$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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — CHI
Jun 3 — Jun 101
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 August or September, booked 50 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 May 4, 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 May 4, 2026.
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/15:00 pm
PIT
- MDW
1 stop4h 20m
Southwest
Tue 6/210:10 am
MDW
- PIT
2 stops6h 45m
Southwest
Deal found 5/4![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 5/1. 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 5/276:25 am
PIT
- ORD
1 stop7h 25m
Southwest
Sat 5/301:55 pm
ORD
- PIT
2 stops8h 10m
Southwest
Deal found 5/1![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/288:00 pm
PIT
- MDW
Nonstop1h 30m
Southwest
Mon 6/13:50 pm
MDW
- PIT
1 stop5h 25m
Southwest
Deal found 5/4![Southwest logo]()
$187
This Delta deal was found by Cheapflights users on 4/30. 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 5/2812:01 pm
PIT
- MDW
1 stop5h 11m
Delta
Mon 6/16:36 pm
MDW
- PIT
1 stop3h 02m
Delta
Deal found 4/30![Delta logo]()
$197
This Delta deal was found by Cheapflights users on 4/29. 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 5/2812:01 pm
PIT
- ORD
1 stop5h 55m
Delta
Mon 6/17:07 am
ORD
- PIT
1 stop4h 37m
Delta
Deal found 4/29![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 4/30. 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.
Tue 6/27:10 pm
PIT
- MDW
Nonstop1h 30m
Southwest
Wed 6/36:20 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 4/30![Southwest logo]()
$200
This Southwest deal was found by Cheapflights users on 5/1. 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.
Mon 6/15:55 am
PIT
- ORD
1 stop7h 55m
Southwest
Wed 6/32:40 pm
ORD
- PIT
1 stop5h 40m
Southwest
Deal found 5/1![Southwest logo]()
$202
This United Airlines deal was found by Cheapflights users on 4/30. 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 6/28:36 am
PIT
- ORD
Nonstop1h 54m
United Airlines
Wed 6/37:15 am
ORD
- PIT
Nonstop1h 43m
United Airlines
Deal found 4/30![United Airlines logo]()
$204
This Southwest deal was found by Cheapflights users on 5/1. 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 5/276:25 am
PIT
- MDW
2 stops10h 20m
Southwest
Sat 5/302:15 pm
MDW
- PIT
1 stop5h 50m
Southwest
Deal found 5/1![Southwest logo]()
$208
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/285:55 am
PIT
- ORD
1 stop7h 55m
Southwest
Mon 6/12:40 pm
ORD
- PIT
2 stops7h 30m
Southwest
Deal found 5/3![Southwest logo]()
$208
This Southwest deal was found by Cheapflights users on 5/1. 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.
Mon 6/81:45 pm
PIT
- MDW
1 stop6h 25m
Southwest
Wed 6/1011:50 am
MDW
- PIT
1 stop6h 15m
Southwest
Deal found 5/1![Southwest logo]()
$212
This KAYAK deal was found by Cheapflights users on 4/30. 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.
Tue 5/266:00 am
PIT
- ORD
Nonstop1h 55m
American Airlines
Thu 5/289:45 am
ORD
- PIT
Nonstop1h 47m
American Airlines
Deal found 4/30![American Airlines logo]()
$212
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 May 4, 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 May 4, 2026.
This Delta deal was found by Cheapflights users on 4/29. 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.
Sat 5/2310:31 am
PIT
- MDW
1 stop3h 11m
Delta
Mon 5/251:22 pm
MDW
- PIT
1 stop4h 27m
Delta
Deal found 4/29![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 4/30. 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 5/298:00 pm
PIT
- MDW
Nonstop1h 30m
Southwest
Tue 6/212:45 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 4/30![Southwest logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/299:29 pm
PIT
- RFD
1 stop12h 52m
Allegiant Air
Sun 5/319:21 am
RFD
- PIT
1 stop12h 45m
Allegiant Air
Deal found 5/3![Allegiant Air logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/288:15 pm
PIT
- RFD
1 stop23h 58m
Multiple Airlines
Sun 5/319:21 am
RFD
- PIT
1 stop12h 45m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$292
This JetBlue deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1712:58 pm
PIT
- ORD
1 stop7h 27m
JetBlue
Sat 7/181:55 pm
ORD
- PIT
1 stop7h 33m
JetBlue
Deal found 5/3![JetBlue logo]()
$343
This United Airlines deal was found by Cheapflights users on 5/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/77:24 pm
PIT
- ORD
Nonstop1h 53m
United Airlines
Sat 9/129:30 pm
ORD
- PIT
Nonstop1h 45m
United Airlines
Deal found 5/1![United Airlines logo]()
$343
This Delta deal was found by Cheapflights users on 5/1. 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.
