What is the most punctual flight time for Pittsburgh to Chicago 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.

How often are flights from Pittsburgh to Chicago delayed?

Historically, on average around 9% 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 131 minutes.

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, Breeze Airways 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 on average per day?

As of November 2025, 36 flights take off from Pittsburgh and land in Chicago each day. The most common flight departure time for this route is 8:00AM, with 53% of daily flights taking off at noon.

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

As of November 2025, 253 flights take off from Pittsburgh and land in Chicago each week. The most common flight departure day for this route is Mon, with 23% of weekly flights taking off on this day.

What airlines fly to Chicago?

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Pittsburgh according to our data. United Airlines is the first choice among our users, with 50% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

Southwest, American Airlines, and United Airlines are the most popular carriers operating from Pittsburgh to Chicago

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

Prices for flights from Pittsburgh Airport to Chicago are updated daily.

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

There are 3 operators available for flights from Pittsburgh Airport to Chicago as of November 2025.

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

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.

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

The necessary travel and health documents for your Chicago 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.

$44 Cheap Flights from Pittsburgh to Chicago in 2025/26

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10:53 am - 6:36 pmPIT-ORD

32h 43m3 stops

3:26 pm - 12:41 amORD-PIT

8h 15m1 stop

$192Spirit Airlines

Find Deal

Sun, Dec 7 - Wed, Dec 10

6:00 am - 6:27 pmPIT-ORD

13h 27m2 stops

3:05 pm - 9:40 amORD-PIT

17h 35m1 stop

$193Multiple Airlines

Find Deal

Wed, Feb 4 - Sun, Feb 8

5:50 pm - 11:46 pmPIT-ORD

6h 56m1 stop

10:07 am - 9:40 amORD-PIT

22h 33m2 stops

$194Spirit Airlines

Find Deal

Thu, Jan 8 - Thu, Jan 15

8:30 am - 6:58 pmPIT-ORD

11h 28m1 stop

1:20 pm - 11:44 pmORD-PIT

9h 24m2 stops

$195Multiple Airlines

Find Deal

Fri, Jan 9 - Wed, Jan 14

12:25 pm - 7:30 pmPIT-MDW

8h 05m2 stops

9:05 am - 4:35 pmMDW-PIT

6h 30m1 stop

$197Southwest

Find Deal

Thu, Jan 15 - Sat, Jan 17

2:55 pm - 7:43 pmPIT-ORD

5h 48m1 stop

7:00 am - 11:42 pmORD-PIT

15h 42m1 stop

$197JetBlue

Find Deal

Sun, Dec 14 - Wed, Dec 17

6:40 am - 7:20 amPIT-MDW

1h 40mnonstop

6:05 pm - 8:30 pmMDW-PIT

1h 25mnonstop

$198Southwest

Find Deal

Wed, Dec 24 - Wed, Dec 31

12:21 pm - 6:32 pmPIT-MDW

7h 11m1 stop

9:32 am - 1:27 pmMDW-PIT

2h 55m1 stop

$217Delta

Find Deal

Wed, Jan 7 - Wed, Jan 14

6:30 am - 4:49 pmPIT-RFD

11h 19m1 stop

5:23 pm - 11:29 pmRFD-PIT

29h 06m1 stop

$443Allegiant Air

Find Deal

Wed, Dec 31 - Sun, Jan 4

8:00 am - 5:45 pmPIT-RFD

10h 45m1 stop

7:29 pm - 1:55 pmRFD-PIT

17h 26m1 stop

$468Allegiant Air

Find Deal

Fri, Dec 19 - Sun, Dec 21

American Airlines flights from Pittsburgh to Chicago

Our best American Airlines deals on Pittsburgh to Chicago flight tickets

American Airlines

Dec 24

PIT8:15 amPittsburgh

1h 52m

ORD9:07 amChicago O'Hare Intl

Dec 31

ORD1:27 pmChicago O'Hare Intl

3h 48m

1 stop

PIT6:15 pmPittsburgh

$212

Find similar

American Airlines

Dec 17

PIT3:30 pmPittsburgh

2h 02m

ORD4:32 pmChicago O'Hare Intl

Dec 18

ORD9:40 amChicago O'Hare Intl

1h 45m

PIT12:25 pmPittsburgh

$222

Find similar

American Airlines

Dec 9

PIT8:15 amPittsburgh

1h 57m

ORD9:12 amChicago O'Hare Intl

Dec 10

ORD6:30 pmChicago O'Hare Intl

1h 30m

PIT9:00 pmPittsburgh

$231

Find similar

Spirit Airlines flights from Pittsburgh to Chicago

Our best Spirit Airlines deals on Pittsburgh to Chicago flight tickets

Spirit Airlines

Dec 7

PIT10:53 amPittsburgh

32h 43m

3 stops

ORD6:36 pmChicago O'Hare Intl

Dec 10

ORD3:26 pmChicago O'Hare Intl

8h 15m

1 stop

PIT12:41 amPittsburgh

$192

