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Flights from Pittsburgh to Chicago
Cheap flight deals from Pittsburgh to Chicago Starting at AED 175
We've found these cheap flights for you. You can book one-way or round-trip flight tickets.
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Round-trip
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One way
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Cheapest nonstopPIT 11:381h 51mNonstopORD 12:29Pittsburgh - Chicago | Tue, Apr 1 | American AirlinesORD 08:301h 33mNonstopPIT 11:03Chicago - Pittsburgh | Wed, Apr 2 | American AirlinesAED 310 AED 45432% OFF32% OFFAED 454 AED 310
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PIT 15:581h 51mNonstopORD 16:49Pittsburgh - Chicago | Tue, Apr 29 | American AirlinesORD 19:051h 37mNonstopPIT 21:42Chicago - Pittsburgh | Tue, May 6 | American AirlinesAED 337 AED 45426% OFF26% OFFAED 454 AED 337
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PIT 20:001h 47mNonstopORD 20:47Pittsburgh - Chicago | Thu, Apr 24 | American AirlinesMDW 07:551h 20mNonstopPIT 10:15Chicago - Pittsburgh | Mon, Apr 28 | Southwest AirlinesAED 343 AED 45425% OFF25% OFFAED 454 AED 343
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PIT 05:251h 51mNonstopORD 06:16Pittsburgh - Chicago | Wed, Apr 9 | American AirlinesORD 19:151h 31mNonstopPIT 21:46Chicago - Pittsburgh | Mon, Apr 14 | American AirlinesAED 36021% OFFAED 454 AED 360
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PIT 06:351h 52mNonstopORD 07:27Pittsburgh - Chicago | Thu, Mar 20 | American AirlinesORD 18:471h 38mNonstopPIT 21:25Chicago - Pittsburgh | Mon, Mar 24 | American AirlinesAED 36719% OFFAED 454 AED 367
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PIT 20:001h 47mNonstopORD 20:47Pittsburgh - Chicago | Mon, Apr 14 | American AirlinesORD 13:511h 27mNonstopPIT 16:18Chicago - Pittsburgh | Wed, Apr 16 | American AirlinesAED 37018% OFFAED 454 AED 370
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PIT 15:581h 51mNonstopORD 16:49Pittsburgh - Chicago | Tue, Apr 8 | American AirlinesORD 16:491h 27mNonstopPIT 19:16Chicago - Pittsburgh | Mon, Apr 14 | American AirlinesAED 37617% OFFAED 454 AED 376
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PIT 11:311h 50mNonstopORD 12:21Pittsburgh - Chicago | Tue, Apr 15 | American AirlinesORD 12:551h 32mNonstopPIT 15:27Chicago - Pittsburgh | Tue, Apr 22 | American AirlinesAED 37817% OFFAED 454 AED 378
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PIT 16:581h 46mNonstopORD 17:44Pittsburgh - Chicago | Thu, Apr 3 | American AirlinesMDW 20:401h 25mNonstopPIT 23:05Chicago - Pittsburgh | Mon, Apr 7 | Southwest AirlinesAED 38216% OFFAED 454 AED 382
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PIT 06:351h 52mNonstopORD 07:27Pittsburgh - Chicago | Thu, Mar 27 | American AirlinesORD 18:471h 38mNonstopPIT 21:25Chicago - Pittsburgh | Mon, Mar 31 | American AirlinesAED 4149% OFFAED 454 AED 414
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PIT 13:0017h 25m1 stopsCHI Invalid DatePittsburgh - Chicago | Tue, Mar 18 | Normal AirlineCHI 15:006hNonstopPIT 16:00Chicago - Pittsburgh | Thu, Mar 20 | Normal AirlineFind More FlightsFind More Flights
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Cheapest nonstopPIT 16:581h 46mNonstopORD 17:44Pittsburgh - Chicago | Wed, Apr 2 | American AirlinesAED 175 AED 22823% OFF23% OFFAED 228 AED 175
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PIT 13:051h 30mNonstopMDW 13:35Pittsburgh - Chicago | Tue, Apr 8 | Southwest AirlinesAED 178 AED 22822% OFF22% OFFAED 228 AED 178
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PIT 05:251h 51mNonstopORD 06:16Pittsburgh - Chicago | Tue, Apr 8 | American AirlinesAED 180 AED 22821% OFF21% OFFAED 228 AED 180
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PIT 06:201h 30mNonstopMDW 06:50Pittsburgh - Chicago | Thu, May 8 | Southwest AirlinesAED 18220% OFFAED 228 AED 182
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PIT 20:001h 30mNonstopMDW 20:30Pittsburgh - Chicago | Wed, Apr 2 | Southwest AirlinesAED 18320% OFFAED 228 AED 183
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PIT 06:451h 30mNonstopMDW 07:15Pittsburgh - Chicago | Thu, Apr 3 | Southwest AirlinesAED 18320% OFFAED 228 AED 183
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PIT 05:251h 51mNonstopORD 06:16Pittsburgh - Chicago | Tue, Apr 22 | American AirlinesAED 18619% OFFAED 228 AED 186
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PIT 16:151h 47mNonstopORD 17:02Pittsburgh - Chicago | Mon, May 12 | American AirlinesAED 18818% OFFAED 228 AED 188
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PIT 16:501h 47mNonstopORD 17:37Pittsburgh - Chicago | Mon, Apr 28 | American AirlinesAED 18818% OFFAED 228 AED 188
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PIT 11:488h 47m1 stopsMDW 19:35Pittsburgh - Chicago | Wed, Apr 2 | Frontier AirlinesAED 2089% OFFAED 228 AED 208
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PIT 13:0017h 25m1 stopsCHI Invalid DatePittsburgh - Chicago | Tue, Mar 18 | Normal AirlineFind More FlightsFind More Flights
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Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.
