/5

1:08 pm-10:50 pm

2 stops8h 42m

Charleston Yeager

Sun 11/9

6:24 am-9:51 am

1 stop4h 27m

$514

ChicagoCharleston

MDW - CRW

MDWCRW

Chicago Midway

Fri 11/14

10:35 am-5:55 pm

1 stop6h 20m

Charleston Yeager

Mon 11/17

3:25 pm-9:44 pm

1 stop7h 19m

$548

ChicagoCharleston

MDW - CRW

MDWCRW

Chicago Midway

Wed 11/5

5:09 pm-10:50 pm

1 stop4h 41m

Charleston Yeager

Sun 11/9

6:24 am-11:55 am

1 stop6h 31m

$598

ChicagoCharleston

MDW - CRW

MDWCRW

Chicago Midway

Fri 11/14

9:30 am-5:55 pm

2 stops7h 25m

Charleston Yeager

Mon 11/17

3:25 pm-9:44 pm

1 stop7h 19m

$604

ChicagoCharleston

MDW - CRW

MDWCRW

Chicago Midway

Fri 9/5

1:08 pm-10:43 pm

2 stops8h 35m

Charleston Yeager

Sun 9/7

3:25 pm-9:26 pm

1 stop7h 01m

$674

ChicagoCharleston

MDW - CRW

MDWCRW

Chicago Midway

Wed 8/27

4:25 pm-10:43 pm

1 stop5h 18m

Charleston Yeager

Sun 8/31

4:05 pm-9:12 pm

1 stop6h 07m

$682

ChicagoCharleston

MDW - CRW

MDWCRW

Chicago Midway

Fri 9/5

4:25 pm-10:43 pm

1 stop5h 18m

Charleston Yeager

Sun 9/7

3:25 pm-9:26 pm

1 stop7h 01m

$708

ChicagoCharleston

MDW - CRW

MDWCRW

Chicago Midway

Wed 8/27

4:25 pm-10:43 pm

1 stop5h 18m

Charleston Yeager

Sun 8/31

6:40 am-12:28 pm

2 stops6h 48m

$734

ChicagoCharleston

MDW - CRW

MDWCRW

Chicago Midway

Fri 9/5

1:08 pm-10:43 pm

2 stops8h 35m

Charleston Yeager

Sun 9/7

11:15 am-6:37 pm

2 stops8h 22m

$759

ChicagoCharleston

MDW - CRW

MDWCRW

Chicago Midway

Thu 9/18

1:08 pm-10:40 pm

2 stops8h 32m

Charleston Yeager

Sun 9/21

6:30 am-11:48 am

1 stop6h 18m

$844

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 resultsSorted by cheapest first
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See travel insights to Charleston from

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

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 day to depart on your flight to Charleston, West Virginia?

On average, the least expensive day to fly to Charleston, West Virginia from Chicago Midway Airport is on a Saturday. momondo users have found tickets for Saturday departures for as low as $249. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to Charleston, West Virginia for around $479.

What is the cheapest time of day to depart on your flight to Charleston, West Virginia?

In the morning is the cheapest time of day to fly from Chicago Midway Airport to Charleston, West Virginia when you can find flight prices for as low as $288. Flying to Charleston, West Virginia in the morning is an ideal time because this is during off-peak travel hours. Try not to purchase tickets at noon because they tend to be around $324. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

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

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

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

Best Price Found

$394

Fastest flight time

4h 41m

Direct flights

None

Airports in Charleston, West Virginia

1 airport
The best one-way flight to Charleston, West Virginia from Chicago Midway Airport in the past 72 hours is $394. The best round-trip flight deal from Chicago Midway Airport to Charleston, West Virginia found on momondo in the last 72 hours is $514.
The fastest flight from Chicago Midway Airport to Charleston, West Virginia takes 4h 41m
There are no direct flights from Chicago Midway Airport to Charleston, West Virginia. Popular non-direct route for this connection is Chicago Midway Airport - Charleston Yeager Airport.
There is 1 airport near Charleston, West Virginia: Charleston Yeager (CRW)
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  • How far is Chicago Midway to Charleston Yeager by plane?

    Chicago Midway and Charleston Yeager are 400.6 mi apart from one another. A reasonable flight in good conditions will take 4h 41m.

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

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Charleston Yeager Airport.

  • What documentation or ID do you need to fly to Charleston Yeager Airport?

    The travel and health documents you'll need for your trip to Charleston Yeager Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Charleston Yeager Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Charleston?

Book flights to Charleston if you plan to visit one of these locations
Cross Lanes

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Charleston from Chicago.

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

Flights from Chicago to Charleston 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 Chicago to Charleston?

Once all potential Chicago to Charleston 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 Chicago to Charleston right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Charleston flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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