$89+ Cheap flights from Pennsylvania to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — CHI
Sep 21 — Sep 281
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 August 22, 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 August 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Mon 10/125:22 pm -
1 stop19h 10m
Thu 10/154:41 pm -
Nonstop2h 23m
Deal found 8/17![Frontier logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Fri 9/1111:54 am -
Nonstop2h 36m
Sat 9/266:20 am -
1 stop10h 54m
Deal found 8/17![Frontier logo]()
$168
This CheapOair deal was found by Cheapflights users on 8/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:54 am -
Nonstop2h 36m
Thu 9/177:25 am -
Nonstop2h 24m
Deal found 8/17![Frontier logo]()
$169
This Priceline deal was found by Cheapflights users on 8/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1811:54 am -
Nonstop2h 36m
Mon 9/217:25 am -
Nonstop2h 24m
Deal found 8/21![Frontier logo]()
$170
This CheapOair deal was found by Cheapflights users on 8/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1111:54 am -
Nonstop2h 36m
Mon 9/147:25 am -
Nonstop2h 24m
Deal found 8/18![Frontier logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Mon 9/2111:54 am -
Nonstop2h 36m
Wed 9/236:20 am -
1 stop10h 54m
Deal found 8/17![Frontier logo]()
$172
This CheapOair deal was found by Cheapflights users on 8/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1411:54 am -
Nonstop2h 36m
Thu 9/176:00 am -
1 stop7h 21m
Deal found 8/17![Frontier logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/1412:35 pm -
1 stop6h 56m
Sat 10/174:41 pm -
Nonstop2h 23m
Deal found 8/17![Frontier logo]()
$174
This Frontier deal was found by Cheapflights users on 8/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/109:09 pm -
Nonstop2h 30m
Sun 10/184:41 pm -
Nonstop2h 23m
Deal found 8/17![Frontier logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Thu 10/159:09 pm -
Nonstop2h 30m
Fri 10/164:41 pm -
Nonstop2h 23m
Deal found 8/17![Frontier logo]()
$176
This CheapOair deal was found by Cheapflights users on 8/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/111:54 am -
Nonstop2h 36m
Mon 10/57:25 am -
Nonstop2h 24m
Deal found 8/19![Frontier logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 9/912:40 pm -
1 stop6h 43m
Mon 9/143:50 pm -
1 stop7h 19m
Deal found 8/17![Frontier logo]()
$178
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 August 22, 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 August 22, 2026.
This Delta deal was found by Cheapflights users on 8/18. 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 11/1811:00 am -
1 stop6h 48m
Mon 11/237:00 am -
1 stop4h 40m
Deal found 8/18![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 8/20. 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.
Mon 9/143:30 pm -
Nonstop2h 22m
Fri 9/182:00 pm -
Nonstop2h 08m
Deal found 8/20![United Airlines logo]()
$216
This JetBlue deal was found by Cheapflights users on 8/21. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/108:05 pm -
Nonstop2h 51m
Wed 10/141:00 pm -
Nonstop2h 20m
Deal found 8/21![JetBlue logo]()
$247
This Southwest deal was found by Cheapflights users on 8/20. 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 10/39:25 am -
Nonstop2h 30m
Sun 10/45:05 am -
Nonstop2h 05m
Deal found 8/20![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 10/282:00 pm -
1 stop6h 11m
Sat 10/3110:35 am -
1 stop5h 57m
Deal found 8/22![Delta logo]()
$197
This Delta deal was found by Cheapflights users on 8/20. 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 10/1510:57 am -
1 stop6h 35m
Mon 10/196:10 am -
1 stop4h 40m
Deal found 8/20![Delta logo]()
$197
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:12 pm -
1 stop6h 45m
Thu 10/225:29 pm -
1 stop4h 47m
Deal found 8/21![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 8/20. 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 9/297:23 am -
Nonstop2h 37m
Sun 10/48:00 am -
Nonstop2h 17m
Deal found 8/20![United Airlines logo]()
$247
This Southwest deal was found by Cheapflights users on 8/18. 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.
Wed 9/1610:55 am -
Nonstop2h 20m
Sat 9/1912:10 pm -
Nonstop2h 10m
Deal found 8/18![Southwest logo]()
$247
This JetBlue deal was found by Cheapflights users on 8/18. 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.
