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$53+ 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 3/25. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — CHI
Mar 2 — Mar 91
Sun 3/2
Sun 3/9
1 adult, Economy
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The best prices from Pittsburgh to Chicago are usually found in August or September, booked 43 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 February 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$152
(Southwest)

One-way from

$53
(Mytrip)

Popular in

January

Cheapest in

August

Average price

$316

Good round-trip deal

$299 or less

Good one-way deal

$196 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. 10% potential increase in price ($33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
Search Deals
Price to beat on a round-trip flight from Pittsburgh to Chicago (CHI).
Search Deals
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 February 25, 2025.

This Southwest deal was found by Cheapflights users on 2/23. 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 5/144:00 pmPIT - MDW
1 stop6h 10mSouthwest
Fri 5/165:45 amMDW - PIT
1 stop5h 20mSouthwest
Deal found 2/23$152
This Southwest deal was found by Cheapflights users on 2/23. 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.
Sat 3/153:25 pmPIT - ORD
1 stop7h 35mSouthwest
Tue 3/184:00 pmORD - PIT
1 stop5h 55mSouthwest
Deal found 2/23$152
This Mytrip deal was found by Cheapflights users on 2/24. 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 4/145:33 amPIT - ORD
1 stop26h 30mSpirit Airlines
Tue 4/156:36 pmORD - PIT
2 stops11h 44mSpirit Airlines
Deal found 2/24$153
This Delta deal was found by Cheapflights users on 2/24. 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.
Wed 4/166:25 amPIT - MDW
1 stop3h 15mDelta
Mon 4/215:59 pmMDW - PIT
1 stop4h 04mDelta
Deal found 2/24$177
This Delta deal was found by Cheapflights users on 2/23. 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.
Tue 4/153:35 pmPIT - ORD
1 stop5h 41mDelta
Tue 4/229:30 amORD - PIT
1 stop2h 57mDelta
Deal found 2/23$177
This JetBlue deal was found by Cheapflights users on 2/24. 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.
Wed 3/2611:09 amPIT - ORD
1 stop6h 16mJetBlue
Wed 4/210:37 amORD - PIT
1 stop9h 19mJetBlue
Deal found 2/24$189
This American Airlines deal was found by Cheapflights users on 2/23. 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.
Sat 3/151:42 pmPIT - ORD
1 stop6h 49mAmerican Airlines
Tue 3/181:55 pmORD - PIT
Nonstop1h 23mAmerican Airlines
Deal found 2/23$202
This United Airlines deal was found by Cheapflights users on 2/23. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/152:06 pmPIT - ORD
Nonstop1h 49mUnited Airlines
Sat 3/156:59 pmORD - PIT
Nonstop1h 33mUnited Airlines
Deal found 2/23$207
This Frontier deal was found by Cheapflights users on 2/24. 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.
Tue 4/12:23 pmPIT - MDW
1 stop6h 28mFrontier
Sun 4/610:19 amMDW - PIT
1 stop9h 09mFrontier
Deal found 2/24$244
This Mytrip deal was found by Cheapflights users on 2/25. 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 3/611:41 amPIT - ORD
2 stops25h 35mMultiple Airlines
Mon 3/107:48 amORD - PIT
2 stops15h 44mMultiple Airlines
Deal found 2/25$255
This Mytrip deal was found by Cheapflights users on 2/25. 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 3/66:00 amPIT - MDW
1 stop12h 36mAllegiant Air
Fri 3/78:40 amMDW - PIT
2 stops37h 53mAllegiant Air
Deal found 2/25$346
This Mytrip deal was found by Cheapflights users on 2/24. 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.
Wed 3/512:00 pmPIT - RFD
1 stop23h 43mMultiple Airlines
Thu 3/69:37 pmRFD - PIT
2 stops25h 55mMultiple Airlines
Deal found 2/24$508

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 February 25, 2025.

