$92+ Cheap flights from Philadelphia (PHL) 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 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — CHI
Oct 19 — Oct 261
Round-trip
1 adult, Economy
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Find cheap flights from Philadelphia 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.Cheapflights Tip: The best prices from Philadelphia to Chicago are usually found in January or November, booked 76 days in advance, depart on a Friday or Thursday and return on a Friday
Cheap flight deals from Philadelphia to Chicago
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Cheapest flights from Philadelphia to ChicagoExplore the most affordable flight options available from Philadelphia to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 19, 2026.
Explore the most affordable flight options available from Philadelphia to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/205:22 pm -
1 stop19h 10m
Mon 10/267:44 pm -
1 stop25h 53m
Deal found 9/18![Frontier logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/2812:36 pm -
1 stop6h 40m
Sat 10/318:00 am -
2 stops14h 06m
Deal found 9/17![Frontier logo]()
$179
This Booking.com deal was found by Cheapflights users on 9/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:50 am -
1 stop19h 34m
Mon 10/267:44 pm -
1 stop10h 37m
Deal found 9/17![Frontier logo]()
$180
This Expedia deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:22 pm -
1 stop7h 21m
Thu 10/226:40 pm -
1 stop11h 41m
Deal found 9/15![Frontier logo]()
$180
This Cheapflightsfares deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/109:09 pm -
Nonstop2h 30m
Mon 10/127:44 pm -
1 stop10h 37m
Deal found 9/17![Frontier logo]()
$181
This Frontier deal was found by Cheapflights users on 9/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:00 am -
1 stop13h 56m
Sat 10/248:04 am -
1 stop13h 08m
Deal found 9/16![Frontier logo]()
$182
This Frontier deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:00 am -
1 stop7h 17m
Wed 10/286:42 pm -
1 stop11h 29m
Deal found 9/15![Frontier logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 9/292:50 pm -
1 stop9h 09m
Sat 10/104:41 pm -
Nonstop2h 23m
Deal found 9/14![Frontier logo]()
$183
This Cheapflightsfares deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/312:36 pm -
1 stop6h 11m
Tue 11/106:42 pm -
1 stop11h 39m
Deal found 9/17![Frontier logo]()
$183
This Mytrip deal was found by Cheapflights users on 9/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2812:36 pm -
2 stops23h 47m
Thu 10/294:42 pm -
Nonstop2h 16m
Deal found 9/17![Frontier logo]()
$184
This CheapOair deal was found by Cheapflights users on 9/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:03 pm -
1 stop6h 44m
Sun 11/16:42 pm -
1 stop11h 39m
Deal found 9/16![Frontier logo]()
$184
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:10 am -
Nonstop2h 26m
Tue 10/139:07 am -
Nonstop2h 18m
Deal found 9/16![United Airlines logo]()
$185
Best flights from Philadelphia to ChicagoDiscover carefully curated flight deals from Philadelphia to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 19, 2026.
Discover carefully curated flight deals from Philadelphia to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 19, 2026.
This United Airlines deal was found by Cheapflights users on 9/17. 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 10/286:15 am -
Nonstop2h 36m
Sat 10/318:50 am -
Nonstop2h 14m
Deal found 9/17![United Airlines logo]()
$185
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 11/1411:30 am -
2 stops6h 55m
Tue 11/1711:30 am -
2 stops9h 40m
Deal found 9/14![Southwest logo]()
$215
This Delta deal was found by Cheapflights users on 9/16. 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 10/2412:32 pm -
1 stop6h 28m
Mon 10/266:44 pm -
1 stop3h 24m
Deal found 9/16![Delta logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Tue 10/275:45 pm -
1 stop15h 59m
Fri 10/307:56 pm -
2 stops21h 23m
Deal found 9/17![Multiple Airlines logo]()
$347
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/147:30 pm -
1 stop5h 02m
Tue 10/209:07 am -
Nonstop2h 18m
Deal found 9/15![United Airlines logo]()
$195
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:40 pm -
1 stop4h 20m
Sat 10/104:20 pm -
Nonstop2h 00m
Deal found 9/15![Southwest logo]()
$221
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/176:00 am -
1 stop4h 37m
Mon 12/216:15 pm -
1 stop3h 56m
Deal found 9/15![Delta logo]()
$231
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/1411:05 am -
Nonstop2h 24m
Thu 10/159:07 am -
Nonstop2h 18m
Deal found 9/14![United Airlines logo]()
$224
This Delta deal was found by Cheapflights users on 9/16. 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.
