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

According to our data, Delta have had the least number of delays on this route over the last 12 months; with no flights being classified as delayed.

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

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

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

As of November 2025, 2 flights take off from Pittsburgh and land in Chicago Midway Airport each day. The most common flight departure time for this route is 6:00AM, with 37% of daily flights taking off at noon.

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

Southwest, Frontier, and Delta are the most popular carriers operating from Pittsburgh to Chicago Midway

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

As of November 2025, 16 flights take off from Pittsburgh and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 19% of weekly flights taking off on this day.

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

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

How often are flights from Pittsburgh to Chicago delayed?

Historically, on average around 12% of flights between Pittsburgh and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 106 minutes.

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

Prices for flights from Pittsburgh Airport to Chicago Midway Airport refresh daily.

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

There is 1 operator available for flights from Pittsburgh Airport to Chicago Midway Airport as of November 2025.

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

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

The necessary travel and health documents for your Chicago Midway 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.

$64 Cheap Flights from Pittsburgh to Chicago Midway Airport in 2025/26

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Cheap round-trip flights

Enter your travel dates to find the best prices.

6:00 am - 1:07 pmPIT-MDW

8h 07m1 stop

5:34 pm - 12:21 amMDW-PIT

5h 47m1 stop

$157Delta

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seg, nov 24 - qui, nov 27

1:55 pm - 2:25 pmPIT-MDW

1h 30mnonstop

9:50 pm - 12:10 amMDW-PIT

1h 20mnonstop

$158Southwest

Find Deal

qui, dez 25 - seg, jan 5

6:45 pm - 7:15 pmPIT-MDW

1h 30mnonstop

4:15 pm - 11:30 pmMDW-PIT

6h 15m1 stop

$168Southwest

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qui, dez 25 - seg, jan 5

1:55 pm - 2:25 pmPIT-MDW

1h 30mnonstop

9:10 am - 5:20 pmMDW-PIT

7h 10m2 stops

$173Southwest

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qui, dez 25 - seg, jan 5

10:42 pm - 1:01 pmPIT-MDW

15h 19m1 stop

8:42 pm - 4:10 pmMDW-PIT

42h 28m2 stops

$175Multiple Airlines

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seg, dez 1 - seg, dez 8

6:00 pm - 6:35 pmPIT-MDW

1h 35mnonstop

12:15 pm - 5:10 pmMDW-PIT

3h 55m1 stop

$178Southwest

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qua, jan 21 - sáb, jan 24

10:45 am - 1:45 pmPIT-MDW

4h 00m1 stop

9:35 am - 5:20 pmMDW-PIT

6h 45m2 stops

$183Southwest

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qui, dez 25 - seg, jan 5

8:38 pm - 11:42 amPIT-MDW

16h 04m1 stop

5:47 pm - 8:19 amMDW-PIT

13h 32m1 stop

$197Multiple Airlines

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sáb, nov 22 - seg, nov 24

6:36 pm - 10:26 amPIT-MDW

16h 50m1 stop

8:32 am - 1:53 pmMDW-PIT

4h 21m1 stop

$211Frontier

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sex, nov 14 - dom, nov 16

2:38 pm - 11:38 amPIT-MDW

22h 00m2 stops

8:41 pm - 2:36 pmMDW-PIT

16h 55m1 stop

$312Frontier

Find Deal

seg, nov 17 - sex, nov 21

Frontier flights from Pittsburgh to Chicago Midway Airport

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

Frontier

Nov 14

PIT6:36 pmPittsburgh

16h 50m

1 stop

MDW10:26 amChicago Midway

Nov 16

MDW8:32 amChicago Midway

4h 21m

1 stop

PIT1:53 pmPittsburgh

$211

Find similar

Frontier

Nov 14

PIT6:36 pmPittsburgh

16h 50m

1 stop

MDW10:26 amChicago Midway

Nov 16

MDW8:32 amChicago Midway

4h 21m

1 stop

PIT1:53 pmPittsburgh

$265

Find similar

Frontier

Nov 17

PIT2:38 pmPittsburgh

22h 00m

2 stops

MDW11:38 amChicago Midway

Nov 21

MDW8:41 pmChicago Midway

16h 55m

1 stop

PIT2:36 pmPittsburgh

$312

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Southwest flights from Pittsburgh to Chicago Midway Airport

