HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$169+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — MDW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Charleston to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 September 11, 2025.

Round-trip from

$278
(Delta)

One-way from

$169
(Delta)

Popular in

December

Cheapest in

February

Average price

$399
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 ($57 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 September 11, 2025.

This Delta deal was found by Cheapflights users on 9/10. 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 10/33:25 pmCRW - MDW
1 stop7h 11mDelta
Sat 10/44:25 pmMDW - CRW
1 stop5h 15mDelta
Deal found 9/10$293
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/92:43 pmCRW - MDW
1 stop26h 37mMultiple Airlines
Thu 10/169:26 pmMDW - CRW
2 stops20h 30mMultiple Airlines
Deal found 9/9$305
This Delta deal was found by Cheapflights users on 9/10. 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.
Thu 10/23:25 pmCRW - MDW
1 stop7h 11mDelta
Sat 10/44:25 pmMDW - CRW
1 stop5h 15mDelta
Deal found 9/10$368
This Delta deal was found by Cheapflights users on 9/9. 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 10/246:48 pmCRW - MDW
1 stop4h 26mDelta
Sun 10/2610:35 amMDW - CRW
1 stop6h 33mDelta
Deal found 9/9$403
This Delta deal was found by Cheapflights users on 9/11. 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.
Fri 9/263:25 pmCRW - MDW
1 stop7h 11mDelta
Tue 9/3012:43 pmMDW - CRW
1 stop4h 25mDelta
Deal found 9/11$473
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/99:58 amCRW - MDW
1 stop14h 57mMultiple Airlines
Sun 11/2312:25 pmMDW - CRW
2 stops29h 31mMultiple Airlines
Deal found 9/9$602
This Delta deal was found by Cheapflights users on 9/9. 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.
Sat 10/44:05 pmCRW - MDW
1 stop6h 05mDelta
Sun 10/510:35 amMDW - CRW
1 stop6h 33mDelta
Deal found 9/9$608
This Delta deal was found by Cheapflights users on 9/8. 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 9/263:25 pmCRW - MDW
1 stop7h 11mDelta
Mon 9/2912:43 pmMDW - CRW
1 stop4h 25mDelta
Deal found 9/8$628
This Delta deal was found by Cheapflights users on 9/10. 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 10/33:25 pmCRW - MDW
1 stop7h 11mDelta
Sun 10/510:35 amMDW - CRW
1 stop6h 33mDelta
Deal found 9/10$643
This Delta deal was found by Cheapflights users on 9/10. 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.
Thu 10/23:25 pmCRW - MDW
1 stop7h 11mDelta
Sun 10/510:35 amMDW - CRW
1 stop6h 33mDelta
Deal found 9/10$668
This Delta deal was found by Cheapflights users on 9/10. 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.
Thu 10/96:25 amCRW - MDW
1 stop4h 15mDelta
Sat 10/114:23 pmMDW - CRW
1 stop5h 27mDelta
Deal found 9/10$683

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 September 11, 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

Wed 3/4

6:24 am-12:01 pm

1 stop6h 37m

Chicago Midway

Sat 3/7

10:35 am-5:54 pm

1 stop6h 19m

$248

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Fri 10/3

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

Fri 10/24

6:48 pm-10:14 pm

1 stop4h 26m

Chicago Midway

Sun 10/26

10:35 am-6:08 pm

1 stop6h 33m

$403

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Fri 9/26

3:25 pm-9:36 pm

1 stop7h 11m

Chicago Midway

Tue 9/30

12:43 pm-6:08 pm

1 stop4h 25m

$473

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Sun 11/9

9:58 am-11:55 pm

1 stop14h 57m

Chicago Midway

Sun 11/23

12:25 pm-6:56 pm

2 stops29h 31m

$602

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Sat 10/4

4:05 pm-9:10 pm

1 stop6h 05m

Chicago Midway

Sun 10/5

10:35 am-6:08 pm

1 stop6h 33m

$608

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Fri 9/26

3:25 pm-9:36 pm

1 stop7h 11m

Chicago Midway

Mon 9/29

12:43 pm-6:08 pm

1 stop4h 25m

$628

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Fri 2/27

3:25 pm-9:46 pm

1 stop7h 21m

$169

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

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 6h 37m. Delta provides one of the quickest options available for as low as $248. 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.

  • What is the cheapest month to book a flight from Charleston, West Virginia to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Charleston, West Virginia to Chicago Midway Airport (average of $160). Flying from Charleston, West Virginia to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.