How many flights depart from Chicago Midway Airport to Pittsburgh on average per week?

As of September 2026, there are 3 flights per week flying from Chicago Midway Airport to Pittsburgh. The most common day of the week flights depart is Mon, with 100% of flights taking off on this day.

Which airline has the best punctuality record on Chicago to Pittsburgh flights?

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 14% of their flights experiencing any sort of delay.

How often are flights from Chicago to Pittsburgh delayed?

Historically, on average around 15% of flights between Chicago and Pittsburgh have experienced a delay on any given week. The average delay length over the past 12 months has been 101 minutes.

What is the most punctual flight time for Chicago to Pittsburgh flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Friday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

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

Southwest is the most popular carrier operating from Chicago Midway to Pittsburgh

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?

As of September 2026, there is 1 operator available to choose from 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.

$125 Cheap Flights from Chicago Midway Airport to Pittsburgh in 2026/27

Find the cheapest flights from Chicago Midway Airport to Pittsburgh

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

1:20 pm - 3:40 pmMDW Chicago Midway-PIT Pittsburgh

1h 20mnonstop

7:45 pm - 8:15 pmPIT Pittsburgh-MDW Chicago Midway

1h 30mnonstop

$277Southwest

Thu, Oct 22 - Thu, Oct 29

7:45 am - 10:05 amMDW Chicago Midway-PIT Pittsburgh

1h 20mnonstop

4:00 pm - 4:35 pmPIT Pittsburgh-MDW Chicago Midway

1h 35mnonstop

$277Southwest

Mon, Oct 26 - Mon, Nov 2

3:35 pm - 6:00 pmMDW Chicago Midway-PIT Pittsburgh

1h 25mnonstop

8:45 am - 9:15 amPIT Pittsburgh-MDW Chicago Midway

1h 30mnonstop

$277Southwest

Sat, Nov 7 - Sat, Nov 14

8:05 am - 10:25 amMDW Chicago Midway-PIT Pittsburgh

1h 20mnonstop

7:45 pm - 8:15 pmPIT Pittsburgh-MDW Chicago Midway

1h 30mnonstop

$277Southwest

Sat, Oct 17 - Mon, Oct 19

5:55 pm - 8:20 pmMDW Chicago Midway-PIT Pittsburgh

1h 25mnonstop

7:45 pm - 8:15 pmPIT Pittsburgh-MDW Chicago Midway

1h 30mnonstop

$277Southwest

Tue, Oct 20 - Thu, Oct 22

1:40 pm - 4:05 pmMDW Chicago Midway-PIT Pittsburgh

1h 25mnonstop

2:20 pm - 2:55 pmPIT Pittsburgh-MDW Chicago Midway

1h 35mnonstop

$277Southwest

Tue, Nov 3 - Wed, Nov 4

8:15 am - 10:40 amMDW Chicago Midway-PIT Pittsburgh

1h 25mnonstop

4:35 pm - 5:05 pmPIT Pittsburgh-MDW Chicago Midway

1h 30mnonstop

$277Southwest

Tue, Dec 1 - Sat, Dec 5

3:35 pm - 6:00 pmMDW Chicago Midway-PIT Pittsburgh

1h 25mnonstop

8:45 am - 9:15 amPIT Pittsburgh-MDW Chicago Midway

1h 30mnonstop

$277Southwest

Sat, Nov 7 - Mon, Nov 9

6:41 pm - 10:57 pmMDW Chicago Midway-PIT Pittsburgh

3h 16m1 stop Detroit Metropolitan Wayne County

12:50 pm - 4:50 pmPIT Pittsburgh-MDW Chicago Midway

5h 00m1 stop Minneapolis St Paul

$297Delta

Wed, Dec 2 - Sat, Dec 5

6:44 pm - 10:59 pmMDW Chicago Midway-PIT Pittsburgh

3h 15m1 stop Detroit Metropolitan Wayne County

6:10 am - 9:46 amPIT Pittsburgh-MDW Chicago Midway

4h 36m1 stop Detroit Metropolitan Wayne County

$297Delta

Sat, Nov 7 - Tue, Nov 10

Cheap last minute flights

Enter your travel dates to find the best prices.

