$69+ Cheap flights from Pittsburgh (PIT) to Illinois
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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — ORD
May 30 — Jun 61
Round-trip
1 adult, Economy
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Cheapest flights from Pittsburgh to IllinoisExplore the most affordable flight options available from Pittsburgh to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 30, 2026.
Explore the most affordable flight options available from Pittsburgh to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 30, 2026.
This Southwest deal was found by Cheapflights users on 4/25. 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.
Sat 5/234:00 pm
PIT
- MDW
Nonstop1h 30m
Southwest
Sat 5/307:45 am
MDW
- PIT
Nonstop1h 20m
Southwest
Deal found 4/25![Southwest logo]()
$177
This United Airlines deal was found by Cheapflights users on 4/26. 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.
Thu 5/282:05 pm
PIT
- ORD
Nonstop1h 45m
United Airlines
Mon 6/19:15 pm
ORD
- PIT
Nonstop1h 44m
United Airlines
Deal found 4/26![United Airlines logo]()
$177
This American Airlines deal was found by Cheapflights users on 4/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:11 pm
PIT
- ORD
Nonstop1h 54m
American Airlines
Mon 5/183:47 pm
ORD
- PIT
Nonstop1h 44m
American Airlines
Deal found 4/25![American Airlines logo]()
$179
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:40 am
PIT
- MDW
1 stop5h 00m
Southwest
Thu 6/47:50 am
MDW
- PIT
2 stops6h 00m
Southwest
Deal found 4/29![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 4/27. 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.
Thu 5/215:55 am
PIT
- ORD
1 stop7h 55m
Southwest
Tue 5/262:40 pm
ORD
- PIT
1 stop5h 40m
Southwest
Deal found 4/27![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 4/27. 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.
Thu 5/2812:35 pm
PIT
- MDW
1 stop5h 25m
Southwest
Mon 6/17:40 am
MDW
- PIT
Nonstop1h 20m
Southwest
Deal found 4/27![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:55 pm
PIT
- MDW
1 stop4h 20m
Southwest
Tue 6/27:50 am
MDW
- PIT
2 stops8h 30m
Southwest
Deal found 4/27![Southwest logo]()
$188
This Southwest deal was found by Cheapflights users on 4/28. 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 6/18:00 pm
PIT
- MDW
Nonstop1h 30m
Southwest
Wed 6/36:20 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 4/28![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 4/27. 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.
Thu 5/2812:35 pm
PIT
- MDW
1 stop5h 25m
Southwest
Tue 6/21:55 pm
MDW
- PIT
1 stop6h 25m
Southwest
Deal found 4/27![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 4/28. 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 5/2812:01 pm
PIT
- ORD
1 stop5h 55m
Delta
Mon 6/15:30 am
ORD
- PIT
1 stop6h 14m
Delta
Deal found 4/28![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 4/26. 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 5/306:08 pm
PIT
- STL
1 stop4h 13m
United Airlines
Wed 6/310:20 am
STL
- PIT
1 stop5h 45m
United Airlines
Deal found 4/26![United Airlines logo]()
$197
This Southwest deal was found by Cheapflights users on 4/27. 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 5/206:40 am
PIT
- MDW
2 stops10h 10m
Southwest
Thu 5/217:40 am
MDW
- PIT
Nonstop1h 20m
Southwest
Deal found 4/27![Southwest logo]()
$198
Best flights from Pittsburgh to IllinoisDiscover carefully curated flight deals from Pittsburgh to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 30, 2026.
Discover carefully curated flight deals from Pittsburgh to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 30, 2026.
This Southwest deal was found by Cheapflights users on 4/26. 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 5/237:05 pm
PIT
- MDW
1 stop4h 30m
Southwest
Mon 5/2512:50 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 4/26![Southwest logo]()
$187
This United Airlines deal was found by Cheapflights users on 4/26. 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.
