$119+ 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 11/23. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — CHI
Oct 28 — Nov 41
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 83 days in advance, depart on a Friday or Thursday and return on a Thursday
Cheap flight deals from Pittsburgh to Chicago
Cheapest
Best
Last-minute
One-way
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 September 28, 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 September 28, 2026.
This Frontier deal was found by Cheapflights users on 9/25. 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 10/178:18 pm -
1 stop12h 13m
Mon 10/198:11 pm -
1 stop21h 45m
Deal found 9/25![Frontier logo]()
$238
This Frontier deal was found by Cheapflights users on 9/23. 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 10/157:51 pm -
1 stop12h 40m
Mon 10/198:11 pm -
1 stop21h 45m
Deal found 9/23![Frontier logo]()
$248
This Gotogate deal was found by Cheapflights users on 9/23. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/126:28 pm -
1 stop15h 50m
Mon 1/115:16 pm -
1 stop22h 58m
Deal found 9/23![Frontier logo]()
$257
This Frontier deal was found by Cheapflights users on 9/24. 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 12/1710:30 am -
1 stop9h 32m
Mon 12/218:07 pm -
1 stop12h 28m
Deal found 9/24![Frontier logo]()
$258
This Priceline deal was found by Cheapflights users on 9/23. 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 10/216:00 am -
1 stop8h 50m
Wed 10/289:51 am -
1 stop6h 41m
Deal found 9/23![Multiple Airlines logo]()
$270
This Frontier deal was found by Cheapflights users on 9/27. 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.
Thu 10/227:51 pm -
1 stop12h 40m
Mon 10/268:11 pm -
1 stop20h 21m
Deal found 9/27![Frontier logo]()
$275
This American Airlines deal was found by Cheapflights users on 9/24. 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.
Thu 10/1510:04 am -
Nonstop1h 55m
Mon 10/196:40 pm -
Nonstop1h 36m
Deal found 9/24![American Airlines logo]()
$276
This Southwest deal was found by Cheapflights users on 9/23. 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 10/151:40 pm -
Nonstop1h 30m
Sat 10/174:10 pm -
Nonstop1h 25m
Deal found 9/23![Southwest logo]()
$277
This American Airlines deal was found by Cheapflights users on 9/28. 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.
Thu 12/179:31 am -
Nonstop2h 04m
Wed 1/65:54 pm -
Nonstop1h 42m
Deal found 9/28![American Airlines logo]()
$277
This American Airlines deal was found by Cheapflights users on 9/27. 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.
Thu 10/226:05 am -
Nonstop1h 54m
Mon 10/269:00 pm -
Nonstop1h 43m
Deal found 9/27![American Airlines logo]()
$279
This Priceline deal was found by Cheapflights users on 9/25. 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 10/286:00 am -
1 stop8h 44m
Fri 10/309:51 am -
1 stop6h 41m
Deal found 9/25![Multiple Airlines logo]()
$280
This Southwest deal was found by Cheapflights users on 9/23. 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 10/157:45 pm -
Nonstop1h 30m
Mon 10/194:30 pm -
1 stop5h 30m
Deal found 9/23![Southwest logo]()
$287
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 September 28, 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 September 28, 2026.
This United Airlines deal was found by Cheapflights users on 9/23. 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 10/156:00 pm -
Nonstop1h 49m
Mon 10/195:55 pm -
Nonstop1h 41m
Deal found 9/23![United Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 9/26. 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.
Mon 12/218:15 pm -
1 stop3h 40m
Fri 12/256:10 pm -
Nonstop1h 30m
Deal found 9/26![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 9/27. 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 12/126:10 am -
1 stop4h 27m
Sat 1/95:35 pm -
1 stop4h 43m
Deal found 9/27![Delta logo]()
$297
This United Airlines deal was found by Cheapflights users on 9/25. 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 12/117:25 pm -
Nonstop1h 55m
Tue 12/156:10 pm -
Nonstop1h 39m
Deal found 9/25![United Airlines logo]()
$287
This Delta deal was found by Cheapflights users on 9/27. 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 12/1210:31 am -
1 stop4h 25m
Sat 1/95:20 pm -
1 stop4h 58m
Deal found 9/27![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 9/25. 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 11/238:00 pm -
Nonstop1h 30m
Fri 11/2711:10 am -
2 stops7h 25m
Deal found 9/25![Southwest logo]()
$302
This Delta deal was found by Cheapflights users on 9/27. 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.
Tue 11/36:05 am -
1 stop8h 03m
Tue 11/102:37 pm -
1 stop4h 50m
Deal found 9/27![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 9/27. 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.
Tue 10/275:40 am -
2 stops8h 40m
Fri 10/305:00 am -
1 stop5h 45m
Deal found 9/27![Southwest logo]()
$312
This Delta deal was found by Cheapflights users on 9/26. 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.
