$122+ 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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — CHI
Nov 29 — Dec 61
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 30, 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 30, 2026.
This Southwest deal was found by Cheapflights users on 10/26. 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 12/52:20 pm -
1 stop6h 15m
Mon 12/78:15 am -
Nonstop1h 25m
Deal found 10/26![Southwest logo]()
$253
This CheapOair deal was found by Cheapflights users on 10/26. 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.
Wed 12/166:00 am -
1 stop8h 30m
Tue 1/55:01 am -
1 stop6h 48m
Deal found 10/26![Multiple Airlines logo]()
$256
This Frontier deal was found by Cheapflights users on 10/26. 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.
Fri 12/116:28 pm -
1 stop7h 40m
Sun 1/105:01 am -
1 stop6h 48m
Deal found 10/26![Frontier logo]()
$258
This Southwest deal was found by Cheapflights users on 10/25. 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 12/114:00 pm -
Nonstop1h 35m
Mon 12/141:40 pm -
Nonstop1h 25m
Deal found 10/25![Southwest logo]()
$263
This Delta deal was found by Cheapflights users on 10/26. 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.
Thu 11/1910:24 am -
1 stop4h 35m
Mon 11/237:05 am -
1 stop3h 32m
Deal found 10/26![Delta logo]()
$263
This CheapOair deal was found by Cheapflights users on 10/27. 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.
Fri 12/46:28 pm -
1 stop15h 50m
Sun 12/65:24 pm -
1 stop23h 09m
Deal found 10/27![Frontier logo]()
$269
This Southwest deal was found by Cheapflights users on 10/26. 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.
Thu 11/1912:20 pm -
2 stops8h 25m
Mon 11/2312:45 pm -
2 stops5h 50m
Deal found 10/26![Southwest logo]()
$273
This Trip.com deal was found by Cheapflights users on 10/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:28 pm -
1 stop23h 48m
Sun 12/138:37 pm -
1 stop19h 56m
Deal found 10/30![Frontier logo]()
$274
This Trip.com deal was found by Cheapflights users on 10/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:28 pm -
1 stop15h 50m
Sun 12/135:24 pm -
1 stop23h 09m
Deal found 10/30![Frontier logo]()
$274
This Expedia deal was found by Cheapflights users on 10/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/116:28 pm -
1 stop7h 40m
Tue 12/157:00 am -
1 stop13h 31m
Deal found 10/30![Multiple Airlines logo]()
$275
This Priceline deal was found by Cheapflights users on 10/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1612:10 pm -
1 stop5h 32m
Sat 1/165:01 am -
1 stop11h 13m
Deal found 10/26![Multiple Airlines logo]()
$276
This Southwest deal was found by Cheapflights users on 10/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/234:00 pm -
Nonstop1h 35m
Tue 12/18:15 am -
Nonstop1h 25m
Deal found 10/30![Southwest logo]()
$277
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 30, 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 30, 2026.
This Southwest deal was found by Cheapflights users on 10/26. 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 12/55:45 am -
2 stops12h 40m
Tue 12/81:15 pm -
2 stops7h 25m
Deal found 10/26![Southwest logo]()
$279
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2411:14 am -
1 stop6h 27m
Fri 11/276:23 am -
1 stop4h 39m
Deal found 10/29![Delta logo]()
$283
This United Airlines deal was found by Cheapflights users on 10/27. 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 12/246:45 am -
Nonstop2h 08m
Tue 12/293:55 pm -
Nonstop1h 45m
Deal found 10/27![United Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 10/27. 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 12/124:35 pm -
Nonstop1h 30m
Thu 1/77:45 am -
1 stop4h 15m
Deal found 10/27![Southwest logo]()
$280
This Delta deal was found by Cheapflights users on 10/26. 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.
Thu 12/176:10 am -
1 stop4h 27m
Mon 12/216:15 pm -
1 stop3h 44m
Deal found 10/26![Delta logo]()
$290
This Southwest deal was found by Cheapflights users on 10/29. 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.
Mon 12/288:15 pm -
1 stop3h 45m
Wed 12/301:05 pm -
Nonstop1h 20m
Deal found 10/29![Southwest logo]()
$307
This Delta deal was found by Cheapflights users on 10/28. 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 12/36:10 am -
1 stop4h 27m
Sun 12/66:41 pm -
1 stop3h 16m
Deal found 10/28![Delta logo]()
$310
This Southwest deal was found by Cheapflights users on 10/28. 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 12/1012:20 pm -
2 stops8h 25m
Sun 12/136:30 am -
1 stop5h 20m
Deal found 10/28![Southwest logo]()
$315
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/152:01 pm -
1 stop4h 59m
Mon 1/186:40 pm -
1 stop3h 33m
Deal found 10/29![Delta logo]()
$317
This United Airlines deal was found by Cheapflights users on 10/29. 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 11/172:07 pm -
Nonstop1h 48m
Thu 11/196:59 am -
Nonstop1h 31m
Deal found 10/29![United Airlines logo]()
$386
This Delta deal was found by Cheapflights users on 10/28. 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.