Thu 11/56:10 am -
1 stop4h 22m
Mon 11/96:44 pm -
1 stop3h 31m
Deal found 9/16![Delta logo]()
$231
This Southwest deal was found by Cheapflights users on 9/16. 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.
Mon 11/97:25 pm -
1 stop4h 20m
Sat 11/143:40 pm -
Nonstop2h 00m
Deal found 9/16![Southwest logo]()
$234
This United Airlines deal was found by Cheapflights users on 9/17. 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 10/236:10 am -
Nonstop2h 25m
Tue 12/86:54 am -
Nonstop2h 03m
Deal found 9/17![United Airlines logo]()
$233
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:15 pm -
1 stop4h 40m
Tue 12/811:30 am -
2 stops9h 35m
Deal found 9/17![Southwest logo]()
$258
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1710:37 am -
1 stop7h 17m
Mon 12/219:20 pm -
Nonstop2h 14m
Deal found 9/15![United Airlines logo]()
$247
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/247:55 am -
Nonstop2h 05m
Sun 10/255:25 pm -
1 stop6h 35m
Deal found 9/14![Southwest logo]()
$258
This United Airlines deal was found by Cheapflights users on 9/18. 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 11/146:15 am -
Nonstop2h 35m
Tue 11/178:50 am -
Nonstop2h 15m
Deal found 9/18![United Airlines logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/109:29 pm -
1 stop13h 58m
Mon 12/1410:16 am -
1 stop6h 29m
Deal found 9/15![Multiple Airlines logo]()
$381
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/147:45 am -
Nonstop2h 05m
Sun 10/1811:10 am -
Nonstop1h 55m
Deal found 9/15![Southwest logo]()
$274
This United Airlines deal was found by Cheapflights users on 9/18. 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 10/279:45 am -
Nonstop2h 35m
Thu 10/2911:07 am -
Nonstop2h 12m
Deal found 9/18![United Airlines logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/33:35 pm -
2 stops18h 43m
Mon 10/510:44 am -
1 stop12h 25m
Deal found 9/14![Multiple Airlines logo]()
$386
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/116:45 am -
Nonstop2h 05m
Thu 11/57:25 pm -
Nonstop1h 55m
Deal found 9/17![Southwest logo]()
$287
This United Airlines deal was found by Cheapflights users on 9/18. 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 10/136:15 am -
1 stop4h 23m
Tue 10/207:00 am -
Nonstop2h 09m
Deal found 9/18![United Airlines logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2912:25 pm -
2 stops45h 15m
Fri 10/28:02 pm -
1 stop14h 00m
Deal found 9/15![Multiple Airlines logo]()
$408
This United Airlines deal was found by Cheapflights users on 9/18. 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 10/2410:40 am -
1 stop4h 46m
Thu 11/57:57 pm -
Nonstop2h 12m
Deal found 9/18![United Airlines logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 9/246:00 pm -
1 stop23h 15m
Fri 10/307:56 pm -
2 stops26h 10m
Deal found 9/14![Multiple Airlines logo]()
$420
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/61:50 pm -
Nonstop2h 15m
Fri 11/203:50 pm -
Nonstop1h 55m
Deal found 9/15![Southwest logo]()
$318
This United Airlines deal was found by Cheapflights users on 9/18. 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 10/107:30 pm -
1 stop5h 01m
Sat 10/1710:54 am -
1 stop6h 48m
Deal found 9/18![United Airlines logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/205:45 pm -
1 stop15h 59m
Wed 10/2111:04 am -
1 stop12h 34m
Deal found 9/18![Multiple Airlines logo]()
$426
This Southwest deal was found by Cheapflights users on 9/18. 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 10/225:10 pm -
1 stop9h 00m
Fri 10/2311:05 am -
2 stops6h 25m
Deal found 9/18![Southwest logo]()
$344
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 11/107:40 pm -
1 stop5h 21m
Wed 11/116:24 pm -
Nonstop2h 14m
Deal found 9/14![United Airlines logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/275:45 pm -
1 stop16h 47m
Sun 10/410:08 am -
2 stops30h 01m
Deal found 9/15![Multiple Airlines logo]()
$442
Last-minute flights from Philadelphia to ChicagoDiscover last-minute flight deals from Philadelphia to Chicago. Data last updated September 19, 2026 and is based on user searches.