Sat 12/511:25 am -
1 stop6h 39m
Mon 12/76:00 am -
1 stop5h 15m
Deal found 9/26![Delta logo]()
$297
This United Airlines deal was found by Cheapflights users on 9/24. 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 11/306:30 am -
Nonstop1h 53m
Tue 12/13:50 pm -
Nonstop1h 34m
Deal found 9/24![United Airlines logo]()
$335
This Southwest deal was found by Cheapflights users on 9/24. 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 10/224:20 pm -
2 stops8h 35m
Fri 10/237:50 am -
2 stops8h 30m
Deal found 9/24![Southwest logo]()
$317
This Delta deal was found by Cheapflights users on 9/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1712:15 pm -
1 stop5h 02m
Wed 1/610:35 am -
1 stop6h 09m
Deal found 9/28![Delta logo]()
$297
This United Airlines deal was found by Cheapflights users on 9/27. 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 11/307:33 pm -
Nonstop1h 56m
Tue 3/26:20 pm -
Nonstop1h 46m
Deal found 9/27![United Airlines logo]()
$335
This Southwest deal was found by Cheapflights users on 9/23. 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 10/156:20 am -
2 stops9h 35m
Mon 10/1911:05 am -
2 stops7h 00m
Deal found 9/23![Southwest logo]()
$317
This Delta deal was found by Cheapflights users on 9/27. 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 10/226:00 am -
1 stop4h 32m
Fri 10/236:44 pm -
1 stop4h 15m
Deal found 9/27![Delta logo]()
$307
This United Airlines deal was found by Cheapflights users on 9/27. 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.
Thu 12/248:45 am -
Nonstop2h 00m
Sat 1/28:52 am -
1 stop4h 30m
Deal found 9/27![United Airlines logo]()
$345
This Southwest deal was found by Cheapflights users on 9/27. 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 11/138:45 am -
Nonstop1h 30m
Sun 11/156:50 pm -
Nonstop1h 30m
Deal found 9/27![Southwest logo]()
$356
This United Airlines deal was found by Cheapflights users on 9/25. 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 10/232:11 pm -
Nonstop1h 44m
Sun 10/2510:30 am -
Nonstop1h 36m
Deal found 9/25![United Airlines logo]()
$356
This Delta deal was found by Cheapflights users on 9/26. 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.
Mon 11/236:35 am -
1 stop6h 15m
Fri 11/275:29 pm -
1 stop4h 32m
Deal found 9/26![Delta logo]()
$338
This Southwest deal was found by Cheapflights users on 9/27. 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 10/307:45 pm -
Nonstop1h 30m
Sun 11/11:00 pm -
1 stop4h 10m
Deal found 9/27![Southwest logo]()
$366
This Delta deal was found by Cheapflights users on 9/25. 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 10/2910:32 am -
1 stop3h 15m
Sun 11/89:29 am -
1 stop4h 49m
Deal found 9/25![Delta logo]()
$366
This Delta deal was found by Cheapflights users on 9/24. 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 11/46:05 am -
1 stop5h 23m
Sun 11/85:29 pm -
1 stop5h 30m
Deal found 9/24![Delta logo]()
$366
Last-minute flights from Pittsburgh to ChicagoDiscover last-minute flight deals from Pittsburgh to Chicago. Data last updated September 28, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Chicago. Data last updated September 28, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 9/23. 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 10/157:51 pm -
1 stop12h 40m
Mon 10/198:11 pm -
1 stop21h 45m
Deal found 9/23![Frontier logo]()
$248
This American Airlines deal was found by Cheapflights users on 9/24. 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.
Thu 10/1510:04 am -
Nonstop1h 55m
Mon 10/196:40 pm -
Nonstop1h 36m
Deal found 9/24![American Airlines logo]()
$276
This Southwest deal was found by Cheapflights users on 9/23. 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 10/157:45 pm -
Nonstop1h 30m
Mon 10/197:45 am -
Nonstop1h 20m
Deal found 9/23![Southwest logo]()
$277
This United Airlines deal was found by Cheapflights users on 9/23. 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 10/156:00 pm -
Nonstop1h 49m
Mon 10/195:55 pm -
Nonstop1h 41m
Deal found 9/23![United Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 9/23. 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 10/151:40 pm -
Nonstop1h 30m
Sat 10/1711:25 am -
2 stops9h 20m
Deal found 9/23![Southwest logo]()
$292
This Frontier deal was found by Cheapflights users on 9/25. 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 10/178:18 pm -
1 stop12h 13m
Mon 10/198:11 pm -
1 stop21h 45m
Deal found 9/25![Frontier logo]()
$238
This Priceline deal was found by Cheapflights users on 9/23. 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 10/216:00 am -
1 stop8h 50m
Wed 10/289:51 am -
1 stop6h 41m
Deal found 9/23![Multiple Airlines logo]()
$270
This Frontier deal was found by Cheapflights users on 9/27. 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.
Thu 10/227:51 pm -
1 stop12h 40m
Mon 10/268:11 pm -
1 stop20h 21m
Deal found 9/27![Frontier logo]()
$275
This American Airlines deal was found by Cheapflights users on 9/27. 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.
