$104+ Cheap flights from Chicago (CHI) to Pittsburgh (PIT)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PIT
Oct 18 — Oct 251
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Pittsburgh 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 Chicago to Pittsburgh are usually found in September or November, booked 50 days in advance, depart on a Thursday or Friday and return on a Friday
Cheap flight deals from Chicago to Pittsburgh
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Cheapest flights from Chicago to PittsburghExplore the most affordable flight options available from Chicago to Pittsburgh. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 18, 2026.
Explore the most affordable flight options available from Chicago to Pittsburgh. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 18, 2026.
This Frontier deal was found by Cheapflights users on 9/17. 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.
Sat 12/55:35 am -
1 stop10h 58m
Mon 12/76:28 pm -
1 stop7h 33m
Deal found 9/17![Frontier logo]()
$244
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/208:46 am -
1 stop9h 10m
Wed 10/217:51 pm -
1 stop12h 40m
Deal found 9/14![Frontier logo]()
$245
This Southwest deal was found by Cheapflights users on 9/15. 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 10/141:00 pm -
Nonstop1h 20m
Wed 10/211:50 pm -
Nonstop1h 30m
Deal found 9/15![Southwest logo]()
$247
This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:15 am -
Nonstop1h 39m
Tue 10/137:46 pm -
Nonstop1h 51m
Deal found 9/14![United Airlines logo]()
$247
This Southwest deal was found by Cheapflights users on 9/13. 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 10/137:55 am -
Nonstop1h 20m
Tue 10/201:50 pm -
Nonstop1h 30m
Deal found 9/13![Southwest logo]()
$248
This Priceline deal was found by Cheapflights users on 9/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:51 am -
1 stop6h 41m
Sat 10/3112:47 pm -
1 stop7h 42m
Deal found 9/16![Multiple Airlines logo]()
$255
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:59 am -
1 stop5h 58m
Tue 10/208:37 pm -
Nonstop1h 53m
Deal found 9/15![American Airlines logo]()
$257
This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/138:46 am -
1 stop9h 10m
Tue 10/207:51 pm -
1 stop13h 00m
Deal found 9/15![Frontier logo]()
$261
This Southwest deal was found by Cheapflights users on 9/16. 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.
Sat 10/178:05 am -
Nonstop1h 20m
Mon 10/197:45 pm -
Nonstop1h 30m
Deal found 9/16![Southwest logo]()
$265
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Sat 10/106:40 pm -
Nonstop1h 36m
Mon 10/126:05 am -
Nonstop1h 54m
Deal found 9/16![American Airlines logo]()
$265
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/69:39 am -
1 stop6h 54m
Wed 10/72:42 pm -
1 stop9h 17m
Deal found 9/14![Multiple Airlines logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/138:04 am -
2 stops10h 22m
Tue 10/207:51 pm -
1 stop13h 00m
Deal found 9/15![Multiple Airlines logo]()
$267
Best flights from Chicago to PittsburghDiscover carefully curated flight deals from Chicago to Pittsburgh that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 18, 2026.
Discover carefully curated flight deals from Chicago to Pittsburgh that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 18, 2026.
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/283:45 pm -
Nonstop1h 34m
Sat 10/317:37 pm -
Nonstop1h 54m
Deal found 9/16![United Airlines logo]()
$247
This Southwest deal was found by Cheapflights users on 9/15. 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 11/116:10 pm -
Nonstop1h 35m
Mon 11/162:20 pm -
Nonstop1h 35m
Deal found 9/15![Southwest logo]()
$265
This Delta deal was found by Cheapflights users on 9/15. 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.
Wed 11/1110:30 am -
1 stop5h 36m
Mon 11/1610:24 am -
1 stop4h 35m
Deal found 9/15![Delta logo]()
$285
This JetBlue deal was found by Cheapflights users on 9/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/299:38 am -
1 stop6h 55m
Sat 10/37:00 am -
1 stop7h 45m
Deal found 9/16![JetBlue logo]()
$400
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/87:26 am -
Nonstop1h 39m
Wed 10/2110:56 am -
Nonstop1h 44m
Deal found 9/16![United Airlines logo]()
$265
This Southwest deal was found by Cheapflights users on 9/17. 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 10/179:55 am -
1 stop5h 35m
Mon 10/197:45 pm -
Nonstop1h 30m
Deal found 9/17![Southwest logo]()
$275
This Southwest deal was found by Cheapflights users on 9/15. 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.
