$91+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — CHI
Nov 3 — Nov 101
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
Cheapest
Best
Last-minute
One-way
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 October 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 October 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:31 pm -
Nonstop2h 44m
Tue 12/18:15 am -
1 stop8h 20m
Deal found 9/29![Frontier logo]()
$183
This Cheapflightsfares deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/288:30 am -
1 stop10h 46m
Fri 10/307:50 pm -
1 stop10h 31m
Deal found 9/30![Frontier logo]()
$184
This Super.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/278:30 am -
1 stop11h 15m
Tue 11/37:28 pm -
1 stop10h 53m
Deal found 9/29![Frontier logo]()
$185
This CheapOair deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/239:09 pm -
Nonstop2h 30m
Sun 10/257:44 pm -
1 stop10h 37m
Deal found 9/30![Frontier logo]()
$186
This Cheapflightsfares deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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 11/59:09 pm -
Nonstop2h 34m
Mon 11/94:42 pm -
Nonstop2h 22m
Deal found 10/4![Frontier logo]()
$187
This Mytrip deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/249:09 pm -
Nonstop2h 30m
Thu 10/296:00 am -
2 stops11h 19m
Deal found 9/30![Frontier logo]()
$188
This Super.com deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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 10/309:09 pm -
Nonstop2h 34m
Mon 11/24:42 pm -
Nonstop2h 16m
Deal found 10/4![Frontier logo]()
$189
This Cheapflightsfares deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/115:22 pm -
1 stop7h 25m
Sat 11/147:25 am -
1 stop9h 54m
Deal found 9/30![Frontier logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/179:09 pm -
Nonstop2h 30m
Wed 10/287:15 am -
1 stop10h 04m
Deal found 9/29![Frontier logo]()
$190
This Super.com deal was found by Cheapflights users on 10/3. 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.
Sat 10/3112:36 pm -
1 stop6h 11m
Tue 11/36:42 pm -
1 stop11h 39m
Deal found 10/3![Frontier logo]()
$190
This Cheapflightsfares deal was found by Cheapflights users on 10/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:30 am -
1 stop11h 01m
Sat 10/244:41 pm -
Nonstop2h 23m
Deal found 10/2![Frontier logo]()
$191
This Cheapflightsfares deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/139:09 pm -
Nonstop2h 34m
Sun 11/154:42 pm -
Nonstop2h 16m
Deal found 9/30![Frontier logo]()
$192
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 October 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 October 4, 2026.
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:15 pm -
1 stop4h 55m
Mon 11/168:10 am -
Nonstop1h 55m
Deal found 9/30![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 10/1. 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 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 10/1![Delta logo]()
$277
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/410:54 am -
Nonstop2h 35m
Sun 11/87:57 pm -
Nonstop2h 12m
Deal found 9/29![United Airlines logo]()
$284
This United Airlines deal was found by Cheapflights users on 10/3. 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.
Sat 12/126:00 am -
1 stop6h 51m
Sat 1/97:00 am -
Nonstop2h 05m
Deal found 10/3![United Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/1411:50 am -
Nonstop2h 10m
Sun 1/175:35 pm -
Nonstop1h 55m
Deal found 9/29![Southwest logo]()
$310
This United Airlines deal was found by Cheapflights users on 10/3. 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.
Tue 2/23:05 pm -
1 stop4h 35m
Tue 2/96:25 pm -
Nonstop2h 15m
Deal found 10/3![United Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 10/2. 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 11/17:30 am -
Nonstop2h 25m
Fri 11/63:50 pm -
Nonstop1h 55m
Deal found 10/2![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:55 am -
2 stops10h 00m
Thu 11/511:10 am -
1 stop11h 10m
Deal found 9/29![Southwest logo]()
$315
This United Airlines deal was found by Cheapflights users on 10/3. 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.
Sun 12/276:24 am -
Nonstop2h 36m
Thu 12/316:26 pm -
Nonstop2h 15m
Deal found 10/3![United Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1912:32 pm -
1 stop5h 00m
Sat 10/246:30 am -
1 stop5h 23m
Deal found 9/29![Delta logo]()
$414
This Southwest deal was found by Cheapflights users on 10/1. 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.
