$90+ Cheap flights from Pennsylvania to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — CHI
Nov 20 — Nov 271
Round-trip
1 adult, Economy
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Find cheap flights from Pennsylvania 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.Cheap flight deals from Pennsylvania to Chicago
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Cheapest flights from Pennsylvania to ChicagoExplore the most affordable flight options available from Pennsylvania to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 21, 2026.
Explore the most affordable flight options available from Pennsylvania to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 21, 2026.
This Mytrip deal was found by Cheapflights users on 10/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1212:36 pm -
2 stops21h 10m
Mon 11/166:00 am -
2 stops24h 21m
Deal found 10/20![Frontier logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/412:36 pm -
1 stop6h 54m
Tue 11/107:35 pm -
1 stop10h 46m
Deal found 10/20![Frontier logo]()
$188
This Southwest deal was found by Cheapflights users on 10/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/42:45 pm -
2 stops9h 25m
Sun 12/63:50 pm -
Nonstop1h 55m
Deal found 10/20![Southwest logo]()
$188
This Cheapflightsfares deal was found by Cheapflights users on 10/20. 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.
Wed 11/1812:36 pm -
1 stop6h 54m
Fri 11/209:20 pm -
Nonstop2h 10m
Deal found 10/20![Frontier logo]()
$189
This Frontier deal was found by Cheapflights users on 10/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:00 am -
1 stop14h 15m
Sun 11/154:42 pm -
Nonstop2h 22m
Deal found 10/20![Frontier logo]()
$190
This Southwest deal was found by Cheapflights users on 10/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/42:45 pm -
2 stops9h 25m
Mon 12/77:35 am -
1 stop5h 25m
Deal found 10/20![Southwest logo]()
$190
This Cheapflightsfares deal was found by Cheapflights users on 10/20. 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.
Wed 11/48:30 am -
1 stop11h 00m
Mon 11/97:50 pm -
1 stop10h 31m
Deal found 10/20![Frontier logo]()
$191
This CheapOair deal was found by Cheapflights users on 10/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/312:36 pm -
1 stop6h 11m
Tue 11/106:42 pm -
1 stop11h 39m
Deal found 10/20![Frontier logo]()
$191
This Cheapflightsfares deal was found by Cheapflights users on 10/20. 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.
Thu 12/104:26 pm -
1 stop17h 52m
Sun 12/138:53 pm -
1 stop13h 03m
Deal found 10/20![Frontier logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 10/17. 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.
Wed 11/115:14 pm -
1 stop7h 33m
Tue 11/176:42 pm -
1 stop11h 39m
Deal found 10/17![Frontier logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/99:09 pm -
Nonstop2h 34m
Wed 11/117:35 pm -
1 stop10h 36m
Deal found 10/16![Frontier logo]()
$193
This Cheapflightsfares deal was found by Cheapflights users on 10/18. 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.
Sun 12/68:40 am -
1 stop8h 26m
Wed 12/912:28 pm -
1 stop9h 43m
Deal found 10/18![Frontier logo]()
$193
Best flights from Pennsylvania to ChicagoDiscover carefully curated flight deals from Pennsylvania to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 21, 2026.
Discover carefully curated flight deals from Pennsylvania to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 21, 2026.
This United Airlines deal was found by Cheapflights users on 10/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/256:15 am -
Nonstop2h 35m
Sat 11/287:07 am -
Nonstop2h 09m
Deal found 10/20![United Airlines logo]()
$237
This Southwest deal was found by Cheapflights users on 10/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:00 am -
1 stop6h 40m
Wed 11/188:10 am -
Nonstop1h 55m
Deal found 10/20![Southwest logo]()
$250
This Delta deal was found by Cheapflights users on 10/19. 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 11/175:17 pm -
1 stop7h 37m
Sat 11/216:15 pm -
1 stop5h 40m
Deal found 10/19![Delta logo]()
$272
This American Airlines deal was found by Cheapflights users on 10/19. 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.
Wed 11/255:14 pm -
1 stop7h 45m
Sat 11/289:15 pm -
Nonstop1h 41m
Deal found 10/19![American Airlines logo]()
$318
This JetBlue deal was found by Cheapflights users on 10/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/512:47 pm -
1 stop7h 30m
Mon 11/91:00 pm -
1 stop5h 53m
Deal found 10/20![JetBlue logo]()
$361
This Southwest deal was found by Cheapflights users on 10/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/227:40 pm -
Nonstop1h 30m
Tue 12/299:25 pm -
Nonstop1h 30m
Deal found 10/20![Southwest logo]()
$251
This United Airlines deal was found by Cheapflights users on 10/19. 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.
