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$113+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — CHI
Dec 28 — Jan 41
Sat 12/28
Sat 1/4
1 adult, Economy
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The best prices from Pittsburgh to Chicago are usually found in February or August, booked 88 days in advance, depart on a Wednesday 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 December 23, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$229
(American Airlines)

One-way from

$113
(Southwest)

Popular in

December

Cheapest in

February

Average price

$340
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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High demand for flights, 11% potential price rise
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Best time to find cheap flights, 2% potential price drop
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Average for round-trip flights in December 2024
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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 December 23, 2024.

This United Airlines deal was found by Cheapflights users on 12/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/282:00 pmPIT - ORD
Nonstop1h 55mUnited Airlines
Sat 12/286:20 pmORD - PIT
2 stops18h 29mUnited Airlines
Deal found 12/22$308
This Priceline deal was found by Cheapflights users on 12/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/316:00 amPIT - ORD
1 stop11h 06mMultiple Airlines
Thu 1/21:07 pmORD - PIT
1 stop6h 59mMultiple Airlines
Deal found 12/21$392
This Southwest deal was found by Cheapflights users on 12/23. 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 12/303:20 pmPIT - MDW
Nonstop1h 25mSouthwest
Wed 1/11:10 pmMDW - PIT
Nonstop1h 20mSouthwest
Deal found 12/23$414
This Delta deal was found by Cheapflights users on 12/22. 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.
Tue 12/316:30 amPIT - MDW
1 stop3h 20mDelta
Fri 1/36:25 pmMDW - PIT
1 stop3h 13mDelta
Deal found 12/22$432
This Southwest deal was found by Cheapflights users on 12/23. 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 12/306:15 amPIT - ORD
1 stop8h 45mSouthwest
Tue 12/315:45 amORD - PIT
1 stop5h 35mSouthwest
Deal found 12/23$432
This American Airlines deal was found by Cheapflights users on 12/23. 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.
Mon 12/305:41 amPIT - ORD
1 stop6h 21mAmerican Airlines
Tue 12/318:50 amORD - PIT
Nonstop1h 35mAmerican Airlines
Deal found 12/23$453
This Delta deal was found by Cheapflights users on 12/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/274:32 pmPIT - ORD
1 stop5h 48mDelta
Tue 12/315:50 pmORD - PIT
1 stop5h 03mDelta
Deal found 12/23$488
This Mytrip deal was found by Cheapflights users on 12/21. 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.
Tue 12/317:33 pmPIT - ORD
3 stops17h 56mSpirit Airlines
Thu 1/29:35 pmORD - PIT
3 stops20h 58mSpirit Airlines
Deal found 12/21$524
This Mytrip deal was found by Cheapflights users on 12/21. 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.
Mon 12/309:09 pmPIT - RFD
2 stops20h 58mMultiple Airlines
Thu 1/210:07 amRFD - PIT
1 stop10h 08mMultiple Airlines
Deal found 12/21$586

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 December 23, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Thu 2/20

6:10 am-12:24 pm

1 stop7h 14m

Chicago O'Hare Intl

Sat 2/22

12:40 pm-3:09 pm

Nonstop1h 29m

$227

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Thu 3/6

11:39 am-5:29 pm

1 stop6h 50m

Chicago O'Hare Intl

Fri 3/14

9:05 am-3:04 pm

1 stop4h 59m

$228

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Sun 1/12

5:17 pm-9:39 am

1 stop17h 22m

Chicago O'Hare Intl

Tue 1/14

3:56 pm-10:16 am

1 stop17h 20m

$230

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sun 1/12

6:27 am-12:46 pm

1 stop7h 19m

Chicago Midway

Tue 1/14

2:08 pm-6:52 pm

1 stop3h 44m

$231

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 3/4

7:15 pm-7:45 pm

Nonstop1h 30m

Chicago Midway

Thu 3/6

8:10 am-10:30 am

Nonstop1h 20m

$232

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Tue 1/7

8:38 pm-11:04 am

1 stop15h 26m

Chicago O'Hare Intl

Sun 1/12

7:25 am-3:41 pm

1 stop7h 16m

$232

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Mon 3/3

1:01 pm-7:55 pm

1 stop7h 54m

Chicago O'Hare Intl

Tue 3/11

10:15 am-8:04 pm

1 stop8h 49m

$242

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Wed 1/15

6:30 am-11:30 am

1 stop6h 00m

Chicago O'Hare Intl

Wed 1/29

11:25 am-8:40 pm

2 stops8h 15m

$256

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Fri 1/17

7:00 am-7:55 am

Nonstop1h 55m

Chicago O'Hare Intl

Mon 1/20

2:20 pm-4:55 pm

Nonstop1h 35m

$277

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Thu 3/6

12:16 pm-12:23 am

1 stop13h 07m

Chicago O'Hare Intl

Sun 3/9

9:25 am-8:46 am

1 stop22h 21m

$318

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/23

Showing 1-10 of 27 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 December.
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 December 20, 2024.

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 88 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 $317). 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 December 23, 2024.

Unlike at noon, when flights are generally more expensive, you can save up to 8% on flights from Pittsburgh to Chicago by exploring options for tickets in the morning.

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 December 16, 2024.

Travelers seeking maximum savings on their Pittsburgh to Chicago flight should consider departing on Wednesday at noon when fares are most often at their lowest. Sunday afternoons 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 December 23, 2024.

The most flights from PIT to CHI are scheduled on a Monday (46 on average). You will have fewer flight options on Wednesday, 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 December 23, 2024.
Peruse reviews from past customers who have flown with Delta, American Airlines and Southwest 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
4,780 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

Food

7.2

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
4,780 reviews
Southwest
8.1
Very good
4,780 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

Food

7.2

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.

Alaska Airlines
8.0
Very good
9,549 reviews
Southwest
8.1
Very good
4,780 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

Food

7.2

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
8,588 reviews
Southwest
8.1
Very good
4,780 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

Food

7.2

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
3,263 reviews
Southwest
8.1
Very good
4,780 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

Food

7.2

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
9,022 reviews
Southwest
8.1
Very good
4,780 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

Food

7.2

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 34 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, American Airlines ($229), Spirit Airlines ($230), and Delta ($231) offers the cheapest pricing from Pittsburgh to Chicago. American Airlines is currently priced 18% 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 $113. However, be on the lookout for offers from Spirit 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 Air Wisconsin (100%), Republic Airways (98%) or SWISS (95%) 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 $149. On average you can expect to pay $1,185. 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 $317). 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

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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.
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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 December 23, 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$122Average$280FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$135Average$308FlexibilityNo cancel feeOn-time69%
DeltaCheapest$155Average$290FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$158Average$303FlexibilityNo cancel feeOn-time63%
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