$88+ Cheap flights from Chicago (CHI) to Pennsylvania
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 7/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PHL
Jul 20 — Jul 271
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Pennsylvania with Cheapflights
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Cheapest flights from Chicago to PennsylvaniaExplore the most affordable flight options available from Chicago to Pennsylvania. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 20, 2026.
Explore the most affordable flight options available from Chicago to Pennsylvania. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 20, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/259:39 am
ORD
- JFK
Nonstop2h 19m
JetBlue
Tue 8/253:30 pm
JFK
- ORD
Nonstop2h 50m
JetBlue
Deal found 6/15![JetBlue logo]()
$177
This flygcity.se deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Mon 8/108:00 pm
JFK
- ORD
Nonstop2h 55m
JetBlue
Deal found 6/15![JetBlue logo]()
$178
This Cheapflightsfares deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Wed 7/223:40 pm
JFK
- ORD
Nonstop2h 54m
JetBlue
Deal found 6/20![JetBlue logo]()
$179
This flygcity.se deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Tue 7/211:20 pm
JFK
- ORD
1 stop6h 55m
JetBlue
Deal found 6/16![JetBlue logo]()
$180
This American Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/212:59 pm
ORD
- LGA
Nonstop2h 20m
American Airlines
Tue 7/219:29 pm
LGA
- ORD
Nonstop3h 01m
American Airlines
Deal found 6/16![American Airlines logo]()
$182
This Cheapflightsfares deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/149:40 am
ORD
- JFK
Nonstop2h 19m
JetBlue
Sat 7/188:00 pm
JFK
- ORD
Nonstop2h 58m
JetBlue
Deal found 6/17![JetBlue logo]()
$182
This Cheapflightsfares deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1510:56 am
ORD
- JFK
1 stop5h 55m
JetBlue
Wed 7/158:00 pm
JFK
- ORD
Nonstop2h 58m
JetBlue
Deal found 6/18![JetBlue logo]()
$183
This American Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/141:14 pm
ORD
- LGA
Nonstop2h 20m
American Airlines
Wed 7/159:44 am
LGA
- ORD
Nonstop2h 46m
American Airlines
Deal found 6/19![American Airlines logo]()
$185
This Super.com deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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.
Sat 7/116:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Tue 7/148:00 pm
JFK
- ORD
Nonstop2h 58m
JetBlue
Deal found 6/19![JetBlue logo]()
$185
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 9/236:00 am
ORD
- JFK
Nonstop2h 21m
Delta
Sat 10/317:35 pm
JFK
- ORD
Nonstop2h 58m
Delta
Deal found 6/18![Delta logo]()
$186
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/1511:30 am
ORD
- LGA
Nonstop2h 30m
Delta
Wed 7/158:45 pm
LGA
- ORD
Nonstop2h 51m
Delta
Deal found 6/19![Delta logo]()
$187
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/145:15 am
MDW
- LGA
Nonstop2h 00m
Southwest
Wed 7/151:35 pm
LGA
- MDW
Nonstop2h 25m
Southwest
Deal found 6/19![Southwest logo]()
$187
Best flights from Chicago to PennsylvaniaDiscover carefully curated flight deals from Chicago to Pennsylvania that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 20, 2026.
Discover carefully curated flight deals from Chicago to Pennsylvania that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 20, 2026.
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/117:00 am
ORD
- LGA
Nonstop2h 14m
Delta
Tue 7/146:00 am
LGA
- ORD
Nonstop2h 32m
Delta
Deal found 6/19![Delta logo]()
$187
This JetBlue deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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.
Wed 8/56:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Sat 8/82:29 pm
JFK
- ORD
Nonstop2h 46m
JetBlue
Deal found 6/17![JetBlue logo]()
$187
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 8/86:00 am
MDW
- LGA
Nonstop2h 00m
Southwest
Mon 8/106:00 am
LGA
- MDW
Nonstop2h 15m
Southwest
Deal found 6/15![Southwest logo]()
$195
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/297:00 am
ORD
- LGA
Nonstop2h 17m
United Airlines
Sun 8/26:10 am
LGA
- ORD
Nonstop2h 39m
United Airlines
Deal found 6/15![United Airlines logo]()
$197
This Expedia deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/912:03 pm
MDW
- IAD
1 stop11h 25m
Frontier
Tue 10/137:00 am
IAD
- MDW
1 stop4h 58m
Frontier
Deal found 6/19![Frontier logo]()
$246
This KAYAK deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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.
