$89+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — CHI
Dec 4 — Dec 111
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 August, booked 65 days in advance, depart on a Friday or Thursday and return on a Thursday
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 November 4, 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 November 4, 2026.
This Justfly.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:34 am -
1 stop11h 29m
Mon 12/79:29 pm -
Nonstop2h 15m
Deal found 11/3![Frontier logo]()
$175
This Cheapflightsfares deal was found by Cheapflights users on 10/30. 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 12/36:45 pm -
Nonstop2h 44m
Sun 12/69:34 pm -
Nonstop2h 15m
Deal found 10/30![Frontier logo]()
$176
This CheapOair deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 12/34:38 pm -
1 stop5h 56m
Mon 12/79:29 pm -
Nonstop2h 15m
Deal found 11/1![Frontier logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 12/76:31 pm -
1 stop20h 59m
Wed 12/94:00 pm -
1 stop6h 11m
Deal found 10/30![Frontier logo]()
$178
This Super.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 12/305:01 am -
1 stop21h 07m
Mon 1/43:30 pm -
Nonstop2h 15m
Deal found 11/2![Frontier logo]()
$179
This Cheapflightsfares deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/22:51 pm -
1 stop24h 09m
Wed 12/98:30 am -
1 stop11h 37m
Deal found 11/3![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 11/236:31 pm -
Nonstop2h 44m
Fri 11/279:20 pm -
Nonstop2h 10m
Deal found 10/30![Frontier logo]()
$181
This Cheapflightsfares deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:34 am -
1 stop9h 33m
Sat 12/512:28 pm -
1 stop9h 43m
Deal found 11/3![Frontier logo]()
$181
This Cheapflightsfares deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/256:31 pm -
Nonstop2h 44m
Mon 11/305:40 am -
1 stop18h 13m
Deal found 11/1![Frontier logo]()
$183
This Expedia deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 12/108:40 am -
1 stop8h 26m
Sat 12/1212:28 pm -
1 stop9h 43m
Deal found 11/3![Frontier logo]()
$183
This Expedia deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 11/256:27 am -
1 stop18h 07m
Fri 11/279:20 pm -
Nonstop2h 10m
Deal found 11/1![Frontier logo]()
$184
This Mytrip deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 11/1812:36 pm -
1 stop6h 54m
Mon 11/239:20 pm -
Nonstop2h 10m
Deal found 11/3![Frontier 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 November 4, 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 November 4, 2026.
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/210:25 am -
1 stop4h 58m
Wed 12/910:40 am -
Nonstop2h 15m
Deal found 11/2![United Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 1/236:00 am -
2 stops11h 50m
Tue 1/268:15 am -
1 stop4h 15m
Deal found 11/1![Southwest logo]()
$224
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 12/88:01 am -
1 stop5h 23m
Sat 1/27:00 am -
1 stop4h 07m
Deal found 10/31![Delta logo]()
$274
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 12/16:00 am -
1 stop4h 37m
Tue 12/82:45 pm -
Nonstop2h 12m
Deal found 11/2![United Airlines logo]()
$238
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 12/1411:45 am -
Nonstop2h 15m
Thu 1/75:30 pm -
Nonstop2h 00m
Deal found 11/2![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 12/116:00 am -
1 stop4h 37m
Mon 1/46:40 pm -
1 stop3h 34m
Deal found 10/31![Delta logo]()
$277
This United Airlines deal was found by Cheapflights users on 10/30. 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 12/259:50 am -
Nonstop2h 36m
Fri 12/256:26 pm -
Nonstop2h 15m
Deal found 10/30![United Airlines logo]()
$257
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 12/184:58 pm -
Nonstop2h 36m
Tue 12/229:20 pm -
Nonstop2h 14m
Deal found 11/2![United Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/245:35 am -
1 stop6h 15m
Wed 1/278:10 am -
Nonstop2h 05m
Deal found 11/2![Southwest logo]()
$294
This Delta deal was found by Cheapflights users on 10/30. 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.
Tue 4/137:29 pm -
1 stop5h 21m
Sat 4/1711:10 am -
1 stop6h 09m
Deal found 10/30![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 10/30. 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.