Sat 6/611:29 am
PIT
- ORD
1 stop6h 27m
Delta
Mon 6/87:17 pm
ORD
- PIT
1 stop3h 50m
Delta
Deal found 5/1![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 5/1. 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.
Fri 6/1912:25 pm
PIT
- MDW
1 stop7h 30m
Southwest
Tue 6/235:10 pm
MDW
- PIT
1 stop3h 35m
Southwest
Deal found 5/1![Southwest logo]()
$260
This Southwest deal was found by Cheapflights users on 4/30. 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 6/58:15 pm
PIT
- MDW
Nonstop1h 30m
Southwest
Mon 6/87:45 am
MDW
- PIT
Nonstop1h 30m
Southwest
Deal found 4/30![Southwest logo]()
$260
This Delta deal was found by Cheapflights users on 4/30. 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.
Sat 9/54:50 pm
PIT
- ORD
1 stop5h 44m
Delta
Tue 9/87:10 am
ORD
- PIT
1 stop7h 30m
Delta
Deal found 4/30![Delta logo]()
$260
This Delta deal was found by Cheapflights users on 5/1. 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.
Fri 6/1912:25 pm
PIT
- ORD
1 stop5h 01m
Delta
Tue 6/2312:27 pm
ORD
- PIT
1 stop5h 21m
Delta
Deal found 5/1![Delta logo]()
$260
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/295:55 am
PIT
- ORD
1 stop7h 55m
Southwest
Tue 6/22:40 pm
ORD
- PIT
1 stop5h 40m
Southwest
Deal found 5/2![Southwest logo]()
$265
This JetBlue deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1612:58 pm
PIT
- ORD
1 stop7h 27m
JetBlue
Sat 7/181:55 pm
ORD
- PIT
1 stop7h 33m
JetBlue
Deal found 5/3![JetBlue logo]()
$343
This United Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 9/117:00 am
PIT
- ORD
Nonstop1h 42m
United Airlines
Sun 9/136:15 pm
ORD
- PIT
Nonstop1h 42m
United Airlines
Deal found 5/3![United Airlines logo]()
$354
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 7/2312:40 pm
PIT
- RFD
1 stop20h 09m
Allegiant Air
Sun 7/269:19 am
RFD
- PIT
1 stop12h 39m
Allegiant Air
Deal found 5/3![Allegiant Air logo]()
$355
This Southwest deal was found by Cheapflights users on 5/1. 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.
Sat 5/234:00 pm
PIT
- MDW
Nonstop1h 30m
Southwest
Sun 5/243:45 pm
MDW
- PIT
1 stop5h 55m
Southwest
Deal found 5/1![Southwest logo]()
$270
This Delta deal was found by Cheapflights users on 4/30. 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.
Fri 6/51:40 pm
PIT
- ORD
1 stop5h 55m
Delta
Mon 6/87:17 pm
ORD
- PIT
1 stop3h 50m
Delta
Deal found 4/30![Delta logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/59:27 pm
PIT
- RFD
1 stop12h 50m
Multiple Airlines
Mon 6/87:53 pm
RFD
- PIT
2 stops16h 02m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$378
This United Airlines deal was found by Cheapflights users on 5/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:16 pm
PIT
- ORD
Nonstop1h 49m
United Airlines
Sun 8/92:20 pm
ORD
- PIT
Nonstop1h 45m
United Airlines
Deal found 5/1![United Airlines logo]()
$354
This Southwest deal was found by Cheapflights users on 5/1. 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.
