$110+ Cheap flights from Pittsburgh (PIT) to Chicago (CHI)
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 11/21. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — CHI
Nov 18 — Nov 251
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 April or February, booked 82 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 October 19, 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 October 19, 2026.
This Priceline deal was found by Cheapflights users on 10/14. 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.
Fri 12/116:28 pm -
1 stop7h 33m
Mon 12/145:35 am -
1 stop10h 58m
Deal found 10/14![Frontier logo]()
$238
This Trip.com deal was found by Cheapflights users on 10/16. 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.
Sat 11/216:59 pm -
1 stop25h 48m
Tue 11/248:42 pm -
1 stop20h 22m
Deal found 10/16![Frontier logo]()
$248
This Frontier deal was found by Cheapflights users on 10/14. 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.
Sat 12/126:28 pm -
1 stop7h 40m
Sat 1/95:01 am -
1 stop11h 13m
Deal found 10/14![Frontier logo]()
$248
This Frontier deal was found by Cheapflights users on 10/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:59 pm -
1 stop6h 44m
Tue 11/245:40 am -
1 stop11h 24m
Deal found 10/16![Frontier logo]()
$249
This Frontier deal was found by Cheapflights users on 10/17. 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 12/56:28 pm -
1 stop7h 40m
Mon 12/75:35 am -
1 stop10h 58m
Deal found 10/17![Frontier logo]()
$259
This Southwest deal was found by Cheapflights users on 10/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:25 pm -
Nonstop1h 30m
Mon 12/78:15 am -
Nonstop1h 25m
Deal found 10/18![Southwest logo]()
$260
This Priceline deal was found by Cheapflights users on 10/16. 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 11/106:00 am -
1 stop8h 42m
Wed 11/119:51 am -
1 stop6h 41m
Deal found 10/16![Multiple Airlines logo]()
$261
This CheapOair deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1612:10 pm -
1 stop5h 32m
Tue 1/55:01 am -
1 stop6h 48m
Deal found 10/16![Multiple Airlines logo]()
$266
This Priceline deal was found by Cheapflights users on 10/16. 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.
Fri 12/116:28 pm -
1 stop7h 40m
Sun 1/105:01 am -
1 stop6h 48m
Deal found 10/16![Frontier logo]()
$269
This Priceline deal was found by Cheapflights users on 10/14. 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.
Wed 11/116:00 am -
1 stop8h 42m
Wed 11/189:51 am -
1 stop6h 41m
Deal found 10/14![Multiple Airlines logo]()
$270
This Trip.com deal was found by Cheapflights users on 10/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:28 pm -
1 stop27h 20m
Sun 12/69:37 pm -
1 stop18h 56m
Deal found 10/14![Frontier logo]()
$275
This Priceline deal was found by Cheapflights users on 10/16. 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.
Wed 12/212:10 pm -
1 stop5h 32m
Mon 12/75:35 am -
1 stop10h 58m
Deal found 10/16![Multiple Airlines logo]()
$275
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 October 19, 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 October 19, 2026.
This Southwest deal was found by Cheapflights users on 10/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/33:45 pm -
2 stops8h 00m
Thu 12/109:40 am -
2 stops7h 15m
Deal found 10/18![Southwest logo]()
$291
This Delta deal was found by Cheapflights users on 10/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:25 am -
1 stop6h 34m
Tue 12/89:37 am -
1 stop4h 36m
Deal found 10/14![Delta logo]()
$297
This United Airlines deal was found by Cheapflights users on 10/15. 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 12/26:27 am -
Nonstop1h 53m
Sat 12/56:10 pm -
Nonstop1h 39m
Deal found 10/15![United Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 10/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/43:55 pm -
1 stop4h 50m
Tue 12/82:39 pm -
1 stop4h 46m
Deal found 10/14![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 10/14. 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.
Fri 12/118:50 pm -
1 stop4h 15m
Mon 12/1411:30 am -
2 stops8h 30m
Deal found 10/14![Southwest logo]()
$302
This United Airlines deal was found by Cheapflights users on 10/16. 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 1/67:20 pm -
Nonstop2h 01m
Sat 1/96:15 pm -
Nonstop1h 45m
Deal found 10/16![United Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 10/16. 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.
Fri 1/156:45 pm -
Nonstop1h 30m
Mon 1/188:00 am -
Nonstop1h 30m
Deal found 10/16![Southwest logo]()
$317
This Delta deal was found by Cheapflights users on 10/15. 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.
Sat 11/2110:20 am -
1 stop3h 31m
Sun 11/226:44 pm -
1 stop3h 05m
Deal found 10/15![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 10/15. 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.
Sat 11/213:55 pm -
1 stop5h 15m
Sun 11/226:30 am -
1 stop5h 20m
Deal found 10/15![Southwest logo]()
$317
This United Airlines deal was found by Cheapflights users on 10/14. 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 11/66:30 am -
Nonstop1h 53m
Fri 11/69:30 pm -
Nonstop1h 29m
Deal found 10/14![United Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 10/15. 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.