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Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Frequently Asked Questions
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When are flight tickets from Pittsburgh (PIT) to Chicago (CHI) the cheapest?
Airlines adjust prices for flights from Pittsburgh to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays. -
How much do flights from Pittsburgh (PIT) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around AED 1,137. -
How long does it take to fly from Pittsburgh (PIT) to Chicago (CHI)?
It takes about 5 hours 23 minutes to fly from Pittsburgh (PIT) to Chicago (CHI). -
What is the transportation method from the main airport to downtown in Chicago?
- The distance from O'Hare International Airport to downtown is about 25 km, by taxi about 40 minutes.
- The distance from Midway International Airport to downtown is about 14 km, by taxi about 30 minutes.
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What are the most popular airlines that fly from Pittsburgh (PIT) to Chicago (CHI)?
Airlines with flights from Pittsburgh (PIT) to Chicago (CHI): United Airlines, Gulf Air, Southwest Airlines, American Airlines, Qantas Airways and Qatar Airways. -
What's the most popular airline for non-stop flights from Pittsburgh (PIT) to Chicago (CHI)?
American Airlines operates 1 non-stop flights from Pittsburgh (PIT) to Chicago (CHI). -
How many airports are there in Chicago (CHI)?
There are 3 airport(s) near Chicago (CHI): Midway International Airport, O'Hare International Airport and Chicago Rockford International Airport.
How to find a cheap flight from Pittsburgh to Chicago
Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Pittsburgh to Chicago. Book your flights at the right time and save more.
Being flexible with your dates to get the cheapest Pittsburgh to Chicago ticket.
Tap "Date" on flight search bar to scan through the calender for Pittsburgh to Chicago airfare over next 6 months in 2025. If you would like to fly in next 3 months, it seems the cheapest date is on Wed, Apr 2 at AED 175 for one-way flights.
Compare cheap Pittsburgh to Chicago flight deals from over hundreds of airlines.
Our extensive search allows you to compare prices from over 500 airlines to choose the cheapest flight tickets from Pittsburgh to Chicago. The cheapest airline operating is American Airlines.
Set up a Price Alert
By setting up a Price Alert for your Pittsburgh to Chicago route, you can easily track the price of your airline tickets from without manually checking every day.
Don't miss cheap Pittsburgh to Chicago flight deals and promo codes.
You can always get the latest deals through Trip.com Deals and Promo Codes for cheap flights. If registering a free membership, you can receive more deals for your flights.
Book early or wait unitl the last minute.
It's always better to book early. Flight tickets tend to be the cheapest when they are first released, normally about a year before the departure date. So, check online as soon as the flights you want become available. If you miss the cheapest time, you can still find lower-priced tickets as the flight date approaches.
Search for flights on the go.
To get the best flight booking experience on the go, download Trip.com and search for cheap flight tickets from Pittsburgh to Chicago to get exclusive deals for you.
Flight Info | Pittsburgh to Chicago
Cheapest direct flight price | AED 175 |
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Cheapest return ticket price | AED 309 |
Off-season for travel | April |
Peak season for travel | December |
Flight distance | 660.47 km |
Average flight time | 5 hours 23 minutes |
Popular airline | American Airlines |
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