Mon 6/83:50 pm
PIT
- MDW
Nonstop1h 30m
Southwest
Fri 6/126:00 pm
MDW
- PIT
1 stop3h 30m
Southwest
Deal found 5/1![Southwest logo]()
$270
This Delta deal was found by Cheapflights users on 5/1. 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.
Mon 6/85:30 am
PIT
- ORD
1 stop5h 43m
Delta
Fri 6/125:30 am
ORD
- PIT
1 stop6h 12m
Delta
Deal found 5/1![Delta logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:29 pm
PIT
- RFD
1 stop12h 52m
Allegiant Air
Fri 6/58:35 am
RFD
- PIT
2 stops12h 31m
Allegiant Air
Deal found 5/1![Allegiant Air logo]()
$374
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 9/38:00 am
PIT
- RFD
1 stop8h 03m
Multiple Airlines
Mon 9/76:02 pm
RFD
- PIT
1 stop16h 19m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$392
This Southwest deal was found by Cheapflights users on 4/30. 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 5/295:45 am
PIT
- MDW
2 stops8h 25m
Southwest
Sat 5/304:00 pm
MDW
- PIT
Nonstop1h 20m
Southwest
Deal found 4/30![Southwest logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/299:29 pm
PIT
- RFD
1 stop12h 52m
Multiple Airlines
Mon 6/18:03 pm
RFD
- PIT
2 stops15h 52m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$396
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Fri 6/129:27 pm
PIT
- RFD
1 stop12h 50m
Allegiant Air
Mon 6/158:35 am
RFD
- PIT
1 stop14h 03m
Allegiant Air
Deal found 4/29![Allegiant Air logo]()
$414
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/66:00 am
PIT
- RFD
1 stop29h 37m
Multiple Airlines
Sat 6/1310:07 am
RFD
- PIT
1 stop24h 07m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$397
This KAYAK deal was found by Cheapflights users on 4/30. 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 5/256:15 am
PIT
- ORD
1 stop9h 45m
Southwest
Thu 5/286:15 am
ORD
- PIT
2 stops12h 05m
Southwest
Deal found 4/30![Southwest logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:45 pm
PIT
- RFD
1 stop20h 00m
Allegiant Air
Sun 5/319:21 am
RFD
- PIT
1 stop12h 45m
Allegiant Air
Deal found 5/1![Allegiant Air logo]()
$414
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/59:27 pm
PIT
- RFD
1 stop12h 50m
Allegiant Air
Sun 6/711:27 am
RFD
- PIT
2 stops10h 37m
Allegiant Air
Deal found 5/4![Allegiant Air logo]()
$420
Last-minute flights from Pittsburgh to ChicagoDiscover last-minute flight deals from Pittsburgh to Chicago. Data last updated May 4, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Chicago. Data last updated May 4, 2026 and is based on user searches.
This KAYAK deal was found by Cheapflights users on 4/30. 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.
Tue 5/266:00 am
PIT
- ORD
Nonstop1h 55m
American Airlines
Thu 5/289:45 am
ORD
- PIT
Nonstop1h 47m
American Airlines
Deal found 4/30![American Airlines logo]()
$212
This Southwest deal was found by Cheapflights users on 5/1. 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 5/276:25 am
PIT
- ORD
1 stop7h 25m
Southwest
Sat 5/301:55 pm
ORD
- PIT
2 stops8h 10m
Southwest
Deal found 5/1![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 5/1. 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 5/276:25 am
PIT
- MDW
2 stops10h 20m
Southwest
Sat 5/302:15 pm
MDW
- PIT
1 stop5h 50m
Southwest
Deal found 5/1![Southwest logo]()
$208
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/288:00 pm
PIT
- MDW
Nonstop1h 30m
Southwest
Mon 6/13:50 pm
MDW
- PIT
1 stop5h 25m
Southwest
Deal found 5/4![Southwest logo]()
$187
This Delta deal was found by Cheapflights users on 4/30. 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 5/2812:01 pm
PIT
- MDW
1 stop5h 11m
Delta
Mon 6/16:36 pm
MDW
- PIT
1 stop3h 02m
Delta
Deal found 4/30![Delta logo]()
$197
This Delta deal was found by Cheapflights users on 4/29. 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 5/2812:01 pm
PIT
- ORD
1 stop5h 55m
Delta
Mon 6/17:07 am
ORD
- PIT
1 stop4h 37m
Delta
Deal found 4/29![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 5/1. 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.