Wed 9/96:45 am -
1 stop8h 00m
Fri 9/1110:59 am -
Nonstop2h 21m
Deal found 8/18![JetBlue logo]()
$250
This Delta deal was found by Cheapflights users on 8/17. 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.
Thu 10/226:05 am -
1 stop4h 12m
Mon 10/269:29 am -
1 stop5h 59m
Deal found 8/17![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 8/21. 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.
Fri 9/258:55 pm -
Nonstop2h 25m
Mon 9/285:10 pm -
Nonstop2h 05m
Deal found 8/21![Southwest logo]()
$247
This United Airlines deal was found by Cheapflights users on 8/17. 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.
Fri 9/1110:27 pm -
Nonstop2h 13m
Fri 10/26:12 pm -
Nonstop2h 05m
Deal found 8/17![United Airlines logo]()
$255
This JetBlue deal was found by Cheapflights users on 8/18. 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 9/13:40 pm -
Nonstop2h 55m
Sun 9/66:00 am -
Nonstop2h 15m
Deal found 8/18![JetBlue logo]()
$257
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:05 am -
1 stop4h 12m
Sat 10/176:44 pm -
1 stop3h 32m
Deal found 8/22![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 10/147:46 am -
Nonstop2h 14m
Mon 10/197:00 am -
Nonstop1h 59m
Deal found 8/22![United Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 8/20. 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 9/1612:05 pm -
1 stop5h 45m
Mon 9/215:00 am -
Nonstop2h 00m
Deal found 8/20![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:00 am -
1 stop4h 42m
Mon 11/95:09 pm -
1 stop6h 30m
Deal found 8/21![Delta logo]()
$197
This JetBlue deal was found by Cheapflights users on 8/17. 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.
Thu 10/153:45 pm -
1 stop8h 59m
Thu 10/221:00 pm -
Nonstop2h 20m
Deal found 8/17![JetBlue logo]()
$265
This United Airlines deal was found by Cheapflights users on 8/18. 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.
Sat 9/1210:27 pm -
Nonstop2h 13m
Sat 9/198:45 am -
Nonstop2h 07m
Deal found 8/18![United Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 8/21. 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.
Wed 9/307:25 am -
Nonstop2h 20m
Fri 10/97:35 pm -
Nonstop2h 05m
Deal found 8/21![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 8/17. 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.
Tue 10/206:12 pm -
1 stop5h 21m
Sat 10/246:44 pm -
1 stop3h 32m
Deal found 8/17![Delta logo]()
$197
This JetBlue deal was found by Cheapflights users on 8/21. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:05 pm -
Nonstop2h 51m
Mon 10/191:00 pm -
Nonstop2h 20m
Deal found 8/21![JetBlue logo]()
$267
This United Airlines deal was found by Cheapflights users on 8/20. 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.
Thu 9/176:13 am -
Nonstop2h 15m
Mon 9/218:42 am -
Nonstop2h 07m
Deal found 8/20![United Airlines logo]()
$257
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:05 am -
1 stop4h 12m
Mon 11/95:09 pm -
1 stop6h 30m
Deal found 8/21![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 8/21. 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.
Tue 9/292:30 pm -
1 stop6h 40m
Sun 10/47:40 am -
1 stop6h 35m
Deal found 8/21![Southwest logo]()
$277
This JetBlue deal was found by Cheapflights users on 8/20. 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 9/108:10 am -
Nonstop2h 48m
Sun 9/137:00 am -
Nonstop2h 27m
Deal found 8/20![JetBlue logo]()
$279
This United Airlines deal was found by Cheapflights users on 8/18. 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 11/183:15 pm -
Nonstop2h 22m
Mon 11/235:55 am -
Nonstop1h 54m
Deal found 8/18![United Airlines logo]()
$257
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 10/136:00 am -
1 stop5h 03m
Thu 10/156:44 pm -
1 stop3h 32m
Deal found 8/22![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 8/20. 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 11/179:30 am -
1 stop8h 55m
Thu 11/199:40 am -
1 stop4h 30m
Deal found 8/20![Southwest logo]()
$277
Last-minute flights from Pennsylvania to ChicagoDiscover last-minute flight deals from Pennsylvania to Chicago. Data last updated August 22, 2026 and is based on user searches.
