$100+ Cheap flights from Philadelphia (PHL) to Midway (MDW)
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 8/22. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — MDW
Aug 30 — Sep 61
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Philadelphia to Midway 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 Midway are usually found in November or October, booked 18 days in advance, depart on a Friday or Wednesday and return on a Thursday
Cheap flight deals from Philadelphia to Midway
Cheapest
Best
Last-minute
One-way
Cheapest flights from Philadelphia to MidwayExplore the most affordable flight options available from Philadelphia to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2026.
Explore the most affordable flight options available from Philadelphia to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2026.
This Priceline deal was found by Cheapflights users on 7/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/294:45 pm
PHL
- MDW
1 stop7h 02m
Frontier
Wed 9/211:50 am
MDW
- PHL
1 stop9h 43m
Frontier
Deal found 7/30![Frontier logo]()
$178
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/274:45 pm
PHL
- MDW
1 stop7h 02m
Frontier
Thu 9/311:50 am
MDW
- PHL
1 stop9h 43m
Frontier
Deal found 7/30![Frontier logo]()
$180
This Jettzy deal was found by Cheapflights users on 7/30. 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1412:40 pm
PHL
- MDW
1 stop6h 11m
Frontier
Mon 9/216:46 pm
MDW
- PHL
1 stop11h 30m
Frontier
Deal found 7/30![Frontier logo]()
$182
This Trip.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:00 am
PHL
- MDW
1 stop7h 07m
Frontier
Wed 10/2112:03 pm
MDW
- PHL
1 stop5h 12m
Frontier
Deal found 7/30![Frontier logo]()
$184
This FlightHub deal was found by Cheapflights users on 7/31. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1612:40 pm
PHL
- MDW
1 stop6h 11m
Frontier
Mon 9/216:46 pm
MDW
- PHL
1 stop11h 30m
Frontier
Deal found 7/31![Frontier logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:00 am
PHL
- MDW
1 stop6h 59m
Frontier
Thu 10/86:40 am
MDW
- PHL
1 stop5h 32m
Frontier
Deal found 7/31![Frontier logo]()
$188
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/222:45 pm
PHL
- MDW
1 stop9h 02m
Frontier
Mon 8/2411:50 am
MDW
- PHL
1 stop9h 43m
Frontier
Deal found 7/30![Frontier logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 9/176:00 am
PHL
- MDW
1 stop6h 59m
Frontier
Wed 9/236:25 am
MDW
- PHL
1 stop10h 49m
Frontier
Deal found 7/30![Frontier logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Sat 9/2612:40 pm
PHL
- MDW
1 stop6h 11m
Frontier
Wed 9/306:25 am
MDW
- PHL
1 stop10h 49m
Frontier
Deal found 7/30![Frontier logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 9/1612:40 pm
PHL
- MDW
1 stop6h 11m
Frontier
Wed 9/236:25 am
MDW
- PHL
1 stop10h 49m
Frontier
Deal found 7/30![Frontier logo]()
$196
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/242:45 pm
PHL
- MDW
1 stop9h 02m
Frontier
Wed 8/2611:50 am
MDW
- PHL
1 stop9h 43m
Frontier
Deal found 7/31![Frontier logo]()
$200
Best flights from Philadelphia to MidwayDiscover carefully curated flight deals from Philadelphia to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 31, 2026.
Discover carefully curated flight deals from Philadelphia to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 31, 2026.
This Southwest deal was found by Cheapflights users on 7/30. 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 9/34:40 pm
PHL
- MDW
1 stop7h 05m
Southwest
Sun 9/68:40 am
MDW
- PHL
Nonstop2h 05m
Southwest
Deal found 7/30![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:00 am
PHL
- MDW
Nonstop2h 05m
Southwest
Mon 9/216:45 pm
MDW
- PHL
Nonstop2h 00m
Southwest
Deal found 7/27![Southwest logo]()
$268
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/235:05 pm
PHL
- MDW
Nonstop2h 05m
Southwest
Wed 9/25:55 pm
MDW
- PHL
Nonstop2h 00m
Southwest
Deal found 7/26![Southwest logo]()
$274
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/252:45 pm
PHL
- MDW
2 stops8h 35m
Southwest
Tue 9/16:00 am
MDW
- PHL
1 stop6h 10m
Southwest
Deal found 7/26![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 7/29. 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.