Fri 7/178:09 pm
ORD
- EWR
Nonstop2h 21m
American Airlines
Sun 7/265:30 am
EWR
- ORD
Nonstop2h 45m
American Airlines
Deal found 6/17![American Airlines logo]()
$297
This United Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 9/25:00 pm
ORD
- LGA
Nonstop2h 25m
United Airlines
Fri 9/47:29 pm
LGA
- ORD
Nonstop2h 44m
United Airlines
Deal found 6/18![United Airlines logo]()
$197
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/77:45 pm
MDW
- LGA
Nonstop2h 15m
Southwest
Sat 7/116:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 6/15![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 8/266:00 am
ORD
- JFK
Nonstop2h 24m
Delta
Fri 8/287:35 pm
JFK
- ORD
Nonstop3h 17m
Delta
Deal found 6/17![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/256:40 pm
MDW
- LGA
Nonstop2h 10m
Southwest
Sun 7/266:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 6/19![Southwest logo]()
$197
This United Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 9/1012:16 pm
ORD
- EWR
Nonstop2h 21m
United Airlines
Sun 9/1311:00 pm
EWR
- ORD
Nonstop2h 28m
United Airlines
Deal found 6/18![United Airlines logo]()
$197
This JetBlue deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/179:42 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Mon 7/208:00 pm
JFK
- ORD
Nonstop2h 58m
JetBlue
Deal found 6/19![JetBlue logo]()
$217
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/261:00 pm
ORD
- JFK
Nonstop2h 33m
Delta
Mon 8/317:35 pm
JFK
- ORD
Nonstop3h 17m
Delta
Deal found 6/16![Delta logo]()
$205
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 8/275:00 am
MDW
- LGA
Nonstop2h 00m
Southwest
Mon 8/318:55 pm
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 6/18![Southwest logo]()
$203
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 8/116:42 pm
MDW
- EWR
1 stop3h 43m
Delta
Wed 8/126:00 am
EWR
- MDW
1 stop4h 59m
Delta
Deal found 6/18![Delta logo]()
$207
This United Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/136:00 pm
ORD
- LGA
Nonstop2h 25m
United Airlines
Tue 7/149:25 pm
LGA
- ORD
Nonstop2h 33m
United Airlines
Deal found 6/18![United Airlines logo]()
$210
This JetBlue deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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.
Mon 6/296:00 am
ORD
- JFK
Nonstop2h 20m
JetBlue
Sun 7/57:00 am
JFK
- ORD
Nonstop2h 45m
JetBlue
Deal found 6/15![JetBlue logo]()
$237
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 8/46:05 am
MDW
- EWR
1 stop5h 13m
Delta
Wed 8/56:00 am
EWR
- MDW
1 stop4h 17m
Delta
Deal found 6/19![Delta logo]()
$207
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 6/307:45 pm
MDW
- LGA
Nonstop2h 10m
Southwest
Tue 7/219:30 pm
LGA
- MDW
Nonstop2h 30m
Southwest
Deal found 6/15![Southwest logo]()
$212
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/19:30 pm
ORD
- EWR
Nonstop2h 23m
United Airlines
Mon 7/67:59 am
EWR
- ORD
Nonstop2h 44m
United Airlines
Deal found 6/15![United Airlines logo]()
$212
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/77:00 am
ORD
- LGA
Nonstop2h 14m
Delta
Wed 7/88:45 pm
LGA
- ORD
Nonstop2h 51m
Delta
Deal found 6/19![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 8/215:00 am
MDW
- LGA
Nonstop2h 00m
Southwest
Sun 8/237:20 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 6/19![Southwest logo]()
$217
This United Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/231:00 pm
ORD
- LGA
Nonstop2h 22m
United Airlines
Fri 7/249:25 pm
LGA
- ORD
Nonstop2h 33m
United Airlines
Deal found 6/19![United Airlines logo]()
$220
This JetBlue deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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.
