HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$99+ 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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — CHI
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Pittsburgh to Chicago with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 November 20, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

January

Cheapest in

February

Round-trip from

$147
(United Airlines)

One-way from

$99
(Southwest)
Provider with most accurate pricing for Pittsburgh-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Pittsburgh-Chicago (CHI) flights.
Search Deals
High demand for flights, 10% potential price rise
Search Deals
Best time to find cheap flights, 22% potential price drop
Search Deals
From Pittsburgh to Chicago (CHI)
Search Deals
One-way flight from Pittsburgh to Chicago (CHI)
Search Deals

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 November 20, 2024.

This United Airlines deal was found by Cheapflights users on 11/19. 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.
Fri 12/137:10 amPIT - ORD
Nonstop1h 40mUnited Airlines
Sun 12/159:05 pmORD - PIT
Nonstop1h 31mUnited Airlines
Deal found 11/19$147
This American Airlines deal was found by Cheapflights users on 11/19. 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.
Thu 12/196:25 amPIT - ORD
Nonstop1h 55mAmerican Airlines
Wed 1/812:21 pmORD - PIT
Nonstop1h 32mAmerican Airlines
Deal found 11/19$152
This Southwest deal was found by Cheapflights users on 11/19. 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 12/178:20 amPIT - MDW
Nonstop1h 35mSouthwest
Thu 12/198:20 amMDW - PIT
Nonstop1h 20mSouthwest
Deal found 11/19$153
This Priceline deal was found by Cheapflights users on 11/19. 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 12/47:33 pmPIT - ORD
1 stop6h 01mMultiple Airlines
Thu 1/97:25 amORD - PIT
1 stop7h 16mMultiple Airlines
Deal found 11/19$153
This Mytrip deal was found by Cheapflights users on 11/18. 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.
Fri 12/68:35 pmPIT - ORD
1 stop14h 42mSpirit Airlines
Wed 12/1110:43 amORD - PIT
1 stop11h 44mSpirit Airlines
Deal found 11/18$163
This Delta deal was found by Cheapflights users on 11/18. 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 12/104:35 pmPIT - MDW
1 stop6h 31mDelta
Tue 12/175:50 pmMDW - PIT
1 stop4h 06mDelta
Deal found 11/18$176
This Delta deal was found by Cheapflights users on 11/20. 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 12/181:00 pmPIT - ORD
1 stop6h 31mDelta
Wed 12/255:50 pmORD - PIT
1 stop5h 03mDelta
Deal found 11/20$176
This Southwest deal was found by Cheapflights users on 11/20. 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 12/184:30 pmPIT - ORD
1 stop6h 00mSouthwest
Sat 12/212:45 pmORD - PIT
1 stop7h 55mSouthwest
Deal found 11/20$309
This Mytrip deal was found by Cheapflights users on 11/19. 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 12/47:33 pmPIT - MDW
2 stops22h 07mMultiple Airlines
Thu 1/99:21 amMDW - PIT
1 stop10h 49mMultiple Airlines
Deal found 11/19$510

