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$49+ 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 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from Pittsburgh to Chicago are usually found in August or April, booked 62 days in advance, depart on a Thursday or Friday and return on a Thursday

Cheap 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 September 15, 2025.

Round-trip from

$97
(Southwest)

One-way from

$49
(Southwest)

Popular in

December

Cheapest in

August

Average price

$265

Good round-trip deal

$250 or less

Good one-way deal

$176 or less
From Pittsburgh to Chicago (CHI)
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One-way flight from Pittsburgh to Chicago (CHI)
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Highest demand for flights based on searches. 8% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Pittsburgh to Chicago (CHI).
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Price to beat on a one-way flight from Pittsburgh to Chicago (CHI).
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Find 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 September 15, 2025.

This Southwest deal was found by Cheapflights users on 9/14. 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.
Tue 10/146:20 amPIT - MDW
Nonstop1h 30mSouthwest
Tue 10/211:25 pmMDW - PIT
Nonstop1h 20mSouthwest
Deal found 9/14$97
This United Airlines deal was found by Cheapflights users on 9/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/158:35 amPIT - ORD
Nonstop1h 50mUnited Airlines
Sat 10/1810:35 amORD - PIT
Nonstop1h 30mUnited Airlines
Deal found 9/13$97
This American Airlines deal was found by Cheapflights users on 9/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/97:17 amPIT - ORD
Nonstop1h 42mAmerican Airlines
Mon 10/138:50 pmORD - PIT
Nonstop1h 29mAmerican Airlines
Deal found 9/13$98
This Southwest deal was found by Cheapflights users on 9/15. 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.
Wed 10/154:00 pmPIT - MDW
Nonstop1h 25mSouthwest
Sat 10/186:30 amMDW - PIT
1 stop7h 40mSouthwest
Deal found 9/15$113
This Southwest deal was found by Cheapflights users on 9/13. 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 10/154:00 pmPIT - MDW
Nonstop1h 25mSouthwest
Fri 10/179:55 pmMDW - PIT
Nonstop1h 20mSouthwest
Deal found 9/13$115
This American Airlines deal was found by Cheapflights users on 9/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/108:31 pmPIT - ORD
Nonstop1h 43mAmerican Airlines
Mon 10/135:11 pmORD - PIT
Nonstop1h 30mAmerican Airlines
Deal found 9/12$115
This Southwest deal was found by Cheapflights users on 9/14. 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.
Thu 10/3012:50 pmPIT - ORD
1 stop4h 35mSouthwest
Sat 11/11:30 pmORD - PIT
1 stop7h 20mSouthwest
Deal found 9/14$122
This United Airlines deal was found by Cheapflights users on 9/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/22:07 pmPIT - ORD
Nonstop1h 44mUnited Airlines
Sun 10/59:07 pmORD - PIT
Nonstop1h 37mUnited Airlines
Deal found 9/12$133
This Southwest deal was found by Cheapflights users on 9/12. 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.
Sun 10/266:20 amPIT - ORD
1 stop7h 25mSouthwest
Tue 10/283:10 pmORD - PIT
1 stop5h 20mSouthwest
Deal found 9/12$135
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/269:34 amPIT - ORD
1 stop11h 10mFrontier
Sun 9/286:10 amORD - PIT
1 stop7h 26mFrontier
Deal found 9/14$144
This Frontier deal was found by Cheapflights users on 9/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/269:34 amPIT - ORD
1 stop11h 10mFrontier
Mon 9/296:10 amORD - PIT
1 stop6h 22mFrontier
Deal found 9/13$145
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/283:31 pmPIT - ORD
1 stop21h 27mFrontier
Thu 10/26:10 amORD - PIT
1 stop7h 26mFrontier
Deal found 9/13$151

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 September 15, 2025.
Use the filters below to find and compare flights from Pittsburgh to Chicago that are best for you.