Tue 7/289:40 am
ORD
- JFK
Nonstop2h 19m
JetBlue
Tue 7/283:40 pm
JFK
- ORD
Nonstop2h 54m
JetBlue
Deal found 6/18![JetBlue logo]()
$267
This Delta deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 8/87:05 am
ORD
- LGA
Nonstop2h 14m
Delta
Mon 8/108:30 pm
LGA
- ORD
Nonstop2h 54m
Delta
Deal found 6/17![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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
ORD
- LGA
Nonstop2h 17m
United Airlines
Mon 9/216:00 am
LGA
- ORD
1 stop4h 38m
United Airlines
Deal found 6/15![United Airlines logo]()
$221
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 8/63:20 pm
MDW
- LGA
1 stop7h 00m
Southwest
Wed 8/129:35 pm
LGA
- MDW
Nonstop2h 15m
Southwest
Deal found 6/17![Southwest logo]()
$222
This JetBlue deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 9/186:00 am
ORD
- JFK
1 stop7h 07m
JetBlue
Fri 9/188:15 pm
JFK
- ORD
Nonstop2h 51m
JetBlue
Deal found 6/15![JetBlue logo]()
$271
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/296:00 am
ORD
- JFK
Nonstop2h 24m
Delta
Sun 8/27:27 am
JFK
- ORD
Nonstop2h 53m
Delta
Deal found 6/15![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 8/296:00 am
MDW
- LGA
Nonstop2h 00m
Southwest
Wed 9/26:00 am
LGA
- MDW
Nonstop2h 15m
Southwest
Deal found 6/19![Southwest logo]()
$222
Last-minute flights from Chicago to PennsylvaniaDiscover last-minute flight deals from Chicago to Pennsylvania. Data last updated June 20, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Pennsylvania. Data last updated June 20, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/77:10 am
ORD
- EWR
Nonstop2h 20m
United Airlines
Sat 7/116:15 pm
EWR
- ORD
Nonstop2h 55m
United Airlines
Deal found 6/15![United Airlines logo]()
$187
This Cheapflightsfares deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/89:40 am
ORD
- JFK
Nonstop2h 19m
JetBlue
Sat 7/117:05 am
JFK
- ORD
Nonstop2h 46m
JetBlue
Deal found 6/17![JetBlue logo]()
$182
This Super.com deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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.
Sat 7/116:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Tue 7/148:00 pm
JFK
- ORD
Nonstop2h 58m
JetBlue
Deal found 6/19![JetBlue logo]()
$185
This American Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/141:14 pm
ORD
- LGA
Nonstop2h 20m
American Airlines
Wed 7/159:44 am
LGA
- ORD
Nonstop2h 46m
American Airlines
Deal found 6/19![American Airlines logo]()
$185
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/145:15 am
MDW
- LGA
Nonstop2h 00m
Southwest
Wed 7/151:35 pm
LGA
- MDW
Nonstop2h 25m
Southwest
Deal found 6/19![Southwest logo]()
$187
This American Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/147:59 pm
ORD
- LGA
Nonstop2h 22m
American Airlines
Sat 7/189:23 pm
LGA
- ORD
Nonstop3h 06m
American Airlines
Deal found 6/19![American Airlines logo]()
$188
This Cheapflightsfares deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1510:56 am
ORD
- JFK
1 stop5h 55m
JetBlue
Wed 7/158:00 pm
JFK
- ORD
Nonstop2h 58m
JetBlue
Deal found 6/18![JetBlue logo]()
$183
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/156:00 am
ORD
- LGA
Nonstop2h 09m
Delta
Wed 7/226:00 am
LGA
- ORD
Nonstop2h 32m
Delta
Deal found 6/19![Delta logo]()
$187
This Delta deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 7/156:00 am
ORD
- JFK
Nonstop2h 24m
Delta
Wed 7/227:20 am
JFK
- ORD
Nonstop2h 53m
Delta
Deal found 6/17![Delta logo]()
$187
This Cheapflightsfares deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Wed 7/223:40 pm
JFK
- ORD
Nonstop2h 54m
JetBlue
Deal found 6/20![JetBlue logo]()
$179
This flygcity.se deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Tue 7/211:20 pm
JFK
- ORD
1 stop6h 55m
JetBlue
Deal found 6/16![JetBlue logo]()
$180
This American Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/212:59 pm
ORD
- LGA
Nonstop2h 20m
American Airlines
Tue 7/219:29 pm
LGA
- ORD
Nonstop3h 01m
American Airlines
Deal found 6/16![American Airlines logo]()
$182
One-way flights from Chicago to PennsylvaniaSearch for one-way flight options from Chicago to Pennsylvania. Find affordable one-way fares based on user searches. Data last updated June 20, 2026.
