$99+ Cheap flights from Chicago (CHI) to Pennsylvania
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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PHL
Oct 31 — Nov 71
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Pennsylvania 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 Chicago to Pennsylvania
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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 October 1, 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 October 1, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/88:15 am -
1 stop8h 20m
Thu 12/106:50 pm -
Nonstop2h 39m
Deal found 9/27![Frontier logo]()
$160
This FlightHub deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:34 pm -
Nonstop2h 10m
Sun 12/66:50 pm -
Nonstop2h 39m
Deal found 9/26![Frontier logo]()
$161
This Cheapflightsfares deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/64:42 pm -
Nonstop2h 16m
Sun 11/89:09 pm -
Nonstop2h 34m
Deal found 9/27![Frontier logo]()
$162
This Cheapflightsfares deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/49:34 pm -
Nonstop2h 10m
Sun 12/66:50 pm -
Nonstop2h 39m
Deal found 9/27![Frontier logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/194:41 pm -
Nonstop2h 23m
Wed 10/2112:35 pm -
1 stop6h 56m
Deal found 9/29![Frontier logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/194:41 pm -
Nonstop2h 23m
Fri 10/239:09 pm -
Nonstop2h 30m
Deal found 9/29![Frontier logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/174:41 pm -
Nonstop2h 23m
Wed 10/215:22 pm -
1 stop16h 59m
Deal found 9/26![Frontier logo]()
$168
This Cheapflightsfares deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:42 pm -
1 stop11h 39m
Fri 11/65:22 pm -
1 stop7h 25m
Deal found 9/29![Frontier logo]()
$169
This Mytrip deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/244:41 pm -
Nonstop2h 23m
Tue 10/274:47 pm -
2 stops21h 04m
Deal found 9/30![Frontier logo]()
$169
This Cheapflightsfares deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/224:41 pm -
Nonstop2h 23m
Sun 10/255:50 am -
1 stop19h 34m
Deal found 9/30![Frontier logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:00 am -
1 stop11h 15m
Thu 10/299:09 pm -
Nonstop2h 34m
Deal found 9/28![Frontier logo]()
$172
This Cheapflightsfares deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:22 am -
1 stop10h 53m
Mon 10/265:22 pm -
1 stop7h 21m
Deal found 9/29![Frontier logo]()
$182
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 October 1, 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 October 1, 2026.
This United Airlines deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2111:25 am -
Nonstop2h 18m
Sat 10/247:10 pm -
Nonstop2h 30m
Deal found 9/27![United Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/291:30 pm -
Nonstop1h 55m
Thu 11/51:50 pm -
Nonstop2h 15m
Deal found 9/30![Southwest logo]()
$266
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:27 am -
1 stop4h 43m
Sat 10/245:29 pm -
1 stop4h 01m
Deal found 9/30![Delta logo]()
$277
This American Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:10 pm -
Nonstop1h 45m
Tue 11/38:01 am -
Nonstop2h 09m
Deal found 9/29![American Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:46 am -
1 stop10h 50m
Wed 10/289:16 pm -
2 stops15h 07m
Deal found 9/29![Multiple Airlines logo]()
$384
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3112:55 pm -
Nonstop2h 05m
Tue 11/36:00 am -
1 stop7h 05m
Deal found 9/28![Southwest logo]()
$267
This United Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:10 pm -
Nonstop1h 39m
Wed 11/46:30 am -
Nonstop1h 53m
Deal found 9/30![United Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/243:15 pm -
1 stop5h 25m
Mon 10/265:29 pm -
1 stop4h 01m
Deal found 9/30![Delta logo]()
$278
This American Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/249:10 pm -
Nonstop1h 45m
Sun 10/258:07 am -
Nonstop2h 03m
Deal found 9/28![American Airlines logo]()
$289
This Southwest deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/244:20 pm -
Nonstop2h 00m
Mon 10/267:10 pm -
Nonstop2h 05m
Deal found 9/27![Southwest logo]()
$284
This United Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/309:30 pm -
Nonstop1h 29m
Tue 11/32:07 pm -
Nonstop1h 48m
Deal found 9/28![United Airlines logo]()
$287
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/711:35 am -
1 stop7h 50m
Wed 12/94:32 pm -
1 stop5h 13m
Deal found 9/28![Delta logo]()
$297
This American Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/244:45 pm -
1 stop4h 51m
Wed 10/288:07 am -
Nonstop2h 03m
Deal found 9/29![American Airlines logo]()
$298
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:45 pm -
Nonstop1h 25m
Mon 10/266:00 pm -
1 stop5h 00m
Deal found 9/28![Southwest logo]()
$287
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/612:59 pm -
Nonstop2h 06m
