--- title: "Pittsburgh to Chicago cheap flights from $105 (PIT to CHI) - Expedia" description: "Book cheap Flights from Pittsburgh (PIT) to Chicago (CHI) start at $105 for one-way and $210 for round trip. Earn your airline miles on top of our rewards!" canonical: "https://www.expedia.com/lp/flights/pit/chi/pittsburgh-to-chicago" language: en-US market: US currency: USD prices_as_of: 2026-11-13T01:27:49Z --- # $105 Cheap Flights from Pittsburgh (PIT) to Chicago (CHI) ![A river with a yellow boat, surrounded by tall buildings and a bridge.](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) [View $105 flight on Sat, Dec 12, 2026](https://www.expedia.com/Flights-Search?leg1=from:PIT,to:ORD,departure:12/12/2026TANYT&trip=oneway&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:104.98&airProductToken=AQphCi8IxnISBDE2MTkYj5oBIMxwKIDRnwMwnNKfAzhFQABYAWoEUENfMXIHUjIxT1hQNAouCMZyEgQxMzQ5GMxwIK4cKI3TnwMwzNSfAzhFQAFYAWoEUENfMXIHUjIxT1hQNBIKCAEQARgBKgJGORgBIgQIARABKAIoAygEMA0) ## Popular airlines from Pittsburgh Intl. Airport (PIT) to Chicago [Delta](https://www.expedia.com/Flights-Search?leg1=from:PIT,to:CHI,departure:11/27/2026TANYT&leg2=from:CHI,to:PIT,departure:12/4/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) [American Airlines](https://www.expedia.com/Flights-Search?leg1=from:PIT,to:CHI,departure:11/27/2026TANYT&leg2=from:CHI,to:PIT,departure:12/4/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) [United](https://www.expedia.com/Flights-Search?leg1=from:PIT,to:CHI,departure:11/27/2026TANYT&leg2=from:CHI,to:PIT,departure:12/4/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) [Frontier Airlines](https://www.expedia.com/Flights-Search?leg1=from:PIT,to:CHI,departure:11/27/2026TANYT&leg2=from:CHI,to:PIT,departure:12/4/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) [JetBlue Airways](https://www.expedia.com/Flights-Search?leg1=from:PIT,to:CHI,departure:11/27/2026TANYT&leg2=from:CHI,to:PIT,departure:12/4/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) [Southwest Airlines](https://www.expedia.com/Flights-Search?leg1=from:PIT,to:CHI,departure:11/27/2026TANYT&leg2=from:CHI,to:PIT,departure:12/4/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) [Alaska Airlines](https://www.expedia.com/Flights-Search?leg1=from:PIT,to:CHI,departure:11/27/2026TANYT&leg2=from:CHI,to:PIT,departure:12/4/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) ### Be in the know Get alerts if flight prices drop or rise\* ### Book smarter Save up to 30% on select hotels after you book a flight\* ### Earn twice Earn your airline miles on top of our OneKeyCash [Learn about One Key](https://www.expedia.com/welcome-one-key) ## Cheap Flights from Pittsburgh to Chicago (PIT-CHI) Prices were available within the past 7 days and start at $105 for one-way flights and $210 for roundtrip, for the period specified. Prices and availability are subject to change. All deals One way Roundtrip [Select Frontier Airlines flight, departing Sat, Dec 12 from Pittsburgh to Chicago, returning Sat, Jan 9, priced at $210 Found 1 hour ago](https://www.expedia.com/Flights-Search?leg1=from:PIT,to:ORD,departure:12/12/2026TANYT&leg2=from:ORD,to:PIT,departure:1/9/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:209.96&airProductToken=AQphCi8IxnISBDE2MTkYj5oBIMxwKIDRnwMwnNKfAzhFQABYAWoEUENfMXIHUjIxT1hQNAouCMZyEgQxMzQ5GMxwIK4cKI3TnwMwzNSfAzhFQAFYAWoEUENfMXIHUjIxT1hQNAphCi4IxnISBDEzNTAYrhwgzHAokYyiAzDGjaIDOEVAAFgBagRQQ18xcgdSMjFPWFA0Ci8IxnISBDE2MjAYzHAgj5oBKLOTogMwzZSiAzhFQAFYAWoEUENfMXIHUjIxT1hQNBIKCAEQARgBKgJGORgBIgQIARABKAIoAygEMA0) Sat, Dec 