Sat 9/122:15 pm
PHL
- MDW
1 stop7h 45m
Southwest
Sun 9/138:20 pm
MDW
- PHL
Nonstop2h 00m
Southwest
Deal found 7/29![Southwest logo]()
$284
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/222:35 pm
PHL
- MDW
1 stop8h 05m
Southwest
Sun 10/258:15 pm
MDW
- PHL
Nonstop1h 55m
Southwest
Deal found 7/28![Southwest logo]()
$284
This Southwest deal was found by Cheapflights users on 7/31. 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.
Tue 9/17:15 am
PHL
- MDW
2 stops9h 10m
Southwest
Sat 9/59:20 am
MDW
- PHL
2 stops11h 10m
Southwest
Deal found 7/31![Southwest logo]()
$298
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/281:05 pm
PHL
- MDW
1 stop8h 10m
Southwest
Sun 8/309:45 am
MDW
- PHL
Nonstop1h 55m
Southwest
Deal found 7/28![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 7/29. 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.
Wed 10/216:00 am
PHL
- MDW
2 stops7h 05m
Southwest
Fri 10/2311:05 am
MDW
- PHL
2 stops6h 25m
Southwest
Deal found 7/29![Southwest logo]()
$304
This Southwest deal was found by Cheapflights users on 7/31. 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.
Fri 8/288:00 am
PHL
- MDW
Nonstop2h 05m
Southwest
Mon 8/316:45 pm
MDW
- PHL
Nonstop1h 55m
Southwest
Deal found 7/31![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:00 am
PHL
- MDW
Nonstop2h 05m
Southwest
Mon 9/72:55 pm
MDW
- PHL
Nonstop2h 00m
Southwest
Deal found 7/28![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:55 am
PHL
- MDW
2 stops12h 50m
Southwest
Mon 10/122:15 pm
MDW
- PHL
1 stop8h 10m
Southwest
Deal found 7/27![Southwest logo]()
$336
Last-minute flights from Philadelphia to MidwayDiscover last-minute flight deals from Philadelphia to Midway. Data last updated July 31, 2026 and is based on user searches.
Discover last-minute flight deals from Philadelphia to Midway. Data last updated July 31, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 8/196:40 pm
PHL
- MDW
2 stops29h 07m
Frontier
Mon 8/3111:50 am
MDW
- PHL
1 stop7h 38m
Frontier
Deal found 7/30![Frontier logo]()
$222
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/214:45 pm
PHL
- MDW
1 stop7h 02m
Frontier
Tue 9/296:25 am
MDW
- PHL
1 stop10h 49m
Frontier
Deal found 7/30![Frontier logo]()
$216
This FlightHub deal was found by Cheapflights users on 7/31. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/214:45 pm
PHL
- MDW
1 stop7h 02m
Frontier
Sat 8/2911:45 am
MDW
- PHL
1 stop7h 43m
Frontier
Deal found 7/31![Frontier logo]()
$219
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/218:15 am
PHL
- MDW
1 stop13h 16m
Frontier
Mon 8/2411:50 am
MDW
- PHL
1 stop7h 38m
Frontier
Deal found 7/31![Frontier logo]()
$227
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/222:45 pm
PHL
- MDW
1 stop9h 02m
Frontier
Mon 8/2411:50 am
MDW
- PHL
1 stop9h 43m
Frontier
Deal found 7/30![Frontier logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Sat 8/224:45 pm
PHL
- MDW
1 stop7h 02m
Frontier
Tue 9/296:25 am
MDW
- PHL
1 stop15h 53m
Frontier
Deal found 7/30![Frontier logo]()
$220
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/242:45 pm
PHL
- MDW
1 stop9h 02m
Frontier
Wed 8/2611:50 am
MDW
- PHL
1 stop9h 43m
Frontier
Deal found 7/31![Frontier logo]()
$200
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/274:45 pm
PHL
- MDW
1 stop7h 02m
Frontier
Thu 9/311:50 am
MDW
- PHL
1 stop9h 43m
Frontier