Discover last-minute flight deals from Philadelphia to Chicago. Data last updated September 19, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 9/292:50 pm -
1 stop9h 09m
Sat 10/104:41 pm -
Nonstop2h 23m
Deal found 9/14![Frontier logo]()
$183
This Cheapflightsfares deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/109:09 pm -
Nonstop2h 30m
Mon 10/127:44 pm -
1 stop10h 37m
Deal found 9/17![Frontier logo]()
$181
This Booking.com deal was found by Cheapflights users on 9/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/121:52 pm -
1 stop26h 38m
Sat 10/174:41 pm -
Nonstop2h 23m
Deal found 9/19![Frontier logo]()
$179
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1411:25 am -
Nonstop2h 05m
Tue 10/207:45 am -
Nonstop1h 55m
Deal found 9/15![Southwest logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/205:22 pm -
1 stop19h 10m
Mon 10/267:44 pm -
1 stop25h 53m
Deal found 9/18![Frontier logo]()
$178
This Expedia deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:22 pm -
1 stop7h 21m
Thu 10/226:40 pm -
1 stop11h 41m
Deal found 9/15![Frontier logo]()
$180
This Booking.com deal was found by Cheapflights users on 9/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:50 am -
1 stop19h 34m
Mon 10/267:44 pm -
1 stop10h 37m
Deal found 9/17![Frontier logo]()
$180
This Frontier deal was found by Cheapflights users on 9/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:00 am -
1 stop13h 56m
Sat 10/248:04 am -
1 stop13h 08m
Deal found 9/16![Frontier logo]()
$182
This Frontier deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:00 am -
1 stop7h 17m
Wed 10/286:42 pm -
1 stop11h 29m
Deal found 9/15![Frontier logo]()
$182
This Mytrip deal was found by Cheapflights users on 9/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2812:36 pm -
2 stops23h 47m
Thu 10/294:42 pm -
Nonstop2h 16m
Deal found 9/17![Frontier logo]()
$184
This United Airlines deal was found by Cheapflights users on 9/17. 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 10/286:15 am -
Nonstop2h 36m
Sat 10/318:50 am -
Nonstop2h 14m
Deal found 9/17![United Airlines logo]()
$185
This CheapOair deal was found by Cheapflights users on 9/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:03 pm -
1 stop6h 44m
Sun 11/16:42 pm -
1 stop11h 39m
Deal found 9/16![Frontier logo]()
$184
One-way flights from Philadelphia to ChicagoSearch for one-way flight options from Philadelphia to Chicago. Find affordable one-way fares based on user searches. Data last updated September 19, 2026.
Search for one-way flight options from Philadelphia to Chicago. Find affordable one-way fares based on user searches. Data last updated September 19, 2026.
This Super.com deal was found by Cheapflights users on 9/18. 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.
Wed 12/28:34 am -
1 stop11h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$92
This Super.com deal was found by Cheapflights users on 9/18. 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.
Tue 11/1712:36 pm -
1 stop6h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$92
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/139:34 am -
Nonstop2h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![United Airlines logo]()
$93
This Southwest deal was found by Cheapflights users on 9/16. 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.
Sat 10/1710:15 am -
Nonstop2h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$93
This Frontier deal was found by Cheapflights users on 9/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:09 pm -
Nonstop2h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$94
This CheapOair deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/612:40 pm -
1 stop6h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 10/2012:35 pm -
2 stops22h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 11/126:03 pm -
1 stop6h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$95
This Super.com deal was found by Cheapflights users on 9/18. 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.
Wed 10/2812:36 pm -
1 stop6h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Wed 12/168:34 am -
1 stop11h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$97
This Super.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1812:36 pm -
1 stop6h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$97
This Super.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2912:36 pm -
1 stop7h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$98
Find flight deals from Philadelphia to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Philadelphia (PHL) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $178 (Kiwi.com) |
One-way from | $92 (Super.com) |
Popular in | June |
Cheapest in | January |
Average price | $296 |
Good round-trip deal | $303 or less |
Good one-way deal | $169 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Philadelphia 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 September 19, 2026.