Thu 11/127:50 am -
Nonstop1h 30m
Tue 11/176:30 pm -
1 stop4h 05m
Deal found 9/15![Southwest logo]()
$275
This Delta deal was found by Cheapflights users on 9/16. 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.
Fri 10/236:44 pm -
1 stop4h 15m
Tue 10/276:30 am -
1 stop6h 17m
Deal found 9/16![Delta logo]()
$303
This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/127:15 am -
Nonstop1h 39m
Mon 10/1910:56 am -
Nonstop1h 44m
Deal found 9/14![United Airlines logo]()
$283
This Southwest deal was found by Cheapflights users on 9/15. 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.
Mon 10/55:00 am -
1 stop5h 45m
Tue 10/66:50 pm -
Nonstop1h 30m
Deal found 9/15![Southwest logo]()
$275
This Delta deal was found by Cheapflights users on 9/18. 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.
Fri 10/167:30 pm -
1 stop3h 29m
Fri 10/233:18 pm -
1 stop7h 59m
Deal found 9/18![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 9/17. 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.
Thu 11/1212:45 pm -
2 stops5h 30m
Sat 11/144:35 pm -
Nonstop1h 30m
Deal found 9/17![Southwest logo]()
$280
This Delta deal was found by Cheapflights users on 9/16. 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.
Fri 10/237:00 am -
1 stop3h 35m
Fri 10/235:45 pm -
1 stop3h 45m
Deal found 9/16![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 9/13. 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.
Thu 10/225:00 am -
1 stop5h 45m
Sat 10/2410:30 am -
2 stops7h 55m
Deal found 9/13![Southwest logo]()
$291
This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/99:20 pm -
Nonstop1h 39m
Mon 10/126:00 pm -
Nonstop1h 49m
Deal found 9/14![United Airlines logo]()
$371
This Delta deal was found by Cheapflights users on 9/16. 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 11/56:44 pm -
1 stop3h 15m
Sun 11/86:00 am -
1 stop4h 32m
Deal found 9/16![Delta logo]()
$369
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:10 pm -
Nonstop1h 39m
Mon 11/168:00 pm -
1 stop5h 02m
Deal found 9/15![United Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 9/18. 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.
Fri 10/97:00 am -
1 stop3h 35m
Tue 10/138:00 am -
1 stop6h 08m
Deal found 9/18![Delta logo]()
$388
This Southwest deal was found by Cheapflights users on 9/13. 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.
Thu 10/81:20 pm -
Nonstop1h 20m
Wed 10/141:50 pm -
Nonstop1h 30m
Deal found 9/13![Southwest logo]()
$359
This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/62:16 pm -
Nonstop1h 39m
Sun 11/86:30 am -
Nonstop1h 53m
Deal found 9/14![United Airlines logo]()
$404
This Southwest deal was found by Cheapflights users on 9/15. 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 10/71:05 pm -
1 stop4h 30m
Sun 10/118:40 am -
Nonstop1h 30m
Deal found 9/15![Southwest logo]()
$368
Last-minute flights from Chicago to PittsburghDiscover last-minute flight deals from Chicago to Pittsburgh. Data last updated September 18, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Pittsburgh. Data last updated September 18, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/69:39 am -
1 stop6h 54m
Wed 10/72:42 pm -
1 stop9h 17m
Deal found 9/14![Multiple Airlines logo]()
$266
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:55 am -
Nonstop1h 20m
Wed 10/146:50 pm -
Nonstop1h 30m
Deal found 9/14![Southwest logo]()
$271
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Sat 10/106:40 pm -
Nonstop1h 36m
Mon 10/126:05 am -
Nonstop1h 54m
Deal found 9/16![American Airlines logo]()
$265
This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:15 am -
Nonstop1h 39m
Tue 10/137:46 pm -
Nonstop1h 51m
Deal found 9/14![United Airlines logo]()
$247
This Southwest deal was found by Cheapflights users on 9/13. 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 10/137:55 am -
Nonstop1h 20m
Tue 10/201:50 pm -
Nonstop1h 30m
Deal found 9/13![Southwest logo]()
$248
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:59 am -
1 stop5h 58m
Tue 10/208:37 pm -
Nonstop1h 53m
Deal found 9/15![American Airlines logo]()
$257
This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/138:46 am -
1 stop9h 10m
Tue 10/207:51 pm -
1 stop13h 00m
Deal found 9/15![Frontier logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/138:04 am -
2 stops10h 22m
Tue 10/207:51 pm -
1 stop13h 00m
Deal found 9/15![Multiple Airlines logo]()
$267
This Southwest deal was found by Cheapflights users on 9/15. 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 10/141:00 pm -
Nonstop1h 20m
Wed 10/211:50 pm -
Nonstop1h 30m
Deal found 9/15![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 9/16. 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.
