HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$49+ 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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — CHI
Apr 21 — Apr 281
Mon 4/21
Mon 4/28
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.

Cheapflights Tip: The best prices from Pittsburgh to Chicago are usually found in August or September, booked 88 days in advance, depart on a Thursday or Friday 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 April 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$97
(American Airlines)

One-way from

$49
(Southwest)

Popular in

January

Cheapest in

August

Average price

$265

Good round-trip deal

$329 or less

Good one-way deal

$162 or less
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
From Pittsburgh to Chicago (CHI)
Search Deals
One-way flight from Pittsburgh to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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).
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 April 16, 2025.

This American Airlines deal was found by Cheapflights users on 4/16. 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 9/88:27 pmPIT - ORD
Nonstop1h 46mAmerican Airlines
Wed 9/108:54 pmORD - PIT
Nonstop1h 50mAmerican Airlines
Deal found 4/16$97
This Southwest deal was found by Cheapflights users on 4/15. 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 5/76:15 amPIT - MDW
2 stops8h 25mSouthwest
Tue 5/138:30 amMDW - PIT
1 stop5h 55mSouthwest
Deal found 4/15$122
This Southwest deal was found by Cheapflights users on 4/16. 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 5/136:00 amPIT - ORD
1 stop6h 50mSouthwest
Wed 5/141:50 pmORD - PIT
1 stop7h 20mSouthwest
Deal found 4/16$122
This KAYAK deal was found by Cheapflights users on 4/15. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/132:10 pmPIT - ORD
Nonstop1h 43mUnited Airlines
Thu 5/1512:45 pmORD - PIT
Nonstop1h 39mUnited Airlines
Deal found 4/15$155
This CheapOair deal was found by Cheapflights users on 4/16. 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 5/96:14 pmPIT - ORD
1 stop6h 18mFrontier
Sun 5/114:15 pmORD - PIT
1 stop24h 09mFrontier
Deal found 4/16$161
This Delta deal was found by Cheapflights users on 4/16. 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.
Thu 5/86:25 amPIT - MDW
1 stop3h 15mDelta
Thu 5/86:25 pmMDW - PIT
1 stop3h 28mDelta
Deal found 4/16$177
This Delta deal was found by Cheapflights users on 4/15. 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.
Thu 5/86:45 amPIT - ORD
1 stop6h 02mDelta
Mon 5/127:10 amORD - PIT
1 stop3h 00mDelta
Deal found 4/15$177
This Mytrip deal was found by Cheapflights users on 4/16. 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 5/69:07 pmPIT - ORD
1 stop11h 20mSpirit Airlines
Wed 5/79:08 pmORD - PIT
1 stop11h 12mSpirit Airlines
Deal found 4/16$179
This Mytrip deal was found by Cheapflights users on 4/16. 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 5/3012:30 pmPIT - ORD
1 stop25h 12mMultiple Airlines
Wed 6/49:08 pmORD - PIT
1 stop11h 12mMultiple Airlines
Deal found 4/16$180
This Mytrip deal was found by Cheapflights users on 4/16. 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 5/303:48 pmPIT - RFD
1 stop17h 18mAllegiant Air
Wed 6/49:35 amRFD - PIT
1 stop9h 55mAllegiant Air
Deal found 4/16$201
This CheapOair deal was found by Cheapflights users on 4/14. 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 6/66:50 pmPIT - MDW
1 stop25h 35mFrontier
Sun 6/89:12 pmMDW - PIT
1 stop19h 48mFrontier
Deal found 4/14$220
This Mytrip deal was found by Cheapflights users on 4/15. 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 5/169:00 amPIT - RFD
1 stop11h 10mMultiple Airlines
Sun 5/1812:28 pmRFD - PIT
1 stop27h 38mMultiple Airlines
Deal found 4/15$278

Cheapflights Fare Finder

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 April 16, 2025.
Use the filters below to find and compare flights from Pittsburgh to Chicago that are best for you.

