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$69+ Cheap flights from Chicago (CHI) to Pittsburgh (PIT)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PIT
Jul 21 — Jul 281
Tue 7/21
Tue 7/28
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Pittsburgh are usually found in August or September, booked 38 days in advance, depart on a Thursday or Wednesday and return on a Friday

Cheap flight deals from Chicago to Pittsburgh

Cheapest flights from Chicago to Pittsburgh
Explore the most affordable flight options available from Chicago to Pittsburgh. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 21, 2026.

This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/15:10 pm
MDW
-
PIT
1 stop3h 35m
Southwest
Wed 7/86:00 am
PIT
-
MDW
2 stops6h 00m
Southwest
Deal found 6/16$204
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/69:24 am
MDW
-
PIT
1 stop5h 09m
Delta
Mon 8/105:50 am
PIT
-
MDW
1 stop7h 01m
Delta
Deal found 6/16$211
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:20 pm
ORD
-
PIT
1 stop5h 44m
Delta
Mon 8/107:05 am
PIT
-
ORD
1 stop8h 04m
Delta
Deal found 6/16$211
This JetBlue deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/310:56 am
ORD
-
PIT
1 stop7h 27m
JetBlue
Tue 7/712:53 pm
PIT
-
ORD
1 stop7h 38m
JetBlue
Deal found 6/18$219
This Super.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1810:56 am
ORD
-
PIT
1 stop7h 27m
JetBlue
Fri 8/2112:58 pm
PIT
-
ORD
1 stop7h 27m
JetBlue
Deal found 6/18$220
This United Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/82:25 pm
ORD
-
PIT
Nonstop1h 45m
United Airlines
Mon 8/107:00 am
PIT
-
ORD
Nonstop1h 48m
United Airlines
Deal found 6/19$227
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/256:35 pm
MDW
-
PIT
1 stop3h 11m
Delta
Tue 7/286:30 am
PIT
-
MDW
1 stop3h 43m
Delta
Deal found 6/20$228
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/255:18 pm
ORD
-
PIT
1 stop4h 28m
Delta
Tue 7/284:55 pm
PIT
-
ORD
1 stop7h 58m
Delta
Deal found 6/20$228
This JetBlue deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/610:56 am
ORD
-
PIT
1 stop7h 52m
JetBlue
Fri 9/111:20 pm
PIT
-
ORD
1 stop7h 02m
JetBlue
Deal found 6/16$229
This Super.com deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/110:56 am
ORD
-
PIT
1 stop7h 27m
JetBlue
Sat 7/46:45 am
PIT
-
ORD
1 stop7h 15m
JetBlue
Deal found 6/19$231
This KAYAK deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1412:37 pm
ORD
-
PIT
Nonstop1h 36m
American Airlines
Thu 9/178:47 pm
PIT
-
ORD
Nonstop2h 00m
American Airlines
Deal found 6/17$234
This American Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/118:00 am
ORD
-
PIT
1 stop7h 56m
American Airlines
Tue 7/143:59 pm
PIT
-
ORD
Nonstop1h 51m
American Airlines
Deal found 6/18$236

Find flight deals from Chicago to Pittsburgh

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Pittsburgh (PIT). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$204
(Southwest)

One-way from

$69
(Southwest)

Popular in

February

Cheapest in

August

Average price

$394

Good round-trip deal

$240 or less

Good one-way deal

$168 or less
Provider with most accurate pricing for Chicago (CHI)-Pittsburgh flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Pittsburgh flights.
Search Deals
From Chicago (CHI) to Pittsburgh
Search Deals
One-way flight from Chicago (CHI) to Pittsburgh
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($74 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Pittsburgh.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Pittsburgh.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Pittsburgh that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 21, 2026.
Use the filters below to find and compare flights from Chicago to Pittsburgh that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Thu 9/17

6:51 pm-11:58 pm

1 stop4h 07m

Pittsburgh

Sat 9/19

5:34 pm-10:25 pm

1 stop5h 51m

$211

ChicagoPittsburgh

ORD - PIT

ORDPIT

Chicago O'Hare Intl

Thu 8/13

6:00 am-2:42 pm

1 stop7h 42m

Pittsburgh

Mon 8/17

5:50 am-10:13 am

1 stop5h 23m

$211

ChicagoPittsburgh

ORD - PIT

ORDPIT

Chicago O'Hare Intl

Sat 8/1

3:46 pm-6:35 pm

Nonstop1h 49m

Pittsburgh

Tue 8/4

10:54 am-11:42 am

Nonstop1h 48m

$240

ChicagoPittsburgh

ORD - PIT

ORDPIT

Chicago O'Hare Intl

Wed 7/1

10:56 am-7:23 pm

1 stop7h 27m

Pittsburgh

Tue 7/7

12:53 pm-7:31 pm

1 stop7h 38m

$242

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Sat 8/1

6:35 pm-10:46 pm

1 stop3h 11m

Pittsburgh

Tue 8/4

7:05 am-11:51 am

1 stop5h 46m

$260

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Fri 9/4

6:42 pm-12:04 am

1 stop4h 22m

Pittsburgh

Sun 9/6

6:35 am-9:17 am

1 stop3h 42m

$260

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Fri 8/14

12:46 pm-8:30 pm

1 stop6h 44m

Pittsburgh

Tue 8/18

5:50 am-9:59 am

1 stop5h 09m

$260

ChicagoPittsburgh

ORD - PIT

ORDPIT

Chicago O'Hare Intl

Mon 7/20

7:17 pm-12:04 am

1 stop3h 47m

Pittsburgh

Wed 7/22

1:00 pm-7:10 pm

1 stop7h 10m

$260

ChicagoPittsburgh

ORD - PIT

ORDPIT

Chicago O'Hare Intl

Sat 7/25

7:05 am-11:42 am

1 stop3h 37m

Pittsburgh

Tue 7/28

6:21 pm-11:53 pm

1 stop6h 32m

$260

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Sun 8/16

7:30 am-1:15 pm

1 stop4h 45m

Pittsburgh

Tue 8/18

8:55 am-9:15 am

Nonstop1h 20m

$261

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/17

Showing 1-10 of 44 resultsSorted by cheapest first
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Compare providers for flights from Chicago to Pittsburgh

