$102+ Cheap flights from Philadelphia (PHL) 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 10/6. 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 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 65 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 August 22, 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 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 Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/59:09 pm -
Nonstop2h 34m
Sun 11/84:42 pm -
Nonstop2h 16m
Deal found 8/19![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 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 11m
Wed 9/166:25 am -
1 stop10h 49m
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
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 August 22, 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 August 22, 2026.
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.
Tue 10/65:08 pm -
Nonstop2h 30m
Wed 10/711:25 am -
Nonstop2h 18m
Deal found 8/17![United Airlines logo]()
$277
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 9/2210:45 am -
Nonstop2h 10m
Sat 9/2611:45 am -
Nonstop1h 55m
Deal found 8/21![Southwest logo]()
$277
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:45 pm -
1 stop15h 14m
Sun 10/410:08 am -
2 stops20h 08m
Deal found 8/18![Multiple Airlines logo]()
$297
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.
Sat 2/139:42 am -
1 stop3h 55m
Sun 2/145:30 am -
1 stop6h 33m
Deal found 8/17![Delta logo]()
$361
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.
Mon 9/146:05 pm -
Nonstop2h 05m
Sat 9/198:10 am -
Nonstop2h 05m
Deal found 8/21![Southwest logo]()
$277
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/19:34 am -
Nonstop2h 25m
Sun 10/44:00 pm -
Nonstop2h 24m
Deal found 8/21![United Airlines logo]()
$284
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.
Wed 10/76:10 am -
Nonstop2h 25m
Fri 10/92:30 pm -
Nonstop2h 24m
Deal found 8/20![United Airlines logo]()
$284
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2410:20 am -
Nonstop2h 05m
Mon 9/283:20 pm -
1 stop5h 45m
Deal found 8/19![Southwest logo]()
$287
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 10/285:28 pm -
2 stops16h 22m
Sun 11/11:12 pm -
1 stop6h 36m
Deal found 8/17![Multiple Airlines logo]()
$332
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.
Sun 9/1311:04 am -
Nonstop2h 25m
Tue 9/156:13 pm -
Nonstop2h 14m
Deal found 8/18![United Airlines logo]()
$284
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 12/165:05 pm -
1 stop6h 30m
Mon 12/213:30 pm -
Nonstop1h 55m
Deal found 8/18![Southwest logo]()
$287
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/105:45 pm -
1 stop16h 07m
Sun 9/139:29 pm -
2 stops15h 52m
Deal found 8/18![Multiple Airlines logo]()
$333
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.
Mon 11/98:15 pm -
1 stop4h 50m
Wed 11/116:25 pm -
Nonstop1h 55m
Deal found 8/20![Southwest logo]()
$287
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.
Fri 9/255:08 pm -
Nonstop2h 30m
Sun 9/279:07 am -
Nonstop2h 18m
Deal found 8/20![United Airlines logo]()
$291
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/35:32 pm -
2 stops16h 46m
Wed 10/79:34 am -
1 stop10h 41m
Deal found 8/18![Multiple Airlines logo]()
$340
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/128:55 am -
1 stop6h 15m
Mon 9/146:45 pm -
Nonstop2h 00m
Deal found 8/17![Southwest logo]()
$287
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 1/112:37 pm -
1 stop4h 56m
Mon 1/258:55 am -
1 stop3h 56m
Deal found 8/20![United Airlines logo]()
$297
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:00 am -
1 stop11h 15m
Sun 9/273:53 pm -
1 stop8h 14m
Deal found 8/20![Multiple Airlines logo]()
$347
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 9/237:15 am -
1 stop7h 15m
Fri 9/252:55 pm -
Nonstop2h 00m
Deal found 8/18![Southwest logo]()
$294
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2110:37 am -
1 stop4h 52m
Mon 12/286:26 pm -
Nonstop2h 15m
Deal found 8/21![United Airlines logo]()
$325
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/174:40 pm -
1 stop7h 05m
Fri 9/181:00 pm -
Nonstop2h 00m
Deal found 8/17![Southwest logo]()
$299
This Kiwi.com 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 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
Thu 10/19:30 am -
1 stop13h 12m
Deal found 8/21![Multiple Airlines logo]()
$380
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.
Sun 10/48:30 pm -
1 stop4h 35m
Sun 10/118:00 am -
Nonstop2h 00m
Deal found 8/20![Southwest logo]()
$301
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1810:15 am -
1 stop4h 57m
Sun 2/218:00 pm -
Nonstop2h 13m
Deal found 8/21![United Airlines logo]()
$351
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:00 am -
2 stops9h 25m
Mon 11/26:30 pm -
1 stop4h 25m
Deal found 8/17![Southwest logo]()
$302
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 10/15:45 pm -
1 stop15h 14m
Mon 10/510:44 am -
1 stop10h 13m
Deal found 8/17![Multiple Airlines logo]()
$418
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2410:54 am -
Nonstop2h 35m
Sun 11/296:35 am -
Nonstop2h 10m
Deal found 8/21![United Airlines logo]()
$351
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.
Fri 12/46:10 am -
Nonstop2h 21m
Sun 12/66:25 pm -
Nonstop2h 07m
Deal found 8/18![United Airlines logo]()
$353
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.
Sun 9/135:45 pm -
1 stop16h 47m
Thu 9/179:29 pm -
2 stops32h 47m
Deal found 8/17![Multiple Airlines logo]()
$428
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/95:10 pm -
1 stop8h 55m
Sat 10/1011:55 am -
2 stops8h 00m
Deal found 8/17![Southwest logo]()
$324
Last-minute flights from Philadelphia to ChicagoDiscover last-minute flight deals from Philadelphia to Chicago. Data last updated August 22, 2026 and is based on user searches.