Fly from

Pittsburgh

Fly to

Chicago

Route

Depart

Return

Price

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Mon 9/8

8:27 pm-9:13 pm

Nonstop1h 46m

Chicago O'Hare Intl

Wed 9/10

8:54 pm-11:44 pm

Nonstop1h 50m

$97

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 5/7

6:15 am-1:40 pm

2 stops8h 25m

Chicago Midway

Tue 5/13

8:30 am-3:25 pm

1 stop5h 55m

$122

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Tue 5/13

6:00 am-11:50 am

1 stop6h 50m

Chicago O'Hare Intl

Wed 5/14

1:50 pm-10:10 pm

1 stop7h 20m

$122

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Tue 5/13

2:10 pm-2:53 pm

Nonstop1h 43m

Chicago O'Hare Intl

Thu 5/15

12:45 pm-3:24 pm

Nonstop1h 39m

$155

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Fri 5/9

6:14 pm-11:32 pm

1 stop6h 18m

Chicago O'Hare Intl

Sun 5/11

4:15 pm-5:24 pm

1 stop24h 09m

$161

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 5/8

6:25 am-8:40 am

1 stop3h 15m

Chicago Midway

Thu 5/8

6:25 pm-10:53 pm

1 stop3h 28m

$177

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Thu 5/8

6:45 am-11:47 am

1 stop6h 02m

Chicago O'Hare Intl

Mon 5/12

3:33 pm-11:59 pm

1 stop7h 26m

$177

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Tue 5/6

9:07 pm-7:27 am

1 stop11h 20m

Chicago O'Hare Intl

Wed 5/7

9:08 pm-9:20 am

1 stop11h 12m

$179

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Fri 5/30

12:30 pm-12:42 pm

1 stop25h 12m

Chicago O'Hare Intl

Wed 6/4

9:08 pm-9:20 am

1 stop11h 12m

$180

PittsburghChicago

PIT - RFD

PITRFD

Pittsburgh

Fri 5/30

3:48 pm-8:06 am

1 stop17h 18m

Chicago Greater Rockford

Wed 6/4

9:35 am-8:30 pm

1 stop9h 55m

$201

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

Showing 1-10 of 29 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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 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 eDreams the most. eDreams 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.

The best insider tips for Pittsburgh to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Pittsburgh to Chicago trip
Airlines
United Airlines

Basic Economy on United allows a personal item only, no carry-on bags.


United Economy Plus offers extra legroom seats towards the front of the economy cabin.

Read more about United Airlinesby Harriet Baskas
Southwest

Southwest offers two free checked bags, even for oversized items like skis.


Southwest's open seating policy allows passengers to choose any available seat.

Read more about Southwestby Marisa Garcia
Airports
PIT

Arrive early at PIT due to ongoing construction and potentially busy security lines, especially for morning flights.

Read more about PITby John Walton
ORD

Use the 'L' train for a reliable and cost-effective way to reach downtown Chicago from ORD.

Read more about ORDby Ramsey Qubein
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Marisa Garcia

Marisa Garcia

Expert on Southwest

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
John Walton

John Walton

Expert on PIT

John Walton

John Walton

Independent aviation journalist John Walton took his first flight at eight weeks old and hasn’t stopped travelling since. A world-renowned expert in airlines and the passenger experience, he writes in depth on aviation, is a resident expert on travel in Japan and France, and offers a uniquely queer perspective on travelling the world.

Read more

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.

Cheapflights Insights

Everything you need to know about your flight from Pittsburgh to Chicago

How far ahead should I book a flight from Pittsburgh to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Pittsburgh to Chicago. Price data was last updated on April 11, 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 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 $321). 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 April 16, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 38% 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 March 30, 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 April 16, 2025.

The most flights from PIT to CHI are scheduled on a Friday (51 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (14 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 April 16, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta 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
8.0
Very good
4,282 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,282 reviews
Southwest
8.0
Very good
4,282 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,916 reviews
Southwest
8.0
Very good
4,282 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,665 reviews
Southwest
8.0
Very good
4,282 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
JetBlue
7.3
Good
2,926 reviews
Southwest
8.0
Very good
4,282 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,282 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 40 flights from Pittsburgh to Chicago per day from 5 different airlines.

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

    According to our current data, American Airlines ($97), Southwest ($122), and Frontier ($161) offers the cheapest pricing from Pittsburgh to Chicago. American Airlines is currently priced 66% 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 $49. However, be on the lookout for offers from United Airlines and American 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 Cathay Pacific (93%), Copa Airlines (92%) or SWISS (91%) 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 $121. On average you can expect to pay $863. The most popular route, (Pittsburgh - Chicago O'Hare Intl), can usually be booked for $97.

  • 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 $321). 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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
John F Kennedy Intl to Midway flights
Philadelphia to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
LaGuardia to Midway flights
Dulles Intl to Midway flights
Newark to St. Louis flights
LaGuardia to St. Louis flights
Reagan-National to Midway flights
John F Kennedy Intl to St. Louis flights
Dulles Intl to St. Louis flights
Philadelphia to Midway flights
Pittsburgh to O'Hare Intl flights
Philadelphia to St. Louis flights
Harrisburg to O'Hare Intl flights
Allentown to O'Hare Intl flights
Reagan-National to St. Louis flights
Pittsburgh to Midway flights
Scranton to O'Hare Intl flights
Harrisburg to Midway flights
Allentown to Midway flights
State College to O'Hare Intl flights
Pittsburgh to St. Louis flights
Dulles Intl to Peoria flights
Reagan-National to Peoria flights
Dulles Intl to Moline flights
Allentown to St. Louis flights
Newark to Rockford flights
Dulles Intl to Bloomington flights
Newark to Peoria flights
Philadelphia to Peoria flights
Philadelphia to Moline flights
John F Kennedy Intl to Bloomington flights
LaGuardia to Bloomington flights
Harrisburg to St. Louis flights
Reagan-National to Moline flights
Scranton to St. Louis flights
Newark to Moline flights
Philadelphia to Evansville flights
Pittsburgh to Rockford flights
Reagan-National to Bloomington flights
LaGuardia to Moline flights
Newark to Evansville flights
John F Kennedy Intl to Moline flights
John F Kennedy Intl to Springfield flights

Top 5 airlines flying from Pittsburgh to Chicago

Discover the top 5 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 April 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$89Average$174FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$119Average$294FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$130Average$322FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$132Average$311FlexibilityNo cancel feeOn-time63%
DeltaCheapest$197Average$456FlexibilityNo 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.