Thu 10/226:05 am -
Nonstop1h 54m
Mon 10/269:00 pm -
Nonstop1h 43m
Deal found 9/27![American Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 9/27. 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 10/226:00 am -
1 stop4h 32m
Fri 10/236:44 pm -
1 stop4h 15m
Deal found 9/27![Delta logo]()
$307
This Southwest deal was found by Cheapflights users on 9/25. 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 10/231:40 pm -
Nonstop1h 30m
Fri 10/307:45 am -
Nonstop1h 20m
Deal found 9/25![Southwest logo]()
$297
This Priceline deal was found by Cheapflights users on 9/25. 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 10/286:00 am -
1 stop8h 44m
Fri 10/309:51 am -
1 stop6h 41m
Deal found 9/25![Multiple Airlines logo]()
$280
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 September 28, 2026.
Search for one-way flight options from Pittsburgh to Chicago. Find affordable one-way fares based on user searches. Data last updated September 28, 2026.
This Frontier deal was found by Cheapflights users on 9/27. 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.
Mon 11/236:59 pm -
1 stop6h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Frontier logo]()
$119
This Frontier deal was found by Cheapflights users on 9/27. 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 10/217:51 pm -
1 stop12h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 9/23. 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 1/117:27 pm -
1 stop21h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Multiple Airlines logo]()
$126
This Frontier deal was found by Cheapflights users on 9/24. 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 12/2110:30 am -
1 stop9h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Frontier logo]()
$129
This CheapOair deal was found by Cheapflights users on 9/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:27 pm -
1 stop23h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 9/23. 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 10/610:17 am -
2 stops30h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Multiple Airlines logo]()
$132
This Frontier deal was found by Cheapflights users on 9/23. 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 10/157:51 pm -
1 stop12h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$135
This Southwest deal was found by Cheapflights users on 9/23. 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 10/157:45 pm -
Nonstop1h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Southwest logo]()
$139
This Frontier deal was found by Cheapflights users on 9/26. 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.
Tue 11/246:59 pm -
1 stop6h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Frontier logo]()
$139
This Southwest deal was found by Cheapflights users on 9/28. 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.
Thu 10/225:50 am -
1 stop5h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Southwest logo]()
$149
This Delta deal was found by Cheapflights users on 9/24. 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 10/261:00 pm -
1 stop7h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Delta logo]()
$149
This KAYAK deal was found by Cheapflights users on 9/26. 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.
Thu 12/2412:13 pm -
1 stop7h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![JetBlue logo]()
$151
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 September 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $238 (Frontier) |
One-way from | $119 (Frontier) |
Popular in | December |
Cheapest in | April |
Average price | $348 |
Good round-trip deal | $344 or less |
Good one-way deal | $187 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 September 28, 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
Thu 11/26
2:05 pm-2:30 pm
Nonstop1h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
PittsburghChicago
PIT Pittsburgh - ORD Chicago O'Hare Intl
PITORD
Pittsburgh
Wed 10/14
10:56 am-11:40 am
Nonstop1h 44m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Tue 10/27
6:50 pm-7:20 pm
Nonstop1h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
PittsburghChicago
PIT Pittsburgh - ORD Chicago O'Hare Intl
PITORD
Pittsburgh
Sat 11/7
5:51 pm-6:39 pm
Nonstop1h 48m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Tue 11/10
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 - ORD Chicago O'Hare Intl
PITORD
Pittsburgh
Wed 10/21
8:56 am-9:45 am
Nonstop1h 49m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Thu 11/26
6:10 am-11:25 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
Thu 10/29
10:32 am-12:47 pm
1 stop3h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Sat 11/7
6:00 am-9:32 am
1 stop4h 32m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Mon 11/2
8:50 pm-12:05 am
1 stop4h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
Showing 1-10 of 45 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 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 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-ORD
PIT-MDW
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-ORD
PIT-MDW
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 September 28, 2026.
Unlike in the afternoon, when flights are generally more expensive, you can save up to 9% 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 September 28, 2026.
The most flights from PIT to CHI are scheduled on a Friday (65 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (51 on average).
How much does it cost to fly round-trip from Pittsburgh to Chicago?
Airfare is typical for this route at the moment.
Pittsburgh to Chicago flights typically cost between $233 and $497 in October.The cheapest round-trip price found within the last 5 days was $238 on Frontier (Oct 17-Oct 19).
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 88 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 September 19, 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 September 28, 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.
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
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
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Pittsburgh
Popular flights
Alternative routes for Pittsburgh to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 28, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Pittsburgh to Chicago by cabin class
Find flights from Pittsburgh to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Pittsburgh and Chicago flights
Browse other Pittsburgh and Chicago flight options. Last updated on September 28, 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 September 28, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 September 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$137 | Average$358 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$145 | Average$342 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$176 | Average$377 | FlexibilityNo cancel fee | On-time69% |