Fly from

Pittsburgh

Fly to

Chicago

Route

Depart

Return

Price

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 10/14

6:20 am-6:50 am

Nonstop1h 30m

Chicago Midway

Tue 10/21

1:25 pm-3:45 pm

Nonstop1h 20m

$97

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Tue 10/14

7:00 pm-7:50 pm

Nonstop1h 50m

Chicago O'Hare Intl

Tue 10/21

10:35 am-1:05 pm

Nonstop1h 30m

$97

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 10/25

6:20 am-6:50 am

Nonstop1h 30m

Chicago Midway

Tue 10/28

8:45 pm-11:05 pm

Nonstop1h 20m

$97

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Wed 10/15

2:07 pm-2:51 pm

Nonstop1h 44m

Chicago O'Hare Intl

Sat 10/18

12:45 pm-3:24 pm

Nonstop1h 39m

$97

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Sat 11/1

11:00 am-11:44 am

Nonstop1h 44m

Chicago O'Hare Intl

Mon 11/3

12:45 pm-3:20 pm

Nonstop1h 35m

$97

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Tue 10/28

7:35 am-8:17 am

Nonstop1h 42m

Chicago O'Hare Intl

Tue 11/4

9:03 am-11:51 am

Nonstop1h 48m

$98

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 10/30

6:20 am-6:50 am

Nonstop1h 30m

Chicago Midway

Sun 11/2

9:40 am-12:05 pm

Nonstop1h 25m

$115

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 10/15

4:00 pm-4:25 pm

Nonstop1h 25m

Chicago Midway

Fri 10/17

9:55 pm-12:15 am

Nonstop1h 20m

$115

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 10/15

1:10 pm-6:30 pm

1 stop6h 20m

Chicago Midway

Sat 10/18

3:25 pm-9:50 pm

2 stops5h 25m

$122

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Fri 10/3

7:05 am-7:48 am

Nonstop1h 43m

Chicago O'Hare Intl

Sun 10/5

7:25 am-10:02 am

Nonstop1h 37m

$133

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 58 results
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The best insider tips for Pittsburgh to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Pittsburgh to Chicago trip
Airports
PIT

Arrive early at PIT due to ongoing construction and potential security delays, especially for morning flights.

Read more about PITby John Walton
ORD

Use the 'L' train for a reliable and traffic-free trip from ORD to downtown Chicago.

Read more about ORDby Ramsey Qubein
MDW

Take the Orange Line from MDW to reach downtown Chicago in under 30 minutes.

Read more about MDWby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

Ramsey Qubein

Ramsey Qubein

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

John Walton

John Walton

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

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

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

Use this chart to determine the optimal time to book a round-trip flight from Pittsburgh to Chicago. Price data was last updated on September 12, 2025.

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 62 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 $245). Flying from Pittsburgh to Chicago in March is currently the most expensive (average of $321). 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 September 15, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 41% on flights from Pittsburgh to Chicago by exploring options for tickets in the evening.

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 September 14, 2025.

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

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 September 15, 2025.

The most flights from PIT to CHI are scheduled on a Monday (64 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (47 on average).

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 September 15, 2025.
Read through reviews of airlines operating flights from Pittsburgh to Chicago, such as Southwest, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,245 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,931 reviews
Southwest
8.0
Very good
4,245 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,245 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,016 reviews
Southwest
8.0
Very good
4,245 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,173 reviews
Southwest
8.0
Very good
4,245 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 54 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 1h 30m. The distance between Pittsburgh and Chicago is about 400 mi. All flights are typically nonstop.

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

    According to our current data, American Airlines ($93), Southwest ($97), and United Airlines ($130) offers the cheapest pricing from Pittsburgh to Chicago. American Airlines is currently priced 67% 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 $49. However, be on the lookout for offers from United Airlines and American 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 Envoy Air (93%), Avianca (92%) or Copa Airlines (91%) 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 $99. On average you can expect to pay $792. The most popular route, (Pittsburgh - Chicago O'Hare Intl), can usually be booked for $97.

  • 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 $245). Flying from Pittsburgh to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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.
John F Kennedy Intl to O'Hare Intl 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$93Average$299FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$97Average$321FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$130Average$319FlexibilityNo cancel feeOn-time69%

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