Fri 11/610:32 am -
1 stop3h 15m
Tue 11/109:30 am -
1 stop4h 39m
Deal found 10/15![Delta logo]()
$337
This United Airlines deal was found by Cheapflights users on 10/14. 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 12/116:00 pm -
Nonstop1h 48m
Tue 12/159:28 pm -
Nonstop1h 31m
Deal found 10/14![United Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 10/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:25 am -
1 stop6h 34m
Sun 12/69:37 am -
1 stop4h 36m
Deal found 10/14![Delta logo]()
$337
This Southwest deal was found by Cheapflights users on 10/15. 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 12/37:25 pm -
Nonstop1h 30m
Sun 12/67:50 am -
Nonstop1h 30m
Deal found 10/15![Southwest logo]()
$347
This United Airlines deal was found by Cheapflights users on 10/14. 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.
Thu 3/112:10 pm -
Nonstop1h 40m
Sun 3/146:55 am -
Nonstop1h 38m
Deal found 10/14![United Airlines logo]()
$404
This United Airlines deal was found by Cheapflights users on 10/17. 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.
Mon 2/11:54 pm -
Nonstop2h 01m
Tue 3/1610:25 am -
Nonstop1h 41m
Deal found 10/17![United Airlines logo]()
$413
This Southwest deal was found by Cheapflights users on 10/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2212:30 pm -
1 stop4h 30m
Wed 11/257:30 pm -
Nonstop1h 30m
Deal found 10/18![Southwest logo]()
$414
This Delta deal was found by Cheapflights users on 10/18. 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.
Tue 12/158:15 am -
1 stop5h 54m
Sat 1/162:30 pm -
1 stop5h 56m
Deal found 10/18![Delta logo]()
$433
This United Airlines deal was found by Cheapflights users on 10/17. 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.
Sat 1/28:45 am -
Nonstop2h 00m
Mon 1/46:10 pm -
1 stop4h 20m
Deal found 10/17![United Airlines logo]()
$423
This Delta deal was found by Cheapflights users on 10/18. 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.
Tue 12/151:00 pm -
1 stop5h 04m
Mon 1/1810:35 am -
1 stop6h 09m
Deal found 10/18![Delta logo]()
$433
This United Airlines deal was found by Cheapflights users on 10/17. 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.
Fri 11/202:07 pm -
Nonstop1h 48m
Mon 11/236:00 am -
1 stop5h 16m
Deal found 10/17![United Airlines logo]()
$423
Last-minute flights from Pittsburgh to ChicagoDiscover last-minute flight deals from Pittsburgh to Chicago. Data last updated October 19, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Chicago. Data last updated October 19, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 10/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:18 pm -
1 stop12h 13m
Mon 10/268:36 am -
1 stop9h 20m
Deal found 10/15![Frontier logo]()
$350
This Frontier deal was found by Cheapflights users on 10/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:51 pm -
1 stop12h 40m
Tue 10/279:51 am -
1 stop6h 41m
Deal found 10/16![Frontier logo]()
$340
This CheapOair deal was found by Cheapflights users on 10/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:27 pm -
1 stop15h 19m
Tue 11/39:51 am -
1 stop6h 41m
Deal found 10/15![Frontier logo]()
$310
This Super.com deal was found by Cheapflights users on 10/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:27 pm -
1 stop15h 19m
Mon 11/29:51 am -
1 stop6h 41m
Deal found 10/15![Frontier logo]()
$345
This Priceline deal was found by Cheapflights users on 10/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:00 am -
1 stop8h 44m
Mon 11/29:51 am -
1 stop6h 41m
Deal found 10/15![Multiple Airlines logo]()
$351
This Southwest deal was found by Cheapflights users on 10/14. 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.
Thu 11/57:55 pm -
Nonstop1h 30m
Mon 11/96:50 pm -
Nonstop1h 30m
Deal found 10/14![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 10/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/610:32 am -
1 stop3h 15m
Tue 11/109:30 am -
1 stop4h 39m
Deal found 10/14![Delta logo]()
$318
This Southwest deal was found by Cheapflights users on 10/14. 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.
Sat 11/75:35 am -
2 stops12h 30m
Mon 11/96:10 pm -
1 stop4h 45m
Deal found 10/14![Southwest logo]()
$308
This Southwest deal was found by Cheapflights users on 10/14. 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 11/117:25 pm -
Nonstop1h 30m
Wed 11/1811:30 am -
2 stops8h 35m
Deal found 10/14![Southwest logo]()
$292
This Trip.com deal was found by Cheapflights users on 10/16. 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.
