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Cheap flights from West Virginia to Chicago from $69

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from West Virginia to Chicago departing on 6/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from West Virginia to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
4:00 pm - 4:30 pm
PIT
-
MDW
1h 30mnonstop
Southwest Logo
6:55 pm - 9:20 pm
MDW
-
PIT
1h 25mnonstop
$177Southwest
Sat, May 9 - Mon, May 11
Southwest Logo
4:00 pm - 4:30 pm
PIT
-
MDW
1h 30mnonstop
Southwest Logo
3:50 pm - 10:15 pm
MDW
-
PIT
5h 25m
1 stop
$187Southwest
Sat, May 9 - Mon, May 11
Southwest Logo
6:25 am - 2:55 pm
PIT
-
MDW
9h 30m
2 stops
Southwest Logo
5:30 am - 12:15 pm
MDW
-
PIT
5h 45m
1 stop
$188Southwest
Tue, May 12 - Thu, May 14
Southwest Logo
10:05 am - 8:05 pm
PIT
-
MDW
11h 00m
2 stops
Southwest Logo
7:40 am - 10:00 am
MDW
-
PIT
1h 20mnonstop
$192Southwest
Sat, May 9 - Mon, May 11
Southwest Logo
6:25 am - 3:45 pm
PIT
-
MDW
10h 20m
2 stops
Southwest Logo
10:05 am - 6:15 pm
MDW
-
PIT
7h 10m
2 stops
$193Southwest
Tue, Jun 2 - Wed, Jun 3
Delta Logo
6:30 am - 8:43 am
PIT
-
MDW
3h 13m
1 stop
Delta Logo
6:36 pm - 10:38 pm
MDW
-
PIT
3h 02m
1 stop
$213Delta
Thu, May 7 - Mon, May 11
Frontier Logo
7:27 pm - 2:12 pm
IAD
-
MDW
19h 45m
2 stops
Frontier Logo
6:00 am - 11:09 pm
MDW
-
IAD
16h 09m
1 stop
$221Frontier
Thu, May 28 - Mon, Jun 1
Frontier Logo
11:07 am - 10:02 pm
IAD
-
MDW
11h 55m
1 stop
Frontier Logo
6:00 am - 4:21 pm
MDW
-
IAD
9h 21m
1 stop
$222Frontier
Thu, May 28 - Sun, May 31
Multiple Airlines Logo
11:07 am - 10:02 pm
IAD
-
MDW
11h 55m
1 stop
Multiple Airlines Logo
2:47 pm - 2:18 pm
MDW
-
IAD
22h 31m
1 stop
$223Multiple Airlines
Tue, May 26 - Sun, May 31
Delta Logo
6:30 am - 8:43 am
PIT
-
MDW
3h 13m
1 stop
Delta Logo
5:29 pm - 12:45 am
MDW
-
PIT
6h 16m
1 stop
$228Delta
Thu, May 7 - Sat, May 9

Southwest flights from West Virginia to Chicago Midway Airport

Our best Southwest deals on West Virginia to Chicago Midway Airport flight tickets
Southwest
May 9
PIT4:00 pmPittsburgh
1h 30m
MDW4:30 pmChicago Midway
May 11
MDW6:55 pmChicago Midway
1h 25m
PIT9:20 pmPittsburgh
$177
Southwest
May 9
PIT4:00 pmPittsburgh
1h 30m
MDW4:30 pmChicago Midway
May 11
MDW3:50 pmChicago Midway
5h 25m
1 stop
PIT10:15 pmPittsburgh
$187
Southwest
May 12
PIT6:25 amPittsburgh
9h 30m
2 stops
MDW2:55 pmChicago Midway
May 14
MDW5:30 amChicago Midway
5h 45m
1 stop
PIT12:15 pmPittsburgh
$188

