$69+ 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — CHI
Sep 30 — Oct 71
Round-trip
1 adult, Economy
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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 September or October, booked 83 days in advance, depart on a Friday or Thursday and return on a Thursday
Cheap flight deals from Pittsburgh to Chicago
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Cheapest flights from Pittsburgh to ChicagoExplore 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 August 31, 2026.
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 August 31, 2026.
This Southwest deal was found by Cheapflights users on 8/27. 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 10/106:20 am -
2 stops9h 30m
Sat 10/176:45 am -
2 stops8h 45m
Deal found 8/27![Southwest logo]()
$173
This CheapOair deal was found by Cheapflights users on 8/27. 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.
Thu 9/242:32 pm -
1 stop9h 27m
Mon 9/283:50 pm -
1 stop20h 57m
Deal found 8/27![Frontier logo]()
$173
This Southwest deal was found by Cheapflights users on 8/26. 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.
Fri 9/251:50 pm -
1 stop6h 40m
Mon 9/287:40 pm -
Nonstop1h 30m
Deal found 8/26![Southwest logo]()
$174
This Southwest deal was found by Cheapflights users on 8/26. 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.
Fri 10/24:20 pm -
2 stops8h 35m
Mon 10/57:45 am -
Nonstop1h 20m
Deal found 8/26![Southwest logo]()
$179
This Frontier deal was found by Cheapflights users on 8/27. 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 9/302:42 pm -
1 stop9h 17m
Sat 10/109:00 am -
1 stop9h 23m
Deal found 8/27![Frontier logo]()
$180
This Southwest deal was found by Cheapflights users on 8/26. 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 9/167:20 pm -
1 stop4h 05m
Thu 9/175:55 am -
1 stop5h 40m
Deal found 8/26![Southwest logo]()
$184
This Delta deal was found by Cheapflights users on 8/26. 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 9/255:40 pm -
1 stop7h 19m
Tue 9/295:30 am -
1 stop6h 01m
Deal found 8/26![Delta logo]()
$184
This CheapOair deal was found by Cheapflights users on 8/26. 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 9/152:42 pm -
1 stop9h 17m
Thu 9/173:50 pm -
1 stop20h 57m
Deal found 8/26![Frontier logo]()
$189
This Southwest deal was found by Cheapflights users on 8/28. 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.
Fri 9/257:30 pm -
Nonstop1h 20m
Fri 10/27:45 am -
Nonstop1h 20m
Deal found 8/28![Southwest logo]()
$191
This American Airlines deal was found by Cheapflights users on 8/28. 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.
Fri 9/258:47 pm -
Nonstop2h 00m
Fri 10/26:50 pm -
Nonstop1h 40m
Deal found 8/28![American Airlines logo]()
$191
This Southwest deal was found by Cheapflights users on 8/27. 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 9/266:10 am -
2 stops7h 55m
Sat 10/38:10 am -
2 stops7h 20m
Deal found 8/27![Southwest logo]()
$194
This KAYAK deal was found by Cheapflights users on 8/26. 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 10/132:11 pm -
Nonstop1h 44m
Thu 10/155:59 am -
Nonstop1h 39m
Deal found 8/26![United Airlines logo]()
$204
Best flights from Pittsburgh to ChicagoDiscover carefully curated flight deals from Pittsburgh to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 31, 2026.
Discover carefully curated flight deals from Pittsburgh to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 31, 2026.
This Southwest deal was found by Cheapflights users on 8/27. 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 10/76:30 am -
1 stop5h 25m
Fri 10/97:45 pm -
Nonstop1h 25m
Deal found 8/27![Southwest logo]()
$174
This Delta deal was found by Cheapflights users on 8/26. 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 11/65:59 pm -
1 stop5h 34m
Tue 11/109:30 am -
1 stop4h 39m
Deal found 8/26![Delta logo]()
$184
This KAYAK deal was found by Cheapflights users on 8/27. 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.
Thu 9/246:34 am -
Nonstop1h 55m
Thu 9/2412:37 pm -
Nonstop1h 36m
Deal found 8/27![American Airlines logo]()
$207
This United Airlines deal was found by Cheapflights users on 8/26. 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 9/305:11 am -
Nonstop1h 48m
Fri 10/25:59 am -
Nonstop1h 39m
Deal found 8/26![United Airlines logo]()
$234
This JetBlue deal was found by Cheapflights users on 8/27. 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.