Mon 11/98:07 pm -
Nonstop2h 23m
Deal found 9/29![United Airlines logo]()
$291
This American Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/95:19 am -
1 stop6h 08m
Sat 12/51:00 pm -
1 stop8h 11m
Deal found 9/29![American Airlines logo]()
$308
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/211:26 pm -
1 stop5h 26m
Sat 1/26:00 am -
1 stop4h 49m
Deal found 9/27![Delta logo]()
$313
This Southwest deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:50 am -
Nonstop1h 30m
Mon 11/162:20 pm -
Nonstop1h 35m
Deal found 9/29![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:29 am -
1 stop5h 49m
Fri 10/3012:20 pm -
1 stop5h 12m
Deal found 9/27![Delta logo]()
$317
This American Airlines deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:20 pm -
Nonstop1h 55m
Sun 11/156:34 am -
Nonstop2h 26m
Deal found 9/26![American Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/176:26 pm -
Nonstop2h 15m
Sun 1/106:00 am -
1 stop4h 44m
Deal found 9/28![United Airlines logo]()
$320
This Southwest deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/811:30 am -
2 stops9h 35m
Thu 12/102:45 pm -
2 stops9h 20m
Deal found 9/29![Southwest logo]()
$296
This KAYAK deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2812:59 pm -
Nonstop2h 06m
Thu 10/298:07 pm -
Nonstop2h 23m
Deal found 9/29![United Airlines logo]()
$325
This American Airlines deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:00 am -
1 stop5h 21m
Tue 10/138:07 am -
Nonstop2h 03m
Deal found 9/26![American Airlines logo]()
$328
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/221:26 pm -
1 stop5h 26m
Sat 1/26:00 am -
1 stop4h 49m
Deal found 9/28![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:45 pm -
Nonstop1h 25m
Tue 10/275:40 am -
2 stops6h 15m
Deal found 9/26![Southwest logo]()
$302
This United Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/182:35 pm -
Nonstop2h 09m
Sat 1/26:51 pm -
Nonstop2h 36m
Deal found 9/30![United Airlines logo]()
$326
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/224:40 pm -
Nonstop1h 55m
Mon 10/267:40 pm -
1 stop4h 30m
Deal found 9/30![Southwest logo]()
$303
This American Airlines deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/199:15 pm -
Nonstop1h 41m
Sun 11/297:55 am -
Nonstop2h 18m
Deal found 9/27![American Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2510:30 am -
1 stop6h 41m
Mon 12/285:54 pm -
1 stop7h 05m
Deal found 9/26![Delta logo]()
$339
Last-minute flights from Chicago to PennsylvaniaDiscover last-minute flight deals from Chicago to Pennsylvania. Data last updated October 1, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Pennsylvania. Data last updated October 1, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/174:41 pm -
Nonstop2h 23m
Wed 10/215:22 pm -
1 stop16h 59m
Deal found 9/26![Frontier logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/194:41 pm -
Nonstop2h 23m
Wed 10/2112:35 pm -
1 stop6h 56m
Deal found 9/29![Frontier logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/194:41 pm -
Nonstop2h 23m
Fri 10/239:09 pm -
Nonstop2h 30m
Deal found 9/29![Frontier logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:00 am -
1 stop11h 15m
Thu 10/299:09 pm -
Nonstop2h 34m
Deal found 9/28![Frontier logo]()
$172
This Cheapflightsfares deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/224:41 pm -
Nonstop2h 23m
Sun 10/255:50 am -
1 stop19h 34m
Deal found 9/30![Frontier logo]()
$171
This Cheapflightsfares deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:22 am -
1 stop10h 53m
Mon 10/265:22 pm -
1 stop7h 21m
Deal found 9/29![Frontier logo]()
$182
This Cheapflightsfares deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/244:41 pm -
Nonstop2h 23m
Mon 10/268:30 am -
1 stop11h 01m
Deal found 9/26![Frontier logo]()
$165
This Mytrip deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/244:41 pm -
Nonstop2h 23m
Tue 10/274:47 pm -
2 stops21h 04m
Deal found 9/30![Frontier logo]()
$169
This Orbitz deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/244:41 pm -
Nonstop2h 23m
Thu 10/293:22 pm -
1 stop18h 24m
Deal found 9/30![Frontier logo]()
$170
This Expedia deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:44 pm -
1 stop10h 37m
Mon 11/29:09 pm -
Nonstop2h 34m
Deal found 9/27![Frontier logo]()
$162
This Cheapflightsfares deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/294:42 pm -
Nonstop2h 16m
Sun 11/19:09 pm -
Nonstop2h 34m
Deal found 9/30![Frontier logo]()
$175
This Cheapflightsfares deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:42 pm -
1 stop11h 39m
Fri 11/65:22 pm -
1 stop7h 25m
Deal found 9/29![Frontier logo]()
$169
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 October 1, 2026.
Search for one-way flight options from Chicago to Pennsylvania. Find affordable one-way fares based on user searches. Data last updated October 1, 2026.