Tue 5/192:08 pm
PIT
- ORD
Nonstop1h 47m
United Airlines
Wed 5/2010:35 am
ORD
- PIT
Nonstop1h 36m
United Airlines
Deal found 4/26![United Airlines logo]()
$207
This Delta deal was found by Cheapflights users on 4/28. 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 9/237:00 am
PIT
- ORD
1 stop6h 08m
Delta
Sat 9/2611:10 am
ORD
- PIT
1 stop5h 00m
Delta
Deal found 4/28![Delta logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Wed 7/226:54 pm
PIT
- RFD
1 stop16h 43m
Multiple Airlines
Sun 7/269:19 am
RFD
- PIT
1 stop12h 39m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$262
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 6/59:27 pm
PIT
- RFD
1 stop12h 50m
Allegiant Air
Sun 6/79:19 am
RFD
- PIT
1 stop12h 45m
Allegiant Air
Deal found 4/29![Allegiant Air logo]()
$281
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/268:42 pm
PIT
- EVV
1 stop4h 39m
American Airlines
Mon 6/296:50 am
EVV
- PIT
1 stop7h 08m
American Airlines
Deal found 4/29![American Airlines logo]()
$367
This Southwest 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 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
Thu 6/47:45 am
MDW
- PIT
Nonstop1h 30m
Southwest
Deal found 4/29![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 4/26. 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 5/185:55 am
PIT
- ORD
1 stop7h 55m
Southwest
Sat 5/301:55 pm
ORD
- PIT
2 stops8h 10m
Southwest
Deal found 4/26![Southwest logo]()
$208
This United Airlines deal was found by Cheapflights users on 4/28. 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.
Wed 9/162:05 pm
PIT
- ORD
Nonstop1h 42m
United Airlines
Fri 9/187:15 am
ORD
- PIT
Nonstop1h 39m
United Airlines
Deal found 4/28![United Airlines logo]()
$240
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:05 pm
PIT
- ORD
1 stop6h 52m
Delta
Tue 9/87:10 am
ORD
- PIT
1 stop7h 30m
Delta
Deal found 4/25![Delta logo]()
$260
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.
Wed 8/56:54 pm
PIT
- RFD
1 stop16h 53m
Multiple Airlines
Sun 8/99:21 am
RFD
- PIT
1 stop12h 49m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
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 4/26![Allegiant Air logo]()
$281
This Delta deal was found by Cheapflights users on 4/28. 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.
Fri 5/291:40 pm
PIT
- ORD
1 stop5h 55m
Delta
Tue 6/26:06 pm
ORD
- PIT
1 stop5h 39m
Delta
Deal found 4/28![Delta logo]()
$260
This Southwest 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 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 6/1010:00 am
MDW
- PIT
2 stops8h 05m
Southwest
Deal found 4/29![Southwest logo]()
$237
This United Airlines deal was found by Cheapflights users on 4/28. 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 5/266:49 am
PIT
- STL
1 stop6h 22m
United Airlines
Wed 5/2711:25 am
STL
- PIT
1 stop4h 45m
United Airlines
Deal found 4/28![United Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:10 pm
PIT
- ORD
1 stop5h 10m
Delta
Mon 5/257:00 am
ORD
- PIT
1 stop3h 13m
Delta
Deal found 4/26![Delta logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Wed 7/296:54 pm
PIT
- RFD
1 stop16h 43m
Multiple Airlines
Sun 8/211:27 am
RFD
- PIT
1 stop29h 22m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$295
This Southwest 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 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 5/246:10 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 4/29![Southwest logo]()
$260
This Delta deal was found by Cheapflights users on 4/27. 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.
Wed 9/234:25 pm
PIT
- ORD
1 stop6h 20m
Delta
Sun 9/2711:30 am
ORD
- PIT
1 stop6h 26m
Delta
Deal found 4/27![Delta logo]()
$271
This United Airlines deal was found by Cheapflights users on 4/28. 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.
Thu 9/177:00 am
PIT
- MLI
1 stop3h 54m
United Airlines
Sun 9/206:30 am
MLI
- PIT
1 stop5h 34m
United Airlines
Deal found 4/28![United Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 4/25. 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.