Thu 11/1910:45 am -
1 stop5h 55m
Mon 11/234:30 pm -
1 stop5h 53m
Deal found 8/27![JetBlue logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 8/27. 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.
Thu 9/102:32 pm -
1 stop19h 20m
Sun 9/133:53 pm -
1 stop6h 00m
Deal found 8/27![Multiple Airlines logo]()
$330
This Delta deal was found by Cheapflights users on 8/27. 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.
Sat 10/105:45 pm -
1 stop3h 45m
Mon 10/127:30 pm -
1 stop3h 29m
Deal found 8/27![Delta logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 8/27. 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.
Fri 11/135:26 pm -
1 stop19h 28m
Sun 11/151:08 pm -
1 stop6h 59m
Deal found 8/27![Allegiant Air logo]()
$392
This Southwest deal was found by Cheapflights users on 8/27. 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 9/177:30 pm -
Nonstop1h 20m
Mon 9/217:40 pm -
Nonstop1h 30m
Deal found 8/27![Southwest logo]()
$210
This Southwest deal was found by Cheapflights users on 8/26. 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 9/2312:40 pm -
2 stops6h 45m
Wed 9/302:00 pm -
2 stops6h 35m
Deal found 8/26![Southwest logo]()
$240
This JetBlue deal was found by Cheapflights users on 8/26. 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.
Wed 9/307:00 am -
1 stop7h 45m
Fri 10/23:00 pm -
1 stop7h 20m
Deal found 8/26![JetBlue logo]()
$281
This Southwest deal was found by Cheapflights users on 8/27. 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 11/193:45 pm -
2 stops7h 55m
Mon 11/232:40 pm -
2 stops8h 15m
Deal found 8/27![Southwest logo]()
$240
This JetBlue deal was found by Cheapflights users on 8/28. 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 9/221:18 pm -
1 stop6h 43m
Sat 9/263:00 pm -
1 stop7h 20m
Deal found 8/28![JetBlue logo]()
$281
This Delta deal was found by Cheapflights users on 8/27. 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 11/510:32 am -
1 stop3h 27m
Sun 11/87:00 am -
1 stop3h 35m
Deal found 8/27![Delta logo]()
$286
This United Airlines deal was found by Cheapflights users on 8/26. 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 11/126:30 am -
Nonstop1h 53m
Sun 11/157:00 am -
1 stop6h 14m
Deal found 8/26![United Airlines logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 8/29. 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 10/62:42 pm -
1 stop19h 02m
Wed 10/1411:04 am -
1 stop21h 37m
Deal found 8/29![Multiple Airlines logo]()
$348
This JetBlue deal was found by Cheapflights users on 8/30. 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.
Fri 10/306:00 am -
1 stop8h 44m
Sun 11/11:00 pm -
1 stop5h 54m
Deal found 8/30![JetBlue logo]()
$295
This Delta deal was found by Cheapflights users on 8/27. 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.
Sat 10/1710:32 am -
1 stop3h 15m
Mon 10/191:27 pm -
1 stop4h 38m
Deal found 8/27![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 8/26. 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.
Fri 10/97:45 pm -
Nonstop1h 30m
Sun 10/118:00 am -
Nonstop1h 20m
Deal found 8/26![Southwest logo]()
$293
This United Airlines deal was found by Cheapflights users on 8/29. 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 10/136:00 pm -
Nonstop1h 49m
Sat 10/175:55 pm -
Nonstop1h 41m
Deal found 8/29![United Airlines logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 8/30. 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.
Thu 10/19:00 am -
1 stop6h 26m
Sun 10/45:47 pm -
1 stop20h 55m
Deal found 8/30![Allegiant Air logo]()
$398
This Kiwi.com deal was found by Cheapflights users on 8/30. 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.
Thu 10/19:00 am -
1 stop6h 26m
Sun 10/410:08 am -
2 stops31h 00m
Deal found 8/30![Multiple Airlines logo]()
$379
This Southwest deal was found by Cheapflights users on 8/27. 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.