Search for one-way flight options from Chicago to Pennsylvania. Find affordable one-way fares based on user searches. Data last updated June 20, 2026.
This Super.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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.
Fri 7/178:58 pm
ORD
- PHL
Nonstop2h 23m
Frontier
Deal found 6/15![Frontier logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/38:00 pm
ORD
- PHL
Nonstop2h 32m
Frontier
Deal found 6/19![Frontier logo]()
$92
This Cheapflightsfares deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Deal found 6/17![JetBlue logo]()
$93
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/117:00 am
ORD
- LGA
Nonstop2h 14m
Delta
Deal found 6/19![Delta logo]()
$94
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 8/1512:10 pm
MDW
- LGA
Nonstop2h 10m
Southwest
Deal found 6/19![Southwest logo]()
$94
This JetBlue deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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.
Wed 8/1210:56 am
ORD
- PHL
1 stop8h 04m
JetBlue
Deal found 6/17![JetBlue logo]()
$94
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 8/121:00 pm
ORD
- JFK
Nonstop2h 33m
Delta
Deal found 6/19![Delta logo]()
$94
This American Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/77:00 am
ORD
- LGA
Nonstop2h 16m
American Airlines
Deal found 6/16![American Airlines logo]()
$95
This Super.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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.
Tue 7/710:56 am
ORD
- PHL
1 stop8h 09m
JetBlue
Deal found 6/15![JetBlue logo]()
$95
This American Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/76:42 am
ORD
- EWR
Nonstop2h 18m
American Airlines
Deal found 6/16![American Airlines logo]()
$95
This Super.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Tue 7/76:30 pm
ORD
- JFK
Nonstop2h 36m
JetBlue
Deal found 6/16![JetBlue logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 8/18:52 pm
ORD
- PHL
Nonstop2h 23m
Frontier
Deal found 6/17![Frontier logo]()
$96
Find flight deals from Chicago to Pennsylvania
Keep the following information in mind while searching for Chicago to Pennsylvania flight deals. Data was last updated June 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $177 (Cheapflightsfares) |
One-way from | $88 (Super.com) |
Popular in | March |
Cheapest in | October |
Average price | $367 |
Good round-trip deal | $240 or less |
Good one-way deal | $125 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Pennsylvania 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 June 20, 2026.