Sat 10/178:05 am -
Nonstop1h 20m
Mon 10/197:45 pm -
Nonstop1h 30m
Deal found 9/16![Southwest logo]()
$265
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/208:46 am -
1 stop9h 10m
Wed 10/217:51 pm -
1 stop12h 40m
Deal found 9/14![Frontier logo]()
$245
This Priceline deal was found by Cheapflights users on 9/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:51 am -
1 stop6h 41m
Sat 10/3112:47 pm -
1 stop7h 42m
Deal found 9/16![Multiple Airlines logo]()
$255
One-way flights from Chicago to PittsburghSearch for one-way flight options from Chicago to Pittsburgh. Find affordable one-way fares based on user searches. Data last updated September 18, 2026.
Search for one-way flight options from Chicago to Pittsburgh. Find affordable one-way fares based on user searches. Data last updated September 18, 2026.
This Priceline deal was found by Cheapflights users on 9/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:51 am -
1 stop6h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$104
This CheapOair deal was found by Cheapflights users on 9/14. 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.
Tue 10/63:50 pm -
1 stop20h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Frontier logo]()
$116
This Frontier deal was found by Cheapflights users on 9/17. 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.
Wed 11/189:51 am -
1 stop6h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/138:04 am -
2 stops10h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$123
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:55 am -
Nonstop1h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$124
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Wed 10/72:13 pm -
Nonstop1h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![United Airlines logo]()
$124
This Frontier deal was found by Cheapflights users on 9/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/108:46 am -
1 stop9h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$125
This Expedia deal was found by Cheapflights users on 9/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:11 pm -
1 stop22h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$126
This Frontier deal was found by Cheapflights users on 9/17. 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.
Mon 12/145:35 am -
1 stop10h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$128
This Trip.com deal was found by Cheapflights users on 9/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/53:50 pm -
1 stop20h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$129
This Delta deal was found by Cheapflights users on 9/16. 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.
Wed 10/76:00 am -
1 stop7h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/168:00 am -
1 stop9h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$135
Find flight deals from Chicago to Pittsburgh
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Pittsburgh (PIT). 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 September 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $244 (Frontier) |
One-way from | $104 (Priceline) |
Popular in | February |
Cheapest in | September |
Average price | $261 |
Good round-trip deal | $242 or less |
Good one-way deal | $151 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Pittsburgh 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 7,457,451 searches. Data last updated September 18, 2026.
Use the filters below to find and compare flights from Chicago to Pittsburgh that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoPittsburgh
MDW Chicago Midway - PIT Pittsburgh
MDWPIT
Chicago Midway
Wed 10/7
7:55 am-10:15 am
Nonstop1h 20m
Pittsburgh
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$124
ChicagoPittsburgh
ORD Chicago O'Hare Intl - PIT Pittsburgh
ORDPIT
Chicago O'Hare Intl
Wed 10/7
2:13 pm-4:57 pm
Nonstop1h 44m
Pittsburgh
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$124
ChicagoPittsburgh
MDW Chicago Midway - PIT Pittsburgh
MDWPIT
Chicago Midway
Sat 10/17
8:05 am-10:25 am
Nonstop1h 20m
Pittsburgh
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$124
ChicagoPittsburgh
MDW Chicago Midway - PIT Pittsburgh
MDWPIT
Chicago Midway
Wed 11/18
6:44 pm-10:49 pm
1 stop3h 05m
Pittsburgh
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$134
ChicagoPittsburgh
ORD Chicago O'Hare Intl - PIT Pittsburgh
ORDPIT
Chicago O'Hare Intl
Wed 11/18
6:00 am-12:16 pm
1 stop5h 16m
Pittsburgh
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$134
ChicagoPittsburgh
ORD Chicago O'Hare Intl - PIT Pittsburgh
ORDPIT
Chicago O'Hare Intl
Wed 10/7
6:00 am-2:37 pm
1 stop7h 37m
Pittsburgh
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$134
ChicagoPittsburgh
ORD Chicago O'Hare Intl - PIT Pittsburgh
ORDPIT
Chicago O'Hare Intl
Tue 12/15
7:05 am-11:40 am
1 stop3h 35m
Pittsburgh
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$134
ChicagoPittsburgh
ORD Chicago O'Hare Intl - PIT Pittsburgh
ORDPIT
Chicago O'Hare Intl
Wed 10/14
