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$64+ Cheap flights from West Virginia 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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — MDW
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Cheap flight deals from West Virginia to Midway

Keep the following information in mind while searching for West Virginia to Midway flight deals. Data was last updated November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$127
(Southwest)

One-way from

$64
(Southwest)

Popular in

December

Cheapest in

February

Average price

$321
Provider with most accurate pricing for Charleston Yeager-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Charleston Yeager-Chicago (CHI) flights.
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From West Virginia to Chicago Midway
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One-way flight from West Virginia to Chicago Midway
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Highest demand for flights based on searches. 13% potential increase in price ($52 potential increase over avg. RT price).
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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 November 2025
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Find flight deals from West Virginia to Midway

Cheapest flights from West Virginia to Midway
Explore the most affordable flight options available from West Virginia to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 2025.

This Southwest deal was found by Cheapflights users on 11/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/36:00 amPIT - MDW
1 stop4h 40mSouthwest
Wed 12/106:05 pmMDW - PIT
Nonstop1h 25mSouthwest
Deal found 11/3$127
This Frontier deal was found by Cheapflights users on 11/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/55:19 pmIAD - MDW
1 stop5h 53mFrontier
Sun 12/76:15 amMDW - IAD
1 stop9h 09mFrontier
Deal found 11/2$141
This Frontier deal was found by Cheapflights users on 11/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:45 amIAD - MDW
1 stop9h 14mFrontier
Sun 12/76:15 amMDW - IAD
1 stop9h 09mFrontier
Deal found 11/3$146
This Frontier deal was found by Cheapflights users on 11/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/135:34 pmIAD - MDW
1 stop5h 29mFrontier
Thu 11/209:30 amMDW - IAD
1 stop6h 01mFrontier
Deal found 11/2$150
This Booking.com deal was found by Cheapflights users on 11/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/88:36 pmIAD - MDW
1 stop13h 36mFrontier
Sat 11/151:37 pmMDW - IAD
1 stop9h 18mFrontier
Deal found 11/1$152
This Delta deal was found by Cheapflights users on 11/2. 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.
Mon 11/246:00 amPIT - MDW
1 stop8h 07mDelta
Thu 11/275:34 pmMDW - PIT
1 stop5h 47mDelta
Deal found 11/2$157
This Southwest deal was found by Cheapflights users on 11/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/251:55 pmPIT - MDW
Nonstop1h 30mSouthwest
Mon 1/59:50 pmMDW - PIT
Nonstop1h 20mSouthwest
Deal found 11/2$158
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/410:38 amIAD - MDW
2 stops12h 34mFrontier
Mon 12/88:42 pmMDW - IAD
1 stop16h 47mFrontier
Deal found 11/2$158
This Expedia deal was found by Cheapflights users on 11/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/128:40 amIAD - MDW
1 stop5h 01mFrontier
Wed 11/191:56 pmMDW - IAD
1 stop5h 24mFrontier
Deal found 11/3$160
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/45:45 amIAD - MDW
1 stop13h 23mFrontier
Sun 12/76:15 amMDW - IAD
1 stop9h 09mFrontier
Deal found 11/2$162
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Fri 12/125:19 pmIAD - MDW
1 stop5h 53mFrontier
Sun 12/142:59 pmMDW - IAD
1 stop23h 06mFrontier
Deal found 11/1$164
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 11/238:44 amIAD - MDW
1 stop8h 46mFrontier
Thu 11/275:30 pmMDW - IAD
1 stop13h 20mFrontier
Deal found 11/2$165

Cheapflights Fare Finder

 
Customize your flight search to find flights from West Virginia 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 November 3, 2025.
Use the filters below to find and compare flights from West Virginia to Chicago Midway Airport that are best for you.

Fly from

West Virginia

Fly to

Midway

Route

Depart

Return

Price

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 12/3

6:00 am-9:40 am

1 stop4h 40m

Chicago Midway

Wed 12/10

6:05 pm-8:30 pm

Nonstop1h 25m

$127

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 12/5

5:19 pm-10:12 pm

1 stop5h 53m

Chicago Midway

Sun 12/7

6:15 am-4:24 pm

1 stop9h 09m

$142

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Mon 11/24

6:00 am-1:07 pm

1 stop8h 07m

Chicago Midway

Thu 11/27

5:34 pm-12:21 am

1 stop5h 47m

$157

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 1/21

6:00 pm-6:35 pm

Nonstop1h 35m

Chicago Midway

Sat 1/24

9:45 am-12:10 pm

Nonstop1h 25m

$168

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 12/25

10:45 am-1:45 pm

1 stop4h 00m

Chicago Midway

Mon 1/5

9:35 am-5:20 pm

2 stops6h 45m

$183

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 11/22

8:38 pm-11:42 am

1 stop16h 04m

Chicago Midway

Mon 11/24

5:47 pm-8:19 am

1 stop13h 32m

$197

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sun 1/18

12:21 pm-6:32 pm

1 stop7h 11m

Chicago Midway

Mon 1/19

6:35 pm-10:39 pm

1 stop3h 04m

$198

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 12/4

2:00 pm-2:30 pm

Nonstop1h 30m

Chicago Midway

Mon 12/8

6:05 pm-8:30 pm

Nonstop1h 25m

$219

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Thu 12/11

6:50 pm-11:47 pm

1 stop5h 57m

Chicago Midway

Sun 12/14

5:13 pm-10:49 pm

1 stop4h 36m

$258

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Fri 12/12

6:50 pm-11:47 pm

1 stop5h 57m

Chicago Midway

Sun 12/14

5:13 pm-10:49 pm

1 stop4h 36m

$258

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 43 results
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Best time to book a flight from West Virginia to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from West Virginia 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.

Cheapflights Insights

Everything you need to know about your flight from West Virginia to Chicago Midway Airport
No data available for this route at this time. Please check back soon.

Related info for your journey

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

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

    There are many flights that can get you from West Virginia to Chicago Midway Airport in 4h 40m. Fly via Southwest, Frontier, or Delta to get the fastest option. The distance from West Virginia to Chicago Midway Airport is about 400 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from West Virginia to Chicago Midway Airport one-way?

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $69. Frontier flights start at $79 while deals on Allegiant Air start at $102 one-way.

  • What are the most popular routes from West Virginia to Chicago Midway Airport?

    The most popular route from West Virginia to Chicago Midway Airport is Washington, D.C. Dulles Intl - Chicago Midway. You may also consider Pittsburgh - Chicago Midway or Charleston Yeager - Chicago Midway.

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

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

  • How can I find direct flights from West Virginia to Midway?

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

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

    Yes. Cheapflights offers flight deals from West Virginia 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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Alternative routes for West Virginia to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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