Find similar

Spirit Airlines

Jan 8

PIT5:50 pmPittsburgh

6h 56m

1 stop

ORD11:46 pmChicago O'Hare Intl

Jan 15

ORD10:07 amChicago O'Hare Intl

22h 33m

2 stops

PIT9:40 amPittsburgh

$194

Find similar

Spirit Airlines

Dec 11

PIT7:59 amPittsburgh

13h 02m

1 stop

ORD8:01 pmChicago O'Hare Intl

Dec 14

ORD5:00 amChicago O'Hare Intl

27h 58m

1 stop

PIT9:58 amPittsburgh

$196

Find similar

Fly from

Fly to

Route

Depart

Return

Price

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Sun 12/7

10:53 am-6:36 pm

3 stops32h 43m

Chicago O'Hare Intl

Wed 12/10

3:26 pm-12:41 am

1 stop8h 15m

$192

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Wed 2/4

6:00 am-6:27 pm

2 stops13h 27m

Chicago O'Hare Intl

Sun 2/8

3:05 pm-9:40 am

1 stop17h 35m

$193

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Thu 1/8

5:50 pm-11:46 pm

1 stop6h 56m

Chicago O'Hare Intl

Thu 1/15

10:07 am-9:40 am

2 stops22h 33m

$194

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Fri 1/9

8:30 am-6:58 pm

1 stop11h 28m

Chicago O'Hare Intl

Wed 1/14

1:20 pm-11:44 pm

2 stops9h 24m

$195

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 1/15

12:25 pm-7:30 pm

2 stops8h 05m

Chicago Midway

Sat 1/17

9:05 am-4:35 pm

1 stop6h 30m

$197

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Sun 12/14

2:55 pm-7:43 pm

1 stop5h 48m

Chicago O'Hare Intl

Wed 12/17

7:00 am-11:42 pm

1 stop15h 42m

$197

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 12/24

6:40 am-7:20 am

Nonstop1h 40m

Chicago Midway

Wed 12/31

6:05 pm-8:30 pm

Nonstop1h 25m

$198

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 1/7

12:21 pm-6:32 pm

1 stop7h 11m

Chicago Midway

Wed 1/14

9:32 am-1:27 pm

1 stop2h 55m

$217

PittsburghChicago

PIT - RFD

PITRFD

Pittsburgh

Wed 12/31

6:30 am-4:49 pm

1 stop11h 19m

Chicago Greater Rockford

Sun 1/4

5:23 pm-11:29 pm

1 stop29h 06m

$443

PittsburghChicago

PIT - RFD

PITRFD

Pittsburgh

Fri 12/19

8:00 am-5:45 pm

1 stop10h 45m

Chicago Greater Rockford

Sun 12/21

7:29 pm-1:55 pm

1 stop17h 26m

$468

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How to get the cheapest flight ticket from Pittsburgh to Chicago

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 typical price of a round-trip flight between Pittsburgh and Chicago?

What is the cheapest month to fly to Chicago?

The month of August is, on average, the cheapest month to fly to Chicago from Pittsburgh, with most prices found around $199. If you’re not able to fly to Chicago in August, then September is your next best option. Flight prices from Pittsburgh to Chicago during September average around $227.

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

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $422. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Pittsburgh to Chicago for around $547.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Pittsburgh to Chicago during this time can be as low as $390. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $658.

What is the cheapest Pittsburgh to Chicago flight route?

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

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Pittsburgh when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $311 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Pittsburgh for as low as $161 on momondo.

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

There are 4 cabin classes available to choose from on Pittsburgh to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Pittsburgh to Chicago flight prices changed over time?

As of November 2025, prices for Pittsburgh to Chicago flights are approximately 16% more expensive when compared to flights at the same time last year.

When to book flights from Pittsburgh to Chicago

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

Estimated round-trip price

Cheap Pittsburgh to Chicago (PIT to CHI) flight deals and tips

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

Best Price Found	$190
Fastest flight time	1h 30m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Pittsburgh in the past 72 hours is $190. The best round-trip flight deal from Pittsburgh to Chicago found on momondo in the last 72 hours is $318.