Thu 5/285:55 am
PIT
- ORD
1 stop7h 55m
Southwest
Sat 5/301:55 pm
ORD
- PIT
2 stops8h 10m
Southwest
Deal found 5/1![Southwest logo]()
$208
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/15:00 pm
PIT
- MDW
1 stop4h 20m
Southwest
Tue 6/210:10 am
MDW
- PIT
2 stops6h 45m
Southwest
Deal found 5/4![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 5/1. 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.
Mon 6/15:55 am
PIT
- ORD
1 stop7h 55m
Southwest
Wed 6/32:40 pm
ORD
- PIT
1 stop5h 40m
Southwest
Deal found 5/1![Southwest logo]()
$202
This Southwest deal was found by Cheapflights users on 4/30. 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.
Tue 6/27:10 pm
PIT
- MDW
Nonstop1h 30m
Southwest
Wed 6/36:20 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 4/30![Southwest logo]()
$200
This United Airlines deal was found by Cheapflights users on 4/30. 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 6/28:36 am
PIT
- ORD
Nonstop1h 54m
United Airlines
Wed 6/37:15 am
ORD
- PIT
Nonstop1h 43m
United Airlines
Deal found 4/30![United Airlines logo]()
$204
This Southwest deal was found by Cheapflights users on 5/1. 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.
Mon 6/81:45 pm
PIT
- MDW
1 stop6h 25m
Southwest
Wed 6/1011:50 am
MDW
- PIT
1 stop6h 15m
Southwest
Deal found 5/1![Southwest logo]()
$212
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 May 4, 2026.
Search for one-way flight options from Pittsburgh to Chicago. Find affordable one-way fares based on user searches. Data last updated May 4, 2026.
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/37:10 pm
PIT
- MDW
Nonstop1h 30m
Southwest
Deal found 5/4![Southwest logo]()
$69
This American Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:00 am
PIT
- ORD
Nonstop1h 55m
American Airlines
Deal found 5/3![American Airlines logo]()
$69
This Delta deal was found by Cheapflights users on 4/29. 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 5/2611:10 am
PIT
- MDW
1 stop7h 46m
Delta
Deal found 4/29![Delta logo]()
$79
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 6/96:20 pm
PIT
- ORD
1 stop6h 39m
Delta
Deal found 5/3![Delta logo]()
$79
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 6/96:30 am
PIT
- MDW
2 stops8h 05m
Southwest
Deal found 5/3![Southwest logo]()
$84
This Southwest deal was found by Cheapflights users on 4/30. 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 5/281:35 pm
PIT
- MDW
Nonstop1h 30m
Southwest
Deal found 4/30![Southwest logo]()
$89
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Sat 6/63:56 pm
PIT
- ORD
Nonstop1h 51m
American Airlines
Deal found 4/30![American Airlines logo]()
$89
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Sat 5/238:37 pm
PIT
- ORD
Nonstop2h 02m
American Airlines
Deal found 4/30![American Airlines logo]()
$90
This Super.com deal was found by Cheapflights users on 5/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/178:15 pm
PIT
- MDW
1 stop20h 42m
Frontier
Deal found 5/1![Frontier logo]()
$95
This Delta deal was found by Cheapflights users on 4/29. 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.
Sat 6/66:30 am
PIT
- MDW
1 stop3h 13m
Delta
Deal found 4/29![Delta logo]()
$99
This Delta deal was found by Cheapflights users on 4/29. 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.