Sat 12/1212:50 pm -
1 stop5h 00m
Sat 1/99:38 am -
1 stop4h 30m
Deal found 10/28![Delta logo]()
$321
This United Airlines deal was found by Cheapflights users on 10/26. 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.
Sat 11/1412:58 pm -
1 stop5h 22m
Mon 11/166:10 pm -
Nonstop1h 39m
Deal found 10/26![United Airlines logo]()
$396
This Delta deal was found by Cheapflights users on 10/26. 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.
Thu 12/1710:27 am -
1 stop4h 29m
Sun 12/205:55 pm -
1 stop4h 04m
Deal found 10/26![Delta logo]()
$330
This Southwest deal was found by Cheapflights users on 10/28. 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 11/3012:30 pm -
2 stops8h 45m
Wed 12/28:15 am -
Nonstop1h 25m
Deal found 10/28![Southwest logo]()
$373
This United Airlines deal was found by Cheapflights users on 10/30. 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 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
Sun 11/2911:55 pm -
Nonstop1h 36m
Deal found 10/30![United Airlines logo]()
$446
This Southwest deal was found by Cheapflights users on 10/28. 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 1/12:20 pm -
Nonstop1h 35m
Sun 1/37:40 am -
Nonstop1h 20m
Deal found 10/28![Southwest logo]()
$396
This Delta deal was found by Cheapflights users on 10/28. 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.
Wed 12/236:00 am -
1 stop4h 49m
Sat 12/263:29 pm -
1 stop6h 44m
Deal found 10/28![Delta logo]()
$375
This Delta deal was found by Cheapflights users on 10/28. 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.
Wed 12/306:00 am -
1 stop4h 49m
Sat 1/23:29 pm -
1 stop6h 44m
Deal found 10/28![Delta logo]()
$406
This KAYAK deal was found by Cheapflights users on 10/27. 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.
Sun 11/1512:15 pm -
1 stop5h 03m
Wed 11/187:00 am -
1 stop7h 19m
Deal found 10/27![Delta logo]()
$441
This KAYAK deal was found by Cheapflights users on 10/27. 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.
Mon 11/163:59 pm -
1 stop5h 46m
Wed 11/188:45 am -
1 stop5h 34m
Deal found 10/27![Delta logo]()
$441
This KAYAK deal was found by Cheapflights users on 10/30. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/306:10 am -
1 stop5h 29m
Tue 12/17:05 am -
1 stop3h 35m
Deal found 10/30![Delta logo]()
$450
Last-minute flights from Pittsburgh to ChicagoDiscover last-minute flight deals from Pittsburgh to Chicago. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Chicago. Data last updated October 30, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 10/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:27 pm -
1 stop23h 40m
Tue 11/109:51 am -
1 stop6h 41m
Deal found 10/25![Frontier logo]()
$275
This Priceline deal was found by Cheapflights users on 10/27. 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 11/1612:47 pm -
1 stop7h 30m
Wed 11/189:51 am -
1 stop6h 41m
Deal found 10/27![Multiple Airlines logo]()
$281
This Southwest deal was found by Cheapflights users on 10/26. 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.
Tue 11/174:00 pm -
1 stop6h 30m
Thu 11/196:10 pm -
Nonstop1h 35m
Deal found 10/26![Southwest logo]()
$253
This Southwest deal was found by Cheapflights users on 10/27. 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 11/1812:20 pm -
2 stops8h 25m
Fri 11/206:50 pm -
Nonstop1h 30m
Deal found 10/27![Southwest logo]()
$278
This Delta deal was found by Cheapflights users on 10/26. 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.
Thu 11/1910:24 am -
1 stop4h 35m
Mon 11/237:05 am -
1 stop3h 32m
Deal found 10/26![Delta logo]()
$263
This Southwest deal was found by Cheapflights users on 10/26. 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.
Thu 11/1912:20 pm -
2 stops8h 25m
Mon 11/2312:45 pm -
2 stops5h 50m
Deal found 10/26![Southwest logo]()
$273
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:24 am -
1 stop3h 27m
Fri 11/2012:30 pm -
1 stop5h 05m
Deal found 10/29![Delta logo]()
$283
This Delta deal was found by Cheapflights users on 10/27. 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.