Sat 5/167:15 am
PIT
- STL
Nonstop1h 50m
Southwest
Mon 5/187:40 pm
STL
- PIT
Nonstop1h 35m
Southwest
Deal found 4/25![Southwest logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 5/298:15 pm
PIT
- RFD
1 stop14h 06m
Multiple Airlines
Mon 6/18:35 am
RFD
- PIT
1 stop14h 03m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$322
This Delta deal was found by Cheapflights users on 4/26. 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.
Fri 6/511:10 am
PIT
- MDW
1 stop7h 46m
Delta
Mon 6/86:58 pm
MDW
- PIT
1 stop4h 09m
Delta
Deal found 4/26![Delta logo]()
$280
This United Airlines deal was found by Cheapflights users on 4/28. 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 9/187:00 am
PIT
- MLI
1 stop3h 54m
United Airlines
Sun 9/208:25 am
MLI
- PIT
1 stop3h 39m
United Airlines
Deal found 4/28![United Airlines logo]()
$321
This Southwest deal was found by Cheapflights users on 4/28. 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 5/295:00 pm
PIT
- MDW
1 stop6h 20m
Southwest
Mon 6/16:55 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 4/28![Southwest logo]()
$270
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Fri 5/229:29 pm
PIT
- RFD
1 stop12h 52m
Allegiant Air
Wed 5/274:45 pm
RFD
- PIT
2 stops29h 21m
Allegiant Air
Deal found 4/26![Allegiant Air logo]()
$396
This Delta deal was found by Cheapflights users on 4/26. 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.
Fri 6/57:50 pm
PIT
- ORD
1 stop5h 09m
Delta
Mon 6/87:17 pm
ORD
- PIT
1 stop3h 50m
Delta
Deal found 4/26![Delta logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Wed 7/810:00 am
PIT
- RFD
1 stop6h 57m
Multiple Airlines
Fri 7/107:50 pm
RFD
- PIT
1 stop21h 25m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$365
This Southwest deal was found by Cheapflights users on 4/27. 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.
Thu 5/286:50 pm
PIT
- STL
1 stop6h 05m
Southwest
Mon 6/110:15 am
STL
- PIT
Nonstop1h 40m
Southwest
Deal found 4/27![Southwest logo]()
$275
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/235:46 pm
PIT
- STL
1 stop3h 53m
Delta
Fri 6/266:10 pm
STL
- PIT
1 stop4h 57m
Delta
Deal found 4/27![Delta logo]()
$280
Last-minute flights from Pittsburgh to IllinoisDiscover last-minute flight deals from Pittsburgh to Illinois. Data last updated April 30, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Illinois. Data last updated April 30, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 4/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:11 pm
PIT
- ORD
Nonstop1h 54m
American Airlines
Mon 5/183:47 pm
ORD
- PIT
Nonstop1h 44m
American Airlines
Deal found 4/25![American Airlines logo]()
$179
This Southwest deal was found by Cheapflights users on 4/27. 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 5/206:40 am
PIT
- MDW
2 stops10h 10m
Southwest
Thu 5/217:40 am
MDW
- PIT
Nonstop1h 20m
Southwest
Deal found 4/27![Southwest logo]()
$198
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/209:19 am
PIT
- ORD
Nonstop1h 49m
American Airlines
Tue 5/266:40 am
ORD
- PIT
1 stop4h 28m
American Airlines
Deal found 4/28![American Airlines logo]()
$202
This Southwest deal was found by Cheapflights users on 4/27. 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.
Thu 5/215:55 am
PIT
- ORD
1 stop7h 55m
Southwest
Tue 5/262:40 pm
ORD
- PIT
1 stop5h 40m
Southwest
Deal found 4/27![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 4/28. 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 5/218:40 am
PIT
- MDW
Nonstop1h 30m
Southwest
Tue 5/266:20 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 4/28![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 4/25. 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.
Sat 5/234:00 pm
PIT
- MDW
Nonstop1h 30m
Southwest
Sat 5/307:45 am
MDW
- PIT
Nonstop1h 20m
Southwest
Deal found 4/25![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:55 pm
PIT
- MDW
1 stop4h 20m
Southwest
Tue 6/27:50 am
MDW
- PIT
2 stops8h 30m
Southwest
Deal found 4/27![Southwest logo]()
$188
This United Airlines deal was found by Cheapflights users on 4/26. 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.