Fri 11/207:25 pm -
1 stop4h 20m
Mon 11/237:25 pm -
Nonstop1h 55m
Deal found 10/1![Southwest logo]()
$320
This United Airlines deal was found by Cheapflights users on 10/3. 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.
Mon 1/186:15 am -
1 stop4h 25m
Sat 1/236:25 pm -
Nonstop2h 15m
Deal found 10/3![United Airlines logo]()
$336
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/101:25 pm -
Nonstop2h 15m
Sun 12/136:30 pm -
1 stop4h 25m
Deal found 9/30![Southwest logo]()
$320
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:24 pm -
Nonstop2h 26m
Thu 10/227:00 am -
Nonstop2h 09m
Deal found 9/29![United Airlines logo]()
$344
This Southwest deal was found by Cheapflights users on 10/3. 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.
Sat 12/127:50 am -
Nonstop2h 20m
Sun 12/138:00 am -
Nonstop2h 00m
Deal found 10/3![Southwest logo]()
$326
This United Airlines deal was found by Cheapflights users on 10/1. 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.
Fri 11/201:16 pm -
Nonstop2h 34m
Sun 11/222:35 pm -
Nonstop2h 12m
Deal found 10/1![United Airlines logo]()
$363
This Southwest deal was found by Cheapflights users on 10/3. 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.
Fri 11/68:15 pm -
1 stop4h 55m
Mon 11/911:10 am -
2 stops12h 00m
Deal found 10/3![Southwest logo]()
$342
This United Airlines deal was found by Cheapflights users on 10/2. 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.
Thu 11/266:15 am -
Nonstop2h 36m
Sun 11/296:35 am -
Nonstop2h 10m
Deal found 10/2![United Airlines logo]()
$389
This Southwest deal was found by Cheapflights users on 10/1. 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.
Thu 11/125:30 am -
2 stops11h 30m
Sun 11/1511:10 am -
2 stops12h 00m
Deal found 10/1![Southwest logo]()
$355
This United Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2410:30 am -
1 stop5h 08m
Sat 11/287:07 am -
Nonstop2h 09m
Deal found 9/30![United Airlines logo]()
$399
Last-minute flights from Philadelphia to ChicagoDiscover last-minute flight deals from Philadelphia to Chicago. Data last updated October 4, 2026 and is based on user searches.
Discover last-minute flight deals from Philadelphia to Chicago. Data last updated October 4, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/179:09 pm -
Nonstop2h 30m
Wed 10/287:15 am -
1 stop10h 04m
Deal found 9/29![Frontier logo]()
$190
This Cheapflightsfares deal was found by Cheapflights users on 10/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:30 am -
1 stop11h 01m
Sat 10/244:41 pm -
Nonstop2h 23m
Deal found 10/2![Frontier logo]()
$191
This CheapOair deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/239:09 pm -
Nonstop2h 30m
Sun 10/257:44 pm -
1 stop10h 37m
Deal found 9/30![Frontier logo]()
$186
This Cheapflightsfares deal was found by Cheapflights users on 10/3. 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.
Fri 10/239:09 pm -
Nonstop2h 30m
Mon 10/267:44 pm -
1 stop10h 37m
Deal found 10/3![Frontier logo]()
$189
This Mytrip deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/249:09 pm -
Nonstop2h 30m
Thu 10/296:00 am -
2 stops11h 19m
Deal found 9/30![Frontier logo]()
$188
This Super.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/278:30 am -
1 stop11h 15m
Tue 11/37:28 pm -
1 stop10h 53m
Deal found 9/29![Frontier logo]()
$185
This Cheapflightsfares deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/288:30 am -
1 stop10h 46m
Fri 10/307:50 pm -
1 stop10h 31m
Deal found 9/30![Frontier logo]()
$184
This Super.com deal was found by Cheapflights users on 10/3. 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.