Fly from

Pittsburgh

Fly to

Chicago

Route

Depart

Return

Price

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 5/14

4:00 pm-9:10 pm

1 stop6h 10m

Chicago Midway

Fri 5/16

5:45 am-12:05 pm

1 stop5h 20m

$152

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Sat 3/15

3:25 pm-10:00 pm

1 stop7h 35m

Chicago O'Hare Intl

Tue 3/18

4:00 pm-10:55 pm

1 stop5h 55m

$152

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Mon 4/14

5:33 am-7:03 am

1 stop26h 30m

Chicago O'Hare Intl

Tue 4/15

6:36 pm-7:20 am

2 stops11h 44m

$153

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 4/16

6:25 am-8:40 am

1 stop3h 15m

Chicago Midway

Mon 4/21

5:59 pm-11:03 pm

1 stop4h 04m

$177

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Tue 4/15

3:35 pm-8:16 pm

1 stop5h 41m

Chicago O'Hare Intl

Tue 4/22

9:30 am-1:27 pm

1 stop2h 57m

$177

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Wed 3/26

11:09 am-4:25 pm

1 stop6h 16m

Chicago O'Hare Intl

Wed 4/2

10:37 am-8:56 pm

1 stop9h 19m

$189

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Sat 3/15

1:42 pm-7:31 pm

1 stop6h 49m

Chicago O'Hare Intl

Tue 3/18

1:55 pm-4:18 pm

Nonstop1h 23m

$202

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Sat 3/15

2:06 pm-2:55 pm

Nonstop1h 49m

Chicago O'Hare Intl

Sat 3/15

6:59 pm-9:32 pm

Nonstop1h 33m

$207

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 4/1

2:23 pm-7:51 pm

1 stop6h 28m

Chicago Midway

Sun 4/6

10:19 am-8:28 pm

1 stop9h 09m

$244

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Thu 3/6

11:41 am-12:16 pm

2 stops25h 35m

Chicago O'Hare Intl

Mon 3/10

7:48 am-12:32 am

2 stops15h 44m

$255

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/24

Showing 1-10 of 26 results
1
2
3

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 February.
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 February 25, 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 43 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 February 25, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 40% 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 February 23, 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 February 25, 2025.

The most flights from PIT to CHI are scheduled on a Tuesday (43 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 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 February 25, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and JetBlue 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
4,374 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Crew

8.7

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Southwest
8.1
Very good
4,374 reviews
Southwest
8.1
Very good
4,374 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Crew

8.7

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Delta
8.0
Very good
8,165 reviews
Southwest
8.1
Very good
4,374 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Crew

8.7

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

JetBlue
7.4
Good
3,052 reviews
Southwest
8.1
Very good
4,374 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Crew

8.7

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

United Airlines
7.4
Good
8,733 reviews
Southwest
8.1
Very good
4,374 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Crew

8.7

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Allegiant Air
7.3
Good
759 reviews
Southwest
8.1
Very good
4,374 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Crew

8.7

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

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 29 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, Southwest ($152), Spirit Airlines ($153), and Delta ($177) offers the cheapest pricing from Pittsburgh to Chicago. Southwest is currently priced 47% 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 Spirit Airlines, with whom users have recently found tickets for as low as $53. However, be on the lookout for offers from Southwest and Delta, 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 Copa Airlines (94%), Royal Jordanian (93%) or Alaska Airlines (92%) 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 $133. On average you can expect to pay $1,015. The most popular route, (Pittsburgh - Chicago O'Hare Intl), can usually be booked for $111.

  • 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
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Pittsburgh to Midway flights
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LaGuardia to Moline flights
John F Kennedy Intl to Moline flights
Newark to Moline flights
Harrisburg to St. Louis flights
Philadelphia to Moline flights
Allentown to St. Louis flights
Dulles Intl to Peoria flights
Reagan-National to Peoria flights
Reagan-National to Moline flights
Philadelphia to Peoria flights
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Elmira to O'Hare Intl flights
State College to St. Louis flights
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LaGuardia to Evansville flights
Scranton to St. Louis flights
Newark to Evansville flights
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John F Kennedy Intl to Bloomington flights
Newark to Bloomington flights
Newark to Champaign flights
Allentown to Moline 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 February 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$129Average$286FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$135Average$320FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$148Average$308FlexibilityNo cancel feeOn-time63%
DeltaCheapest$176Average$463FlexibilityNo cancel feeOn-timeN/A
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