Fri 1/1512:25 pm -
1 stop5h 00m
Mon 1/187:55 am -
2 stops7h 45m
Deal found 8/27![Southwest logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 8/30. 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.
Sun 9/137:30 am -
1 stop27h 02m
Thu 9/173:53 pm -
1 stop6h 00m
Deal found 8/30![Allegiant Air logo]()
$413
This United Airlines deal was found by Cheapflights users on 8/29. 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 10/77:46 pm -
Nonstop1h 51m
Sun 10/115:59 am -
Nonstop1h 39m
Deal found 8/29![United Airlines logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 8/29. 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.
Thu 10/87:51 pm -
1 stop13h 11m
Wed 10/1411:04 am -
1 stop21h 37m
Deal found 8/29![Multiple Airlines logo]()
$392
This Kiwi.com deal was found by Cheapflights users on 8/29. 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.
Thu 11/1212:10 pm -
1 stop21h 28m
Sun 11/151:08 pm -
1 stop6h 59m
Deal found 8/29![Allegiant Air logo]()
$421
This Kiwi.com deal was found by Cheapflights users on 8/30. 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.
Thu 9/242:32 pm -
1 stop19h 20m
Mon 9/284:50 pm -
1 stop19h 06m
Deal found 8/30![Multiple Airlines logo]()
$409
This Southwest deal was found by Cheapflights users on 8/29. 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.
Fri 10/97:45 pm -
Nonstop1h 30m
Sat 10/174:10 pm -
Nonstop1h 25m
Deal found 8/29![Southwest logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 8/29. 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.
Thu 10/87:51 pm -
1 stop13h 11m
Mon 10/126:13 pm -
1 stop17h 43m
Deal found 8/29![Multiple Airlines logo]()
$419
Last-minute flights from Pittsburgh to ChicagoDiscover last-minute flight deals from Pittsburgh to Chicago. Data last updated August 31, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Chicago. Data last updated August 31, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 8/26. 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 9/152:42 pm -
1 stop9h 17m
Thu 9/173:50 pm -
1 stop20h 57m
Deal found 8/26![Frontier logo]()
$189
This Southwest deal was found by Cheapflights users on 8/26. 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 9/167:20 pm -
1 stop4h 05m
Thu 9/175:55 am -
1 stop5h 40m
Deal found 8/26![Southwest logo]()
$184
This Southwest deal was found by Cheapflights users on 8/27. 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 9/177:30 pm -
Nonstop1h 20m
Mon 9/217:40 pm -
Nonstop1h 30m
Deal found 8/27![Southwest logo]()
$210
This Delta deal was found by Cheapflights users on 8/26. 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 9/187:45 pm -
1 stop5h 14m
Wed 9/236:00 am -
1 stop5h 10m
Deal found 8/26![Delta logo]()
$184
This American Airlines deal was found by Cheapflights users on 8/27. 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 9/226:34 am -
Nonstop1h 55m
Sat 9/268:50 am -
1 stop8h 11m
Deal found 8/27![American Airlines logo]()
$210
This CheapOair deal was found by Cheapflights users on 8/27. 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.
Thu 9/242:32 pm -
1 stop9h 27m
Mon 9/283:50 pm -
1 stop20h 57m
Deal found 8/27![Frontier logo]()
$173
This KAYAK deal was found by Cheapflights users on 8/27. 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.
Thu 9/246:34 am -
Nonstop1h 55m
Thu 9/2412:37 pm -
Nonstop1h 36m
Deal found 8/27![American Airlines logo]()
$207
This Southwest deal was found by Cheapflights users on 8/26. 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.
Fri 9/251:50 pm -
1 stop6h 40m
Mon 9/287:40 pm -
Nonstop1h 30m
Deal found 8/26![Southwest logo]()
$174
This Southwest deal was found by Cheapflights users on 8/28. 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.
Fri 9/257:30 pm -
Nonstop1h 20m
Fri 10/27:45 am -
Nonstop1h 20m
Deal found 8/28![Southwest logo]()
$191
This American Airlines deal was found by Cheapflights users on 8/28. 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.