8:45 am - 11:20 amMDW Chicago Midway-PIT Pittsburgh

1h 35mnonstop

6:55 pm - 7:20 pmPIT Pittsburgh-MDW Chicago Midway

1h 25mnonstop

$539Southwest

Tue, Sep 29 - Tue, Sep 29

8:45 am - 11:20 amMDW Chicago Midway-PIT Pittsburgh

1h 35mnonstop

1:55 pm - 2:20 pmPIT Pittsburgh-MDW Chicago Midway

1h 25mnonstop

$539Southwest

Tue, Sep 29 - Wed, Sep 30

4:10 pm - 6:30 pmMDW Chicago Midway-PIT Pittsburgh

1h 20mnonstop

6:50 pm - 7:20 pmPIT Pittsburgh-MDW Chicago Midway

1h 30mnonstop

$539Southwest

Sat, Oct 3 - Tue, Oct 6

8:45 am - 11:20 amMDW Chicago Midway-PIT Pittsburgh

1h 35mnonstop

1:55 pm - 2:20 pmPIT Pittsburgh-MDW Chicago Midway

1h 25mnonstop

$539Southwest

Wed, Sep 30 - Wed, Sep 30

12:50 pm - 3:10 pmMDW Chicago Midway-PIT Pittsburgh

1h 20mnonstop

7:20 pm - 10:25 pmPIT Pittsburgh-MDW Chicago Midway

4h 05m1 stop Nashville Intl

$549Southwest

Tue, Sep 29 - Tue, Sep 29

8:15 am - 1:05 pmMDW Chicago Midway-PIT Pittsburgh

3h 50m1 stop Lambert-St Louis

8:55 am - 9:15 amPIT Pittsburgh-MDW Chicago Midway

1h 20mnonstop

$549Southwest

Tue, Sep 29 - Wed, Sep 30

8:45 am - 11:20 amMDW Chicago Midway-PIT Pittsburgh

1h 35mnonstop

7:20 pm - 10:25 pmPIT Pittsburgh-MDW Chicago Midway

4h 05m1 stop Nashville Intl

$549Southwest

Wed, Sep 30 - Wed, Sep 30

8:40 am - 4:35 pmMDW Chicago Midway-PIT Pittsburgh

6h 55m1 stop Nashville Intl

6:50 pm - 7:20 pmPIT Pittsburgh-MDW Chicago Midway

1h 30mnonstop

$549Southwest

Sat, Oct 3 - Tue, Oct 6

7:01 pm - 11:58 pmMDW Chicago Midway-PIT Pittsburgh

3h 57m1 stop Detroit Metropolitan Wayne County

10:25 am - 12:39 pmPIT Pittsburgh-MDW Chicago Midway

3h 14m1 stop Detroit Metropolitan Wayne County

$559Delta

Tue, Sep 29 - Sat, Oct 3

7:01 pm - 11:58 pmMDW Chicago Midway-PIT Pittsburgh

3h 57m1 stop Detroit Metropolitan Wayne County

6:35 am - 1:20 pmPIT Pittsburgh-MDW Chicago Midway

7h 45m1 stop Minneapolis St Paul

$559Delta

Tue, Sep 29 - Sat, Oct 3

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Delta flights from Chicago Midway Airport to Pittsburgh

