$69+ Cheap flights from Pittsburgh (PIT) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — CHI
Aug 31 — Sep 71
Round-trip
1 adult, Economy
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Find cheap flights from Pittsburgh to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Pittsburgh to Chicago are usually found in September or January, booked 83 days in advance, depart on a Friday or Wednesday 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 August 1, 2026.
Explore the most affordable flight options available from Pittsburgh to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 1, 2026.
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/511:06 am
PIT
- MDW
1 stop5h 38m
Delta
Tue 9/85:37 pm
MDW
- PIT
1 stop4h 18m
Delta
Deal found 7/31![Delta logo]()
$184
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/54:55 pm
PIT
- ORD
1 stop8h 02m
Delta
Mon 9/76:59 am
ORD
- PIT
1 stop3h 20m
Delta
Deal found 7/31![Delta logo]()
$184
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:30 am
PIT
- MDW
1 stop6h 17m
Delta
Mon 10/2612:27 pm
MDW
- PIT
1 stop4h 38m
Delta
Deal found 7/27![Delta logo]()
$188
This Delta deal was found by Cheapflights users on 7/30. 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.
Thu 8/205:50 am
PIT
- ORD
1 stop5h 23m
Delta
Sat 8/225:18 pm
ORD
- PIT
1 stop4h 33m
Delta
Deal found 7/30![Delta logo]()
$188
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/111:50 pm
PIT
- MDW
2 stops9h 10m
Southwest
Mon 9/143:15 pm
MDW
- PIT
1 stop6h 35m
Southwest
Deal found 7/31![Southwest logo]()
$189
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 9/16:55 pm
PIT
- MDW
Nonstop1h 25m
Southwest
Tue 9/86:20 pm
MDW
- PIT
Nonstop1h 30m
Southwest
Deal found 8/1![Southwest logo]()
$191
This American Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 8/2711:21 am
PIT
- ORD
Nonstop1h 53m
American Airlines
Mon 8/319:15 pm
ORD
- PIT
Nonstop1h 44m
American Airlines
Deal found 8/1![American Airlines logo]()
$191
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/148:47 pm
PIT
- ORD
Nonstop2h 00m
American Airlines
Mon 9/219:46 am
ORD
- PIT
Nonstop1h 46m
American Airlines
Deal found 7/30![American Airlines logo]()
$192
This Priceline deal was found by Cheapflights users on 7/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:15 am
PIT
- ORD
1 stop8h 24m
Multiple Airlines
Mon 8/246:05 am
ORD
- PIT
1 stop11h 10m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$200
This KAYAK deal was found by Cheapflights users on 7/27. 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 8/176:09 pm
PIT
- ORD
Nonstop1h 50m
United Airlines
Thu 8/207:10 am
ORD
- PIT
Nonstop1h 39m
United Airlines
Deal found 7/27![United Airlines logo]()
$204
This KAYAK deal was found by Cheapflights users on 7/27. 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 8/177:30 pm
PIT
- MDW
Nonstop1h 20m
Southwest
Thu 8/207:40 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 7/27![Southwest logo]()
$207
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Tue 9/17:50 pm
PIT
- ORD
Nonstop1h 50m
United Airlines
Thu 9/107:10 am
ORD
- PIT
Nonstop1h 39m
United Airlines
Deal found 7/30![United Airlines logo]()
$207
Best flights from Pittsburgh to ChicagoDiscover carefully curated flight deals from Pittsburgh to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 1, 2026.
Discover carefully curated flight deals from Pittsburgh to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 1, 2026.