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

Direct flights go from Pittsburgh to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

Search flight deals

How far is Pittsburgh to Chicago by plane?
Pittsburgh and Chicago are 408.7 mi apart from one another. In terms of flight time, this usually takes a little over 1h 30m.
When did momondo last update prices for flights from Pittsburgh Airport to Chicago?
Prices for flights from Pittsburgh Airport to Chicago are updated daily.
How many operators does momondo search for flights from Pittsburgh Airport to Chicago?
There are 3 operators available for flights from Pittsburgh Airport to Chicago as of November 2025.
How old do you have to be to fly from Pittsburgh Airport to Chicago?
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.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago 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?
Based on momondo bookings for flights between Pittsburgh and Chicago, the leading plane model is Boeing 737-800, making up 17.61% of the total bookings. Other popular models include Boeing 737 MAX 8 with 12.19%, Embraer 175 (Enhanced Winglets) with 11.30%, and Embraer 175 with 10.99%.
What is the most popular airline from Pittsburgh to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Pittsburgh to Chicago is Southwest (38% of total bookings). The next most popular airlines are United Airlines (32%), American Airlines (28%), and Frontier (1%).

Best airlines flying from Pittsburgh to Chicago

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

Airline	Rating	Free Cancellation	Price
American Airlines	PriceFrom $92	Free Cancellation	Rating 7.2 11,038 reviews	Search American Airlines flights
Southwest	PriceFrom $97	Free Cancellation	Rating 8.0 4,254 reviews	Search Southwest flights
United Airlines	PriceFrom $126	Free Cancellation	Rating 7.4 9,046 reviews	Search United Airlines flights

Southwest Flights From Pittsburgh to Chicago
The lowest priced Southwest flight from Pittsburgh to Chicago from the last 72 hours was $97. Generally, Southwest has 16 flights on this route every week with an average price of $318. Southwest is rated 8.0/10 by our users.
United Airlines Flights From Pittsburgh to Chicago
United Airlines is also a popular choice for this route. United Airlines flight deals for Pittsburgh to Chicago start from as low as $126 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around $322. United Airlines operates 25 flights to Chicago from Pittsburgh in an average week. Users have rated it 7.4/10 across 9,046 reviews.

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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?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Pittsburgh to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

Flights from Pittsburgh to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search for Pittsburgh to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Of course. momondo tracks the price of Pittsburgh 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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Cheap flights from Pittsburgh to Chicago from $44

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 12/9. 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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American Airlines flights from Pittsburgh to Chicago

Our best American Airlines deals on Pittsburgh to Chicago flight tickets

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Our best Spirit Airlines deals on Pittsburgh to Chicago flight tickets

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How to get the cheapest flight ticket from Pittsburgh to Chicago

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 typical price of a round-trip flight between Pittsburgh and Chicago?

What is the cheapest month to fly to Chicago?

The month of August is, on average, the cheapest month to fly to Chicago from Pittsburgh, with most prices found around $199. If you’re not able to fly to Chicago in August, then September is your next best option. Flight prices from Pittsburgh to Chicago during September average around $227.

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

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Pittsburgh to Chicago during this time can be as low as $390. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $658.

What is the cheapest Pittsburgh to Chicago flight route?

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

How far in advance should I book a flight to Chicago?

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

There are 4 cabin classes available to choose from on Pittsburgh to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Pittsburgh to Chicago flight prices changed over time?

As of November 2025, prices for Pittsburgh to Chicago flights are approximately 16% more expensive when compared to flights at the same time last year.

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

Southwest, American Airlines, and United Airlines are the most popular carriers operating from Pittsburgh to Chicago

What airlines fly to Chicago?

How often are flights from Pittsburgh to Chicago delayed?

Historically, on average around 9% 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 131 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 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?

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, Breeze Airways 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 on average per day?

As of November 2025, 36 flights take off from Pittsburgh and land in Chicago each day. The most common flight departure time for this route is 8:00AM, with 53% of daily flights taking off at noon.

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

As of November 2025, 253 flights take off from Pittsburgh and land in Chicago each week. The most common flight departure day for this route is Mon, with 23% of weekly flights taking off on this day.

When to book flights from Pittsburgh to Chicago

Cheap Pittsburgh to Chicago (PIT to CHI) flight deals and tips

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

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

How far is Pittsburgh to Chicago by plane?

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

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

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

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

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

What is the most popular airline from Pittsburgh to Chicago?

Best airlines flying from Pittsburgh to Chicago

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

Southwest Flights From Pittsburgh to Chicago

United Airlines Flights From Pittsburgh to Chicago

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 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.