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 7% of flights being delayed.

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.

How often are flights from Pittsburgh to Chicago delayed?

About 9% of weekly flights between Pittsburgh and Chicago have experienced delays in the past year, with the average delay time being 132 minutes.

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

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

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

Airfare is typical for this route at the moment. Pittsburgh to Chicago flights typically cost between $171 and $425 in February. The cheapest round-trip price found within the last 3 days was $171 on Southwest (Feb 19-Feb 23).

How long is the flight from Pittsburgh to Chicago?

Departing from Pittsburgh to Chicago will take you 1h 35m. 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 ($91), Southwest ($97), and United Airlines ($106) 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 $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.

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 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, November is the cheapest month in which you can book a flight from Pittsburgh to Chicago (average of $76). Flying from Pittsburgh to Chicago in February is currently the most expensive (average of $155). 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 day to fly from Pittsburgh to Chicago?

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

Weekly flight availability from Pittsburgh to Chicago

The most flights from PIT to CHI are scheduled on a Friday (51 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 on average).

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 cheapest flights from Pittsburgh to Chicago?

The cheapest flight price from Pittsburgh to Chicago is $117. On average you can expect to pay $1,111. The most popular route, (Pittsburgh - Chicago O'Hare Intl), can usually be booked for $119.

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 (100%), GoJet (100%) or ANA (80%) as they are the most reliable in getting you off to your destination on time.

What are the most popular airlines that fly from Pittsburgh to Chicago?

Consider United Airlines, American Airlines or Southwest when booking your flight. These represent the most popular airlines when flying from Pittsburgh to Chicago.

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

Unlike at noon, when flights are generally more expensive, you can save up to 22% on flights from Pittsburgh to Chicago by exploring options for tickets in the evening.

Most accurate provider : When it comes to deals on Pittsburgh-Chicago flights, users find the pricing of CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on Pittsburgh-Chicago flight deals on Cheapflights vs. CheapOair >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 CheapOair the most. CheapOair 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.

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 42 flights from Pittsburgh to Chicago per day from 3 different airlines.

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.

$51+ Flights from Pittsburgh to Chicago

Most accurate provider	CheapOair 3 stars
Most trusted provider	CheapOair 3 stars
Round-trip from	$171 (Southwest)
One-way from	$51 (Booking.com)
Popular in	December
Cheapest in	August
Average price	$258
Good round-trip deal	$319 or less
Good one-way deal	$176 or less

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy2 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*1 star
eDreams	Price Accuracy3 stars	Trust Score*3 stars
CheapOair	Price Accuracy3 stars	Trust Score*3 stars
Priceline	Price Accuracy1 star	Trust Score*3 stars

PIT

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

ORD

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

MDW

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

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$91	Average$292	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$97	Average$320	FlexibilityNo cancel fee	On-time63%
United Airlines	Cheapest$106	Average$303	FlexibilityNo cancel fee	On-time69%

$51+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.

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Cheapest flights from Pittsburgh to ChicagoExplore 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 January 12, 2026.

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 January 12, 2026.

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

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 January.

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.

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 January 9, 2026.

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

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 January 12, 2026.

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 January 3, 2026.

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 January 12, 2026.

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

How often are flights from Pittsburgh to Chicago delayed?

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

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

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

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

Airports

PIT

ORD

MDW

Our travel experts

Reviews of airlines servicing Chicago

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.

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?

How long is the flight from Pittsburgh to Chicago?

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

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

What are the most popular routes from Pittsburgh to Chicago?

What are the most reliable airlines from Pittsburgh to Chicago?

What are the cheapest flights from Pittsburgh to Chicago?

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

How can I find direct flights from Pittsburgh to Chicago?

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

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

Traveling to a place near Chicago?

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Alternative routes for Pittsburgh to Chicago

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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 January 12, 2026.