This Delta deal was found by Cheapflights users on 7/28. 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 8/2011:59 am
PIT
- ORD
1 stop6h 02m
Delta
Mon 8/247:30 pm
ORD
- PIT
1 stop3h 34m
Delta
Deal found 7/28![Delta logo]()
$188
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Tue 9/16:09 pm
PIT
- ORD
Nonstop1h 50m
United Airlines
Wed 9/97:10 am
ORD
- PIT
Nonstop1h 39m
United Airlines
Deal found 7/30![United Airlines logo]()
$207
This Southwest deal was found by Cheapflights users on 7/27. 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 8/218:40 am
PIT
- MDW
Nonstop1h 20m
Southwest
Mon 8/241:05 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 7/27![Southwest logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:00 am
PIT
- RFD
1 stop8h 09m
Multiple Airlines
Mon 8/245:13 pm
RFD
- PIT
1 stop17h 08m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:00 am
PIT
- RFD
1 stop26h 54m
Allegiant Air
Sun 10/251:12 pm
RFD
- PIT
1 stop7h 28m
Allegiant Air
Deal found 7/29![Allegiant Air logo]()
$309
This United Airlines deal was found by Cheapflights users on 7/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:50 pm
PIT
- ORD
Nonstop1h 50m
United Airlines
Sat 9/1212:29 pm
ORD
- PIT
Nonstop1h 38m
United Airlines
Deal found 7/28![United Airlines logo]()
$207
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 11/234:55 pm
PIT
- MDW
1 stop4h 30m
Southwest
Tue 12/13:00 pm
MDW
- PIT
1 stop7h 15m
Southwest
Deal found 7/31![Southwest logo]()
$211
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/265:03 pm
PIT
- ORD
1 stop7h 49m
Delta
Tue 10/2711:30 am
ORD
- PIT
1 stop7h 57m
Delta
Deal found 7/31![Delta logo]()
$211
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Thu 8/207:52 pm
PIT
- ORD
Nonstop1h 52m
United Airlines
Fri 8/214:30 pm
ORD
- PIT
Nonstop1h 41m
United Airlines
Deal found 7/30![United Airlines logo]()
$210
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 12/13:45 pm
PIT
- MDW
1 stop5h 40m
Southwest
Wed 12/23:50 pm
MDW
- PIT
1 stop4h 00m
Southwest
Deal found 7/31![Southwest logo]()
$211
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/223:19 pm
PIT
- ORD
1 stop7h 59m
Delta
Sat 9/263:40 pm
ORD
- PIT
1 stop4h 59m
Delta
Deal found 7/31![Delta logo]()
$211
This United Airlines deal was found by Cheapflights users on 7/29. 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.
Fri 10/165:11 am
PIT
- ORD
Nonstop1h 48m
United Airlines
Mon 10/192:13 pm
ORD
- PIT
Nonstop1h 44m
United Airlines
Deal found 7/29![United Airlines logo]()
$210
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/42:45 pm
PIT
- MDW
Nonstop1h 20m
Southwest
Sun 9/69:10 am
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 7/28![Southwest logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/102:32 pm
PIT
- RFD
1 stop19h 20m
Multiple Airlines
Sun 9/133:53 pm
RFD
- PIT
1 stop6h 00m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$275
This Delta deal was found by Cheapflights users on 7/30. 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.
Wed 9/210:26 am
PIT
- ORD
1 stop3h 42m
Delta
Mon 9/76:59 am
ORD
- PIT
1 stop3h 20m
Delta
Deal found 7/30![Delta logo]()
$230
This United Airlines deal was found by Cheapflights users on 7/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:50 pm
PIT
- ORD
Nonstop1h 50m
United Airlines
Sun 9/64:30 pm
ORD
- PIT
Nonstop1h 41m
United Airlines
Deal found 7/28![United Airlines logo]()
$215
This Delta deal was found by Cheapflights users on 7/29. 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 10/233:59 pm
PIT
- ORD
1 stop6h 37m
Delta
Mon 10/262:29 pm
ORD
- PIT
1 stop7h 27m
Delta
Deal found 7/29![Delta logo]()
$230
This Southwest deal was found by Cheapflights users on 7/29. 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.
