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$147+ Cheap flights from Charleston, WV (CRW) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — MDW
nov. 27 — déc. 41
jeu. 11/27
jeu. 12/4
1 adult, Economy
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Find flight deals from Charleston to Midway

Cheapest flights from Charleston to Midway
Explore the most affordable flight options available from Charleston to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octobre 28, 2025.

This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 11/74:05 pmCRW - MDW
1 stop7h 09mDelta
mar. 11/1112:47 pmMDW - CRW
1 stop4h 23mDelta
Deal found 10/28$338
This Kiwi.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 11/279:58 amCRW - MDW
2 stops13h 45mMultiple Airlines
jeu. 12/47:44 amMDW - CRW
1 stop5h 19mMultiple Airlines
Deal found 10/28$393
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 11/271:15 pmCRW - MDW
1 stop4h 24mDelta
jeu. 12/45:13 pmMDW - CRW
1 stop4h 36mDelta
Deal found 10/28$408
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/309:58 amCRW - MDW
2 stops37h 14mMultiple Airlines
dim. 1/47:44 amMDW - CRW
1 stop5h 19mMultiple Airlines
Deal found 10/27$427
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/309:58 amCRW - MDW
2 stops29h 39mMultiple Airlines
sam. 1/32:16 pmMDW - CRW
1 stop18h 02mMultiple Airlines
Deal found 10/27$471
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/116:50 pmCRW - MDW
1 stop5h 50mDelta
sam. 11/154:28 pmMDW - CRW
1 stop5h 22mDelta
Deal found 10/27$498
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 10/296:25 amCRW - MDW
1 stop4h 20mDelta
sam. 11/14:23 pmMDW - CRW
1 stop5h 27mDelta
Deal found 10/26$573
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/106:50 pmCRW - MDW
1 stop5h 50mDelta
ven. 11/1412:47 pmMDW - CRW
1 stop4h 23mDelta
Deal found 10/25$576
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 11/14:05 pmCRW - MDW
1 stop7h 09mDelta
dim. 11/25:04 pmMDW - CRW
1 stop4h 46mDelta
Deal found 10/28$663

Cheap flight deals from Charleston to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Charleston (CRW) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated octobre 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$208
(Delta)

One-way from

$147
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$334
Provider with most accurate pricing for Charleston Yeager-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Charleston Yeager-Chicago Midway flights.
Search Deals
From Charleston Yeager to Chicago Midway
Search Deals
One-way flight from Charleston Yeager to Chicago Midway
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($52 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Charleston to Midway 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, Cheapflights users made 2,558,603 searches. Data last updated octobre 28, 2025.
Use the filters below to find and compare flights from Charleston to Chicago Midway Airport that are best for you.

Fly from

Charleston

Fly to

Midway

Route

Depart

Return

Price

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

sam. 2/21

12:02 pm-3:25 pm

1 stop4h 23m

Chicago Midway

mer. 2/25

5:25 pm-10:34 pm

1 stop4h 09m

$208

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

ven. 11/7

4:05 pm-10:14 pm

1 stop7h 09m

Chicago Midway

mar. 11/11

12:47 pm-6:10 pm

1 stop4h 23m

$338

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

jeu. 11/27

9:58 am-10:43 pm

2 stops13h 45m

Chicago Midway

jeu. 12/4

7:44 am-2:03 pm

1 stop5h 19m

$393

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

jeu. 11/27

1:15 pm-4:39 pm

1 stop4h 24m

Chicago Midway

jeu. 12/4

5:13 pm-10:49 pm

1 stop4h 36m

$408

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

mar. 12/30

9:58 am-2:37 pm

2 stops29h 39m

Chicago Midway

sam. 1/3

2:16 pm-9:18 am

1 stop18h 02m

$471

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

mer. 3/4

6:24 am-12:01 pm

1 stop6h 37m

Chicago Midway

sam. 3/7

6:00 am-11:29 am

1 stop4h 29m

$488

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

mar. 11/11

6:50 pm-11:40 pm

1 stop5h 50m

Chicago Midway

sam. 11/15

4:28 pm-10:50 pm

1 stop5h 22m

$498

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

lun. 11/10

7:36 pm-12:41 pm

3 stops42h 05m

$147

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

dim. 11/9

9:58 am-11:55 pm

1 stop14h 57m

$256

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

lun. 11/10

6:50 pm-11:40 pm

1 stop5h 50m

$298

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Compare providers for flights from Charleston to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Charleston to Midway in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Charleston, West Virginia-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Charleston, West Virginia-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Charleston, West Virginia-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Charleston, West Virginia-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Charleston, West Virginia-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Charleston to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Charleston with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

Find useful and relevant information for your journey from Charleston to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Charleston to Chicago Midway?

    If you book a flight to Chicago Midway from Charleston, you will be flying from Yeager, which is the city’s only airport. Charleston Yeager (CRW) is located 2.7 mi from the center of Charleston. There are 0 flights from Yeager to Chicago Midway per day from 0 different airlines.

  • How long is the flight from Charleston, West Virginia to Chicago Midway Airport?

    A quick flight from Charleston, West Virginia to Chicago Midway Airport can take about 4h 23m. Delta provides one of the quickest options available for as low as $208. There are 401 mi between Charleston, West Virginia and Chicago Midway Airport.

  • Can I find deals for flights from Charleston to Midway that include hotel bookings?

    Yes. In addition to deals on Charleston to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Charleston to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Charleston to Midway.

  • Can I find deals for business class flights from Charleston to Midway?

    Yes. Cheapflights offers flight deals from Charleston to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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