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

Southwest

Dec 25

PIT1:55 pmPittsburgh

1h 30m

MDW2:25 pmChicago Midway

Jan 5

MDW9:50 pmChicago Midway

1h 20m

PIT12:10 amPittsburgh

$158

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Southwest

Dec 25

PIT6:45 pmPittsburgh

1h 30m

MDW7:15 pmChicago Midway

Jan 5

MDW4:15 pmChicago Midway

6h 15m

1 stop

PIT11:30 pmPittsburgh

$168

Find similar

Southwest

Dec 25

PIT1:55 pmPittsburgh

1h 30m

MDW2:25 pmChicago Midway

Jan 5

MDW9:10 amChicago Midway

7h 10m

2 stops

PIT5:20 pmPittsburgh

$173

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momondo Fare Finder

Use the filters below to find and compare flights from Pittsburgh to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

seg 11/24

6:00 am-1:07 pm

1 stop8h 07m

Chicago Midway

qui 11/27

5:34 pm-12:21 am

1 stop5h 47m

$157

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

qui 12/25

1:55 pm-2:25 pm

Nonstop1h 30m

Chicago Midway

seg 1/5

9:50 pm-12:10 am

Nonstop1h 20m

$158

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

qui 12/25

6:45 pm-7:15 pm

Nonstop1h 30m

Chicago Midway

seg 1/5

4:15 pm-11:30 pm

1 stop6h 15m

$168

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

qui 12/25

1:55 pm-2:25 pm

Nonstop1h 30m

Chicago Midway

seg 1/5

9:10 am-5:20 pm

2 stops7h 10m

$173

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

seg 12/1

10:42 pm-1:01 pm

1 stop15h 19m

Chicago Midway

seg 12/8

8:42 pm-4:10 pm

2 stops42h 28m

$175

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

qua 1/21

6:00 pm-6:35 pm

Nonstop1h 35m

Chicago Midway

sáb 1/24

12:15 pm-5:10 pm

1 stop3h 55m

$178

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

qui 12/25

10:45 am-1:45 pm

1 stop4h 00m

Chicago Midway

seg 1/5

9:35 am-5:20 pm

2 stops6h 45m

$183

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

sáb 11/22

8:38 pm-11:42 am

1 stop16h 04m

Chicago Midway

seg 11/24

5:47 pm-8:19 am

1 stop13h 32m

$197

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

sex 11/14

6:36 pm-10:26 am

1 stop16h 50m

Chicago Midway

dom 11/16

8:32 am-1:53 pm

1 stop4h 21m

$211

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

seg 11/17

2:38 pm-11:38 am

2 stops22h 00m

Chicago Midway

sex 11/21

8:41 pm-2:36 pm

1 stop16h 55m

$312

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 Pittsburgh 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

Prices

Airlines

Delays

Other information

What is the cheapest month to fly to Chicago Midway Airport?

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from Pittsburgh, with most prices found around $201. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Pittsburgh during the month December is also very affordable. Most momondo users find prices during this month for around $236.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Pittsburgh. The lowest ticket price found for a Wednesday departure recently was $354. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Saturday is the most expensive day to depart from Pittsburgh because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $440.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Pittsburgh in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $362 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $404. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Pittsburgh to Chicago Midway flight route?

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

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

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

When to book flights from Pittsburgh to Chicago Midway Airport

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

Estimated round-trip price

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

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

Best Price Found	$201
Fastest flight time	1h 30m
Direct flights	Every day

The best one-way flight to Chicago Midway Airport from Pittsburgh in the past 72 hours is $201. The best round-trip flight deal from Pittsburgh to Chicago Midway Airport found on momondo in the last 72 hours is $286.

