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$54+ 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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — CHI
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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Cheapflights Tip: The best prices from Pittsburgh to Chicago are usually found in August or September, booked 86 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 October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$107
(Southwest)

One-way from

$54
(Frontier)

Popular in

December

Cheapest in

August

Average price

$282

Good round-trip deal

$275 or less

Good one-way deal

$175 or less
Provider with most accurate pricing for Pittsburgh-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Pittsburgh-Chicago (CHI) flights.
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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. 9% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 14, 2025.

This Southwest deal was found by Cheapflights users on 10/14. 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 12/410:45 amPIT - MDW
1 stop4h 00mSouthwest
Mon 12/86:05 pmMDW - PIT
Nonstop1h 25mSouthwest
Deal found 10/14$107
This United Airlines deal was found by Cheapflights users on 10/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/238:45 amPIT - ORD
Nonstop1h 59mUnited Airlines
Thu 12/259:18 pmORD - PIT
Nonstop1h 41mUnited Airlines
Deal found 10/14$107
This Frontier deal was found by Cheapflights users on 10/13. 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.
Mon 11/105:30 pmPIT - ORD
1 stop7h 45mFrontier
Mon 11/178:26 amORD - PIT
1 stop4h 27mFrontier
Deal found 10/13$108
This United Airlines deal was found by Cheapflights users on 10/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/165:50 pmPIT - ORD
Nonstop1h 44mUnited Airlines
Thu 12/187:24 amORD - PIT
Nonstop1h 43mUnited Airlines
Deal found 10/14$109
This Southwest deal was found by Cheapflights users on 10/14. 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 11/201:20 pmPIT - MDW
1 stop4h 30mSouthwest
Mon 11/2411:00 amMDW - PIT
1 stop5h 20mSouthwest
Deal found 10/14$114
This CheapOair deal was found by Cheapflights users on 10/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/410:15 amPIT - ORD
1 stop11h 12mSpirit Airlines
Wed 11/510:52 amORD - PIT
1 stop9h 19mSpirit Airlines
Deal found 10/14$114
This Priceline deal was found by Cheapflights users on 10/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1210:15 amPIT - ORD
1 stop11h 12mMultiple Airlines
Thu 11/138:26 amORD - PIT
1 stop4h 27mMultiple Airlines
Deal found 10/13$116
This Southwest deal was found by Cheapflights users on 10/14. 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 11/46:00 amPIT - ORD
1 stop7h 15mSouthwest
Tue 11/41:45 pmORD - PIT
1 stop6h 20mSouthwest
Deal found 10/14$117
This Southwest deal was found by Cheapflights users on 10/14. 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 12/166:00 amPIT - ORD
1 stop7h 15mSouthwest
Thu 12/181:45 pmORD - PIT
1 stop7h 30mSouthwest
Deal found 10/14$122
This Kiwi.com deal was found by Cheapflights users on 10/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/510:06 pmPIT - ORD
1 stop15h 39mMultiple Airlines
Wed 11/127:34 pmORD - PIT
1 stop9h 47mMultiple Airlines
Deal found 10/14$124
This Kiwi.com deal was found by Cheapflights users on 10/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/510:06 pmPIT - ORD
1 stop15h 39mMultiple Airlines
Thu 11/136:40 amORD - PIT
1 stop22h 41mMultiple Airlines
Deal found 10/14$125
This Priceline deal was found by Cheapflights users on 10/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1210:15 amPIT - ORD
1 stop11h 12mSpirit Airlines
Wed 11/1910:52 amORD - PIT
1 stop9h 19mSpirit Airlines
Deal found 10/13$126

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 October 14, 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

Thu 12/4

10:45 am-1:45 pm

1 stop4h 00m

Chicago Midway

Mon 12/8

6:05 pm-8:30 pm

Nonstop1h 25m

$107

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Tue 11/4

6:00 am-12:15 pm

1 stop7h 15m

Chicago O'Hare Intl

Tue 11/4

1:45 pm-9:05 pm

1 stop6h 20m

$117

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Thu 11/6

12:14 pm-12:27 am

1 stop13h 13m

Chicago O'Hare Intl

Sat 11/8

10:52 am-9:11 pm

1 stop9h 19m

$157

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 11/20

3:30 pm-8:45 pm

1 stop6h 15m

Chicago Midway

Mon 11/24

11:00 am-5:20 pm

1 stop5h 20m

$175

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Tue 11/4

6:00 am-12:15 pm

1 stop7h 15m

Chicago O'Hare Intl

Wed 11/5

11:55 am-9:15 pm

1 stop8h 20m

$177

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Fri 10/31

5:47 pm-6:31 pm

Nonstop1h 44m

Chicago O'Hare Intl

Sun 11/2

7:25 am-9:54 am

Nonstop1h 29m

$186

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Fri 10/31

7:00 am-7:30 am

Nonstop1h 30m

Chicago Midway

Sun 11/2

9:40 am-12:05 pm

Nonstop1h 25m

$186

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Fri 10/31

12:50 pm-1:15 pm

Nonstop1h 25m

Chicago Midway

Mon 11/3

10:15 am-12:45 pm

Nonstop1h 30m

$186

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Thu 11/20

6:00 am-10:19 am

1 stop5h 19m

Chicago O'Hare Intl

Mon 11/24

6:45 am-11:12 am

1 stop3h 27m

$208

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Sat 11/22

3:01 pm-7:50 pm

1 stop5h 49m

Chicago O'Hare Intl

Sun 11/23

1:20 pm-10:45 pm

1 stop8h 25m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

Showing 1-10 of 52 results
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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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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

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 October 10, 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 86 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 $91). Flying from Pittsburgh to Chicago in February is currently the most expensive (average of $153). 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 October 14, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 36% 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 October 5, 2025.

Travelers seeking maximum savings on their Pittsburgh to Chicago flight should consider departing on Saturday afternoons when fares are most often at their lowest. Thursday 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 October 14, 2025.

The most flights from PIT to CHI are scheduled on a Monday (61 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (44 on average).

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

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 October 14, 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
4,238 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

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
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

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
8,976 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

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
11,042 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

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
3,135 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

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 44m. 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 ($93), Southwest ($97), and United Airlines ($128) 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 $56. However, be on the lookout for offers from Delta and Allegiant Air, 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 GoJet (100%), Copa Airlines (96%) or SWISS (94%) 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 $68. On average you can expect to pay $857. The most popular route, (Pittsburgh - Chicago O'Hare Intl), can usually be booked for $134.

  • 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 $91). Flying from Pittsburgh to Chicago in February is currently the most expensive (average of $153). 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
Porter
Benton Harbor
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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$93Average$297FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$97Average$317FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$128Average$322FlexibilityNo cancel feeOn-time69%

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