Our best Delta deals on Chicago Midway Airport to Pittsburgh flight tickets

Delta

Oct 22

MDW6:44 pmChicago Midway

4h 15m

1 stop

PIT11:59 pmPittsburgh

Oct 24

PIT12:49 pmPittsburgh

4h 58m

1 stop

MDW4:47 pmChicago Midway

$297

Delta

Oct 23

MDW6:44 pmChicago Midway

4h 15m

1 stop

PIT11:59 pmPittsburgh

Oct 31

PIT6:00 amPittsburgh

4h 32m

1 stop

MDW9:32 amChicago Midway

$307

Delta

Oct 26

MDW5:31 pmChicago Midway

4h 53m

1 stop

PIT11:24 pmPittsburgh

Oct 27

PIT10:32 amPittsburgh

3h 15m

1 stop

MDW12:47 pmChicago Midway

$338

Southwest flights from Chicago Midway Airport to Pittsburgh

Our best Southwest deals on Chicago Midway Airport to Pittsburgh flight tickets

Southwest

Oct 22

MDW7:45 pmChicago Midway

1h 25m

PIT10:10 pmPittsburgh

Oct 26

PIT1:40 pmPittsburgh

1h 30m

MDW2:10 pmChicago Midway

$277

Southwest

Oct 22

MDW7:45 pmChicago Midway

1h 25m

PIT10:10 pmPittsburgh

Oct 26

PIT6:00 pmPittsburgh

5h 00m

1 stop

MDW10:00 pmChicago Midway

$287

Southwest

Oct 22

MDW1:20 pmChicago Midway

1h 20m

PIT3:40 pmPittsburgh

Oct 26

PIT4:20 pmPittsburgh

8h 35m

2 stops

MDW11:55 pmChicago Midway

$292

momondo Fare Finder

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

Cheapest round-trip

Quickest round-trip

ChicagoPittsburgh

MDW Chicago Midway - PIT Pittsburgh

MDWPIT

Chicago Midway

Thu 10/22

1:20 pm-3:40 pm

Nonstop1h 20m

Pittsburgh

Thu 10/29

7:45 pm-8:15 pm

Nonstop1h 30m

$277

ChicagoPittsburgh

MDW Chicago Midway - PIT Pittsburgh

MDWPIT

Chicago Midway

Mon 10/26

7:45 am-10:05 am

Nonstop1h 20m

Pittsburgh

Mon 11/2

4:00 pm-4:35 pm

Nonstop1h 35m

$277

ChicagoPittsburgh

MDW Chicago Midway - PIT Pittsburgh

MDWPIT

Chicago Midway

Sat 11/7

3:35 pm-6:00 pm

Nonstop1h 25m

Pittsburgh

Sat 11/14

8:45 am-9:15 am

Nonstop1h 30m

$277

ChicagoPittsburgh

MDW Chicago Midway - PIT Pittsburgh

MDWPIT

Chicago Midway

Sat 10/17

8:05 am-10:25 am

Nonstop1h 20m

Pittsburgh

Mon 10/19

7:45 pm-8:15 pm

Nonstop1h 30m

$277

ChicagoPittsburgh

MDW Chicago Midway - PIT Pittsburgh

MDWPIT

Chicago Midway

Tue 10/20

5:55 pm-8:20 pm

Nonstop1h 25m

Pittsburgh

Thu 10/22

7:45 pm-8:15 pm

Nonstop1h 30m

$277

ChicagoPittsburgh

MDW Chicago Midway - PIT Pittsburgh

MDWPIT

Chicago Midway

Tue 11/3

1:40 pm-4:05 pm

Nonstop1h 25m

Pittsburgh

Wed 11/4

2:20 pm-2:55 pm

Nonstop1h 35m

$277

ChicagoPittsburgh

MDW Chicago Midway - PIT Pittsburgh

MDWPIT

Chicago Midway

Tue 12/1

8:15 am-10:40 am

Nonstop1h 25m

Pittsburgh

Sat 12/5

4:35 pm-5:05 pm

Nonstop1h 30m

$277

ChicagoPittsburgh

MDW Chicago Midway - PIT Pittsburgh

MDWPIT

Chicago Midway

Sat 11/7

3:35 pm-6:00 pm

Nonstop1h 25m

Pittsburgh

Mon 11/9

8:45 am-9:15 am

Nonstop1h 30m

$277

ChicagoPittsburgh

MDW Chicago Midway - PIT Pittsburgh

MDWPIT

Chicago Midway

Wed 12/2

6:41 pm-10:57 pm

1 stop3h 16m

Pittsburgh

Sat 12/5

12:50 pm-4:50 pm

1 stop5h 00m

$297

ChicagoPittsburgh

MDW Chicago Midway - PIT Pittsburgh

MDWPIT

Chicago Midway

Sat 11/7

6:44 pm-10:59 pm

1 stop3h 15m

Pittsburgh

Tue 11/10

6:10 am-9:46 am

1 stop4h 36m

$297

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Delays

Other information

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 $286. 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 Monday will generally be more expensive and average around $467. 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 at noon. Our users have found flights to Pittsburgh at noon for as low as $374. Flights to Pittsburgh are more costly in the evening, with an average ticket price of $410. Departure times in the evening 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 Airport to Pittsburgh flights?

There is only 1 cabin class available to choose from on Chicago Midway Airport 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?

You could potentially save up to 43% on your flight if you consider stops on a Chicago Midway Airport to Pittsburgh flight.

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	$125
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 $125. The best round-trip flight deal from Chicago Midway Airport to Pittsburgh found on momondo in the last 72 hours is $277.

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 in Pittsburgh. From Chicago Midway Airport there are direct flights to Pittsburgh (PIT).

Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Pittsburgh

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?
As of September 2026, there is 1 operator available to choose from 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?
Based on momondo bookings for flights between Chicago Midway Airport and Pittsburgh, the leading plane model is Airbus A320-100/200, making up 18.99% of the total bookings. Other popular models include Airbus A319 with 15.92%, Embraer 175 (Enhanced Winglets) with 12.01%, and Boeing 737 MAX 8 with 11.17%.
What is the most popular airline from Chicago Midway Airport to Pittsburgh?
momondo data reveals that the most frequently booked airline on the route from Chicago Midway Airport to Pittsburgh is Southwest, representing 100% of all bookings.

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
Southwest	PriceFrom $137	Free Cancellation	Rating 8.0 4,201 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 3 flights/week on average for this route. A good Southwest flight deal for Chicago Midway Airport to Pittsburgh starts from $137 round-trip, up to an average price of $343. Our users have rated Southwest at 8.0/10.

Washington

Monroeville

Wheeling

Butler

Canonsburg

New Castle

West Mifflin

Moon

Belle Vernon

Coraopolis

Triadelphia

Steubenville

Mars

Bridgeport

Wexford

Cadiz

Chester

Edgewood

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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.