The fastest flight from Pittsburgh to Chicago Midway Airport takes 1h 30m

Direct flights go from Pittsburgh to Chicago Midway Airport every day.

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How far is Pittsburgh to Chicago Midway by plane?
The straight-line distance from Pittsburgh to Chicago Midway is 413.5 mi. 1h 30m is a normal flight duration for this route.
When did momondo last update prices for flights from Pittsburgh Airport to Chicago Midway Airport?
Prices for flights from Pittsburgh Airport to Chicago Midway Airport refresh daily.
How many operators does momondo search for flights from Pittsburgh Airport to Chicago Midway Airport?
There is 1 operator available for flights from Pittsburgh Airport to Chicago Midway Airport as of November 2025.
How old do you have to be to fly from Pittsburgh Airport to Chicago Midway 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 Pittsburgh Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The necessary travel and health documents for your Chicago Midway 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 Pittsburgh to Chicago Midway Airport?
Based on momondo bookings for flights between Pittsburgh and Chicago Midway Airport, the leading plane model is Boeing 737-800, making up 15.73% of the total bookings. Other popular models include Boeing 737 MAX 8 with 15.65%, Boeing 737-800 Passenger/BBJ2 (winglets) with 10.27%, and Embraer 175 (Enhanced Winglets) with 9.86%.
What is the most popular airline from Pittsburgh to Chicago Midway Airport?
momondo data reveals that the most frequently booked airline on the route from Pittsburgh to Chicago Midway Airport is Southwest, representing 100% of all bookings.

Best airlines flying from Pittsburgh to Chicago Midway Airport

Compare and see reviews for airlines that fly from Pittsburgh to Chicago Midway Airport with momondo

Airline	Rating	Free Cancellation	Price
Southwest	PriceFrom $97	Free Cancellation	Rating 8.0 4,238 reviews		Search Southwest flights

Southwest Flights From Pittsburgh to Chicago Midway Airport
The lowest priced Southwest flight from Pittsburgh to Chicago Midway Airport from the last 72 hours was $97. Generally, Southwest has 16 flights on this route every week with an average price of $319. Southwest is rated 8.0/10 by our users.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

It is quick and easy to find Pittsburgh 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 Pittsburgh to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Pittsburgh to Chicago flights to just show those with flexible booking policies.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Pittsburgh.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Pittsburgh and alert you when they change.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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qua 12/3

qua 12/10

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Cheap flights from Pittsburgh to Chicago from $64

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Pittsburgh to Chicago departing on 12/31. 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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Frontier flights from Pittsburgh to Chicago Midway Airport

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Use the filters below to find and compare flights from Pittsburgh to Chicago Midway Airport that are best for you.

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

What is the cheapest day to depart on your flight to Chicago Midway Airport?

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

What is the cheapest Pittsburgh to Chicago Midway flight route?

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

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

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

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

Southwest, Frontier, and Delta are the most popular carriers operating from Pittsburgh to Chicago Midway

How often are flights from Pittsburgh to Chicago delayed?

Historically, on average around 12% of flights between Pittsburgh and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 106 minutes.

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

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

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

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

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

According to our data, Delta have had the least number of delays on this route over the last 12 months; with no flights being classified as delayed.

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

As of November 2025, 2 flights take off from Pittsburgh and land in Chicago Midway Airport each day. The most common flight departure time for this route is 6:00AM, with 37% of daily flights taking off at noon.

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

As of November 2025, 16 flights take off from Pittsburgh and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 19% of weekly flights taking off on this day.

When to book flights from Pittsburgh to Chicago Midway Airport

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

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

Best Price Found

Fastest flight time

Direct flights

How far is Pittsburgh to Chicago Midway by plane?

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

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

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

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

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

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

Best airlines flying from Pittsburgh to Chicago Midway Airport

Compare and see reviews for airlines that fly from Pittsburgh to Chicago Midway Airport with momondo

Southwest Flights From Pittsburgh to Chicago Midway Airport

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Chicago

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Popular flights according to clicks in the last 7 days on momondo