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Cheap flights from Chicago Midway Airport to Pittsburgh 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 Chicago Midway Airport to Pittsburgh departing on 12/17. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
7:05 am - 3:15 pmMDW-PIT
7h 10m1 stop
Southwest Logo
6:00 pm - 6:35 pmPIT-MDW
1h 35mnonstop
$117Southwest
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Wed, Dec 17 - Sat, Jan 17
Southwest Logo
1:30 pm - 3:50 pmMDW-PIT
1h 20mnonstop
Southwest Logo
10:25 am - 6:40 pmPIT-MDW
9h 15m2 stops
$122Southwest
Find Deal
Wed, Dec 17 - Sat, Jan 17
Southwest Logo
9:25 am - 5:35 pmMDW-PIT
7h 10m2 stops
Southwest Logo
9:15 am - 3:20 pmPIT-MDW
7h 05m1 stop
$132Southwest
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Wed, Dec 17 - Sat, Jan 17
Southwest Logo
2:30 pm - 9:55 pmMDW-PIT
6h 25m2 stops
Southwest Logo
10:25 am - 6:40 pmPIT-MDW
9h 15m2 stops
$137Southwest
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Wed, Dec 17 - Sat, Jan 17
Southwest Logo
6:05 pm - 8:30 pmMDW-PIT
1h 25mnonstop
Southwest Logo
6:40 am - 7:20 amPIT-MDW
1h 40mnonstop
$144Southwest
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Thu, Dec 11 - Tue, Dec 16
Southwest Logo
5:35 am - 12:30 pmMDW-PIT
5h 55m1 stop
Southwest Logo
6:40 am - 7:20 amPIT-MDW
1h 40mnonstop
$154Southwest
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Thu, Dec 11 - Tue, Dec 16
Delta Logo
10:47 am - 4:18 pmMDW-PIT
4h 31m1 stop
Delta Logo
11:43 am - 4:39 pmPIT-MDW
5h 56m1 stop
$157Delta
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Mon, Nov 24 - Thu, Nov 27
Southwest Logo
6:05 pm - 8:30 pmMDW-PIT
1h 25mnonstop
Southwest Logo
6:00 am - 2:55 pmPIT-MDW
9h 55m2 stops
$159Southwest
Find Deal
Thu, Dec 11 - Tue, Dec 16
Southwest Logo
5:35 am - 12:30 pmMDW-PIT
5h 55m1 stop
Southwest Logo
6:00 am - 2:55 pmPIT-MDW
9h 55m2 stops
$169Southwest
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Thu, Dec 11 - Tue, Dec 16
Southwest Logo
1:30 pm - 3:50 pmMDW-PIT
1h 20mnonstop
Southwest Logo
6:45 pm - 7:15 pmPIT-MDW
1h 30mnonstop
$171Southwest
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Thu, Dec 4 - Mon, Dec 8

Southwest flights from Chicago Midway Airport to Pittsburgh

Our best Southwest deals on Chicago Midway Airport to Pittsburgh flight tickets
Southwest
Dec 17
MDW7:05 amChicago Midway
7h 10m
1 stop
PIT3:15 pmPittsburgh
Jan 17
PIT6:00 pmPittsburgh
1h 35m
MDW6:35 pmChicago Midway
$117
Find similar
Southwest
Dec 17
MDW1:30 pmChicago Midway
1h 20m
PIT3:50 pmPittsburgh
Jan 17
PIT10:25 amPittsburgh
9h 15m
2 stops
MDW6:40 pmChicago Midway
$122
Find similar
Southwest
Dec 17
MDW9:25 amChicago Midway
7h 10m
2 stops
PIT5:35 pmPittsburgh
Jan 17
PIT9:15 amPittsburgh
7h 05m
1 stop
MDW3:20 pmChicago Midway
$132
Find similar

Delta flights from Chicago Midway Airport to Pittsburgh

Our best Delta deals on Chicago Midway Airport to Pittsburgh flight tickets
Delta
Nov 24
MDW12:47 pmChicago Midway
4h 53m
1 stop
PIT6:40 pmPittsburgh
Nov 27
PIT6:26 amPittsburgh
3h 28m
1 stop
MDW8:54 amChicago Midway
$157
Find similar
Delta
Jan 1
MDW6:08 pmChicago Midway
3h 28m
1 stop
PIT10:36 pmPittsburgh
Jan 5
PIT6:00 amPittsburgh
3h 54m
1 stop
MDW8:54 amChicago Midway
$174
Find similar
Delta
Dec 6
MDW6:46 pmChicago Midway
3h 26m
1 stop
PIT11:12 pmPittsburgh
Dec 8
PIT7:45 pmPittsburgh
5h 02m
1 stop
MDW11:47 pmChicago Midway
$191
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momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Pittsburgh 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 November 13, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Pittsburgh that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Wed 12/17