Use the filters below to find and compare flights from Philadelphia 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
Sat 11/14
7:50 am-9:10 am
Nonstop2h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$93
PhiladelphiaChicago
PHL Philadelphia - RFD Chicago Greater Rockford
PHLRFD
Philadelphia
Tue 10/20
12:35 pm-10:14 am
2 stops22h 39m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$97
PhiladelphiaChicago
PHL Philadelphia - ORD Chicago O'Hare Intl
PHLORD
Philadelphia
Sat 10/10
6:10 am-10:24 am
1 stop5h 14m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$103
PhiladelphiaChicago
PHL Philadelphia - ORD Chicago O'Hare Intl
PHLORD
Philadelphia
Tue 12/1
6:00 am-11:51 am
1 stop6h 51m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$103
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Thu 11/19
1:25 pm-2:40 pm
Nonstop2h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$106
PhiladelphiaChicago
PHL Philadelphia - ORD Chicago O'Hare Intl
PHLORD
Philadelphia
Thu 10/15
6:10 am-10:29 am
1 stop5h 19m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$116
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Mon 10/12
5:16 pm-10:33 pm
1 stop6h 17m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$116
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Sat 10/10
10:15 am-11:25 am
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$119
PhiladelphiaChicago
PHL Philadelphia - ORD Chicago O'Hare Intl
PHLORD
Philadelphia
Sat 11/7
1:16 pm-2:51 pm
Nonstop2h 35m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$129
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Thu 12/10
6:20 pm-7:35 pm
Nonstop2h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$129
Showing 1-10 of 60 resultsSorted by cheapest first
Compare providers for flights from Philadelphia to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Philadelphia to Chicago in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Philadelphia-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Philadelphia-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Philadelphia-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Philadelphia-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Philadelphia-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Philadelphia to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Philadelphia with our price prediction graph.
PHL-CHI
PHL-ORD
PHL-MDW
PHL-RFD
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 Philadelphia to Chicago
PHL-CHI
PHL-ORD
PHL-MDW
PHL-RFD
What is the cheapest month to book a flight from Philadelphia to Chicago?
Currently, January is the cheapest month in which you can book a flight from Philadelphia to Chicago (average of $233). Flying from Philadelphia to Chicago in March 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 PHL to CHI?
Find hourly flight availability from Philadelphia 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 September 19, 2026.
It’s optimal to fly from Philadelphia to Chicago in the afternoon. By choosing this option you can save up to 15% on the cost of your flight, compared to a flight in the morning.
Weekly flight availability from Philadelphia to Chicago
Explore weekly flight availability from Philadelphia 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 September 19, 2026.
The most flights from PHL to CHI are scheduled on a Friday (54 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (21 on average).
How much does it cost to fly round-trip from Philadelphia to Chicago?
Airfare is below average for this route at the moment.
Philadelphia to Chicago flights typically cost between $208 and $349 in November.The cheapest round-trip price found within the last 5 days was $178 on Frontier (Nov 3-Nov 12).
How often are flights from Philadelphia to Chicago delayed?
About 18% of weekly flights between Philadelphia and Chicago have experienced delays in the past year, with the average delay time being 140 minutes.
What is the most punctual flight time for Philadelphia to Chicago flights?
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Friday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Philadelphia to Chicago flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 9% of flights being delayed.
How far ahead should I book a flight from Philadelphia to Chicago?
The price you pay for your flight from Philadelphia to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 77 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest day to fly from Philadelphia to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Philadelphia to Chicago. Price data was last updated on September 12, 2026.
Travelers seeking maximum savings on their Philadelphia to Chicago flight should consider departing on Friday afternoons 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.
The best insider tips for Philadelphia to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Philadelphia to Chicago trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 19, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican Airlines from Philadelphia to Chicago. 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.
Entertainment
7.5
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Philadelphia 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
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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 September 19, 2026.
Complete your trip
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Philadelphia and Chicago flights
Browse other Philadelphia and Chicago flight options. Last updated on September 19, 2026.
Other flights from Philadelphia
Browse through other flights departing from Philadelphia. Flights are based on user searches made on Cheapflights and were last updated on September 19, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Philadelphia to Chicago
Discover the top 5 airlines that operate flights from Philadelphia 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 September 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$73 | Average$190 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$133 | Average$281 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$177 | Average$361 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$177 | Average$371 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$179 | Average$335 | FlexibilityNo cancel fee | On-time71% |