12 - Sat, Jan 9 · PIT · ORD · Roundtrip [Select Frontier Airlines flight, departing Tue, Feb 2 from Pittsburgh to Chicago, returning Wed, Feb 10, priced at $220 Just found](https://www.expedia.com/Flights-Search?leg1=from:PIT,to:ORD,departure:2/2/2027TANYT&leg2=from:ORD,to:PIT,departure:2/10/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:219.97&airProductToken=AQpfCi4IxnISBDM4MTkYj5oBIMxwKOSXpAMw%5FpikAzhSQABYAWoDRUNPcgdSMjFPWFA0Ci0IxnISBDEzNDkYzHAgrhwo35ukAzCknaQDOFJAAVgBagNFQ09yB1IyMU9YUDQKXwotCMZyEgQxOTAxGK4cIMxwKJXupAMwwe-kAzhSQABYAWoDRUNPcgdSMjFPWFA0Ci4IxnISBDM4MjAYzHAgj5oBKJPwpAMwsvGkAzhSQAFYAWoDRUNPcgdSMjFPWFA0EgoIARABGAEqAkY5GAEiBAgBEAEoAigDKAQwAQ) Tue, Feb 2 - Wed, Feb 10 · PIT · Pittsbur · gh · ORD · Roundtrip [Select Frontier Airlines flight, departing Sat, Dec 12 from Pittsburgh to Chicago, returning Sat, Jan 9, priced at $230 Found 1 hour ago](https://www.expedia.com/Flights-Search?leg1=from:PIT,to:ORD,departure:12/12/2026TANYT&leg2=from:ORD,to:PIT,departure:1/9/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:229.96&airProductToken=AQphCi8IxnISBDE2MTkYj5oBIMxwKIDRnwMwnNKfAzhFQABYAWoEUENfMXIHUjIxT1hQNAouCMZyEgQxMzQ5GMxwIK4cKI3TnwMwzNSfAzhFQAFYAWoEUENfMXIHUjIxT1hQNAphCi4IxnISBDE5MDEYrhwgzHAolYaiAzDDh6IDOEVAAFgBagRQQ18xcgdHMTRPWFA0Ci8IxnISBDE2MjAYzHAgj5oBKJOIogMwrYmiAzhFQAFYAWoEUENfMXIHRzE0T1hQNBIKCAEQARgBKgJGORgBIgQIARABKAIoAygEMA0) Sat, Dec 12 - Sat, Jan 9 · PIT · ORD · Roundtrip [Select Frontier Airlines flight, departing Mon, Jan 4 from Pittsburgh to Chicago, returning Sat, Jan 9, priced at $240 Found 4 hours ago](https://www.expedia.com/Flights-Search?leg1=from:PIT,to:ORD,departure:1/4/2027TANYT&leg2=from:ORD,to:PIT,departure:1/9/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:239.96&airProductToken=AQphCi8IxnISBDE2MTkYj5oBIMxwKM%5FToQMw69ShAzhFQABYAWoEUENfMXIHRzIxVlhQMgouCMZyEgQxMzQ5GMxwIK4cKO3VoQMwrNehAzhFQAFYAWoEUENfMXIHRzIxVlhQMgphCi4IxnISBDEzNTAYrhwgzHAokYyiAzDGjaIDOEVAAFgBagRQQ18xcgdSMjFPWFA0Ci8IxnISBDE2MjAYzHAgj5oBKLOTogMwzZSiAzhFQAFYAWoEUENfMXIHUjIxT1hQNBIKCAEQARgBKgJGORgBIgQIARABKAIoAygEMA0) Mon, Jan 4 - Sat, Jan 9 · PIT · ORD · Roundtrip [Select Frontier Airlines flight, departing Mon, Jan 4 from Pittsburgh to Chicago, returning Tue, Jan 5, priced at $245 Found 1 day ago](https://www.expedia.com/Flights-Search?leg1=from:PIT,to:ORD,departure:1/4/2027TANYT&leg2=from:ORD,to:PIT,departure:1/5/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:244.37&airProductToken=AQpfCi4IxnISBDE2MTkYj5oBIMxwKM%5FToQMw69ShAzhHQABYAWoDRUNPcgdHMjFWWFAyCi0IxnISBDEzNDkYzHAgrhwo7dWhAzCs16EDOEdAAVgBagNFQ09yB0cyMVZYUDIKXwotCMZyEgQxOTAxGK4cIMxwKJXZoQMww9qhAzhSQABYAWoDRUNPcgdSMjFPWFA0Ci4IxnISBDE2MjAYzHAgj5oBKJPboQMwrdyhAzhSQAFYAWoDRUNPcgdSMjFPWFA0EgoIARABGAEqAkY5GAEiBAgBEAEoAigDKAQwAQ) Mon, Jan 4 - Tue, Jan 5 · PIT · ORD · Roundtrip [Select Frontier Airlines flight, departing Fri, Jan 15 from Pittsburgh to Chicago, returning Wed, Jan 20, priced at $245 Found 6 hours ago](https://www.expedia.com/Flights-Search?leg1=from:PIT,to:ORD,departure:1/15/2027TANYT&leg2=from:ORD,to:PIT,departure:1/20/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:244.96&airProductToken=AQphCi8IxnISBDE2MTkYj5oBIMxwKKTPogMwv9CiAzhFQABYAWoEUENfMXIHRzIxR1hQMgouCMZyEgQxMzQ5GMxwIK4cKKHRogMw5tKiAzhFQAFYAWoEUENfMXIHRzIxR1hQMgphCi4IxnISBDEzNTAYrhwgzHAo0oejAzCIiaMDOEVAAFgBagRQQ18xcgdSMjFPWFA0Ci8IxnISBDM4MjAYzHAgj5oBKJOPowMwspCjAzhFQAFYAWoEUENfMXIHUjIxT1hQNBIKCAEQARgBKgJGORgBIgQIARABKAIoAygEMA0) Fri, Jan 15 - Wed, Jan 20 · PIT · ORD · Roundtrip [Select United