Fri 1/157:50 am -
Nonstop2h 10m
Sun 1/171:25 pm -
Nonstop1h 55m
Deal found 10/30![Southwest logo]()
$313
This United Airlines deal was found by Cheapflights users on 10/30. 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.
Tue 12/297:37 pm -
1 stop5h 24m
Fri 1/18:45 am -
1 stop4h 28m
Deal found 10/30![United Airlines logo]()
$286
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/246:05 am -
2 stops9h 50m
Tue 1/2612:50 pm -
2 stops7h 25m
Deal found 10/31![Southwest logo]()
$314
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 3/276:00 am -
1 stop3h 58m
Mon 3/2911:10 am -
1 stop6h 09m
Deal found 10/31![Delta logo]()
$366
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 1/81:19 pm -
Nonstop2h 36m
Sun 1/1011:06 am -
Nonstop2h 13m
Deal found 10/31![United Airlines logo]()
$313
This Southwest deal was found by Cheapflights users on 10/30. 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.
Tue 11/247:40 am -
Nonstop2h 25m
Mon 11/307:05 pm -
Nonstop2h 05m
Deal found 10/30![Southwest logo]()
$320
This Southwest deal was found by Cheapflights users on 10/30. 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.
Sun 1/107:50 am -
Nonstop2h 10m
Thu 1/147:45 am -
1 stop5h 00m
Deal found 10/30![Southwest logo]()
$323
This United Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 11/3010:54 am -
Nonstop2h 35m
Wed 12/210:40 am -
Nonstop2h 15m
Deal found 11/1![United Airlines logo]()
$353
This Southwest deal was found by Cheapflights users on 10/30. 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 12/245:05 pm -
1 stop6h 35m
Sun 12/277:35 am -
Nonstop1h 50m
Deal found 10/30![Southwest logo]()
$338
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 12/85:35 am -
2 stops9h 55m
Thu 12/1011:30 am -
2 stops9h 40m
Deal found 11/3![Southwest logo]()
$343
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 11/209:45 am -
Nonstop2h 35m
Tue 12/16:54 am -
Nonstop2h 03m
Deal found 11/3![United Airlines logo]()
$380
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 12/2312:10 pm -
Nonstop2h 10m
Sun 12/2712:50 pm -
1 stop9h 20m
Deal found 10/31![Southwest logo]()
$362
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 12/202:15 pm -
Nonstop2h 05m
Wed 12/237:05 pm -
Nonstop2h 05m
Deal found 11/3![Southwest logo]()
$367
Last-minute flights from Philadelphia to ChicagoDiscover last-minute flight deals from Philadelphia to Chicago. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from Philadelphia to Chicago. Data last updated November 4, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 11/1812:36 pm -
1 stop6h 54m
Wed 11/259:20 pm -
Nonstop2h 10m
Deal found 11/3![Frontier logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 11/236:31 pm -
Nonstop2h 44m
Fri 11/279:20 pm -
Nonstop2h 10m
Deal found 10/30![Frontier logo]()
$181
This Cheapflightsfares deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/256:31 pm -
Nonstop2h 44m
Mon 11/305:40 am -
1 stop18h 13m
Deal found 11/1![Frontier logo]()
$183
This Expedia deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 11/256:27 am -
1 stop18h 07m
Fri 11/279:20 pm -
Nonstop2h 10m
Deal found 11/1![Frontier logo]()
$184
This Cheapflightsfares deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/22:51 pm -
1 stop24h 09m
Wed 12/98:30 am -
1 stop11h 37m
Deal found 11/3![Frontier logo]()
$180
This Cheapflightsfares deal was found by Cheapflights users on 10/30. 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 12/36:45 pm -
Nonstop2h 44m
Sun 12/69:34 pm -
Nonstop2h 15m
Deal found 10/30![Frontier logo]()
$176
This CheapOair deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 12/34:38 pm -
1 stop5h 56m
Mon 12/79:29 pm -
Nonstop2h 15m
Deal found 11/1![Frontier logo]()
$177
This Cheapflightsfares deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:34 am -
1 stop9h 33m
Sat 12/512:28 pm -
1 stop9h 43m
Deal found 11/3![Frontier logo]()
$181
This Justfly.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:34 am -
1 stop11h 29m
Mon 12/79:29 pm -
Nonstop2h 15m
Deal found 11/3![Frontier logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 12/76:31 pm -
1 stop20h 59m
Wed 12/94:00 pm -
1 stop6h 11m
Deal found 10/30![Frontier logo]()
$178
This Expedia deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 12/108:40 am -
1 stop8h 26m
Sat 12/1212:28 pm -
1 stop9h 43m
Deal found 11/3![Frontier logo]()
$183
This Super.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 12/305:01 am -
1 stop21h 07m
Mon 1/43:30 pm -
Nonstop2h 15m
Deal found 11/2![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 November 4, 2026.