5:29 pm-11:59 pm
1 stop5h 30m
Pittsburgh
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$134
ChicagoPittsburgh
ORD Chicago O'Hare Intl - PIT Pittsburgh
ORDPIT
Chicago O'Hare Intl
Sat 10/24
5:59 am-8:38 am
Nonstop1h 39m
Pittsburgh
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$139
ChicagoPittsburgh
MDW Chicago Midway - PIT Pittsburgh
MDWPIT
Chicago Midway
Mon 12/14
1:40 pm-4:05 pm
Nonstop1h 25m
Pittsburgh
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$142
Showing 1-10 of 40 resultsSorted by cheapest first
Compare providers for flights from Chicago to Pittsburgh
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 Chicago to Pittsburgh in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Pittsburgh flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Pittsburgh flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Pittsburgh flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Pittsburgh 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 Chicago-Pittsburgh 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 Chicago to Pittsburgh
Have a flexible travel schedule? Discover the best time to fly to Pittsburgh from Chicago with our price prediction graph.
CHI-PIT
MDW-PIT
ORD-PIT
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 Chicago to Pittsburgh
CHI-PIT
MDW-PIT
ORD-PIT
What is the cheapest month to book a flight from Chicago to Pittsburgh?
Currently, September is the cheapest month in which you can book a flight from Chicago to Pittsburgh (average of $261). Flying from Chicago to Pittsburgh in February is currently the most expensive (average of $466). 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 CHI to PIT?
Find hourly flight availability from Chicago to Pittsburgh. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 18, 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago to Pittsburgh in the evening. If you’re flexible enough to do this you can expect to save up to 19% on your trip compared to booking a flight in the afternoon.
Weekly flight availability from Chicago to Pittsburgh
Explore weekly flight availability from Chicago to Pittsburgh. 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 September 18, 2026.
The most flights from CHI to PIT are scheduled on a Wednesday (58 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (33 on average).
How much does it cost to fly round-trip from Chicago to Pittsburgh?
Airfare is typical for this route at the moment.
Chicago to Pittsburgh flights typically cost between $207 and $440 in December.The cheapest round-trip price found within the last 5 days was $244 on Frontier (Dec 5-Dec 7).
How often are flights from Chicago to Pittsburgh delayed?
About 15% of weekly flights between Chicago and Pittsburgh have experienced delays in the past year, with the average delay time being 101 minutes.
What is the most punctual flight time for Chicago to Pittsburgh flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Friday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Pittsburgh flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 14% of flights being delayed.
How far ahead should I book a flight from Chicago to Pittsburgh?
The best time to book flights from Chicago to Pittsburgh is 49 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest day to fly from Chicago to Pittsburgh?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Pittsburgh. Price data was last updated on September 12, 2026.
Travelers seeking maximum savings on their Chicago to Pittsburgh flight should consider departing on Thursday afternoons when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Chicago to Pittsburgh flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Pittsburgh trip
Our travel experts
Reviews of airlines servicing Pittsburgh
Get insights into the airlines that provide service to Pittsburgh. 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 Pittsburgh. Reviews last updated September 18, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican Airlines from Chicago to Pittsburgh. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago to Pittsburgh. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Pittsburgh?
Book flights to Pittsburgh if you plan to visit one of these locationsMonroeville
Washington
Chester
Mars
Wexford
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Chicago and Pittsburgh flights
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Other flights from Chicago
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Top 3 airlines flying from Chicago to Pittsburgh
Discover the top 3 airlines that operate flights from Chicago to Pittsburgh. 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 7,457,451 searches. Data last updated September 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$137 | Average$343 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$137 | Average$337 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$137 | Average$414 | FlexibilityNo cancel fee | On-time69% |