Sat 10/3112:36 pm -
1 stop6h 11m
Tue 11/36:42 pm -
1 stop11h 39m
Deal found 10/3![Frontier logo]()
$190
This Cheapflightsfares deal was found by Cheapflights users on 10/3. 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 11/59:09 pm -
Nonstop2h 34m
Mon 11/94:42 pm -
Nonstop2h 22m
Deal found 10/3![Frontier logo]()
$187
This Cheapflightsfares deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/115:22 pm -
1 stop7h 25m
Sat 11/147:25 am -
1 stop9h 54m
Deal found 9/30![Frontier logo]()
$189
This Cheapflightsfares deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/139:09 pm -
Nonstop2h 34m
Sun 11/154:42 pm -
Nonstop2h 16m
Deal found 9/30![Frontier logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:31 pm -
Nonstop2h 44m
Tue 12/18:15 am -
1 stop8h 20m
Deal found 9/29![Frontier logo]()
$183
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 October 4, 2026.
Search for one-way flight options from Philadelphia to Chicago. Find affordable one-way fares based on user searches. Data last updated October 4, 2026.
This Super.com deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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.
Sat 11/1412:36 pm -
1 stop6h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Frontier logo]()
$91
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/115:22 pm -
1 stop16h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$92
This Cheapflightsfares deal was found by Cheapflights users on 10/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/412:36 pm -
1 stop6h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Frontier logo]()
$93
This Cheapflightsfares deal was found by Cheapflights users on 10/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3112:36 pm -
1 stop6h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Frontier logo]()
$93
This Cheapflightsfares deal was found by Cheapflights users on 10/1. 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.
Sun 10/259:09 pm -
Nonstop2h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Frontier logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:34 am -
1 stop7h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 10/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/312:36 pm -
1 stop6h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![Frontier logo]()
$97
This Cheapflightsfares deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/309:09 pm -
Nonstop2h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Frontier logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/96:40 pm -
1 stop13h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 10/2. 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 12/14:38 pm -
1 stop15h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 10/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/312:36 pm -
1 stop6h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![Frontier logo]()
$105
This Super.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/224:39 pm -
1 stop9h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$107
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 October 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $183 (Kiwi.com) |
One-way from | $91 (Super.com) |
Popular in | June |
Cheapest in | January |
Average price | $287 |
Good round-trip deal | $324 or less |
Good one-way deal | $179 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 October 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 - MDW Chicago Midway
PHLMDW
Philadelphia
Fri 2/5
12:35 pm-1:45 pm
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$138
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Fri 11/13
1:50 pm-3:05 pm
Nonstop2h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$138
PhiladelphiaChicago
PHL Philadelphia - ORD Chicago O'Hare Intl
PHLORD
Philadelphia
Tue 12/1
6:19 am-7:55 am
Nonstop2h 36m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$145
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Tue 2/2
11:50 am-1:00 pm
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$145
PhiladelphiaChicago
PHL Philadelphia - ORD Chicago O'Hare Intl
PHLORD
Philadelphia
Fri 12/25
10:37 am-4:54 pm
1 stop7h 17m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$148
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Fri 1/29
1:15 pm-9:50 pm
2 stops9h 35m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$153
Quickest round-trip
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Mon 10/26
11:30 am-12:35 pm
Nonstop2h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$156
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Sun 10/25
6:45 am-7:50 am
Nonstop2h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$156
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Tue 12/1
5:35 am-2:40 pm
2 stops10h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$160
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Wed 11/18
5:35 am-2:40 pm
2 stops10h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$160
Showing 1-10 of 41 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 October.
| 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 | |
| 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 $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 October 4, 2026.
It’s optimal to fly from Philadelphia to Chicago in the afternoon. By choosing this option you can save up to 16% 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 October 4, 2026.
The most flights from PHL to CHI are scheduled on a Friday (52 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (12 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 $203 and $365 in November.The cheapest round-trip price found within the last 5 days was $183 on Frontier (Nov 23-Dec 1).
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 September 26, 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 October 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.
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Overall
7.9
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Overall
7.9
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Overall
7.9
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Overall
7.9
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Overall
7.9
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
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Philadelphia
Popular flights
Alternative routes for Philadelphia to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 4, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Philadelphia to Chicago by cabin class
Find flights from Philadelphia to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Philadelphia and Chicago flights
Browse other Philadelphia and Chicago flight options. Last updated on October 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 October 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 October 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$69 | Average$192 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$133 | Average$281 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$190 | Average$368 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$190 | Average$375 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$190 | Average$337 | FlexibilityNo cancel fee | On-time71% |