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

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

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

As of December 2025, 306 flights take off from Pittsburgh and land in Chicago each week. The most common flight departure day for this route is Wed, with 18% of weekly flights taking off on this day.

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 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.

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, 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, 43 flights take off from Pittsburgh and land in Chicago each day. The most common flight departure time for this route is 3:00PM, with 58% 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 131 minutes.

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.

$32 Cheap Flights from Pittsburgh to Chicago in 2025/26

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Pittsburgh to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:00 am - 4:52 pm

PIT

ORD

11h 52m2 stops

8:43 pm - 9:40 am

ORD

PIT

11h 57m1 stop

$195Multiple Airlines

Tue, Jan 13 - Mon, Jan 19

12:25 pm - 7:30 pm

PIT

MDW

8h 05m2 stops

9:55 am - 3:40 pm

MDW

PIT

4h 45m1 stop

$196Southwest

Thu, Jan 15 - Sun, Jan 18

6:00 am - 9:03 pm

PIT

ORD

16h 03m1 stop

12:44 pm - 11:44 pm

ORD

PIT

10h 00m2 stops

$196Spirit Airlines

Mon, Jan 12 - Sat, Jan 17

6:00 am - 9:03 pm

PIT

ORD

16h 03m1 stop

12:44 pm - 11:44 pm

ORD

PIT

10h 00m2 stops

$197Spirit Airlines

Mon, Jan 12 - Sat, Jan 17

12:20 pm - 12:50 pm

PIT

MDW

1h 30mnonstop

1:25 pm - 3:45 pm

MDW

PIT

1h 20mnonstop

$197Southwest

Thu, Jan 8 - Mon, Jan 12

5:32 am - 9:03 pm

PIT

ORD

16h 31m2 stops

8:43 pm - 9:40 am

ORD

PIT

11h 57m1 stop

$198Spirit Airlines

Sat, Jan 17 - Mon, Jan 19

8:15 am - 9:07 am

PIT

ORD

1h 52mnonstop

6:07 am - 11:33 am

ORD

PIT

4h 26m1 stop

$200American Airlines

Thu, Jan 1 - Sat, Jan 3

10:05 am - 2:01 pm

PIT

ORD

4h 56m1 stop

8:37 am - 11:13 am

ORD

PIT

1h 36mnonstop

$204American Airlines

Thu, Jan 22 - Sun, Jan 25

6:00 am - 8:53 am

PIT

MDW

3h 53m1 stop

6:17 pm - 10:37 pm

MDW

PIT

3h 20m1 stop

$217Delta

Thu, Feb 19 - Thu, Feb 19

6:19 am - 8:52 am

PIT

MDW

3h 33m1 stop

6:30 pm - 11:42 pm

MDW

PIT

4h 12m1 stop

$218Delta

Sat, Jan 10 - Sun, Jan 11

Spirit Airlines flights from Pittsburgh to Chicago

Our best Spirit Airlines deals on Pittsburgh to Chicago flight tickets

Spirit Airlines

Jan 12

PIT6:00 amPittsburgh

16h 03m

1 stop

ORD9:03 pmChicago O'Hare Intl

Jan 17

ORD12:44 pmChicago O'Hare Intl

10h 00m

2 stops

PIT11:44 pmPittsburgh

$196

Find similar

Spirit Airlines

Jan 12

PIT6:00 amPittsburgh

16h 03m

1 stop

ORD9:03 pmChicago O'Hare Intl

Jan 17

ORD12:44 pmChicago O'Hare Intl

10h 00m

2 stops

PIT11:44 pmPittsburgh

$197

Find similar

Spirit Airlines

Jan 17

PIT5:32 amPittsburgh

16h 31m

2 stops

ORD9:03 pmChicago O'Hare Intl

Jan 19

ORD8:43 pmChicago O'Hare Intl

11h 57m

1 stop

PIT9:40 amPittsburgh

$198

Find similar

American Airlines flights from Pittsburgh to Chicago

Our best American Airlines deals on Pittsburgh to Chicago flight tickets

American Airlines

Jan 1

PIT8:15 amPittsburgh

1h 52m

ORD9:07 amChicago O'Hare Intl

Jan 3

ORD6:07 amChicago O'Hare Intl

4h 26m

1 stop

PIT11:33 amPittsburgh

$200

Find similar

American Airlines

Jan 22

PIT10:05 amPittsburgh

4h 56m

1 stop

ORD2:01 pmChicago O'Hare Intl

Jan 25

ORD8:37 amChicago O'Hare Intl

1h 36m

PIT11:13 amPittsburgh

$204

Find similar

American Airlines

Jan 17

PIT6:25 amPittsburgh

2h 04m

ORD7:29 amChicago O'Hare Intl

Jan 17

ORD6:34 pmChicago O'Hare Intl

1h 38m

PIT9:12 pmPittsburgh

$205

Find similar

Fly from

Fly to

Route

Depart

Return

Price

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Tue 1/13

6:00 am-4:52 pm

2 stops11h 52m

Chicago O'Hare Intl

Mon 1/19

8:43 pm-9:40 am

1 stop11h 57m

$195

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 1/15

12:25 pm-7:30 pm

2 stops8h 05m

Chicago Midway

Sun 1/18

9:55 am-3:40 pm

1 stop4h 45m

$196

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Mon 1/12

6:00 am-9:03 pm

1 stop16h 03m

Chicago O'Hare Intl

Sat 1/17

12:44 pm-11:44 pm

2 stops10h 00m

$196

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Mon 1/12

6:00 am-9:03 pm

1 stop16h 03m

Chicago O'Hare Intl

Sat 1/17

12:44 pm-11:44 pm

2 stops10h 00m

$197

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 1/8

12:20 pm-12:50 pm

Nonstop1h 30m

