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

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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — CHI
Aug 15 — Aug 221
Sat 8/15
Sat 8/22
1 adult, Economy
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Cheapflights Tip: The best prices from Pittsburgh to Chicago are usually found in August or September, booked 50 days in advance, depart on a Friday or Thursday and return on a Thursday

Cheap flight deals from Pittsburgh to Chicago

Cheapest flights from Pittsburgh to Chicago
Explore the most affordable flight options available from Pittsburgh to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 16, 2026.

This Southwest deal was found by Cheapflights users on 7/12. 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.
Sat 8/226:20 am
PIT
-
MDW
2 stops8h 00m
Southwest
Tue 8/251:00 pm
MDW
-
PIT
2 stops7h 30m
Southwest
Deal found 7/12$167
This Delta deal was found by Cheapflights users on 7/15. 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.
Tue 8/184:55 pm
PIT
-
ORD
1 stop5h 00m
Delta
Wed 8/266:59 am
ORD
-
PIT
1 stop3h 20m
Delta
Deal found 7/15$167
This Southwest deal was found by Cheapflights users on 7/14. 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.
Sat 10/1010:30 am
PIT
-
MDW
2 stops12h 10m
Southwest
Mon 10/127:50 am
MDW
-
PIT
1 stop4h 05m
Southwest
Deal found 7/14$168
This Southwest deal was found by Cheapflights users on 7/12. 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.
Sat 8/86:50 am
PIT
-
MDW
1 stop3h 40m
Southwest
Sat 8/157:45 am
MDW
-
PIT
Nonstop1h 25m
Southwest
Deal found 7/12$169
This Southwest deal was found by Cheapflights users on 7/15. 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.
Sat 9/266:10 am
PIT
-
MDW
2 stops10h 55m
Southwest
Wed 9/307:40 am
MDW
-
PIT
2 stops8h 55m
Southwest
Deal found 7/15$173
This Southwest deal was found by Cheapflights users on 7/13. 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 8/1210:10 am
PIT
-
MDW
2 stops7h 40m
Southwest
Sat 8/157:45 am
MDW
-
PIT
Nonstop1h 25m
Southwest
Deal found 7/13$174
This Southwest deal was found by Cheapflights users on 7/11. 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.
Thu 9/34:10 pm
PIT
-
MDW
1 stop4h 05m
Southwest
Mon 9/77:55 am
MDW
-
PIT
1 stop4h 15m
Southwest
Deal found 7/11$179
This Delta deal was found by Cheapflights users on 7/15. 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 8/84:55 pm
PIT
-
MDW
1 stop6h 41m
Delta
Sat 8/156:42 pm
MDW
-
PIT
1 stop3h 09m
Delta
Deal found 7/15$188
This Delta deal was found by Cheapflights users on 7/15. 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 8/84:55 pm
PIT
-
ORD
1 stop5h 00m
Delta
Sat 8/155:18 pm
ORD
-
PIT
1 stop4h 33m
Delta
Deal found 7/15$188
This Southwest deal was found by Cheapflights users on 7/15. 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.
Sat 8/226:10 am
PIT
-
MDW
2 stops7h 55m
Southwest
Mon 8/248:00 am
MDW
-
PIT
2 stops8h 40m
Southwest
Deal found 7/15$189
This Delta deal was found by Cheapflights users on 7/15. 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 8/206:19 pm
PIT
-
MDW
1 stop5h 17m
Delta
Mon 8/246:42 pm
MDW
-
PIT
1 stop4h 22m
Delta
Deal found 7/15$198
This Delta deal was found by Cheapflights users on 7/16. 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 8/1312:17 pm
PIT
-
ORD
1 stop5h 00m
Delta
Thu 8/2011:23 am
ORD
-
PIT
1 stop4h 51m
Delta
Deal found 7/16$198

Find flight deals from Pittsburgh to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Pittsburgh (PIT) to Chicago (CHI). 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 July 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$167
(Southwest)

One-way from

$69
(Southwest)

Popular in

December

Cheapest in

August

Average price

$353

Good round-trip deal

$353 or less

Good one-way deal

$173 or less
Provider with most accurate pricing for Pittsburgh-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Pittsburgh-Chicago (CHI) flights.
Search Deals
From Pittsburgh to Chicago (CHI)
Search Deals
One-way flight from Pittsburgh to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($5 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Pittsburgh to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Pittsburgh to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pittsburgh to Chicago 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 July 16, 2026.
Use the filters below to find and compare flights from Pittsburgh to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 8/22

