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 49% 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.

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

As of December 2025, 35 flights take off from Pittsburgh and land in Chicago each day. The most common flight departure time for this route is 1:00PM, with 49% of daily flights taking off in the afternoon.

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 132 minutes.

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

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 7% of their flights experiencing any sort of delay.

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

As of December 2025, 250 flights take off from Pittsburgh and land in Chicago each week. The most common flight departure day for this route is Tue, with 20% of weekly flights taking off on this day.

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

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

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

Tuesday 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.

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.

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 December 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.

$49 Cheap Flights from Pittsburgh to Chicago in 2025/26

Q: What is the typical price of a round-trip flight between Pittsburgh and Chicago?

Prices are currently typical for flights on this route. Typical prices usually range from $170 to $378. The lowest price recently found on this route was $171.

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Round-trip

One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

6:00 pm - 6:35 pm

PIT

MDW

1h 35mnonstop

5:40 pm - 8:00 pm

MDW

PIT

1h 20mnonstop

$171Southwest

Thu, Jan 22 - Mon, Jan 26

8:56 am - 9:55 am

PIT

ORD

1h 59mnonstop

6:04 pm - 8:41 pm

ORD

PIT

1h 37mnonstop

$171United Airlines

Thu, Jan 22 - Mon, Jan 26

5:39 pm - 6:48 pm

PIT

ORD

2h 09mnonstop

8:37 am - 11:13 am

ORD

PIT

1h 36mnonstop

$172American Airlines

Sat, Jan 24 - Mon, Jan 26

6:00 am - 7:36 pm

PIT

ORD

14h 36m1 stop

7:45 am - 2:41 pm

ORD

PIT

5h 56m1 stop

$173JetBlue

Wed, Jan 21 - Wed, Jan 28

6:00 am - 7:41 pm

PIT

ORD

14h 41m2 stops

2:52 pm - 11:44 pm

ORD

PIT

7h 52m1 stop

$174Multiple Airlines

Wed, Feb 4 - Thu, Feb 5

9:00 am - 5:43 pm

PIT

ORD

9h 43m1 stop

7:45 am - 2:41 pm

ORD

PIT

5h 56m1 stop

$175JetBlue

Tue, Jan 20 - Wed, Jan 21

5:50 pm - 11:46 pm

PIT

ORD

6h 56m1 stop

8:43 pm - 9:40 am

ORD

PIT

11h 57m1 stop

$176Spirit Airlines

Wed, Jan 14 - Fri, Jan 16

5:50 pm - 11:46 pm

PIT

ORD

6h 56m1 stop

8:43 pm - 9:40 am

ORD

PIT

11h 57m1 stop

$177Spirit Airlines

Tue, Jan 13 - Fri, Jan 16

10:23 am - 12:49 pm

PIT

MDW

3h 26m1 stop

6:00 am - 1:50 pm

MDW

PIT

6h 50m1 stop

$177Delta

Wed, Jan 21 - Wed, Jan 28

3:55 pm - 7:00 pm

PIT

MDW

4h 05m1 stop

1:25 pm - 3:45 pm

MDW

PIT

1h 20mnonstop

$181Southwest

Thu, Jan 22 - Mon, Jan 26

United Airlines flights from Pittsburgh to Chicago

Our best United Airlines deals on Pittsburgh to Chicago flight tickets

United Airlines

Jan 22

PIT8:56 amPittsburgh

1h 59m

ORD9:55 amChicago O'Hare Intl

Jan 26

ORD6:04 pmChicago O'Hare Intl

1h 37m

PIT8:41 pmPittsburgh

$171

Find similar

United Airlines

Jan 20

PIT8:56 amPittsburgh

1h 59m

ORD9:55 amChicago O'Hare Intl

Jan 21

ORD6:04 pmChicago O'Hare Intl

1h 37m

PIT8:41 pmPittsburgh

$193

Find similar

United Airlines

Feb 12

PIT7:00 amPittsburgh

1h 52m

ORD7:52 amChicago O'Hare Intl

Feb 12

ORD2:21 pmChicago O'Hare Intl

1h 35m

PIT4:56 pmPittsburgh

$231

Find similar

JetBlue flights from Pittsburgh to Chicago

Our best JetBlue deals on Pittsburgh to Chicago flight tickets

JetBlue

Jan 21

PIT6:00 amPittsburgh

14h 36m

1 stop

ORD7:36 pmChicago O'Hare Intl

Jan 28

ORD7:45 amChicago O'Hare Intl

5h 56m

1 stop

PIT2:41 pmPittsburgh

$173

Find similar

JetBlue

Jan 20

PIT9:00 amPittsburgh

9h 43m

1 stop

ORD5:43 pmChicago O'Hare Intl

Jan 21

ORD7:45 amChicago O'Hare Intl

5h 56m

1 stop

PIT2:41 pmPittsburgh

$175

Find similar

JetBlue

Jan 13

PIT6:00 amPittsburgh

14h 36m

1 stop

ORD7:36 pmChicago O'Hare Intl

Jan 14

ORD9:40 amChicago O'Hare Intl

13h 15m

1 stop

PIT11:55 pmPittsburgh

$184

Find similar

Fly from

Fly to

Route

Depart

Return

Price

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 1/22

6:00 pm-6:35 pm

Nonstop1h 35m

Chicago Midway

Mon 1/26

5:40 pm-8:00 pm

Nonstop1h 20m

$171

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Thu 1/22

8:56 am-9:55 am

Nonstop1h 59m

Chicago O'Hare Intl

Mon 1/26

6:04 pm-8:41 pm

Nonstop1h 37m

$171

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Sat 1/24

5:39 pm-6:48 pm

Nonstop2h 09m

Chicago O'Hare Intl

Mon 1/26

8:37 am-11:13 am

Nonstop1h 36m

$172

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Wed 1/21

6:00 am-7:36 pm

1 stop14h 36m

Chicago O'Hare Intl

Wed 1/28

7:45 am-2:41 pm

1 stop5h 56m

$173

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Wed 2/4

6:00 am-7:41 pm

2 stops14h 41m