Fri 11/206:10 am -
1 stop5h 29m
Sat 11/217:25 am -
1 stop3h 15m
Deal found 10/27![Delta logo]()
$283
This Frontier deal was found by Cheapflights users on 10/26. 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.
Sun 11/226:59 pm -
1 stop6h 44m
Thu 12/35:35 am -
1 stop10h 53m
Deal found 10/26![Frontier logo]()
$279
This Southwest deal was found by Cheapflights users on 10/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/234:00 pm -
Nonstop1h 35m
Tue 12/18:15 am -
Nonstop1h 25m
Deal found 10/30![Southwest logo]()
$277
This Frontier deal was found by Cheapflights users on 10/27. 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 44m
Fri 11/275:40 am -
1 stop11h 24m
Deal found 10/27![Frontier logo]()
$277
This Priceline deal was found by Cheapflights users on 10/27. 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 11/306:59 pm -
1 stop6h 44m
Thu 12/35:35 am -
1 stop10h 53m
Deal found 10/27![Frontier 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 October 30, 2026.
Search for one-way flight options from Pittsburgh to Chicago. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This Southwest deal was found by Cheapflights users on 10/26. 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 11/162:20 pm -
Nonstop1h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Southwest logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Tue 11/106:27 pm -
1 stop23h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$125
This American Airlines deal was found by Cheapflights users on 10/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/78:21 pm -
Nonstop2h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![American Airlines logo]()
$127
This Jetabroad deal was found by Cheapflights users on 10/28. 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 Jetabroad 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 10/28![Frontier logo]()
$129
This CheapOair deal was found by Cheapflights users on 10/28. 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 11/176:27 pm -
1 stop23h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Frontier logo]()
$131
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:10 am -
1 stop4h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Delta logo]()
$132
This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/11:00 pm -
1 stop7h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Delta logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/77:59 pm -
2 stops16h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/77:59 pm -
2 stops27h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$133
This Trip.com deal was found by Cheapflights users on 10/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/216:11 pm -
1 stop26h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Frontier logo]()
$134
This Southwest deal was found by Cheapflights users on 10/26. 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.
Tue 11/1712:20 pm -
2 stops8h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Southwest logo]()
$137
This Priceline deal was found by Cheapflights users on 10/27. 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.
Sun 11/226:59 pm -
1 stop6h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier 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 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $253 (Southwest) |
One-way from | $122 (Southwest) |
Popular in | December |
Cheapest in | April |
Average price | $384 |
Good round-trip deal | $346 or less |
Good one-way deal | $168 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 30, 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
Mon 11/16
5:35 am-9:00 am
1 stop4h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$132
PittsburghChicago
PIT Pittsburgh - ORD Chicago O'Hare Intl
PITORD
Pittsburgh
Tue 12/1
1:00 pm-7:25 pm
1 stop7h 25m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$132
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Wed 12/16
7:10 pm-10:45 pm
1 stop4h 35m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$132
PittsburghChicago
PIT Pittsburgh - ORD Chicago O'Hare Intl
PITORD
Pittsburgh
Wed 12/16
4:59 pm-9:36 pm
1 stop5h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$132
PittsburghChicago
PIT Pittsburgh - ORD Chicago O'Hare Intl
PITORD
Pittsburgh
Thu 11/19
7:20 am-12:46 pm
1 stop6h 26m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$132
PittsburghChicago
PIT Pittsburgh - ORD Chicago O'Hare Intl
PITORD
Pittsburgh
Thu 12/31
8:45 am-9:45 am
Nonstop2h 00m
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 - MDW Chicago Midway
PITMDW
Pittsburgh
Sat 11/21
6:10 am-9:46 am
1 stop4h 36m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Fri 11/27
6:10 am-11:25 am
1 stop6h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
PittsburghChicago
PIT Pittsburgh - ORD Chicago O'Hare Intl
PITORD
Pittsburgh
Thu 11/19
11:43 am-12:13 am
2 stops13h 30m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$160
Showing 1-10 of 40 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 | |
| Price Accuracy2 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 $412). 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 30, 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.
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 $277 and $455 in December.The cheapest round-trip price found within the last 5 days was $253 on Southwest (Dec 5-Dec 7).
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 24, 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 30, 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
7.9
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.4
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.4
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.4
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.4
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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Pittsburgh and Chicago flights
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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 October 30, 2026.
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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 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$137 | Average$384 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$157 | Average$342 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$178 | Average$390 | FlexibilityNo cancel fee | On-time69% |