Wed 12/309:50 am -
Nonstop2h 36m
Tue 1/52:35 pm -
Nonstop2h 09m
Deal found 10/19![United Airlines logo]()
$254
This Southwest deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/218:25 pm -
Nonstop1h 30m
Fri 11/2711:10 am -
2 stops7h 25m
Deal found 10/21![Southwest logo]()
$258
This United Airlines deal was found by Cheapflights users on 10/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:30 am -
Nonstop1h 53m
Mon 11/232:16 pm -
Nonstop1h 39m
Deal found 10/20![United Airlines logo]()
$259
This Southwest deal was found by Cheapflights users on 10/18. 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.
Fri 1/225:20 am -
2 stops12h 10m
Mon 1/251:45 pm -
2 stops6h 30m
Deal found 10/18![Southwest logo]()
$260
This American Airlines deal was found by Cheapflights users on 10/16. 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 1/197:00 am -
1 stop8h 20m
Fri 1/299:14 pm -
Nonstop1h 47m
Deal found 10/16![American Airlines logo]()
$318
This United Airlines deal was found by Cheapflights users on 10/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/103:05 pm -
1 stop7h 39m
Wed 11/188:50 am -
Nonstop2h 15m
Deal found 10/20![United Airlines logo]()
$275
This Delta deal was found by Cheapflights users on 10/19. 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 12/1512:50 pm -
1 stop7h 19m
Tue 1/193:00 pm -
1 stop6h 46m
Deal found 10/19![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 10/18. 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 12/32:20 pm -
Nonstop1h 35m
Thu 12/107:35 am -
1 stop4h 10m
Deal found 10/18![Southwest logo]()
$270
This American Airlines deal was found by Cheapflights users on 10/16. 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.
Fri 11/136:37 pm -
Nonstop2h 40m
Sun 11/158:10 pm -
Nonstop2h 04m
Deal found 10/16![American Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 10/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/307:37 pm -
1 stop5h 24m
Sat 1/28:52 am -
1 stop4h 22m
Deal found 10/20![United Airlines logo]()
$284
This Delta deal was found by Cheapflights users on 10/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:58 pm -
1 stop6h 58m
Sun 12/65:30 am -
1 stop5h 36m
Deal found 10/20![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 10/19. 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.
Thu 12/103:45 pm -
2 stops8h 00m
Mon 12/1411:30 am -
2 stops8h 35m
Deal found 10/19![Southwest logo]()
$273
This American Airlines deal was found by Cheapflights users on 10/19. 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 11/38:01 am -
Nonstop2h 09m
Sat 11/79:15 pm -
Nonstop1h 38m
Deal found 10/19![American Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 10/19. 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.
Sat 12/55:00 am -
Nonstop2h 28m
Mon 12/76:55 am -
Nonstop2h 06m
Deal found 10/19![United Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 10/17. 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.
Fri 1/81:00 pm -
1 stop6h 32m
Tue 1/129:50 am -
2 stops11h 56m
Deal found 10/17![Delta logo]()
$364
This American Airlines deal was found by Cheapflights users on 10/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:10 pm -
1 stop6h 22m
Sun 11/85:19 am -
1 stop4h 57m
Deal found 10/18![American Airlines logo]()
$343
This Southwest deal was found by Cheapflights users on 10/18. 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.
Fri 12/45:05 pm -
1 stop6h 35m
Mon 12/76:25 pm -
Nonstop2h 00m
Deal found 10/18![Southwest logo]()
$289
This United Airlines deal was found by Cheapflights users on 10/18. 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.
Tue 11/176:05 am -
Nonstop2h 23m
Tue 11/249:20 pm -
Nonstop2h 06m
Deal found 10/18![United Airlines logo]()
$291
This United Airlines deal was found by Cheapflights users on 10/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/158:07 pm -
Nonstop2h 23m
Sun 11/229:20 pm -
Nonstop2h 06m
Deal found 10/17![United Airlines logo]()
$291
This Southwest deal was found by Cheapflights users on 10/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/107:30 am -
Nonstop2h 20m
Mon 12/148:10 am -
Nonstop1h 55m
Deal found 10/16![Southwest logo]()
$295
This Delta deal was found by Cheapflights users on 10/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:03 pm -
1 stop6h 54m
Sat 11/711:19 am -
2 stops10h 00m
Deal found 10/20![Delta logo]()
$404
This United Airlines deal was found by Cheapflights users on 10/19. 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.