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Pittsburgh in June.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Pittsburgh flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Pittsburgh flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Pittsburgh flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Pittsburgh flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Pittsburgh flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Pittsburgh

Have a flexible travel schedule? Discover the best time to fly to Pittsburgh from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Pittsburgh

What is the cheapest month to book a flight from Chicago to Pittsburgh?

Currently, September is the cheapest month in which you can book a flight from Chicago to Pittsburgh (average of $67). Flying from Chicago to Pittsburgh in March is currently the most expensive (average of $163). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to PIT?

Find hourly flight availability from Chicago to Pittsburgh. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 21, 2026.

A simple way to save on the total cost of your ticket is to fly from Chicago to Pittsburgh in the afternoon. If you’re flexible enough to do this you can expect to save up to 13% on your trip compared to booking a flight in the evening.

Weekly flight availability from Chicago to Pittsburgh

Explore weekly flight availability from Chicago to Pittsburgh. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 21, 2026.

The most flights from CHI to PIT are scheduled on a Friday (60 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (47 on average).

How much does it cost to fly round-trip from Chicago to Pittsburgh?

How often are flights from Chicago to Pittsburgh delayed?

About 15% of weekly flights between Chicago and Pittsburgh have experienced delays in the past year, with the average delay time being 103 minutes.

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

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.

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

Wednesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

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

Over the last year, Southwest have had the lowest number of delays on this route, with just 14% of flights being delayed.

How far ahead should I book a flight from Chicago to Pittsburgh?

The best time to book flights from Chicago to Pittsburgh is 35 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest day to fly from Chicago to Pittsburgh?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Pittsburgh. Price data was last updated on June 20, 2026.

Travelers seeking maximum savings on their Chicago to Pittsburgh flight should consider departing on Thursday afternoons when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

The best insider tips for Chicago to Pittsburgh flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Pittsburgh trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
John Walton

John Walton

Expert on PIT

Independent aviation journalist John Walton took his first flight at eight weeks old and hasn’t stopped travelling since. A world-renowned expert in airlines and the passenger experience, he writes in depth on aviation, is a resident expert on travel in Japan and France, and offers a uniquely queer perspective on travelling the world.

Read more

Reviews of airlines servicing Pittsburgh

Get insights into the airlines that provide service to Pittsburgh. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Pittsburgh. Reviews last updated June 21, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican Airlines from Chicago to Pittsburgh. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,241 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
7.9
Good
4,241 reviews
Southwest
7.9
Good
4,241 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
9,865 reviews
Southwest
7.9
Good
4,241 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.1
Good
11,716 reviews
Southwest
7.9
Good
4,241 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

Find useful and relevant information for your journey from Chicago to Pittsburgh. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Pittsburgh from Chicago?

    If you book a flight to Pittsburgh from Chicago, you will be flying to Pittsburgh, which is the city’s only airport. Pittsburgh (PIT) is located 13.5 mi from the center of Pittsburgh. There are 53 flights from Chicago to Pittsburgh per day from 3 different airlines.

  • How long is the flight from Chicago to Pittsburgh?

    For as low as $240, Delta can have you in Pittsburgh from Chicago in 1h 49m. Chicago and Pittsburgh are separated by a distance of 411 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago to Pittsburgh round-trip?

    Our cheapest airline available from Chicago to Pittsburgh is American Airlines. Our recent data shows that you can find tickets from as low as $97 on this airline. Additional options worth looking into are Southwest and United Airlines, starting at $116 and $133 round-trip. You may be able to fly from Chicago to Pittsburgh for 69% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Chicago to Pittsburgh one-way?

    One-way options have recently been found by users for as low as $48 on American Airlines. Other airlines that offer cheap prices include Frontier from $72 and United Airlines from $78 one-way.

  • What are the most reliable airlines from Chicago to Pittsburgh?

    Consider Avianca (95%), Republic Airways (89%) or SkyWest Airlines (84%) when booking your flight. These represent the most reliable airlines when flying from Chicago to Pittsburgh.

  • What are the cheapest flights from Chicago to Pittsburgh?

    Looking at all options, your cheapest flight can be booked for $68. While the most popular route (Chicago O'Hare Intl - Pittsburgh) can be booked for $137 on average, our data indicates $335 when flying from Chicago to Pittsburgh.

  • Can I find deals for flights from Chicago to Pittsburgh that include hotel bookings?

    Yes. In addition to deals on Chicago to Pittsburgh flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Pittsburgh?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Pittsburgh.

  • Can I find deals for business class flights from Chicago to Pittsburgh?

    Yes. Cheapflights offers flight deals from Chicago to Pittsburgh by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Pittsburgh?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Pittsburgh (average of $67). Flying from Chicago to Pittsburgh in March is currently the most expensive (average of $163). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Pittsburgh?

Book flights to Pittsburgh if you plan to visit one of these locations
Washington
Mars
Chester
Steubenville
Monroeville
Wexford
Belle Vernon

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Top 3 airlines flying from Chicago to Pittsburgh

Discover the top 3 airlines that operate flights from Chicago to Pittsburgh. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$97Average$308FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$116Average$311FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$133Average$383FlexibilityNo cancel feeOn-time69%

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