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$55+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — CHI
Jan 28 — Feb 41
Tue 1/28
Tue 2/4
1 adult, Economy
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Find cheap flights from Pittsburgh to Chicago with Cheapflights

1. Tell us where you want to go
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3. Compare prices and book
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The best prices from Pittsburgh to Chicago are usually found in August or February, booked 71 days in advance, depart on a Friday or Thursday and return on a Saturday

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 January 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$181
(CheapOair)

One-way from

$55
(Frontier)

Popular in

January

Cheapest in

August

Average price

$325

Good round-trip deal

$351 or less

Good one-way deal

$212 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)
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
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 January 2025
Search Deals
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 January 23, 2025.

This CheapOair deal was found by Cheapflights users on 1/23. 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.
Fri 3/711:41 amPIT - ORD
1 stop21h 03mSpirit Airlines
Mon 3/107:42 pmORD - PIT
1 stop20h 27mSpirit Airlines
Deal found 1/23$181
This Southwest deal was found by Cheapflights users on 1/23. 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 2/197:15 pmPIT - MDW
Nonstop1h 30mSouthwest
Fri 2/218:10 amMDW - PIT
Nonstop1h 25mSouthwest
Deal found 1/23$182
This American Airlines deal was found by Cheapflights users on 1/23. 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.
Tue 3/412:17 pmPIT - ORD
Nonstop1h 40mAmerican Airlines
Thu 3/61:55 pmORD - PIT
Nonstop1h 29mAmerican Airlines
Deal found 1/23$182
This United deal was found by Cheapflights users on 1/23. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/62:06 pmPIT - ORD
Nonstop1h 49mUnited Airlines
Mon 3/109:10 pmORD - PIT
Nonstop1h 32mUnited Airlines
Deal found 1/23$197
This Southwest deal was found by Cheapflights users on 1/23. 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.
Mon 4/75:50 pmPIT - ORD
1 stop4h 40mSouthwest
Wed 4/91:30 pmORD - PIT
1 stop7h 30mSouthwest
Deal found 1/23$217
This Mytrip deal was found by Cheapflights users on 1/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/26:05 pmPIT - ORD
1 stop16h 34mMultiple Airlines
Sat 2/85:11 amORD - PIT
2 stops14h 01mMultiple Airlines
Deal found 1/21$229
This Delta deal was found by Cheapflights users on 1/22. 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.
Fri 4/186:00 amPIT - ORD
1 stop4h 24mDelta
Mon 4/214:56 pmORD - PIT
1 stop5h 08mDelta
Deal found 1/22$233
This Delta deal was found by Cheapflights users on 1/22. 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.
Mon 4/144:55 pmPIT - MDW
1 stop6h 34mDelta
Wed 4/236:00 amMDW - PIT
1 stop6h 44mDelta
Deal found 1/22$258
This JetBlue deal was found by Cheapflights users on 1/21. 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.
Mon 8/119:40 amPIT - ORD
1 stop8h 16mJetBlue
Wed 8/208:40 amORD - PIT
1 stop6h 07mJetBlue
Deal found 1/21$331
This FlightHub deal was found by Cheapflights users on 1/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/64:41 pmPIT - MDW
1 stop8h 36mFrontier
Sun 2/97:15 amMDW - PIT
1 stop7h 29mFrontier
Deal found 1/21$336
This Mytrip deal was found by Cheapflights users on 1/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/278:35 pmPIT - RFD
1 stop14h 25mMultiple Airlines
Sun 3/99:37 pmRFD - PIT
2 stops25h 52mMultiple Airlines
Deal found 1/23$377
This Mytrip deal was found by Cheapflights users on 1/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/244:55 pmPIT - MDW
2 stops17h 46mAllegiant Air
Mon 7/288:03 amMDW - PIT
1 stop6h 09mAllegiant Air
Deal found 1/22$481

Find flights from Pittsburgh to Chicago within your budget

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 January 23, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Fri 3/7