Frontier flights from West Virginia to Chicago Midway Airport

Our best Frontier deals on West Virginia to Chicago Midway Airport flight tickets
Frontier
May 28
IAD7:27 pmWashington, D.C. Dulles Intl
19h 45m
2 stops
MDW2:12 pmChicago Midway
Jun 1
MDW6:00 amChicago Midway
16h 09m
1 stop
IAD11:09 pmWashington, D.C. Dulles Intl
$221
Frontier
May 28
IAD11:07 amWashington, D.C. Dulles Intl
11h 55m
1 stop
MDW10:02 pmChicago Midway
May 31
MDW6:00 amChicago Midway
9h 21m
1 stop
IAD4:21 pmWashington, D.C. Dulles Intl
$222
Frontier
Jul 1
IAD11:17 amWashington, D.C. Dulles Intl
11h 54m
1 stop
MDW10:11 pmChicago Midway
Jul 7
MDW6:00 amChicago Midway
9h 20m
1 stop
IAD4:20 pmWashington, D.C. Dulles Intl
$224

momondo Fare Finder

 
Customize your flight search to find flights from West Virginia to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated April 21, 2026.
Use the filters below to find and compare flights from West Virginia to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 5/9

4:00 pm-4:30 pm

Nonstop1h 30m

Chicago Midway

Mon 5/11

6:55 pm-9:20 pm

Nonstop1h 25m

$177

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 5/9

4:00 pm-4:30 pm

Nonstop1h 30m

Chicago Midway

Mon 5/11

3:50 pm-10:15 pm

1 stop5h 25m

$187

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 5/12

6:25 am-2:55 pm

2 stops9h 30m

Chicago Midway

Thu 5/14

5:30 am-12:15 pm

1 stop5h 45m

$188

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 5/9

10:05 am-8:05 pm

2 stops11h 00m

Chicago Midway

Mon 5/11

7:40 am-10:00 am

Nonstop1h 20m

$192

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 6/2

6:25 am-3:45 pm

2 stops10h 20m

Chicago Midway

Wed 6/3

10:05 am-6:15 pm

2 stops7h 10m

$193

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 5/7

6:30 am-8:43 am

1 stop3h 13m

Chicago Midway

Mon 5/11

6:36 pm-10:38 pm

1 stop3h 02m

$213

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 5/28

7:27 pm-2:12 pm

2 stops19h 45m

Chicago Midway

Mon 6/1

6:00 am-11:09 pm

1 stop16h 09m

$221

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 5/28

11:07 am-10:02 pm

1 stop11h 55m

Chicago Midway

Sun 5/31

6:00 am-4:21 pm

1 stop9h 21m

$222

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 5/26

11:07 am-10:02 pm

1 stop11h 55m

Chicago Midway

Sun 5/31

2:47 pm-2:18 pm

1 stop22h 31m

$223

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 5/7

6:30 am-8:43 am

1 stop3h 13m

Chicago Midway

Sat 5/9

5:29 pm-12:45 am

1 stop6h 16m

$228

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from West Virginia to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from West Virginia to Chicago Midway?

Southwest and Delta are the most popular carriers operating from West Virginia to Chicago Midway

Cheap West Virginia to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from West Virginia to Chicago Midway Airport

Fastest flight time

1h 20m

Direct flights

Every day
The fastest flight from West Virginia to Chicago Midway Airport takes 1h 20m
Direct flights go from West Virginia to Chicago Midway Airport every day.
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Frequently asked questions about flying from West Virginia to Chicago Midway Airport

  • When did momondo last update prices for flights from West Virginia to Chicago Midway Airport?

    Prices for flights from West Virginia to Chicago Midway Airport were last updated today.

  • How many operators does momondo search for flights from West Virginia to Chicago Midway Airport?

  • How old do you have to be to fly from West Virginia to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from West Virginia to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from West Virginia to Chicago?

It is quick and easy to find West Virginia to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from West Virginia to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from West Virginia with this policy.

How can momondo help me find flights from West Virginia to Chicago?

Once all potential West Virginia to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from West Virginia to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of West Virginia to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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