Thu 8/204:10 pm
PIT
- MDW
2 stops7h 10m
Southwest
Mon 8/2412:20 pm
MDW
- PIT
2 stops9h 25m
Southwest
Deal found 7/29![Southwest logo]()
$240
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:19 pm
PIT
- ORD
1 stop6h 38m
Delta
Fri 8/286:25 pm
ORD
- PIT
1 stop5h 11m
Delta
Deal found 7/27![Delta logo]()
$230
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/277:00 am
PIT
- ORD
Nonstop1h 43m
United Airlines
Fri 8/287:10 am
ORD
- PIT
Nonstop1h 39m
United Airlines
Deal found 7/31![United Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/102:32 pm
PIT
- RFD
1 stop19h 20m
Multiple Airlines
Mon 9/145:20 pm
RFD
- PIT
1 stop18h 36m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:20 pm
PIT
- RFD
1 stop18h 32m
Allegiant Air
Sun 10/411:12 am
RFD
- PIT
1 stop6h 26m
Allegiant Air
Deal found 7/27![Allegiant Air logo]()
$355
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 11/134:55 pm
PIT
- MDW
2 stops8h 10m
Southwest
Sat 11/143:35 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 7/31![Southwest logo]()
$252
This Southwest deal was found by Cheapflights users on 7/28. 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 9/107:30 pm
PIT
- MDW
Nonstop1h 20m
Southwest
Sun 9/136:00 pm
MDW
- PIT
Nonstop1h 30m
Southwest
Deal found 7/28![Southwest logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/19:00 am
PIT
- RFD
1 stop6h 26m
Multiple Airlines
Mon 10/56:31 pm
RFD
- PIT
1 stop17h 25m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:30 am
PIT
- RFD
1 stop12h 38m
Allegiant Air
Sun 11/151:08 pm
RFD
- PIT
1 stop6h 59m
Allegiant Air
Deal found 7/28![Allegiant Air logo]()
$382
This Southwest deal was found by Cheapflights users on 7/30. 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.
Thu 1/72:00 pm
PIT
- MDW
Nonstop1h 45m
Southwest
Sun 1/101:25 pm
MDW
- PIT
Nonstop1h 20m
Southwest
Deal found 7/30![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 7/30. 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.
Sun 9/137:30 pm
PIT
- MDW
1 stop4h 30m
Southwest
Thu 9/177:40 pm
MDW
- PIT
Nonstop1h 30m
Southwest
Deal found 7/30![Southwest logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/158:00 am
PIT
- RFD
2 stops27h 47m
Multiple Airlines
Fri 8/216:56 pm
RFD
- PIT
1 stop22h 19m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$404
This Kiwi.com deal was found by Cheapflights users on 7/27. 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.
Sun 10/44:34 pm
PIT
- RFD
1 stop18h 20m
Allegiant Air
Thu 10/85:23 pm
RFD
- PIT
1 stop28h 39m
Allegiant Air
Deal found 7/27![Allegiant Air logo]()
$489
Last-minute flights from Pittsburgh to ChicagoDiscover last-minute flight deals from Pittsburgh to Chicago. Data last updated August 1, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Chicago. Data last updated August 1, 2026 and is based on user searches.
This KAYAK deal was found by Cheapflights users on 7/27. 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 8/176:09 pm
PIT
- ORD
Nonstop1h 50m
United Airlines
Thu 8/207:10 am
ORD
- PIT
Nonstop1h 39m
United Airlines
Deal found 7/27![United Airlines logo]()
$204
This KAYAK deal was found by Cheapflights users on 7/27. 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 8/177:30 pm
PIT
- MDW
Nonstop1h 20m
Southwest
Thu 8/207:40 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 7/27![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 7/30. 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.
Thu 8/205:50 am
PIT
- ORD
1 stop5h 23m
Delta
Sat 8/225:18 pm
ORD
- PIT
1 stop4h 33m
Delta
Deal found 7/30![Delta logo]()
$188
This United Airlines deal was found by Cheapflights users on 7/29. 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.
Thu 8/204:11 pm
PIT
- ORD
Nonstop1h 49m
United Airlines
Mon 8/246:05 pm
ORD
- PIT
Nonstop1h 42m
United Airlines
Deal found 7/29![United Airlines logo]()
$207
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Thu 8/207:52 pm
PIT
- ORD
Nonstop1h 52m
United Airlines
Fri 8/214:30 pm
ORD
- PIT
Nonstop1h 41m
United Airlines
Deal found 7/30![United Airlines logo]()
$210
This Delta deal was found by Cheapflights users on 7/30. 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.
Thu 8/205:50 am
PIT
- MDW
1 stop5h 09m
Delta
Sat 8/226:42 pm
MDW
- PIT
1 stop3h 09m
Delta
Deal found 7/30![Delta logo]()
$218
This Delta deal was found by Cheapflights users on 7/30. 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.
Thu 8/2012:17 pm
PIT
- ORD
1 stop5h 00m
Delta
Mon 8/247:30 pm
ORD
- PIT
1 stop3h 34m
Delta
Deal found 7/30![Delta logo]()
$218
This Priceline deal was found by Cheapflights users on 7/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:15 am
PIT
- ORD
1 stop8h 24m
Multiple Airlines
Mon 8/246:05 am
ORD
- PIT
1 stop11h 10m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$200
This Southwest deal was found by Cheapflights users on 7/30. 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.