Fri 9/258:47 pm -
Nonstop2h 00m
Fri 10/26:50 pm -
Nonstop1h 40m
Deal found 8/28![American Airlines logo]()
$191
This Southwest deal was found by Cheapflights users on 8/27. 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 9/266:10 am -
2 stops7h 55m
Sat 10/38:10 am -
2 stops7h 20m
Deal found 8/27![Southwest logo]()
$194
This Frontier deal was found by Cheapflights users on 8/27. 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 9/302:42 pm -
1 stop9h 17m
Sat 10/109:00 am -
1 stop9h 23m
Deal found 8/27![Frontier logo]()
$180
One-way flights from Pittsburgh to ChicagoSearch for one-way flight options from Pittsburgh to Chicago. Find affordable one-way fares based on user searches. Data last updated August 31, 2026.
Search for one-way flight options from Pittsburgh to Chicago. Find affordable one-way fares based on user searches. Data last updated August 31, 2026.
This Southwest deal was found by Cheapflights users on 8/27. 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 9/238:55 am -
Nonstop1h 20m
Deal found 8/27![Southwest logo]()
$69
This United Airlines deal was found by Cheapflights users on 8/27. 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 9/214:13 pm -
Nonstop1h 49m
Deal found 8/27![United Airlines logo]()
$69
This Frontier deal was found by Cheapflights users on 8/26. 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 10/108:18 pm -
1 stop12h 13m
Deal found 8/26![Frontier logo]()
$75
This Delta deal was found by Cheapflights users on 8/27. 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 9/2311:35 am -
1 stop7h 44m
Deal found 8/27![Delta logo]()
$79
This Delta deal was found by Cheapflights users on 8/27. 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.
Mon 10/265:45 pm -
1 stop3h 45m
Deal found 8/27![Delta logo]()
$79
This Southwest deal was found by Cheapflights users on 8/26. 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 9/266:10 am -
2 stops7h 55m
Deal found 8/26![Southwest logo]()
$84
This Priceline deal was found by Cheapflights users on 8/27. 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.
Mon 9/282:32 pm -
1 stop9h 27m
Deal found 8/27![Frontier logo]()
$86
This Frontier deal was found by Cheapflights users on 8/28. 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.
Fri 10/22:32 pm -
1 stop9h 27m
Deal found 8/28![Frontier logo]()
$87
This Southwest deal was found by Cheapflights users on 8/28. 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 9/211:50 pm -
2 stops9h 35m
Deal found 8/28![Southwest logo]()
$90
This Frontier deal was found by Cheapflights users on 8/28. 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 9/292:42 pm -
1 stop9h 17m
Deal found 8/28![Frontier logo]()
$90
This Frontier deal was found by Cheapflights users on 8/26. 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.
Thu 9/242:32 pm -
1 stop9h 27m
Deal found 8/26![Frontier logo]()
$94
This Southwest deal was found by Cheapflights users on 8/26. 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.
Fri 9/257:30 pm -
Nonstop1h 20m
Deal found 8/26![Southwest logo]()
$96
Find 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 August 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $173 (Southwest) |
One-way from | $69 (Southwest) |
Popular in | December |
Cheapest in | September |
Average price | $355 |
Good round-trip deal | $315 or less |
Good one-way deal | $197 or less |
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 7,457,451 searches. Data last updated August 31, 2026.