7:05 am-3:15 pm

1 stop7h 10m

Pittsburgh

Sat 1/17

6:00 pm-6:35 pm

Nonstop1h 35m

$117

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Wed 12/17

1:30 pm-3:50 pm

Nonstop1h 20m

Pittsburgh

Sat 1/17

10:25 am-6:40 pm

2 stops9h 15m

$122

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Wed 12/17

9:25 am-5:35 pm

2 stops7h 10m

Pittsburgh

Sat 1/17

9:15 am-3:20 pm

1 stop7h 05m

$132

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Wed 12/17

2:30 pm-9:55 pm

2 stops6h 25m

Pittsburgh

Sat 1/17

10:25 am-6:40 pm

2 stops9h 15m

$137

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Thu 12/11

6:05 pm-8:30 pm

Nonstop1h 25m

Pittsburgh

Tue 12/16

6:40 am-7:20 am

Nonstop1h 40m

$144

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Thu 12/11

5:35 am-12:30 pm

1 stop5h 55m

Pittsburgh

Tue 12/16

6:40 am-7:20 am

Nonstop1h 40m

$154

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Mon 11/24

10:47 am-4:18 pm

1 stop4h 31m

Pittsburgh

Thu 11/27

11:43 am-4:39 pm

1 stop5h 56m

$157

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Thu 12/11

6:05 pm-8:30 pm

Nonstop1h 25m

Pittsburgh

Tue 12/16

6:00 am-2:55 pm

2 stops9h 55m

$159

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Thu 12/11

5:35 am-12:30 pm

1 stop5h 55m

Pittsburgh

Tue 12/16

6:00 am-2:55 pm

2 stops9h 55m

$169

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Thu 12/4

1:30 pm-3:50 pm

Nonstop1h 20m

Pittsburgh

Mon 12/8

6:45 pm-7:15 pm

Nonstop1h 30m

$171

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Pittsburgh from

How to get the cheapest flight ticket from Chicago Midway Airport to Pittsburgh

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 month to fly to Pittsburgh?

In general, September is the cheapest month to fly from Chicago Midway Airport to Pittsburgh. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $114. The month of February is another great option to travel to Pittsburgh, with average flight prices from Chicago Midway Airport averaging around $137.

What is the cheapest day to depart on your flight to Pittsburgh?

The cheapest day to depart on your flight to Pittsburgh is on a Thursday when prices can be found for as low as $273. This is often the case because there is less demand to fly during this day of the week. Flights from Chicago Midway Airport to Pittsburgh on a Sunday will generally be more expensive and average around $431. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Pittsburgh?

Our data shows that the cheapest Chicago Midway Airport to Pittsburgh flights are usually those with departure times in the morning. Our users have found flights to Pittsburgh in the morning for as low as $299. Flights to Pittsburgh are more costly in the afternoon, with an average ticket price of $342. Departure times in the afternoon fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago Midway to Pittsburgh flight route?

Fly from Chicago Midway to Pittsburgh for the best Chicago Midway - Pittsburgh flight prices

What cabin class options are available on Chicago Midway to Pittsburgh flights?

There is only 1 cabin class available to choose from on Chicago Midway to Pittsburgh flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago Midway Airport to Pittsburgh flights?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Pittsburgh.

When to book flights from Chicago Midway Airport to Pittsburgh

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Pittsburgh according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Pittsburgh (MDW to PIT) flight deals and tips

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

Best Price Found

$48

Fastest flight time

1h 20m

Direct flights

Every day

Airports in Pittsburgh

1 airport
The best one-way flight to Pittsburgh from Chicago Midway Airport in the past 72 hours is $48. The best round-trip flight deal from Chicago Midway Airport to Pittsburgh found on momondo in the last 72 hours is $266.
The fastest flight from Chicago Midway Airport to Pittsburgh takes 1h 20m
Direct flights go from Chicago Midway Airport to Pittsburgh every day.
There is 1 airport near Pittsburgh: Pittsburgh (PIT)
Search flight deals

  • How far is Chicago Midway to Pittsburgh by plane?

    There are 413.5 mi between Chicago Midway and Pittsburgh. Flights usually cover this in 1h 20m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Chicago Midway Airport to Pittsburgh Airport are refreshed on a daily basis.

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Pittsburgh Airport.

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

    The necessary travel and health documents for your Pittsburgh Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to Pittsburgh?

  • What is the most popular airline from Chicago Midway Airport to Pittsburgh?

Best airlines flying from Chicago Midway Airport to Pittsburgh

Compare and see reviews for airlines that fly from Chicago Midway Airport to Pittsburgh with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $103Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Pittsburgh

    Southwest is one of the most popular airlines flying from Chicago Midway Airport to Pittsburgh, operating 18 flights/week on average for this route. A good Southwest flight deal for Chicago Midway Airport to Pittsburgh starts from $103 round-trip, up to an average price of $291. Our users have rated Southwest at 8.0/10.

Traveling to a place near Pittsburgh?

Book flights to Pittsburgh if you plan to visit one of these locations
Washington
Monroeville
Wheeling
Butler
Canonsburg
Belle Vernon
Triadelphia
New Castle
West Mifflin
Steubenville
Moon
Coraopolis
Wexford
Mars
Cadiz
Freeport
Chester
Bridgeport

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Pittsburgh for you.

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

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

How can momondo help me find flights from Chicago to Pittsburgh?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Pittsburgh.

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

Yes. momondo can track prices for Chicago to Pittsburgh flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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