Wed 3/172:57 pm -
Nonstop2h 29m
Sun 3/219:20 pm -
Nonstop2h 08m
Deal found 10/19![United Airlines logo]()
$291
This Southwest deal was found by Cheapflights users on 10/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:00 am -
1 stop7h 05m
Wed 11/253:05 pm -
2 stops8h 15m
Deal found 10/20![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 10/16. 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.
Sat 10/312:30 pm -
1 stop7h 08m
Wed 11/410:55 am -
2 stops10h 24m
Deal found 10/16![Delta logo]()
$404
Last-minute flights from Pennsylvania to ChicagoDiscover last-minute flight deals from Pennsylvania to Chicago. Data last updated October 21, 2026 and is based on user searches.
Discover last-minute flight deals from Pennsylvania to Chicago. Data last updated October 21, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 10/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/312:36 pm -
1 stop6h 11m
Tue 11/106:42 pm -
1 stop11h 39m
Deal found 10/20![Frontier logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/412:36 pm -
1 stop6h 54m
Tue 11/107:35 pm -
1 stop10h 46m
Deal found 10/20![Frontier logo]()
$188
This Cheapflightsfares deal was found by Cheapflights users on 10/20. 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.
Wed 11/46:00 am -
1 stop10h 31m
Mon 11/97:50 pm -
1 stop10h 31m
Deal found 10/20![Frontier logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/99:09 pm -
Nonstop2h 34m
Wed 11/117:35 pm -
1 stop10h 36m
Deal found 10/16![Frontier logo]()
$193
This Southwest deal was found by Cheapflights users on 10/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/102:55 pm -
1 stop5h 10m
Wed 11/1111:30 am -
2 stops9h 40m
Deal found 10/20![Southwest logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 10/19. 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.
Tue 11/1010:37 am -
1 stop7h 30m
Tue 11/177:35 pm -
1 stop10h 46m
Deal found 10/19![Frontier logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 10/17. 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.
Wed 11/115:14 pm -
1 stop7h 33m
Tue 11/176:42 pm -
1 stop11h 39m
Deal found 10/17![Frontier logo]()
$192
This Mytrip deal was found by Cheapflights users on 10/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1212:36 pm -
2 stops21h 10m
Mon 11/166:00 am -
2 stops24h 21m
Deal found 10/20![Frontier logo]()
$187
This Frontier deal was found by Cheapflights users on 10/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:00 am -
1 stop14h 15m
Sun 11/154:42 pm -
Nonstop2h 22m
Deal found 10/20![Frontier logo]()
$190
This Cheapflightsfares deal was found by Cheapflights users on 10/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/139:09 pm -
Nonstop2h 34m
Mon 11/167:50 pm -
1 stop10h 31m
Deal found 10/19![Frontier logo]()
$192
This Cheapflightsfares deal was found by Cheapflights users on 10/20. 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.
Wed 11/1812:36 pm -
1 stop6h 54m
Fri 11/209:20 pm -
Nonstop2h 10m
Deal found 10/20![Frontier logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2112:38 pm -
1 stop20h 36m
Thu 12/105:02 pm -
1 stop5h 38m
Deal found 10/20![Frontier logo]()
$194
One-way flights from Pennsylvania to ChicagoSearch for one-way flight options from Pennsylvania to Chicago. Find affordable one-way fares based on user searches. Data last updated October 21, 2026.
Search for one-way flight options from Pennsylvania to Chicago. Find affordable one-way fares based on user searches. Data last updated October 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/129:09 pm -
Nonstop2h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$90
This American Airlines deal was found by Cheapflights users on 10/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/229:16 am -
Nonstop2h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![American Airlines logo]()
$91
This Southwest deal was found by Cheapflights users on 10/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/177:35 am -
Nonstop2h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Southwest logo]()
$91
This Frontier deal was found by Cheapflights users on 10/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/139:09 pm -
Nonstop2h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Frontier logo]()
$92
This Delta deal was found by Cheapflights users on 10/19. 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 11/216:10 pm -
1 stop6h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Delta logo]()
$93
This Southwest deal was found by Cheapflights users on 10/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/218:35 pm -
1 stop4h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Southwest logo]()
$93
This Trip.com deal was found by Cheapflights users on 10/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/312:49 pm -
1 stop9h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Frontier logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 10/19. 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.