Use the filters below to find and compare flights from Pittsburgh to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Wed 10/7
6:30 am-10:55 am
1 stop5h 25m
Chicago Midway
Fri 10/9
7:45 pm-10:10 pm
Nonstop1h 25m
$174
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Fri 11/6
5:59 pm-10:33 pm
1 stop5h 34m
Chicago Midway
Tue 11/10
9:30 am-3:09 pm
1 stop4h 39m
$184
PittsburghChicago
PIT Pittsburgh - ORD Chicago O'Hare Intl
PITORD
Pittsburgh
Sat 10/10
5:45 pm-8:30 pm
1 stop3h 45m
Chicago O'Hare Intl
Mon 10/12
7:30 pm-11:59 pm
1 stop3h 29m
$184
PittsburghChicago
PIT Pittsburgh - ORD Chicago O'Hare Intl
PITORD
Pittsburgh
Thu 9/24
6:34 am-7:29 am
Nonstop1h 55m
Chicago O'Hare Intl
Thu 9/24
12:37 pm-3:13 pm
Nonstop1h 36m
$207
Quickest round-trip
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Thu 9/17
7:30 pm-7:50 pm
Nonstop1h 20m
Chicago Midway
Mon 9/21
7:40 pm-10:10 pm
Nonstop1h 30m
$210
PittsburghChicago
PIT Pittsburgh - ORD Chicago O'Hare Intl
PITORD
Pittsburgh
Wed 9/30
5:11 am-5:59 am
Nonstop1h 48m
Chicago O'Hare Intl
Fri 10/2
5:59 am-8:38 am
Nonstop1h 39m
$234
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Wed 9/23
12:40 pm-6:25 pm
2 stops6h 45m
Chicago Midway
Wed 9/30
2:00 pm-9:35 pm
2 stops6h 35m
$240
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Thu 11/19
3:45 pm-10:40 pm
2 stops7h 55m
Chicago Midway
Mon 11/23
2:40 pm-11:55 pm
2 stops8h 15m
$240
PittsburghChicago
PIT Pittsburgh - ORD Chicago O'Hare Intl
PITORD
Pittsburgh
Thu 11/19
10:45 am-3:40 pm
1 stop5h 55m
Chicago O'Hare Intl
Mon 11/23
4:30 pm-11:23 pm
1 stop5h 53m
$281
PittsburghChicago
PIT Pittsburgh - ORD Chicago O'Hare Intl
PITORD
Pittsburgh
Wed 9/30
7:00 am-1:45 pm
1 stop7h 45m
Chicago O'Hare Intl
Fri 10/2
3:00 pm-11:20 pm
1 stop7h 20m
$281
Showing 1-10 of 60 resultsSorted by cheapest first
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 August.
| 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 Pittsburgh-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Pittsburgh-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Pittsburgh-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Pittsburgh-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Pittsburgh-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Pittsburgh to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Pittsburgh with our price prediction graph.
PIT-CHI
PIT-MDW
PIT-ORD
PIT-RFD
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
PIT-CHI
PIT-MDW
PIT-ORD
PIT-RFD
What is the cheapest month to book a flight from Pittsburgh to Chicago?
Currently, October is the cheapest month in which you can book a flight from Pittsburgh to Chicago (average of $289). Flying from Pittsburgh to Chicago in July is currently the most expensive (average of $410). 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 August 31, 2026.
Unlike in the afternoon, when flights are generally more expensive, you can save up to 7% on flights from Pittsburgh to Chicago by exploring options for tickets in the evening.
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 August 31, 2026.
The most flights from PIT to CHI are scheduled on a Sunday (64 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (50 on average).
How much does it cost to fly round-trip from Pittsburgh to Chicago?
Airfare is below average for this route at the moment.
Pittsburgh to Chicago flights typically cost between $207 and $413 in October.The cheapest round-trip price found within the last 5 days was $173 on Southwest (Oct 10-Oct 17).
How often are flights from Pittsburgh to Chicago delayed?
About 11% of weekly flights between Pittsburgh and Chicago have experienced delays in the past year, with the average delay time being 128 minutes.
What is the most punctual flight time for Pittsburgh to Chicago 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?
Thursday 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 Pittsburgh to Chicago flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 7% of flights being delayed.
How far ahead should I book a flight from Pittsburgh to Chicago?
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 26 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
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 August 29, 2026.
Travelers seeking maximum savings on their Pittsburgh to Chicago flight should consider departing on Saturday at noon when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Pittsburgh to Chicago 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 Pittsburgh to Chicago trip
Our travel experts
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 August 31, 2026.
Read through reviews of airlines operating flights from Pittsburgh to Chicago, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Alternative routes for Pittsburgh to Chicago
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Other flights to Chicago
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Pittsburgh and Chicago flights
Browse other Pittsburgh and Chicago flight options. Last updated on August 31, 2026.
Other flights from Pittsburgh
Browse through other flights departing from Pittsburgh. Flights are based on user searches made on Cheapflights and were last updated on August 31, 2026.
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Consider these flights traveling from Pittsburgh to Chicago.
Top 3 airlines flying from Pittsburgh to Chicago
Discover the top 3 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 7,457,451 searches. Data last updated August 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$137 | Average$355 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$152 | Average$338 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$171 | Average$372 | FlexibilityNo cancel fee | On-time69% |