Use the filters below to find and compare flights from Chicago to Pennsylvania that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoNew York
ORD - LGA
ORDLGA
Chicago O'Hare Intl
Sat 7/11
7:00 am-10:14 am
Nonstop2h 14m
New York LaGuardia
Tue 7/14
6:00 am-7:32 am
Nonstop2h 32m
$187
ChicagoNew York
ORD - JFK
ORDJFK
Chicago O'Hare Intl
Wed 8/5
6:00 am-9:17 am
Nonstop2h 17m
New York John F Kennedy Intl
Sat 8/8
2:29 pm-4:15 pm
Nonstop2h 46m
$187
Quickest round-trip
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Sat 8/8
6:00 am-9:00 am
Nonstop2h 00m
New York LaGuardia
Mon 8/10
6:00 am-7:15 am
Nonstop2h 15m
$195
ChicagoNew York
ORD - LGA
ORDLGA
Chicago O'Hare Intl
Wed 7/29
7:00 am-10:17 am
Nonstop2h 17m
New York LaGuardia
Sun 8/2
6:10 am-7:49 am
Nonstop2h 39m
$197
ChicagoNew York
ORD - LGA
ORDLGA
Chicago O'Hare Intl
Wed 9/2
5:00 pm-8:25 pm
Nonstop2h 25m
New York LaGuardia
Fri 9/4
7:29 pm-9:13 pm
Nonstop2h 44m
$197
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Tue 7/7
7:45 pm-11:00 pm
Nonstop2h 15m
New York LaGuardia
Sat 7/11
6:00 am-7:20 am
Nonstop2h 20m
$197
ChicagoNew York
ORD - JFK
ORDJFK
Chicago O'Hare Intl
Wed 8/26
6:00 am-9:24 am
Nonstop2h 24m
New York John F Kennedy Intl
Fri 8/28
7:35 pm-9:52 pm
Nonstop3h 17m
$197
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Sat 7/25
6:40 pm-9:50 pm
Nonstop2h 10m
New York LaGuardia
Sun 7/26
6:00 am-7:20 am
Nonstop2h 20m
$197
ChicagoNewark
ORD - EWR
ORDEWR
Chicago O'Hare Intl
Thu 9/10
12:16 pm-3:37 pm
Nonstop2h 21m
Newark
Sun 9/13
11:00 pm-12:28 am
Nonstop2h 28m
$197
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Thu 8/27
5:00 am-8:00 am
Nonstop2h 00m
New York LaGuardia
Mon 8/31
8:55 pm-10:15 pm
Nonstop2h 20m
$203
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Pennsylvania
Have a flexible travel schedule? Discover the best time to fly to Pennsylvania from Chicago with our price prediction graph.
ORD-JFK
ORD-LGA
MDW-LGA
ORD-EWR
ORD-PHL
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 Chicago to Pennsylvania
CHI-USPA
ORD-JFK
ORD-LGA
MDW-LGA
ORD-EWR
What is the cheapest month to book a flight from Chicago to Pennsylvania?
Currently, October is the cheapest month in which you can book a flight from Chicago to Pennsylvania (average of $219). Flying from Chicago to Pennsylvania in February is currently the most expensive (average of $612). 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 CHI to PA?
Find hourly flight availability from Chicago to Pennsylvania. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 20, 2026.
One of the essential ways to save on airfare from Chicago to Pennsylvania is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 7% on airfare.
Weekly flight availability from Chicago to Pennsylvania
Explore weekly flight availability from Chicago to Pennsylvania. 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 June 20, 2026.
The most flights from CHI to USPA are scheduled on a Thursday (56 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (23 on average).
How much does it cost to fly round-trip from Chicago to Pennsylvania?
How far ahead should I book a flight from Chicago to Pennsylvania?
Booking 35 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Pennsylvania. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Chicago to Pennsylvania?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Pennsylvania. Price data was last updated on June 13, 2026.
Travelers seeking maximum savings on their Chicago to Pennsylvania flight should consider departing on Thursday afternoons when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Pennsylvania
Get insights into the airlines that provide service to Pennsylvania. 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 Pennsylvania. Reviews last updated June 20, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican Airlines from Chicago to Pennsylvania have to say. 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
Comfort
8.0
Boarding
8.1
Overall
7.9
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
7.9
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
7.9
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
7.9
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
7.9
Entertainment
7.5
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 Chicago to Pennsylvania. 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 Chicago to Pennsylvania
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Pennsylvania by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Pennsylvania by cabin class
Find flights from Chicago to Pennsylvania, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Pennsylvania flights
Browse other Chicago and Pennsylvania flight options. Last updated on June 20, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Pennsylvania flights
Consider these flights traveling from Chicago to Pennsylvania.
Top 4 airlines flying from Chicago to Pennsylvania
Discover the top 4 airlines that operate flights from Chicago to Pennsylvania. 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 June 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$67 | Average$165 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$97 | Average$345 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$116 | Average$348 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$134 | Average$388 | FlexibilityNo cancel fee | On-time69% |