Discover last-minute flight deals from Pennsylvania to Chicago. Data last updated August 22, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 9/912:40 pm -
1 stop6h 43m
Mon 9/143:50 pm -
1 stop7h 19m
Deal found 8/17![Frontier logo]()
$178
This Trip.com deal was found by Cheapflights users on 8/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:35 am -
1 stop24h 03m
Fri 9/1110:26 am -
1 stop5h 52m
Deal found 8/19![Frontier logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Thu 9/1011:54 am -
Nonstop2h 36m
Tue 9/156:20 am -
1 stop10h 54m
Deal found 8/17![Frontier logo]()
$169
This CheapOair deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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.
Thu 9/1011:54 am -
Nonstop2h 36m
Mon 9/147:25 am -
Nonstop2h 24m
Deal found 8/22![Frontier logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Fri 9/1111:54 am -
Nonstop2h 36m
Sat 9/266:20 am -
1 stop10h 54m
Deal found 8/17![Frontier logo]()
$168
This CheapOair deal was found by Cheapflights users on 8/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1111:54 am -
Nonstop2h 36m
Mon 9/147:25 am -
Nonstop2h 24m
Deal found 8/18![Frontier logo]()
$171
This Expedia deal was found by Cheapflights users on 8/17. 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.
Mon 9/1411:54 am -
Nonstop2h 36m
Wed 9/167:28 pm -
1 stop10h 48m
Deal found 8/17![Frontier logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Mon 9/1411:54 am -
Nonstop2h 36m
Fri 9/257:25 am -
Nonstop2h 24m
Deal found 8/17![Frontier logo]()
$176
This Priceline deal was found by Cheapflights users on 8/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1811:54 am -
Nonstop2h 36m
Mon 9/217:25 am -
Nonstop2h 24m
Deal found 8/21![Frontier logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Mon 9/2111:54 am -
Nonstop2h 36m
Wed 9/236:20 am -
1 stop10h 54m
Deal found 8/17![Frontier logo]()
$172
This Super.com deal was found by Cheapflights users on 8/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2411:54 am -
Nonstop2h 36m
Mon 10/57:25 am -
Nonstop2h 24m
Deal found 8/17![Frontier logo]()
$174
This Mytrip deal was found by Cheapflights users on 8/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:15 am -
1 stop16h 44m
Mon 9/287:25 am -
Nonstop2h 24m
Deal found 8/18![Frontier logo]()
$179
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 August 22, 2026.
Search for one-way flight options from Pennsylvania to Chicago. Find affordable one-way fares based on user searches. Data last updated August 22, 2026.
This United Airlines deal was found by Cheapflights users on 8/18. 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 9/145:10 pm -
Nonstop2h 23m
Deal found 8/18![United Airlines logo]()
$89
This United Airlines deal was found by Cheapflights users on 8/17. 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.
Wed 9/1610:41 am -
Nonstop2h 18m
Deal found 8/17![United Airlines logo]()
$89
This American Airlines deal was found by Cheapflights users on 8/19. 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 9/236:19 pm -
Nonstop2h 40m
Deal found 8/19![American Airlines logo]()
$90
This CheapOair deal was found by Cheapflights users on 8/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/811:12 am -
1 stop21h 19m
Deal found 8/19![Frontier logo]()
$90
This Trip.com deal was found by Cheapflights users on 8/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:13 pm -
1 stop21h 32m
Deal found 8/20![Frontier logo]()
$91
This Booking.com deal was found by Cheapflights users on 8/18. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:50 am -
1 stop11h 01m
Deal found 8/18![Frontier logo]()
$91
This Super.com deal was found by Cheapflights users on 8/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1612:30 pm -
1 stop12h 56m
Deal found 8/18![Frontier logo]()
$92
This Super.com deal was found by Cheapflights users on 8/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:00 am -
1 stop24h 38m
Deal found 8/18![Frontier logo]()
$93
This Super.com deal was found by Cheapflights users on 8/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:50 am -
1 stop11h 01m
Deal found 8/17![Frontier logo]()
$93
This Jetabroad deal was found by Cheapflights users on 8/21. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/161:15 pm -
1 stop6h 46m
Deal found 8/21![JetBlue logo]()
$94
This Expedia deal was found by Cheapflights users on 8/17. 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.