Search for one-way flight options from Philadelphia to Chicago. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 1/108:00 am -
Nonstop2h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$89
This Super.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 12/114:31 pm -
1 stop5h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Frontier logo]()
$90
This Super.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 1/226:37 pm -
1 stop6h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Frontier logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 2/46:15 am -
1 stop6h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$91
This Super.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 12/221:38 pm -
Nonstop2h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Frontier logo]()
$92
This Trip.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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.
Tue 1/126:37 pm -
1 stop6h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$94
This Booking.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 12/76:50 pm -
Nonstop2h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Frontier logo]()
$95
This Super.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 12/1612:31 pm -
1 stop9h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 2/166:15 am -
1 stop6h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 12/226:32 am -
1 stop6h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Frontier logo]()
$98
This Super.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 11/245:05 am -
1 stop18h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$99
This CheapOair deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 12/37:34 am -
1 stop9h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$99
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 November 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $174 (Cheapflightsfares) |
One-way from | $89 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $300 |
Good round-trip deal | $299 or less |
Good one-way deal | $195 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 November 4, 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 12/8
6:24 am-8:00 am
Nonstop2h 36m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$100
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Tue 1/5
7:30 am-8:50 am
Nonstop2h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$100
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Tue 12/8
7:30 am-8:50 am
Nonstop2h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$100
PhiladelphiaChicago
PHL Philadelphia - ORD Chicago O'Hare Intl
PHLORD
Philadelphia
Thu 12/10
6:31 pm-7:20 am
1 stop13h 49m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$102
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Wed 1/13
6:05 am-2:45 pm
2 stops9h 40m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$115
Quickest round-trip
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Fri 12/11
11:40 am-12:50 pm
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$129
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Thu 11/26
1:25 pm-2:35 pm
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$129
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Fri 1/22
1:25 pm-2:35 pm
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$129
PhiladelphiaChicago
PHL Philadelphia - ORD Chicago O'Hare Intl
PHLORD
Philadelphia
Thu 11/26
10:30 am-2:39 pm
1 stop5h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Fri 11/20
7:25 pm-10:45 pm
1 stop4h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
Showing 1-10 of 42 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 November.
| 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 Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy1 star | 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
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
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 $240). Flying from Philadelphia to Chicago in June is currently the most expensive (average of $364). 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 November 4, 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 November 4, 2026.
The most flights from PHL to CHI are scheduled on a Monday (50 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (25 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 $193 and $396 in December.The cheapest round-trip price found within the last 5 days was $174 on Frontier (Dec 9-Dec 13).
How often are flights from Philadelphia to Chicago delayed?
About 17% of weekly flights between Philadelphia and Chicago have experienced delays in the past year, with the average delay time being 138 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 October 31, 2026.
Travelers seeking maximum savings on their Philadelphia to Chicago flight should consider departing on Saturday evenings 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 November 4, 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.
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
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
Merrillville
Lansing
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 November 4, 2026.
Complete your trip
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Search flights from Philadelphia to Chicago by cabin class
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Philadelphia and Chicago flights
Browse other Philadelphia and Chicago flight options. Last updated on November 4, 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 November 4, 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 November 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$199 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$83 | Average$281 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$189 | Average$374 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$194 | Average$338 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$213 | Average$378 | FlexibilityNo cancel fee | On-time63% |