Fri 8/218:40 am
PIT
- MDW
Nonstop1h 20m
Southwest
Mon 8/248:15 am
MDW
- PIT
Nonstop1h 30m
Southwest
Deal found 7/30![Southwest logo]()
$210
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/268:55 am
PIT
- MDW
Nonstop1h 20m
Southwest
Sat 8/293:10 pm
MDW
- PIT
Nonstop1h 20m
Southwest
Deal found 7/31![Southwest logo]()
$191
This American Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 8/2711:21 am
PIT
- ORD
Nonstop1h 53m
American Airlines
Mon 8/319:15 pm
ORD
- PIT
Nonstop1h 44m
American Airlines
Deal found 8/1![American Airlines logo]()
$191
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 8/271:00 pm
PIT
- ORD
1 stop6h 03m
Delta
Mon 8/316:40 am
ORD
- PIT
1 stop5h 12m
Delta
Deal found 8/1![Delta logo]()
$211
One-way flights from Pittsburgh to ChicagoSearch for one-way flight options from Pittsburgh to Chicago. Find affordable one-way fares based on user searches. Data last updated August 1, 2026.
Search for one-way flight options from Pittsburgh to Chicago. Find affordable one-way fares based on user searches. Data last updated August 1, 2026.
This Southwest deal was found by Cheapflights users on 7/29. 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.
Thu 8/277:30 pm
PIT
- MDW
Nonstop1h 20m
Southwest
Deal found 7/29![Southwest logo]()
$69
This United Airlines deal was found by Cheapflights users on 7/29. 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.
Thu 8/277:00 am
PIT
- ORD
Nonstop1h 43m
United Airlines
Deal found 7/29![United Airlines logo]()
$69
This American Airlines deal was found by Cheapflights users on 7/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/64:06 pm
PIT
- ORD
Nonstop1h 53m
American Airlines
Deal found 7/29![American Airlines logo]()
$74
This Delta deal was found by Cheapflights users on 7/29. 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 8/275:50 am
PIT
- MDW
1 stop5h 09m
Delta
Deal found 7/29![Delta logo]()
$79
This Delta deal was found by Cheapflights users on 7/29. 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 8/271:00 pm
PIT
- ORD
1 stop6h 03m
Delta
Deal found 7/29![Delta logo]()
$79
This Delta deal was found by Cheapflights users on 7/29. 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.
Sun 9/66:29 pm
PIT
- ORD
1 stop6h 28m
Delta
Deal found 7/29![Delta logo]()
$84
This Expedia deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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.
Wed 9/232:42 pm
PIT
- ORD
1 stop9h 17m
Frontier
Deal found 7/31![Frontier logo]()
$86
This Frontier deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/142:32 pm
PIT
- ORD
1 stop9h 27m
Frontier
Deal found 7/31![Frontier logo]()
$87
This Frontier deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/152:42 pm
PIT
- ORD
1 stop9h 17m
Frontier
Deal found 7/31![Frontier logo]()
$88
This Expedia deal was found by Cheapflights users on 7/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/242:32 pm
PIT
- ORD
1 stop9h 27m
Frontier
Deal found 7/29![Frontier logo]()
$91
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:55 pm
PIT
- MDW
Nonstop1h 25m
Southwest
Deal found 8/1![Southwest logo]()
$96
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/224:09 pm
PIT
- ORD
Nonstop1h 49m
United Airlines
Deal found 7/31![United Airlines logo]()
$96
Find flight deals from Pittsburgh to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Pittsburgh (PIT) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $184 (Delta) |
One-way from | $69 (Southwest) |
Popular in | December |
Cheapest in | September |
Average price | $275 |
Good round-trip deal | $344 or less |
Good one-way deal | $184 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 2,558,603 searches. Data last updated August 1, 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 - ORD
PITORD
Pittsburgh
Thu 8/20
11:59 am-5:01 pm
1 stop6h 02m
Chicago O'Hare Intl
Mon 8/24
7:30 pm-12:04 am
1 stop3h 34m
$188
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Tue 9/1
6:09 pm-6:59 pm
Nonstop1h 50m
Chicago O'Hare Intl
Wed 9/9
7:10 am-9:49 am
Nonstop1h 39m
$207
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Tue 9/8
7:50 pm-8:40 pm
Nonstop1h 50m
Chicago O'Hare Intl
Sat 9/12
12:29 pm-3:07 pm
Nonstop1h 38m
$207
Quickest round-trip
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Fri 8/21
8:40 am-9:00 am
Nonstop1h 20m
Chicago Midway
Mon 8/24
1:05 pm-3:30 pm
Nonstop1h 25m
$210
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Thu 8/20
7:52 pm-8:44 pm
Nonstop1h 52m
Chicago O'Hare Intl
Fri 8/21
4:30 pm-7:11 pm
Nonstop1h 41m
$210
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Fri 10/16
5:11 am-5:59 am
Nonstop1h 48m
Chicago O'Hare Intl
Mon 10/19
2:13 pm-4:57 pm