Discover last-minute flight deals from Philadelphia 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 11m
Wed 9/166:25 am -
1 stop10h 49m
Deal found 8/17![Frontier logo]()
$172
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
Sat 9/126:00 am -
1 stop7h 21m
Deal found 8/17![Frontier logo]()
$176
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 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 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 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.
Sat 9/127:50 am -
1 stop8h 30m
Thu 9/247:25 am -
Nonstop2h 24m
Deal found 8/17![Frontier logo]()
$175
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 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 Philadelphia to ChicagoSearch for one-way flight options from Philadelphia to Chicago. Find affordable one-way fares based on user searches. Data last updated August 22, 2026.
Search for one-way flight options from Philadelphia to Chicago. Find affordable one-way fares based on user searches. Data last updated August 22, 2026.
This Jetabroad 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/612:40 pm -
1 stop6h 43m
Deal found 8/20![Frontier logo]()
$102
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.
Mon 10/51:50 pm -
1 stop26h 30m
Deal found 8/18![Frontier logo]()
$103
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/211:50 pm -
1 stop26h 30m
Deal found 8/17![Frontier logo]()
$105
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.
Sat 10/3112:43 pm -
1 stop10h 10m
Deal found 8/17![Frontier logo]()
$105
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2211:57 am -
1 stop28h 23m
Deal found 8/21![Frontier logo]()
$106
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.
Tue 10/2712:43 pm -
1 stop10h 10m
Deal found 8/17![Frontier logo]()
$106
This Jetabroad 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/312:43 pm -
1 stop10h 10m
Deal found 8/18![Frontier logo]()
$107
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1711:54 am -
Nonstop2h 36m
Deal found 8/19![Frontier logo]()
$109
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 10/1612:35 pm -
1 stop6h 56m
Deal found 8/18![Frontier logo]()
$110
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 10/165:22 pm -
1 stop7h 21m
Deal found 8/18![Frontier logo]()
$110
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.
Fri 9/113:30 pm -
1 stop8h 29m
Deal found 8/17![Frontier logo]()
$111
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.
Fri 9/115:32 pm -
1 stop7h 12m
Deal found 8/17![Frontier logo]()
$111
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 August 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $167 (Kiwi.com) |
One-way from | $102 (Jetabroad) |
Popular in | June |
Cheapest in | January |
Average price | $277 |
Good round-trip deal | $279 or less |
Good one-way deal | $184 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 August 22, 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 - ORD Chicago O'Hare Intl
PHLORD
Philadelphia
Tue 10/6
5:08 pm-6:38 pm
Nonstop2h 30m
Chicago O'Hare Intl
Wed 10/7
11:25 am-2:43 pm
Nonstop2h 18m
$277
Quickest round-trip
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Tue 9/22
10:45 am-11:55 am
Nonstop2h 10m
Chicago Midway
Sat 9/26
11:45 am-2:40 pm
Nonstop1h 55m
$277
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Mon 9/14
6:05 pm-7:10 pm
Nonstop2h 05m
Chicago Midway
Sat 9/19
8:10 am-11:15 am
Nonstop2h 05m
$277
PhiladelphiaChicago
PHL Philadelphia - ORD Chicago O'Hare Intl
PHLORD
Philadelphia
Thu 10/1
9:34 am-10:59 am
Nonstop2h 25m
Chicago O'Hare Intl
Sun 10/4
4:00 pm-7:24 pm
Nonstop2h 24m
$284
PhiladelphiaChicago
PHL Philadelphia - ORD Chicago O'Hare Intl
PHLORD
Philadelphia
Wed 10/7
6:10 am-7:35 am
Nonstop2h 25m
Chicago O'Hare Intl
Fri 10/9
2:30 pm-5:54 pm
Nonstop2h 24m
$284
PhiladelphiaChicago
PHL Philadelphia - ORD Chicago O'Hare Intl
PHLORD
Philadelphia
Sun 9/13
11:04 am-12:29 pm
Nonstop2h 25m
Chicago O'Hare Intl
Tue 9/15
6:13 pm-9:27 pm
Nonstop2h 14m
$284
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Thu 9/24
10:20 am-11:25 am
Nonstop2h 05m
Chicago Midway
Mon 9/28
3:20 pm-10:05 pm
1 stop5h 45m
$287
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Wed 12/16
5:05 pm-10:35 pm
1 stop6h 30m
Chicago Midway
Mon 12/21
3:30 pm-6:25 pm
Nonstop1h 55m
$287
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Mon 11/9
8:15 pm-12:05 am
1 stop4h 50m
Chicago Midway
Wed 11/11
6:25 pm-9:20 pm
Nonstop1h 55m
$287
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Sat 9/12
8:55 am-2:10 pm
1 stop6h 15m
Chicago Midway
Mon 9/14
6:45 pm-9:45 pm
Nonstop2h 00m
$287
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 August.
| 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 Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*1 star | |
| 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 $230). 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 August 22, 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 August 22, 2026.
The most flights from PHL to CHI are scheduled on a Thursday (52 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (31 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 $182 and $332 in October.The cheapest round-trip price found within the last 5 days was $167 on Frontier (Oct 12-Oct 15).
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 141 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?
Saturday 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 August 15, 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 evenings 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 August 22, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited 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.
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Boarding
8.1
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 August 22, 2026.
Complete your trip
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Philadelphia and Chicago flights
Browse other Philadelphia and Chicago flight options. Last updated on August 22, 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 August 22, 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 August 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$75 | Average$184 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$133 | Average$266 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$330 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$176 | Average$352 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$177 | Average$369 | FlexibilityNo cancel fee | On-time63% |