Mon 12/74:31 pm -
1 stop20h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Frontier logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/178:30 am -
2 stops15h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/165:14 pm -
1 stop25h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$97
This Expedia deal was found by Cheapflights users on 10/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/112:49 pm -
1 stop9h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Frontier logo]()
$98
This Southwest deal was found by Cheapflights users on 10/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:25 am -
2 stops9h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Southwest logo]()
$98
Find flight deals from Pennsylvania to Chicago
Keep the following information in mind while searching for Pennsylvania to Chicago flight deals. Data was last updated October 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $187 (Mytrip) |
One-way from | $90 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $311 |
Good round-trip deal | $312 or less |
Good one-way deal | $154 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Pennsylvania to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 21, 2026.
Use the filters below to find and compare flights from Pennsylvania to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Sun 1/17
7:35 am-8:55 am
Nonstop2h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$91
PhiladelphiaChicago
PHL Philadelphia - ORD Chicago O'Hare Intl
PHLORD
Philadelphia
Fri 11/20
7:40 pm-12:01 am
1 stop5h 21m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$93
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Tue 12/1
6:00 am-9:37 am
1 stop4h 37m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$93
PhiladelphiaChicago
PHL Philadelphia - ORD Chicago O'Hare Intl
PHLORD
Philadelphia
Sat 11/21
7:40 pm-12:01 am
1 stop5h 21m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$93
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Wed 11/18
1:55 pm-7:30 pm
1 stop6h 35m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$93
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Sat 1/16
1:20 pm-7:40 pm
1 stop7h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$93
PhiladelphiaChicago
PHL Philadelphia - ORD Chicago O'Hare Intl
PHLORD
Philadelphia
Sat 2/6
5:30 am-10:07 am
1 stop5h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$109
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Mon 12/7
6:15 pm-7:30 pm
Nonstop2h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$115
Quickest round-trip
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Wed 11/18
2:20 pm-2:50 pm
Nonstop1h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$122
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Sat 12/12
4:35 pm-5:05 pm
Nonstop1h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$122
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Pennsylvania to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Pennsylvania with our price prediction graph.
PHL-ORD
PHL-MDW
ERI-ORD
PIT-ORD
PIT-MDW
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 Pennsylvania to Chicago
USPA-CHI
PHL-ORD
PHL-MDW
ERI-ORD
PIT-ORD
What is the cheapest month to book a flight from Pennsylvania to Chicago?
Currently, January is the cheapest month in which you can book a flight from Pennsylvania to Chicago (average of $289). Flying from Pennsylvania to Chicago in June is currently the most expensive (average of $365). 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 PA to CHI?
Find hourly flight availability from Pennsylvania to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 21, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 24% on flights from Pennsylvania to Chicago by exploring options for tickets at noon.
Weekly flight availability from Pennsylvania to Chicago
Explore weekly flight availability from Pennsylvania 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 October 21, 2026.
The most flights from USPA to CHI are scheduled on a Monday (50 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (12 on average).
How much does it cost to fly round-trip from Pennsylvania to Chicago?
Airfare is below average for this route at the moment.
Pennsylvania to Chicago flights typically cost between $198 and $382 in November.The cheapest round-trip price found within the last 5 days was $187 on Frontier (Nov 12-Nov 16).
How far ahead should I book a flight from Pennsylvania to Chicago?
The best time to book flights from Pennsylvania to Chicago is 77 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest day to fly from Pennsylvania to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Pennsylvania to Chicago. Price data was last updated on October 17, 2026.
Travelers seeking maximum savings on their Pennsylvania to Chicago flight should consider departing on Saturday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from Pennsylvania to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
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Alternative routes for Pennsylvania to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
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 October 21, 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 Pennsylvania to Chicago by cabin class
Find flights from Pennsylvania to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Pennsylvania and Chicago flights
Browse other Pennsylvania and Chicago flight options. Last updated on October 21, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Pennsylvania to Chicago flights
Consider these flights traveling from Pennsylvania to Chicago.
Top 5 airlines flying from Pennsylvania to Chicago
Discover the top 5 airlines that operate flights from Pennsylvania to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$70 | Average$193 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$83 | Average$305 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$137 | Average$378 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$157 | Average$342 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$178 | Average$380 | FlexibilityNo cancel fee | On-time69% |