Chicago O'Hare Intl

Thu 2/5

2:52 pm-11:44 pm

1 stop7h 52m

$174

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Tue 1/20

9:00 am-5:43 pm

1 stop9h 43m

Chicago O'Hare Intl

Wed 1/21

7:45 am-2:41 pm

1 stop5h 56m

$175

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Wed 1/14

5:50 pm-11:46 pm

1 stop6h 56m

Chicago O'Hare Intl

Fri 1/16

8:43 pm-9:40 am

1 stop11h 57m

$176

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Tue 1/13

5:50 pm-11:46 pm

1 stop6h 56m

Chicago O'Hare Intl

Fri 1/16

8:43 pm-9:40 am

1 stop11h 57m

$177

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 1/21

10:23 am-12:49 pm

1 stop3h 26m

Chicago Midway

Wed 1/28

6:00 am-1:50 pm

1 stop6h 50m

$177

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 1/22

3:55 pm-7:00 pm

1 stop4h 05m

Chicago Midway

Mon 1/26

1:25 pm-3:45 pm

Nonstop1h 20m

$181

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

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 $197. 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 $418. 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 $549.

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 $387. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $657.

What is the cheapest Pittsburgh to Chicago flight route?

Fly from Pittsburgh to Chicago O'Hare Intl 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 $308 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 $188 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 December 2025, prices for Pittsburgh to Chicago flights are approximately 49% 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	$194
Fastest flight time	1h 25m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Pittsburgh in the past 72 hours is $194. The best round-trip flight deal from Pittsburgh to Chicago found on momondo in the last 72 hours is $341.

The fastest flight from Pittsburgh to Chicago takes 1h 25m

Direct flights go from Pittsburgh to Chicago every day.

There are 3 airports in Chicago. From Pittsburgh there are direct flights to 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 25m.
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 December 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 15.53% of the total bookings. Other popular models include Airbus A319 with 13.64%, Embraer 175 with 11.64%, and Embraer 175 (Enhanced Winglets) with 11.41%.
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 (34%), American Airlines (27%), and Frontier (2%).

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 $91	Free Cancellation	Rating 7.2 11,074 reviews	Search American Airlines flights
Southwest	PriceFrom $97	Free Cancellation	Rating 8.0 4,251 reviews	Search Southwest flights
United Airlines	PriceFrom $104	Free Cancellation	Rating 7.4 9,124 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 10 flights on this route every week with an average price of $315. 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 $104 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around $308. United Airlines operates 17 flights to Chicago from Pittsburgh in an average week. Users have rated it 7.4/10 across 9,124 reviews.

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Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Munster

Crown Point

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 $49

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 2/3. 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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See travel insights to Chicago from

How to get the cheapest flight ticket from Pittsburgh to Chicago

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 $197. 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 $387. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $657.

What is the cheapest Pittsburgh to Chicago flight route?

Fly from Pittsburgh to Chicago O'Hare Intl 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 December 2025, prices for Pittsburgh to Chicago flights are approximately 49% more expensive when compared to flights at the same time last year.

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

Southwest, United Airlines, and Spirit 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 132 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?

Tuesday 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, United Airlines have had the least number of delays on this route over the last 12 months; with about 7% of their flights experiencing any sort of delay.

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

As of December 2025, 35 flights take off from Pittsburgh and land in Chicago each day. The most common flight departure time for this route is 1:00PM, with 49% of daily flights taking off in the afternoon.

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

As of December 2025, 250 flights take off from Pittsburgh and land in Chicago each week. The most common flight departure day for this route is Tue, with 20% 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.

Find better results for your trip to the United States