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Midway

$69+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — MDW
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This Priceline deal was found by Cheapflights users on 1/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2311:41 am
IAD
-
MDW
1 stop9h 06m
Frontier
Mon 3/26:00 am
MDW
-
IAD
1 stop9h 08m
Frontier
Deal found 1/27$148
This Frontier deal was found by Cheapflights users on 1/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:22 am
IAD
-
MDW
1 stop5h 54m
Frontier
Mon 3/26:00 am
MDW
-
IAD
1 stop9h 08m
Frontier
Deal found 1/28$150
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Thu 2/2611:22 am
IAD
-
MDW
1 stop5h 54m
Frontier
Thu 3/57:30 am
MDW
-
IAD
1 stop8h 13m
Frontier
Deal found 1/28$156
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Fri 2/275:37 pm
IAD
-
MDW
1 stop6h 00m
Frontier
Thu 3/57:30 am
MDW
-
IAD
1 stop8h 13m
Frontier
Deal found 1/28$160
This Booking.com deal was found by Cheapflights users on 1/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/235:22 pm
IAD
-
MDW
1 stop6h 07m
Frontier
Thu 2/267:30 am
MDW
-
IAD
1 stop22h 50m
Frontier
Deal found 1/27$163
This Southwest deal was found by Cheapflights users on 1/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:25 am
PIT
-
MDW
2 stops8h 55m
Southwest
Tue 3/31:25 pm
MDW
-
PIT
Nonstop1h 20m
Southwest
Deal found 1/27$172
This Expedia deal was found by Cheapflights users on 1/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:22 am
IAD
-
MDW
1 stop12h 07m
Frontier
Sat 2/288:00 am
MDW
-
IAD
1 stop24h 25m
Frontier
Deal found 1/27$175
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Mon 3/25:22 pm
IAD
-
MDW
1 stop6h 07m
Frontier
Fri 3/69:51 pm
MDW
-
IAD
1 stop8h 33m
Frontier
Deal found 1/27$177
This Priceline deal was found by Cheapflights users on 1/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1810:51 am
IAD
-
MDW
1 stop9h 40m
Frontier
Mon 4/202:20 pm
MDW
-
IAD
1 stop9h 16m
Frontier
Deal found 1/28$180
This Orbitz deal was found by Cheapflights users on 1/27. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/49:51 am
IAD
-
MDW
1 stop10h 40m
Frontier
Wed 5/62:20 pm
MDW
-
IAD
1 stop9h 16m
Frontier
Deal found 1/27$181
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Fri 2/275:37 pm
IAD
-
MDW
1 stop6h 00m
Frontier
Fri 3/69:51 pm
MDW
-
IAD
1 stop8h 33m
Frontier
Deal found 1/28$182
This Southwest deal was found by Cheapflights users on 1/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:55 pm
PIT
-
MDW
Nonstop1h 35m
Southwest
Wed 2/251:50 pm
MDW
-
PIT
1 stop6h 00m
Southwest
Deal found 1/28$185

Find 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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$148
(Priceline)

One-way from

$69
(Super.com)

Popular in

July

Cheapest in

February

Average price

$312
Provider with most accurate pricing for Charleston Yeager-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Charleston Yeager-Chicago (CHI) flights.
Search Deals
From West Virginia to Chicago Midway
Search Deals
One-way flight from West Virginia to Chicago Midway
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($58 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 29, 2026.
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

Tue 2/24

6:00 pm-6:35 pm

Nonstop1h 35m

Chicago Midway

Tue 3/3

5:40 pm-8:00 pm

Nonstop1h 20m

$175

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 4/7

7:10 pm-7:40 pm

Nonstop1h 30m

Chicago Midway

Wed 4/8

7:50 am-10:15 am

Nonstop1h 25m

$175

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Mon 2/23

5:40 am-6:30 am

Nonstop1h 50m

Chicago Midway

Wed 2/25

1:25 pm-8:45 pm

2 stops6h 20m

$190

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 2/12

5:37 pm-10:34 pm

1 stop5h 57m

Chicago Midway

Mon 2/23

6:00 am-4:08 pm

1 stop9h 08m

$193

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 4/15

10:20 am-4:29 pm

1 stop7h 09m

Chicago Midway

Thu 4/16

9:27 am-1:22 pm

1 stop2h 55m

$195

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 3/18

12:15 pm-12:45 pm

Nonstop1h 30m

Chicago Midway

Tue 3/31

6:30 am-11:35 am

1 stop4h 05m

$203

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 2/19

7:05 pm-10:30 pm

1 stop4h 25m

Chicago Midway

Mon 2/23

1:25 pm-3:45 pm

Nonstop1h 20m

$203

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Mon 2/23

5:40 am-6:30 am

Nonstop1h 50m

Chicago Midway

Thu 2/26

6:40 am-12:05 pm

1 stop4h 25m

$203

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 2/26

11:22 am-10:29 pm

1 stop12h 07m

Chicago Midway

Thu 3/5

5:16 pm-7:24 am

2 stops13h 08m

$214

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 4/30

8:09 am-8:04 am

1 stop24h 55m

Chicago Midway

Sun 5/3

9:14 am-7:27 am

1 stop21h 13m

$215

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 53 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 1h 35m. 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 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
Lansing
Merrillville
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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