This Trip.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:22 am -
1 stop10h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$99
This Cheapflightsfares deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:50 pm -
1 stop10h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$99
This Cheapflightsfares deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:21 am -
1 stop10h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Frontier logo]()
$101
This Super.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:26 am -
1 stop6h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$101
This Super.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/912:28 pm -
1 stop9h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:44 pm -
1 stop25h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$102
This Booking.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:42 pm -
1 stop11h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:44 pm -
1 stop21h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Frontier logo]()
$103
This CheapOair deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:16 am -
1 stop11h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Frontier logo]()
$104
This CheapOair deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:42 pm -
1 stop11h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/318:00 am -
2 stops14h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$105
This Cheapflightsfares deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:44 pm -
1 stop10h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$106
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 October 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $160 (Cheapflightsfares) |
One-way from | $99 (Trip.com) |
Popular in | June |
Cheapest in | January |
Average price | $254 |
Good round-trip deal | $277 or less |
Good one-way deal | $151 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 7,457,451 searches. Data last updated October 1, 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
ChicagoPhiladelphia
MDW Chicago Midway - PHL Philadelphia
MDWPHL
Chicago Midway
Thu 10/22
4:40 pm-7:35 pm
Nonstop1h 55m
Philadelphia
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$129
ChicagoPhiladelphia
ORD Chicago O'Hare Intl - PHL Philadelphia
ORDPHL
Chicago O'Hare Intl
Sat 11/21
7:20 pm-10:27 pm
Nonstop2h 07m
Philadelphia
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$129
ChicagoPhiladelphia
MDW Chicago Midway - PHL Philadelphia
MDWPHL
Chicago Midway
Mon 11/2
3:50 pm-6:45 pm
Nonstop1h 55m
Philadelphia
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$129
ChicagoPhiladelphia
MDW Chicago Midway - PHL Philadelphia
MDWPHL
Chicago Midway
Fri 10/23
4:40 pm-7:35 pm
Nonstop1h 55m
Philadelphia
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$138
ChicagoPhiladelphia
MDW Chicago Midway - PHL Philadelphia
MDWPHL
Chicago Midway
Fri 11/13
7:25 pm-10:20 pm
Nonstop1h 55m
Philadelphia
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$138
ChicagoPittsburgh
ORD Chicago O'Hare Intl - PIT Pittsburgh
ORDPIT
Chicago O'Hare Intl
Thu 10/29
12:48 pm-3:19 pm
Nonstop1h 31m
Pittsburgh
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$139
ChicagoPittsburgh
MDW Chicago Midway - PIT Pittsburgh
MDWPIT
Chicago Midway
Wed 10/28
5:55 pm-8:20 pm
Nonstop1h 25m
Pittsburgh
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$139
Quickest round-trip
ChicagoPittsburgh
MDW Chicago Midway - PIT Pittsburgh
MDWPIT
Chicago Midway
Mon 10/19
7:45 am-10:05 am
Nonstop1h 20m
Pittsburgh
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$139
ChicagoPhiladelphia
ORD Chicago O'Hare Intl - PHL Philadelphia
ORDPHL
Chicago O'Hare Intl
Fri 11/27
2:44 pm-7:41 pm
1 stop3h 57m
Philadelphia
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$148
ChicagoPittsburgh
MDW Chicago Midway - PIT Pittsburgh
MDWPIT
Chicago Midway
Sat 10/31
5:31 pm-11:24 pm
1 stop4h 53m
Pittsburgh
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$149
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-PHL
MDW-PHL
ORD-ERI
ORD-PIT
MDW-PIT
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-PHL
MDW-PHL
ORD-ERI
ORD-PIT
What is the cheapest month to book a flight from Chicago to Pennsylvania?
Currently, January is the cheapest month in which you can book a flight from Chicago to Pennsylvania (average of $268). Flying from Chicago to Pennsylvania in July is currently the most expensive (average of $393). 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 October 1, 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 evening could potentially save you up to 24% 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 October 1, 2026.
The most flights from CHI to USPA are scheduled on a Tuesday (51 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (24 on average).
How much does it cost to fly round-trip from Chicago to Pennsylvania?
Airfare is typical for this route at the moment.
Chicago to Pennsylvania flights typically cost between $153 and $319 in December.The cheapest round-trip price found within the last 5 days was $160 on Frontier (Dec 8-Dec 10).
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 September 26, 2026.
Travelers seeking maximum savings on their Chicago to Pennsylvania flight should consider departing on Thursday mornings when fares are most often at their lowest. Sunday at noon 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 October 1, 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.
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
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 October 1, 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 7,457,451 searches. Data last updated October 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$69 | Average$177 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$137 | Average$373 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$137 | Average$361 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$156 | Average$405 | FlexibilityNo cancel fee | On-time69% |