11:41 am-7:44 am

1 stop21h 03m

Chicago O'Hare Intl

Mon 3/10

7:42 pm-5:09 pm

1 stop20h 27m

$181

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Fri 2/14

10:28 am-1:05 pm

1 stop3h 37m

Chicago Midway

Mon 2/17

6:28 pm-10:40 pm

1 stop3h 12m

$182

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Fri 2/14

7:42 pm-11:49 pm

1 stop5h 07m

Chicago O'Hare Intl

Mon 2/17

6:15 pm-10:40 pm

1 stop3h 25m

$182

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Fri 2/21

8:36 pm-9:15 am

1 stop13h 39m

Chicago O'Hare Intl

Sun 2/23

5:15 am-1:40 pm

1 stop7h 25m

$183

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Fri 2/14

9:00 pm-12:15 am

1 stop4h 15m

Chicago Midway

Mon 2/17

1:40 pm-4:00 pm

Nonstop1h 20m

$192

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Thu 2/27

2:06 pm-2:55 pm

Nonstop1h 49m

Chicago O'Hare Intl

Wed 3/12

9:10 pm-11:42 pm

Nonstop1h 32m

$197

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Wed 2/12

11:07 am-11:50 am

Nonstop1h 43m

Chicago O'Hare Intl

Thu 2/13

1:35 pm-4:01 pm

Nonstop1h 26m

$201

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Mon 4/7

5:50 pm-9:30 pm

1 stop4h 40m

Chicago O'Hare Intl

Wed 4/9

4:00 pm-9:10 pm

1 stop4h 10m

$217

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sun 3/9

9:14 pm-7:35 pm

1 stop23h 21m

Chicago Midway

Sun 3/16

12:36 pm-8:46 am

1 stop19h 10m

$338

PittsburghChicago

PIT - RFD

PITRFD

Pittsburgh

Thu 2/27

8:35 pm-10:00 am

1 stop14h 25m

Chicago Greater Rockford

Sun 3/9

9:37 pm-12:29 am

2 stops25h 52m

$377

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/23

Showing 1-10 of 26 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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice 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.

Travel insights for flights from Pittsburgh to Chicago

Get recent, data-driven insights about flights from Pittsburgh to Chicago including ideal travel times, pricing trends, and more.

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 17, 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 71 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 $322). 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 January 23, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 42% 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 January 21, 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 January 23, 2025.

The most flights from PIT to CHI are scheduled on a Monday (45 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

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.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

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).

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 January 23, 2025.
Peruse reviews from past customers who have flown with Spirit Airlines, American Airlines and United Airlines from Pittsburgh to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,647 reviews

Boarding

8.2

Crew

8.7

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,647 reviews
Southwest
8.1
Very good
4,647 reviews

Boarding

8.2

Crew

8.7

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,508 reviews
Southwest
8.1
Very good
4,647 reviews

Boarding

8.2

Crew

8.7

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,185 reviews
Southwest
8.1
Very good
4,647 reviews

Boarding

8.2

Crew

8.7

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,970 reviews
Southwest
8.1
Very good
4,647 reviews

Boarding

8.2

Crew

8.7

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.4
Good
801 reviews
Southwest
8.1
Very good
4,647 reviews

Boarding

8.2

Crew

8.7

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 36 flights from Pittsburgh to Chicago per day from 4 different airlines.

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

    According to our current data, Spirit Airlines ($181), Delta ($182), and Southwest ($192) offers the cheapest pricing from Pittsburgh to Chicago. Spirit Airlines is currently priced 36% 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 Frontier, with whom users have recently found tickets for as low as $55. However, be on the lookout for offers from Southwest 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 Air Wisconsin (100%), SWISS (96%) or Qantas Airways (89%) 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 $143. On average you can expect to pay $1,255. 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 $245). Flying from Pittsburgh to Chicago in March is currently the most expensive (average of $322). 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
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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
Newark to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Newark to Midway flights
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John F Kennedy Intl to Midway flights
Philadelphia to O'Hare Intl flights
LaGuardia to Midway flights
Reagan-National to Midway flights
Philadelphia to Midway flights
Dulles Intl to Midway flights
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LaGuardia to St. Louis flights
John F Kennedy Intl to St. Louis flights
Pittsburgh to O'Hare Intl flights
Dulles Intl to St. Louis flights
Harrisburg to O'Hare Intl flights
Philadelphia to St. Louis flights
Reagan-National to St. Louis flights
Pittsburgh to Midway flights
Allentown to O'Hare Intl flights
Scranton to O'Hare Intl flights
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Allentown to Midway flights
Pittsburgh to St. Louis flights
Dulles Intl to Moline flights
LaGuardia to Peoria flights
Scranton to St. Louis flights
Newark to Peoria flights
Reagan-National to Moline flights
Newark to Moline flights
Harrisburg to St. Louis flights
LaGuardia to Moline flights
State College to Peoria flights
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Philadelphia to Moline flights
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Harrisburg to Bloomington flights
Harrisburg to Peoria flights
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Dulles Intl to Peoria flights
Newark to Champaign flights
John F Kennedy Intl to Champaign flights

Top 4 airlines flying from Pittsburgh to Chicago

Discover the top 4 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 January 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$123Average$284FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$134Average$316FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$153Average$303FlexibilityNo cancel feeOn-time63%
DeltaCheapest$155Average$363FlexibilityNo cancel feeOn-timeN/A
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