Chicago Midway

Mon 1/12

1:25 pm-3:45 pm

Nonstop1h 20m

$197

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Sat 1/17

5:32 am-9:03 pm

2 stops16h 31m

Chicago O'Hare Intl

Mon 1/19

8:43 pm-9:40 am

1 stop11h 57m

$198

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Thu 1/1

8:15 am-9:07 am

Nonstop1h 52m

Chicago O'Hare Intl

Sat 1/3

6:07 am-11:33 am

1 stop4h 26m

$200

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Thu 1/22

10:05 am-2:01 pm

1 stop4h 56m

Chicago O'Hare Intl

Sun 1/25

8:37 am-11:13 am

Nonstop1h 36m

$204

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 2/19

6:00 am-8:53 am

1 stop3h 53m

Chicago Midway

Thu 2/19

6:17 pm-10:37 pm

1 stop3h 20m

$217

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 1/10

6:19 am-8:52 am

1 stop3h 33m

Chicago Midway

Sun 1/11

6:30 pm-11:42 pm

1 stop4h 12m

$218

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 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 $423. 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 $550.

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 $662.

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 $310 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	$178
Fastest flight time	1h 25m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Pittsburgh in the past 72 hours is $178. The best round-trip flight deal from Pittsburgh to Chicago found on momondo in the last 72 hours is $340.

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

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 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 16.66% of the total bookings. Other popular models include Airbus A319 with 11.27%, Embraer 175 (Enhanced Winglets) with 11.22%, and Embraer 175 with 11.22%.
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 (33%), 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 11,047 reviews	Search American Airlines flights
Southwest	PriceFrom $97	Free Cancellation	Rating 8.0 4,250 reviews	Search Southwest flights
United Airlines	PriceFrom $117	Free Cancellation	Rating 7.4 9,066 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 15 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 $117 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around $316. United Airlines operates 29 flights to Chicago from Pittsburgh in an average week. Users have rated it 7.4/10 across 9,066 reviews.

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?

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.

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.

Start using Trips

Find my bookings

Get notified when prices go down

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

1 adult

Sat 1/3

Sat 1/10

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Popular cities in the United States

Flights to New Yorkfrom $48

Flights to Los Angelesfrom $40

Flights to Miamifrom $47

Flights to Orlandofrom $41

Flights to San Franciscofrom $49

Flights to Las Vegasfrom $40

Flights to Washington, D.C.from $41

Flights to Bostonfrom $57

Flights to Atlantafrom $49

Flights to Dallasfrom $51

Flights to Seattlefrom $56

Flights to Denverfrom $48

Cheap flights from Pittsburgh to Chicago from $32

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 1/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Pittsburgh to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Spirit Airlines flights from Pittsburgh to Chicago

Our best Spirit Airlines deals on Pittsburgh to Chicago flight tickets

American Airlines flights from Pittsburgh to Chicago

Our best American Airlines deals on Pittsburgh to Chicago flight tickets

momondo Fare Finder

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

See travel insights to Chicago from

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 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 $662.

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 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 Allegiant Air 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, 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, 43 flights take off from Pittsburgh and land in Chicago each day. The most common flight departure time for this route is 3:00PM, with 58% of daily flights taking off in the afternoon.

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

As of December 2025, 306 flights take off from Pittsburgh and land in Chicago each week. The most common flight departure day for this route is Wed, with 18% 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