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$198+ Cheap flights from Charleston, WV (CRW) to Midway (MDW)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — MDW
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap 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 December 12, 2025.

This Delta deal was found by Cheapflights users on 12/9. 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.
Wed 12/106:50 pmCRW - MDW
1 stop5h 57mDelta
Tue 12/1610:49 amMDW - CRW
1 stop6h 16mDelta
Deal found 12/9$343
This Delta deal was found by Cheapflights users on 12/9. 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.
Wed 12/106:50 pmCRW - MDW
1 stop5h 57mDelta
Sat 12/134:29 pmMDW - CRW
1 stop5h 20mDelta
Deal found 12/9$398
This Delta deal was found by Cheapflights users on 12/11. 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.
Sat 12/136:00 amCRW - MDW
1 stop4h 54mDelta
Sun 12/145:13 pmMDW - CRW
1 stop4h 36mDelta
Deal found 12/11$473
This Delta deal was found by Cheapflights users on 12/11. 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.
Sun 12/2112:25 pmCRW - MDW
1 stop4h 55mDelta
Sun 1/1111:21 amMDW - CRW
1 stop4h 19mDelta
Deal found 12/11$528
This Delta deal was found by Cheapflights users on 12/9. 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.
Wed 12/106:50 pmCRW - MDW
1 stop5h 57mDelta
Sun 12/1412:50 pmMDW - CRW
1 stop4h 19mDelta
Deal found 12/9$593
This Delta deal was found by Cheapflights users on 12/9. 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.
Wed 12/106:50 pmCRW - MDW
1 stop5h 57mDelta
Thu 12/189:59 amMDW - CRW
2 stops11h 50mDelta
Deal found 12/9$676
This Delta deal was found by Cheapflights users on 12/9. 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.
Fri 12/126:50 pmCRW - MDW
1 stop5h 57mDelta
Sun 12/1412:50 pmMDW - CRW
1 stop4h 19mDelta
Deal found 12/9$683
This Delta deal was found by Cheapflights users on 12/10. 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.
Fri 12/196:54 pmCRW - MDW
1 stop5h 53mDelta
Sun 12/216:00 amMDW - CRW
1 stop4h 45mDelta
Deal found 12/10$708
This Delta deal was found by Cheapflights users on 12/9. 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.
Tue 12/166:50 pmCRW - MDW
1 stop5h 57mDelta
Thu 12/185:26 pmMDW - CRW
1 stop4h 23mDelta
Deal found 12/9$766
This Delta deal was found by Cheapflights users on 12/9. 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.
Wed 12/106:50 pmCRW - MDW
1 stop5h 57mDelta
Mon 12/157:02 pmMDW - CRW
2 stops19h 05mDelta
Deal found 12/9$780
This Delta deal was found by Cheapflights users on 12/9. 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.
Wed 12/106:50 pmCRW - MDW
1 stop5h 57mDelta
Fri 12/127:02 pmMDW - CRW
2 stops26h 47mDelta
Deal found 12/9$795

Find 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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$198
(Delta)

Popular in

July

Cheapest in

February

Average price

$269
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
Highest demand for flights based on searches. 10% potential increase in price ($39 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 12, 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

Sat 1/17

12:20 pm-4:29 pm

1 stop5h 09m

Chicago Midway

Tue 1/20

12:48 pm-5:53 pm

1 stop4h 05m

$198

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Wed 1/7

12:20 pm-4:29 pm

1 stop5h 09m

Chicago Midway

Wed 1/14

11:21 am-4:40 pm

1 stop4h 19m

$198

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Fri 3/20

6:56 pm-10:29 pm

1 stop4h 33m

Chicago Midway

Tue 3/24

12:47 pm-6:16 pm

1 stop4h 29m

$213

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Wed 4/8

6:56 pm-10:29 pm

1 stop4h 33m

Chicago Midway

Sat 4/11

4:30 pm-10:38 pm

1 stop5h 08m

$318

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Sat 1/10

5:20 pm-10:07 pm

1 stop5h 47m

Chicago Midway

Sun 1/11

11:21 am-4:40 pm

1 stop4h 19m

$373

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Sun 1/18

12:20 pm-4:29 pm

1 stop5h 09m

Chicago Midway

Wed 1/21

10:46 am-5:53 pm

1 stop6h 07m

$436

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Sun 1/18

5:20 pm-10:07 pm

1 stop5h 47m

Chicago Midway

Tue 1/20

10:48 am-5:53 pm

1 stop6h 05m

$436

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Thu 2/19

6:37 pm-10:42 pm

1 stop5h 05m

Chicago Midway

Mon 2/23

10:53 am-5:55 pm

1 stop6h 02m

$443

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Sun 12/21

12:25 pm-4:20 pm

1 stop4h 55m

Chicago Midway

Sun 1/11

11:21 am-4:40 pm

1 stop4h 19m

$528

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Thu 5/28

3:25 pm-9:45 pm

1 stop7h 20m

Chicago Midway

Mon 6/1

10:35 am-5:55 pm

1 stop6h 20m

$548

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 12 results
1
2

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 December.
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 5h 09m. Delta provides one of the quickest options available for as low as $198. 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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