Sat 11/216:59 pm -
1 stop25h 48m
Tue 11/248:42 pm -
1 stop20h 22m
Deal found 10/16![Frontier logo]()
$248
This Southwest deal was found by Cheapflights users on 10/15. 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.
Sat 11/218:25 pm -
Nonstop1h 30m
Sun 11/227:40 am -
Nonstop1h 30m
Deal found 10/15![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 10/15. 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.
Sat 11/2110:20 am -
1 stop3h 31m
Sun 11/226:44 pm -
1 stop3h 05m
Deal found 10/15![Delta logo]()
$317
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 October 19, 2026.
Search for one-way flight options from Pittsburgh to Chicago. Find affordable one-way fares based on user searches. Data last updated October 19, 2026.
This Frontier deal was found by Cheapflights users on 10/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:59 pm -
1 stop6h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$110
This Frontier deal was found by Cheapflights users on 10/18. 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.
Tue 1/51:44 pm -
1 stop12h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Frontier logo]()
$116
This Super.com deal was found by Cheapflights users on 10/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:28 pm -
1 stop7h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Frontier logo]()
$117
This Trip.com deal was found by Cheapflights users on 10/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:27 pm -
1 stop23h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Frontier logo]()
$124
This Expedia deal was found by Cheapflights users on 10/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:28 pm -
1 stop27h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Frontier logo]()
$125
This Orbitz deal was found by Cheapflights users on 10/14. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:59 pm -
1 stop6h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Frontier logo]()
$129
This Southwest deal was found by Cheapflights users on 10/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:25 pm -
Nonstop1h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Southwest logo]()
$130
This CheapOair deal was found by Cheapflights users on 10/14. 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.
Wed 11/116:27 pm -
1 stop15h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 10/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/159:00 am -
2 stops34h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Multiple Airlines logo]()
$133
This Expedia deal was found by Cheapflights users on 10/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:59 pm -
1 stop25h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Frontier logo]()
$135
This Orbitz deal was found by Cheapflights users on 10/15. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/66:09 pm -
1 stop7h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Frontier logo]()
$135
This Southwest deal was found by Cheapflights users on 10/14. 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.
Thu 12/102:20 pm -
Nonstop1h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Southwest logo]()
$139
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 October 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $238 (Priceline) |
One-way from | $110 (Frontier) |
Popular in | October |
Cheapest in | April |
Average price | $396 |
Good round-trip deal | $346 or less |
Good one-way deal | $154 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 October 19, 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
Quickest round-trip
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Tue 12/1
7:25 pm-7:55 pm
Nonstop1h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Tue 11/17
6:35 am-11:50 am
1 stop6h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Fri 12/18
3:10 pm-3:40 pm
Nonstop1h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
PittsburghChicago
PIT Pittsburgh - ORD Chicago O'Hare Intl
PITORD
Pittsburgh
Sat 1/16
6:00 am-8:58 am
1 stop3h 58m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
PittsburghChicago
PIT Pittsburgh - ORD Chicago O'Hare Intl
PITORD
Pittsburgh
Fri 12/11
11:17 am-4:43 pm
1 stop6h 26m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
PittsburghChicago
PIT Pittsburgh - ORD Chicago O'Hare Intl
PITORD
Pittsburgh
Tue 12/15
11:17 am-2:53 pm
1 stop4h 36m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
PittsburghChicago
PIT Pittsburgh - ORD Chicago O'Hare Intl
PITORD
Pittsburgh
Fri 1/15
10:23 am-12:37 pm
1 stop3h 14m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
PittsburghChicago
PIT Pittsburgh - ORD Chicago O'Hare Intl
PITORD
Pittsburgh
Fri 11/13
7:33 pm-8:29 pm
Nonstop1h 56m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Fri 11/13
8:45 am-9:15 am
Nonstop1h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
PittsburghChicago
PIT Pittsburgh - ORD Chicago O'Hare Intl
PITORD
Pittsburgh
Fri 1/22
6:09 pm-12:55 am
1 stop7h 46m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$160
Showing 1-10 of 42 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 October.
| 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
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
What is the cheapest month to book a flight from Pittsburgh to Chicago?
Currently, April is the cheapest month in which you can book a flight from Pittsburgh to Chicago (average of $300). 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 October 19, 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 October 19, 2026.
The most flights from PIT to CHI are scheduled on a Friday (64 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (47 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 $287 and $569 in December.The cheapest round-trip price found within the last 5 days was $238 on Frontier (Dec 11-Dec 14).
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 125 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?
Saturday 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 89 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 October 17, 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. Sunday afternoons 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 October 19, 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.
Entertainment
7.5
Overall
7.9
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
7.9
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
7.9
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
7.9
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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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 October 19, 2026.
Other flights from Pittsburgh
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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 October 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$137 | Average$380 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$157 | Average$342 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$178 | Average$386 | FlexibilityNo cancel fee | On-time69% |