Thu 5/282:05 pm
PIT
- ORD
Nonstop1h 45m
United Airlines
Mon 6/19:15 pm
ORD
- PIT
Nonstop1h 44m
United Airlines
Deal found 4/26![United Airlines logo]()
$177
This Southwest deal was found by Cheapflights users on 4/27. 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.
Thu 5/2812:35 pm
PIT
- MDW
1 stop5h 25m
Southwest
Mon 6/17:40 am
MDW
- PIT
Nonstop1h 20m
Southwest
Deal found 4/27![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 4/27. 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.
Thu 5/2812:35 pm
PIT
- MDW
1 stop5h 25m
Southwest
Tue 6/21:55 pm
MDW
- PIT
1 stop6h 25m
Southwest
Deal found 4/27![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 4/28. 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 5/2812:01 pm
PIT
- ORD
1 stop5h 55m
Delta
Mon 6/15:30 am
ORD
- PIT
1 stop6h 14m
Delta
Deal found 4/28![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 4/26. 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 5/306:08 pm
PIT
- STL
1 stop4h 13m
United Airlines
Wed 6/310:20 am
STL
- PIT
1 stop5h 45m
United Airlines
Deal found 4/26![United Airlines logo]()
$197
One-way flights from Pittsburgh to IllinoisSearch for one-way flight options from Pittsburgh to Illinois. Find affordable one-way fares based on user searches. Data last updated April 30, 2026.
Search for one-way flight options from Pittsburgh to Illinois. Find affordable one-way fares based on user searches. Data last updated April 30, 2026.
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/267:10 pm
PIT
- MDW
Nonstop1h 30m
Southwest
Deal found 4/29![Southwest logo]()
$69
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/268:37 pm
PIT
- ORD
Nonstop2h 02m
American Airlines
Deal found 4/29![American Airlines logo]()
$69
This Delta deal was found by Cheapflights users on 4/28. 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 6/2410:25 am
PIT
- MDW
1 stop3h 16m
Delta
Deal found 4/28![Delta logo]()
$79
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.
Wed 6/243:35 pm
PIT
- ORD
1 stop7h 59m
Delta
Deal found 4/30![Delta logo]()
$79
This Southwest deal was found by Cheapflights users on 4/27. 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.
Thu 5/218:40 am
PIT
- MDW
Nonstop1h 30m
Southwest
Deal found 4/27![Southwest logo]()
$89
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/66:00 am
PIT
- ORD
Nonstop1h 55m
American Airlines
Deal found 4/29![American Airlines logo]()
$89
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:59 am
PIT
- ORD
Nonstop2h 01m
American Airlines
Deal found 4/29![American Airlines logo]()
$91
This Super.com deal was found by Cheapflights users on 4/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/138:15 pm
PIT
- ORD
1 stop27h 58m
Frontier
Deal found 4/28![Frontier logo]()
$95
This Delta deal was found by Cheapflights users on 4/28. 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 5/234:45 pm
PIT
- MDW
1 stop5h 24m
Delta
Deal found 4/28![Delta logo]()
$99
This Delta deal was found by Cheapflights users on 4/28. 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 5/236:07 pm
PIT
- ORD
1 stop3h 07m
Delta
Deal found 4/28![Delta logo]()
$99
This Trip.com deal was found by Cheapflights users on 4/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/138:15 pm
PIT
- STL
1 stop29h 06m
Frontier
Deal found 4/27![Frontier logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Wed 6/246:54 pm
PIT
- RFD
1 stop16h 43m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$101
Find flight deals from Pittsburgh to Illinois
Keep the following information in mind while searching for Pittsburgh to Illinois flight deals. Data was last updated April 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $177 (Southwest) |
One-way from | $69 (Southwest) |
Popular in | December |
Cheapest in | August |
Average price | $316 |
Good round-trip deal | $351 or less |
Good one-way deal | $222 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Pittsburgh to Illinois 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 April 30, 2026.