6:20 am-1:20 pm

2 stops8h 00m

Chicago Midway

Tue 8/25

1:00 pm-9:30 pm

2 stops7h 30m

$167

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Sat 8/15

5:56 pm-8:30 pm

1 stop3h 34m

Chicago O'Hare Intl

Thu 8/20

7:30 pm-12:04 am

1 stop3h 34m

$167

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 8/29

6:20 am-1:20 pm

2 stops8h 00m

Chicago Midway

Sat 9/5

9:55 am-8:45 pm

2 stops9h 50m

$167

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Tue 8/18

12:17 pm-4:17 pm

1 stop5h 00m

Chicago O'Hare Intl

Thu 8/27

5:20 pm-12:04 am

1 stop5h 44m

$167

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 8/13

4:10 pm-10:20 pm

2 stops7h 10m

Chicago Midway

Sat 8/22

7:55 am-5:50 pm

2 stops8h 55m

$167

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Thu 8/27

1:00 pm-6:03 pm

1 stop6h 03m

Chicago O'Hare Intl

Mon 8/31

6:40 am-12:52 pm

1 stop5h 12m

$167

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Tue 8/18

4:55 pm-8:55 pm

1 stop5h 00m

Chicago O'Hare Intl

Wed 8/26

6:59 am-11:19 am

1 stop3h 20m

$167

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Mon 8/10

6:10 am-3:25 pm

2 stops10h 15m

Chicago Midway

Mon 8/17

11:00 am-5:50 pm

1 stop5h 50m

$168

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 8/22

6:10 am-1:05 pm

2 stops7h 55m

Chicago Midway

Mon 8/24

8:00 am-5:40 pm

2 stops8h 40m

$189

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Thu 9/17

6:00 am-10:19 am

1 stop5h 19m

Chicago O'Hare Intl

Mon 9/21

5:10 pm-11:58 pm

1 stop5h 48m

$218

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/11

Showing 1-10 of 58 resultsSorted by cheapest first
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Compare providers for flights from Pittsburgh to Chicago

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 Pittsburgh to Chicago in July.
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 Pittsburgh-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Pittsburgh-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Pittsburgh-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Pittsburgh-Chicago 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 Pittsburgh-Chicago 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 Pittsburgh to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Pittsburgh 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 Pittsburgh to Chicago

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

Currently, August is the cheapest month in which you can book a flight from Pittsburgh to Chicago (average of $61). Flying from Pittsburgh to Chicago in April is currently the most expensive (average of $145). 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 PIT to CHI?

Find hourly flight availability from Pittsburgh to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 16, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 14% on flights from Pittsburgh to Chicago by exploring options for tickets in the evening.

Weekly flight availability from Pittsburgh to Chicago

Explore weekly flight availability from Pittsburgh to Chicago. 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 July 16, 2026.

The most flights from PIT to CHI are scheduled on a Monday (65 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (27 on average).

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

How often are flights from Pittsburgh to Chicago delayed?

About 11% of weekly flights between Pittsburgh and Chicago have experienced delays in the past year, with the average delay time being 130 minutes.

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

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

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

Saturday 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 Pittsburgh to Chicago flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 8% of flights being delayed.

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

The price you pay for your flight from Pittsburgh to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 21 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Use this chart to determine the cheapest time to fly round-trip from Pittsburgh to Chicago. Price data was last updated on July 11, 2026.

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

The best insider tips for Pittsburgh to Chicago 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 Pittsburgh to Chicago 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 Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated July 16, 2026.
Read through reviews of airlines operating flights from Pittsburgh to Chicago, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

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
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

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
9,994 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

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
11,816 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Frontier
5.6
Fair
2,794 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

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 Pittsburgh to Chicago. 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 from for flights from Pittsburgh to Chicago?

    If you book a flight to Chicago from Pittsburgh, you will be flying from Pittsburgh, which is the city’s only airport. Pittsburgh (PIT) is located 13.5 mi from the center of Pittsburgh. There are 55 flights from Pittsburgh to Chicago per day from 3 different airlines.

  • How long is the flight from Pittsburgh to Chicago?

    Departing from Pittsburgh to Chicago will take you 3h 34m. The distance between Pittsburgh and Chicago is about 411 mi. This flight may include one or multiple stops.

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

    According to our current data, American Airlines ($91), Southwest ($121), and United Airlines ($137) offers the cheapest pricing from Pittsburgh to Chicago. American Airlines is currently priced 70% below the average price you’ll pay for this route.

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

    The cheapest airline one-way is Southwest, with whom users have recently found tickets for as low as $38. However, be on the lookout for offers from American Airlines and United Airlines, as they are both options that can get you from Pittsburgh to Chicago for a low price.

  • What are the most popular routes from Pittsburgh to Chicago?

    When deciding which route to take from Pittsburgh to Chicago consider Pittsburgh - Chicago O'Hare Intl, Pittsburgh - Chicago Midway or Pittsburgh - Chicago Greater Rockford as they are the most popular.

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

    No one likes to see their flight delayed. When booking a flight from Pittsburgh to Chicago consider choosing Japan Airlines (93%), Republic Airways (92%) or Avianca (87%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Pittsburgh to Chicago?

    The cheapest flight price from Pittsburgh to Chicago is $103. On average you can expect to pay $1,407. The most popular route, (Pittsburgh - Chicago O'Hare Intl), can usually be booked for $137.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Pittsburgh to Chicago 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 Pittsburgh to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Pittsburgh to Chicago (average of $61). Flying from Pittsburgh to Chicago in April is currently the most expensive (average of $145). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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Alternative routes for Pittsburgh to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Newark to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
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Dulles Intl to O'Hare Intl flights
LaGuardia to Midway flights
John F Kennedy Intl to Midway flights
Dulles Intl to Midway flights
Philadelphia to Midway flights
Newark to St. Louis flights
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John F Kennedy Intl to St. Louis flights
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Philadelphia to St. Louis flights
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Philadelphia to Rockford flights
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Harrisburg to Midway flights
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LaGuardia to Moline flights
Harrisburg to St. Louis flights
Allentown to St. Louis flights
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Newark to Peoria flights
Pittsburgh to Rockford flights
Reagan-National to Peoria flights
Dulles Intl to Peoria flights
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Philadelphia to Moline flights
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Top 3 airlines flying from Pittsburgh to Chicago

Discover the top 3 airlines that operate flights from Pittsburgh to Chicago. 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 July 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$91Average$304FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$121Average$346FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$137Average$346FlexibilityNo cancel feeOn-time69%

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