Sat 6/66:07 pm
PIT
- ORD
1 stop3h 07m
Delta
Deal found 4/29![Delta logo]()
$99
This United Airlines deal was found by Cheapflights users on 4/30. 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 5/267:39 pm
PIT
- ORD
Nonstop1h 57m
United Airlines
Deal found 4/30![United Airlines logo]()
$104
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 May 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $182 (Southwest) |
One-way from | $69 (Southwest) |
Popular in | December |
Cheapest in | August |
Average price | $307 |
Good round-trip deal | $354 or less |
Good one-way deal | $210 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 May 4, 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 - MDW
PITMDW
Pittsburgh
Sat 5/23
10:31 am-12:42 pm
1 stop3h 11m
Chicago Midway
Mon 5/25
1:22 pm-6:49 pm
1 stop4h 27m
$197
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Sat 6/6
11:29 am-4:56 pm
1 stop6h 27m
Chicago O'Hare Intl
Mon 6/8
7:17 pm-12:07 am
1 stop3h 50m
$197
Quickest round-trip
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Fri 5/29
8:00 pm-8:30 pm
Nonstop1h 30m
Chicago Midway
Tue 6/2
12:45 pm-3:10 pm
Nonstop1h 25m
$240
PittsburghChicago
PIT - RFD
PITRFD
Pittsburgh
Fri 5/29
9:29 pm-9:21 am
1 stop12h 52m
Chicago Greater Rockford
Sun 5/31
9:21 am-11:06 pm
1 stop12h 45m
$246
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Fri 6/19
12:25 pm-6:55 pm
1 stop7h 30m
Chicago Midway
Tue 6/23
5:10 pm-9:45 pm
1 stop3h 35m
$260
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Fri 6/5
8:15 pm-8:45 pm
Nonstop1h 30m
Chicago Midway
Mon 6/8
7:45 am-10:15 am
Nonstop1h 30m
$260
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Sat 9/5
4:50 pm-9:34 pm
1 stop5h 44m
Chicago O'Hare Intl
Tue 9/8
7:10 am-3:40 pm
1 stop7h 30m
$260
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Fri 6/19
12:25 pm-4:26 pm
1 stop5h 01m
Chicago O'Hare Intl
Tue 6/23
12:27 pm-6:48 pm
1 stop5h 21m
$260
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Fri 5/29
5:55 am-12:50 pm
1 stop7h 55m
Chicago O'Hare Intl
Tue 6/2
2:40 pm-9:20 pm
1 stop5h 40m
$265
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Sat 5/23
4:00 pm-4:30 pm
Nonstop1h 30m
Chicago Midway
Sun 5/24
3:45 pm-10:40 pm
1 stop5h 55m
$270
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 May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Pittsburgh-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Pittsburgh-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Pittsburgh-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Pittsburgh-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Pittsburgh-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Pittsburgh to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Pittsburgh with our price prediction graph.
PIT-CHI
PIT-MDW
PIT-ORD
PIT-RFD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Pittsburgh to Chicago
PIT-CHI
PIT-MDW
PIT-ORD
PIT-RFD
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 61 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Pittsburgh to Chicago?
Currently, August is the cheapest month in which you can book a flight from Pittsburgh to Chicago (average of $61). Flying from Pittsburgh to Chicago in April is currently the most expensive (average of $145). 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 May 4, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 21% on flights from Pittsburgh to Chicago by exploring options for tickets in the evening.
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 May 2, 2026.
Travelers seeking maximum savings on their Pittsburgh to Chicago flight should consider departing on Wednesday at noon when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
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 May 4, 2026.
The most flights from PIT to CHI are scheduled on a Monday (62 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (49 on average).
How much does it cost to fly round-trip from Pittsburgh to Chicago?
How often are flights from Pittsburgh to Chicago delayed?
About 10% of weekly flights between Pittsburgh and Chicago have experienced delays in the past year, with the average delay time being 132 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.
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 May 4, 2026.
Read through reviews of airlines operating flights from Pittsburgh to Chicago, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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
Hammond
Porter
Browse thousands of different options on Cheapflights for your next trip
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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 May 4, 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 May 4, 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 May 4, 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 2,558,603 searches. Data last updated May 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$92 | Average$289 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$97 | Average$318 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$137 | Average$312 | FlexibilityNo cancel fee | On-time69% |