flight, departing Tue, Feb 2 from Pittsburgh to Chicago, returning Wed, Feb 10, priced at $260 Just found](https://www.expedia.com/Flights-Search?leg1=from:PIT,to:ORD,departure:2/2/2027TANYT&leg2=from:ORD,to:PIT,departure:2/10/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:259.38&airProductToken=AQo5CjcI1YIBEgQzNTkxGI-aASCuHCi0mqQDMK2bpAM4TkAAWAFqCjFfYmFzaWNlY29yCFRBSzJBS0JTEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwCw) Tue, Feb 2 - Wed, Feb 10 · PIT · ORD · Roundtrip [Select JetBlue Airways flight, departing Mon, Feb 8 from Pittsburgh to Chicago, returning Tue, Feb 16, priced at $266 Just found](https://www.expedia.com/Flights-Search?leg1=from:PIT,to:ORD,departure:2/8/2027TANYT&leg2=from:ORD,to:PIT,departure:2/16/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:265.79&airProductToken=AQpgCi8IwmwSBDIxODYYj5oBIMGTASiu2KQDMJjZpAM4TEAAWAFqAkROcghQQzJBVUVZMQotCMJsEgM4MTEYwZMBIK4cKK3apAMw5dukAzhMQAFYAWoCRE5yCFBDMkFVRVkxEgoIARABGAEqAkI2GAEiBAgBEAEoAigDKAQwAQ) Mon, Feb 8 - Tue, Feb 16 · PIT · ORD · Roundtrip [Select Delta flight, departing Tue, Feb 2 from Pittsburgh to Chicago, returning Wed, Feb 10, priced at $275 Just found](https://www.expedia.com/Flights-Search?leg1=from:PIT,to:ORD,departure:2/2/2027TANYT&leg2=from:ORD,to:PIT,departure:2/10/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:274.18&airProductToken=AQpvCjYIxJgBEgQ1MDg2GI-aASCpUSiOl6QDMO-XpAM4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU0gzQkMKNQjEmAESBDQ5MTUYqVEgrhwoxpikAzD3maQDOEVAAVgBaglNQUlOQkFTSUNyCFZBVlNIM0JDEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) Tue, Feb 2 - Wed, Feb 10 · PIT · ORD · Roundtrip [Select Southwest Airlines flight, departing Sat, Dec 5 from Pittsburgh to Chicago, returning Wed, Dec 9, priced at $309 Found 2 hours ago](https://www.expedia.com/Flights-Search?leg1=from:PIT,to:MDW,departure:12/5/2026TANYT&leg2=from:MDW,to:PIT,departure:12/9/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:308.80&airProductToken=AQoyCjAI15wBEgQyMzEzGI-aASDssAEo2f2eAzCz%5Fp4DOEFAAFgBagNXR0FyB0FETlZOMkUKMgowCNecARIEMzY0MxjssAEgj5oBKPeqnwMwzKufAzhBQABYAWoDV0dBcgdBRE5WTjJFEgoIARABGAEqAldOGAEiBAgBEAEoAigDKAQwAQ) Sat, Dec 5 - Wed, Dec 9 · PIT · MDW · Roundtrip ## Alternative airports near Chicago Prices were available within the past 7 days. Prices and availability are subject to change. [Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $529](https://www.expedia.com/Flights-Search?leg1=from:PIT,to:ORD,departure:11/27/2026TANYT&leg2=from:ORD,to:PIT,departure:11/29/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) 23 min [Select flight to Midway Intl. MDW. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $529](https://www.expedia.com/Flights-Search?leg1=from:PIT,to:MDW,departure:11/27/2026TANYT&leg2=from:MDW,to:PIT,departure:11/29/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) 16 min ## Book with confidence ### Pittsburgh to Chicago Flights #### The cheapest times to fly from Pittsburgh to Chicago On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Pittsburgh to Chicago are during the month of December. You can find some of the cheapest flights from Pittsburgh to Chicago with Expedia's search tool and vast selection of airlines. #### The best time to book a flight from Pittsburgh to Chicago Sunday is one of the best days to book for cheap flights from Pittsburgh to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance. #### How to find cheap round-trip tickets from Pittsburgh to Chicago Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Pittsburgh to Chicago in 2026\. You can also book with separate airlines for your outbound and return journeys, from $105 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference\*. This is available for a small fee, and is free to One Key Gold and Platinum tier members. Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Pittsburgh to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps. You could also save big by booking one of Expedia's [vacation packages](https://www.expedia.com/package-deals). Bundling together your Pittsburgh to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures. *\*Terms apply.* *Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023\. The percentages you see are averages.* ## Travel information | Origin airport | Pittsburgh Intl. Airport | | ------------------- | -------------------------------------------- | | Destination airport | Chicago Midway Airport | | Distance | 399 miles away | | Airlines serving | Southwest Airlines, Delta, Frontier Airlines | | Popular airline | Southwest Airlines | | Roundtrip price | $210 | | Average flight time | 1 hour 31 mins | ## Explore a world of travel with Expedia - [Flights](?equalTargetTab=tab-0) - [Flights from Houston (IAH) to Chicago (CHI)](https://www.expedia.com/lp/flights/iah/chi/houston-to-chicago) - [Flights from Richmond (RIC) to Chicago (ORD)](https://www.expedia.com/lp/flights/ric/ord/richmond-to-chicago) - [Flights from Los Angeles (LAX) to Chicago (CHI)](https://www.expedia.com/lp/flights/lax/chi/los-angeles-to-chicago) - [Flights from Las Vegas (LAS) to Chicago (ORD)](https://www.expedia.com/lp/flights/las/ord/las-vegas-to-chicago) - [Flights from Hartford (BDL) to Chicago (CHI)](https://www.expedia.com/lp/flights/bdl/chi/hartford-to-chicago) - [Flights from Denver (DEN) to Chicago (CHI)](https://www.expedia.com/lp/flights/den/chi/denver-to-chicago) - 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[Flights from Newark Liberty Intl. Airport (EWR) to Chicago (CHI)](https://www.expedia.com/lp/flights/ewr/chi/newark-liberty-intl-airport-to-chicago) - [Flights from Phoenix (PHX) to Chicago (CHI)](https://www.expedia.com/lp/flights/phx/chi/phoenix-to-chicago) - [Flights from Seattle (SEA) to Chicago (CHI)](https://www.expedia.com/lp/flights/sea/chi/seattle-to-chicago) - [Flights from New York (JFK) to Chicago (ORD)](https://www.expedia.com/lp/flights/jfk/ord/new-york-to-chicago) \*Available to One Key members. ## Other language versions ```yaml hreflang: x-default: https://www.expedia.com/lp/flights/pit/chi/pittsburgh-to-chicago en-IN: https://www.expedia.co.in/lp/flights/pit/chi/pittsburgh-to-chicago en-US: https://www.expedia.com/lp/flights/pit/chi/pittsburgh-to-chicago en-TW: https://www.expedia.com.tw/en/lp/flights/pit/chi/pittsburgh-to-chicago en-CA: https://www.expedia.ca/lp/flights/pit/chi/pittsburgh-to-chicago ar: https://www.expedia.sa/lp/flights/pit/chi/pittsburgh-to-chicago zh-CN: https://www.expedia.com/cn/lp/flights/pit/chi/pittsburgh-to-chicago es-MX: https://www.expedia.mx/lp/vuelos/pit/chi/pittsburgh-a-todos-los-aeropuertos-de-chicago fr-CA: https://www.expedia.ca/fr/lp/vols/pit/chi/pittsburgh-a-chicago en-SG: https://www.expedia.com.sg/lp/flights/pit/chi/pittsburgh-to-chicago id-ID: https://www.expedia.co.id/lp/flights/pit/chi/pittsburgh-to-semua-bandara-chicago en-GB: https://www.expedia.co.uk/lp/flights/pit/chi/pittsburgh-to-chicago ko-KR: https://www.expedia.co.kr/lp/flights/pit/chi/pittsburgh-to-chicago es: https://www.expedia.com/es/lp/vuelos/pit/chi/pittsburgh-a-todos-los-aeropuertos-de-chicago ```