Use the filters below to find and compare flights from Pittsburgh to Illinois that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Sat 5/23
7:05 pm-10:35 pm
1 stop4h 30m
Chicago Midway
Mon 5/25
12:50 pm-3:15 pm
Nonstop1h 25m
$187
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Tue 6/2
7:10 pm-7:40 pm
Nonstop1h 30m
Chicago Midway
Thu 6/4
7:45 am-10:15 am
Nonstop1h 30m
$192
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Tue 5/19
2:08 pm-2:55 pm
Nonstop1h 47m
Chicago O'Hare Intl
Wed 5/20
10:35 am-1:11 pm
Nonstop1h 36m
$207
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Mon 5/18
5:55 am-12:50 pm
1 stop7h 55m
Chicago O'Hare Intl
Sat 5/30
1:55 pm-11:05 pm
2 stops8h 10m
$208
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Mon 6/8
1:45 pm-7:10 pm
1 stop6h 25m
Chicago Midway
Wed 6/10
10:00 am-7:05 pm
2 stops8h 05m
$237
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Wed 9/16
2:05 pm-2:47 pm
Nonstop1h 42m
Chicago O'Hare Intl
Fri 9/18
7:15 am-9:54 am
Nonstop1h 39m
$240
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Wed 9/23
7:00 am-12:08 pm
1 stop6h 08m
Chicago O'Hare Intl
Sat 9/26
11:10 am-5:10 pm
1 stop5h 00m
$260
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Sat 9/5
6:05 pm-11:57 pm
1 stop6h 52m
Chicago O'Hare Intl
Tue 9/8
7:10 am-3:40 pm
1 stop7h 30m
$260
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Fri 5/29
1:40 pm-6:35 pm
1 stop5h 55m
Chicago O'Hare Intl
Tue 6/2
6:06 pm-12:45 am
1 stop5h 39m
$260
Quickest round-trip
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Sat 5/23
4:00 pm-4:30 pm
Nonstop1h 30m
Chicago Midway
Sun 5/24
6:10 pm-8:35 pm
Nonstop1h 25m
$260
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Pittsburgh to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Pittsburgh with our price prediction graph.
PIT-MDW
PIT-ORD
PIT-STL
PIT-RFD
PIT-MLI
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 Illinois
PIT-USIL
PIT-MDW
PIT-ORD
PIT-STL
PIT-RFD
How far ahead should I book a flight from Pittsburgh to Illinois?
To ensure you get the cheapest price possible for a flight from Pittsburgh to Illinois, you should look to book at least 61 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Pittsburgh to Illinois?
Currently, August is the cheapest month in which you can book a flight from Pittsburgh to Illinois (average of $61). Flying from Pittsburgh to Illinois 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 IL?
Find hourly flight availability from Pittsburgh to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 30, 2026.
It’s optimal to fly from Pittsburgh to Illinois in the evening. By choosing this option you can save up to 21% on the cost of your flight, compared to a flight at noon.
What is the cheapest day to fly from Pittsburgh to Illinois?
Use this chart to determine the cheapest time to fly round-trip from Pittsburgh to Illinois. Price data was last updated on April 25, 2026.
Travelers seeking maximum savings on their Pittsburgh to Illinois flight should consider departing on Wednesday 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.
Weekly flight availability from Pittsburgh to Illinois
Explore weekly flight availability from Pittsburgh to Illinois. 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 April 30, 2026.
The most flights from PIT to USIL are scheduled on a Wednesday (56 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (14 on average).
How much does it cost to fly round-trip from Pittsburgh to Illinois?
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated April 30, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican Airlines from Pittsburgh to Illinois. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
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 Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Pittsburgh to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Illinois by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Pittsburgh to Illinois by cabin class
Find flights from Pittsburgh to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Pittsburgh and Illinois flights
Browse other Pittsburgh and Illinois flight options. Last updated on April 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Pittsburgh to Illinois flights
Consider these flights traveling from Pittsburgh to Illinois.
Top 3 airlines flying from Pittsburgh to Illinois
Discover the top 3 airlines that operate flights from Pittsburgh to Illinois. 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 April 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$91 | Average$402 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$97 | Average$323 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$137 | Average$327 | FlexibilityNo cancel fee | On-time69% |