Fri 9/117:50 am -
1 stop11h 01m
Deal found 8/17![Frontier logo]()
$94
This CheapOair deal was found by Cheapflights users on 8/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:50 am -
1 stop11h 01m
Deal found 8/17![Frontier logo]()
$95
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 August 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $168 (Kiwi.com) |
One-way from | $89 (United Airlines) |
Popular in | June |
Cheapest in | January |
Average price | $278 |
Good round-trip deal | $279 or less |
Good one-way deal | $180 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 August 22, 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
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl
DCAORD
Washington, D.C. Reagan-National
Wed 11/18
11:00 am-4:48 pm
1 stop6h 48m
Chicago O'Hare Intl
Mon 11/23
7:00 am-12:40 pm
1 stop4h 40m
$197
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl
DCAORD
Washington, D.C. Reagan-National
Wed 10/28
2:00 pm-7:11 pm
1 stop6h 11m
Chicago O'Hare Intl
Sat 10/31
10:35 am-5:32 pm
1 stop5h 57m
$197
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl
IADORD
Washington, D.C. Dulles Intl
Thu 10/15
10:57 am-4:32 pm
1 stop6h 35m
Chicago O'Hare Intl
Mon 10/19
6:10 am-11:50 am
1 stop4h 40m
$197
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl
IADORD
Washington, D.C. Dulles Intl
Wed 10/14
6:12 pm-11:57 pm
1 stop6h 45m
Chicago O'Hare Intl
Thu 10/22
5:29 pm-11:16 pm
1 stop4h 47m
$197
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - MDW Chicago Midway
IADMDW
Washington, D.C. Dulles Intl
Thu 10/22
6:05 am-9:17 am
1 stop4h 12m
Chicago Midway
Mon 10/26
9:29 am-4:28 pm
1 stop5h 59m
$197
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - MDW Chicago Midway
IADMDW
Washington, D.C. Dulles Intl
Sat 10/17
6:05 am-9:17 am
1 stop4h 12m
Chicago Midway
Sat 10/17
6:44 pm-11:16 pm
1 stop3h 32m
$197
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - MDW Chicago Midway
IADMDW
Washington, D.C. Dulles Intl
Mon 11/9
6:00 am-9:42 am
1 stop4h 42m
Chicago Midway
Mon 11/9
5:09 pm-12:39 am
1 stop6h 30m
$197
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - MDW Chicago Midway
IADMDW
Washington, D.C. Dulles Intl
Tue 10/20
6:12 pm-10:33 pm
1 stop5h 21m
Chicago Midway
Sat 10/24
6:44 pm-11:16 pm
1 stop3h 32m
$197
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - MDW Chicago Midway
IADMDW
Washington, D.C. Dulles Intl
Thu 11/5
6:05 am-9:17 am
1 stop4h 12m
Chicago Midway
Mon 11/9
5:09 pm-12:39 am
1 stop6h 30m
$197
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - MDW Chicago Midway
IADMDW
Washington, D.C. Dulles Intl
Tue 10/13
6:00 am-10:03 am
1 stop5h 03m
Chicago Midway
Thu 10/15
6:44 pm-11:16 pm
1 stop3h 32m
$197
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
IAD-ORD
DCA-ORD
IAD-MDW
LGA-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
IAD-ORD
DCA-ORD
IAD-MDW
What is the cheapest month to book a flight from Pennsylvania to Chicago?
Currently, October is the cheapest month in which you can book a flight from Pennsylvania to Chicago (average of $273). 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 August 22, 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 August 22, 2026.
The most flights from USPA to CHI are scheduled on a Friday (54 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (30 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 $186 and $336 in September.The cheapest round-trip price found within the last 5 days was $168 on Frontier (Sep 11-Sep 26).
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 August 22, 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
Lansing
Merrillville
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
Chicago flight routes
Complete your trip
Flights by cabin class
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Top destinations
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 August 22, 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 August 22, 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 August 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$75 | Average$184 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$97 | Average$346 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$133 | Average$314 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$137 | Average$361 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$165 | Average$365 | FlexibilityNo cancel fee | On-time69% |