Nonstop1h 44m
$210
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Mon 11/23
4:55 pm-8:25 pm
1 stop4h 30m
Chicago Midway
Tue 12/1
3:00 pm-11:15 pm
1 stop7h 15m
$211
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Mon 10/26
5:03 pm-11:52 pm
1 stop7h 49m
Chicago O'Hare Intl
Tue 10/27
11:30 am-8:27 pm
1 stop7h 57m
$211
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Tue 12/1
3:45 pm-8:25 pm
1 stop5h 40m
Chicago Midway
Wed 12/2
3:50 pm-8:50 pm
1 stop4h 00m
$211
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Tue 9/22
3:19 pm-10:18 pm
1 stop7h 59m
Chicago O'Hare Intl
Sat 9/26
3:40 pm-9:39 pm
1 stop4h 59m
$211
Showing 1-10 of 60 resultsSorted by cheapest first
Compare providers for flights from Pittsburgh to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Pittsburgh to Chicago in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Pittsburgh-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Pittsburgh-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Pittsburgh-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Pittsburgh-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Pittsburgh-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Pittsburgh to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Pittsburgh with our price prediction graph.
PIT-CHI
PIT-ORD
PIT-MDW
PIT-RFD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Pittsburgh to Chicago
PIT-CHI
PIT-ORD
PIT-MDW
PIT-RFD
What is the cheapest month to book a flight from Pittsburgh to Chicago?
Currently, October is the cheapest month in which you can book a flight from Pittsburgh to Chicago (average of $278). Flying from Pittsburgh to Chicago in July is currently the most expensive (average of $391). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from PIT to CHI?
Find hourly flight availability from Pittsburgh to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 1, 2026.
Unlike at noon, 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 August 1, 2026.
The most flights from PIT to CHI are scheduled on a Monday (65 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (30 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 $157 and $365 in September.The cheapest round-trip price found within the last 5 days was $184 on Delta (Sep 5-Sep 8).
How often are flights from Pittsburgh to Chicago delayed?
About 11% of weekly flights between Pittsburgh and Chicago have experienced delays in the past year, with the average delay time being 128 minutes.
What is the most punctual flight time for Pittsburgh to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Thursday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Pittsburgh to Chicago flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 7% of flights being delayed.
How far ahead should I book a flight from Pittsburgh to Chicago?
The price you pay for your flight from Pittsburgh to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 84 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest day to fly from Pittsburgh to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Pittsburgh to Chicago. Price data was last updated on August 1, 2026.
Travelers seeking maximum savings on their Pittsburgh to Chicago flight should consider departing on Saturday at noon when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Pittsburgh to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Pittsburgh to Chicago trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated August 1, 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.
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Pittsburgh to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Pittsburgh to Chicago
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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 August 1, 2026.
Complete your trip
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Pittsburgh and Chicago flights
Browse other Pittsburgh and Chicago flight options. Last updated on August 1, 2026.
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Browse through other flights departing from Pittsburgh. Flights are based on user searches made on Cheapflights and were last updated on August 1, 2026.
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Consider these flights traveling from Pittsburgh to Chicago.
Top 3 airlines flying from Pittsburgh to Chicago
Discover the top 3 airlines that operate flights from Pittsburgh to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$97 | Average$319 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$133 | Average$348 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$158 | Average$358 | FlexibilityNo cancel fee | On-time69% |