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Fri 12/13

7:10 am-7:50 am

Nonstop1h 40m

Chicago O'Hare Intl

Sun 12/15

9:05 pm-11:36 pm

Nonstop1h 31m

$147

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Thu 12/19

6:25 am-7:20 am

Nonstop1h 55m

Chicago O'Hare Intl

Tue 1/7

6:15 pm-8:53 pm

Nonstop1h 38m

$152

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 12/17

8:20 am-8:55 am

Nonstop1h 35m

Chicago Midway

Thu 12/19

8:20 am-10:40 am

Nonstop1h 20m

$153

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Wed 12/4

7:33 pm-12:34 am

1 stop6h 01m

Chicago O'Hare Intl

Thu 1/9

7:25 am-3:41 pm

1 stop7h 16m

$153

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sun 1/12

4:41 pm-12:13 am

1 stop8h 32m

Chicago Midway

Thu 1/16

7:15 am-3:44 pm

1 stop7h 29m

$157

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Fri 12/6

8:35 pm-10:17 am

1 stop14h 42m

Chicago O'Hare Intl

Wed 12/11

10:43 am-11:27 pm

1 stop11h 44m

$163

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Fri 2/14

8:19 pm-9:15 am

1 stop13h 56m

Chicago O'Hare Intl

Sun 2/16

8:14 am-7:29 pm

1 stop10h 15m

$168

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 12/10

4:35 pm-10:06 pm

1 stop6h 31m

Chicago Midway

Tue 12/17

5:50 pm-10:56 pm

1 stop4h 06m

$176

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Wed 12/18

1:00 pm-6:31 pm

1 stop6h 31m

Chicago O'Hare Intl

Wed 12/25

5:50 pm-11:53 pm

1 stop5h 03m

$176

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Sun 1/12

11:20 am-5:53 pm

1 stop7h 33m

Chicago O'Hare Intl

Tue 1/14

9:05 am-2:55 pm

1 stop4h 50m

$188

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 27 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 November.
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 November 15, 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, September is the cheapest month in which you can book a flight from Pittsburgh to Chicago (average of $232). Flying from Pittsburgh to Chicago in June is currently the most expensive (average of $308). 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 November 20, 2024.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 7% 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 November 18, 2024.

Travelers seeking maximum savings on their Pittsburgh to Chicago flight should consider departing on Saturday evenings 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 November 20, 2024.

The most flights from PIT to CHI are scheduled on a Tuesday (43 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (12 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 November 20, 2024.
Peruse reviews from past customers who have flown with American Airlines, Spirit 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
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

JetBlue
7.5
Good
3,394 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,171 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

WestJet
7.3
Good
2,811 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 31 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, United Airlines ($147), American Airlines ($152), and Southwest ($153) offers the cheapest pricing from Pittsburgh to Chicago. United Airlines 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 Southwest, with whom users have recently found tickets for as low as $99. However, be on the lookout for offers from United Airlines and Spirit 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 SkyWest Airlines (100%), GoJet (100%) or Republic Airways (99%) 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 $157. On average you can expect to pay $976. 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, September is the cheapest month in which you can book a flight from Pittsburgh to Chicago (average of $232). Flying from Pittsburgh to Chicago in June is currently the most expensive (average of $308). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
LaGuardia to O'Hare Intl flights
Newark to O'Hare Intl flights
Newark to Midway flights
Dulles Intl to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Reagan-National to O'Hare Intl flights
LaGuardia to Midway flights
Dulles Intl to Midway flights
Philadelphia to Midway flights
Newark to St. Louis flights
LaGuardia to St. Louis flights
Dulles Intl to St. Louis flights
John F Kennedy Intl to St. Louis flights
Reagan-National to Midway flights
Reagan-National to St. Louis flights
Pittsburgh to O'Hare Intl flights
Allentown to O'Hare Intl flights
Harrisburg to O'Hare Intl flights
Philadelphia to St. Louis flights
Allentown to Midway flights
Pittsburgh to Midway flights
State College to O'Hare Intl flights
Scranton to O'Hare Intl flights
LaGuardia to Moline flights
Newark to Moline flights
Harrisburg to Midway flights
Pittsburgh to St. Louis flights
LaGuardia to Evansville flights
Dulles Intl to Moline flights
John F Kennedy Intl to Evansville flights
John F Kennedy Intl to Moline flights
Harrisburg to St. Louis flights
Reagan-National to Moline flights
Allentown to St. Louis flights
Reagan-National to Peoria flights
State College to St. Louis flights
Dulles Intl to Peoria flights
LaGuardia to Peoria flights
Newark to Evansville flights
Newark to Peoria flights
John F Kennedy Intl to Bloomington flights
Newark to Bloomington flights
LaGuardia to Bloomington flights
Scranton to Peoria flights
John F Kennedy Intl to Peoria flights
John F Kennedy Intl to Springfield flights
Philadelphia to Moline flights
Scranton to St. Louis 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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$118Average$278FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$136Average$303FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$148Average$296FlexibilityNo cancel feeOn-time63%
DeltaCheapest$155Average$290FlexibilityNo cancel feeOn-timeN/A
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
View all available airlines