Deal found 7/30![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Fri 8/284:45 pm
PHL
- MDW
1 stop7h 02m
Frontier
Mon 8/3111:50 am
MDW
- PHL
1 stop7h 38m
Frontier
Deal found 7/30![Frontier logo]()
$231
This Priceline deal was found by Cheapflights users on 7/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/294:45 pm
PHL
- MDW
1 stop7h 02m
Frontier
Wed 9/211:50 am
MDW
- PHL
1 stop9h 43m
Frontier
Deal found 7/30![Frontier logo]()
$178
One-way flights from Philadelphia to MidwaySearch for one-way flight options from Philadelphia to Midway. Find affordable one-way fares based on user searches. Data last updated July 31, 2026.
Search for one-way flight options from Philadelphia to Midway. Find affordable one-way fares based on user searches. Data last updated July 31, 2026.
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/224:45 pm
PHL
- MDW
1 stop7h 02m
Frontier
Deal found 7/31![Frontier logo]()
$100
This Expedia deal was found by Cheapflights users on 7/31. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/272:45 pm
PHL
- MDW
1 stop9h 02m
Frontier
Deal found 7/31![Frontier logo]()
$106
This Trip.com deal was found by Cheapflights users on 7/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/184:45 pm
PHL
- MDW
1 stop7h 02m
Frontier
Deal found 7/29![Frontier logo]()
$112
This Super.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/244:45 pm
PHL
- MDW
1 stop7h 02m
Frontier
Deal found 7/28![Frontier logo]()
$119
This Frontier deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/254:45 pm
PHL
- MDW
1 stop7h 02m
Frontier
Deal found 7/27![Frontier logo]()
$120
This Priceline deal was found by Cheapflights users on 7/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/294:45 pm
PHL
- MDW
1 stop7h 02m
Frontier
Deal found 7/29![Frontier logo]()
$121
This Super.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/34:45 pm
PHL
- MDW
1 stop7h 02m
Frontier
Deal found 7/27![Frontier logo]()
$122
This Trip.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/194:45 pm
PHL
- MDW
1 stop7h 02m
Frontier
Deal found 7/27![Frontier logo]()
$123
This Frontier deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2812:43 pm
PHL
- MDW
1 stop10h 10m
Frontier
Deal found 7/27![Frontier logo]()
$126
This Frontier deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/284:45 pm
PHL
- MDW
1 stop7h 02m
Frontier
Deal found 7/27![Frontier logo]()
$127
Find flight deals from Philadelphia to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Philadelphia (PHL) to Midway (MDW). 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 July 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $178 (Priceline) |
One-way from | $100 (Frontier) |
Popular in | March |
Cheapest in | November |
Average price | $435 |
Good round-trip deal | $345 or less |
Good one-way deal | $219 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Philadelphia to Midway 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 2,558,603 searches. Data last updated July 31, 2026.
Use the filters below to find and compare flights from Philadelphia to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PhiladelphiaChicago
PHL - MDW
PHLMDW
Philadelphia
Thu 9/3
4:40 pm-10:45 pm
1 stop7h 05m
Chicago Midway
Sun 9/6
8:40 am-11:45 am
Nonstop2h 05m
$267
PhiladelphiaChicago
PHL - MDW
PHLMDW
Philadelphia
Thu 9/17
8:00 am-9:05 am
Nonstop2h 05m
Chicago Midway
Mon 9/21
6:45 pm-9:45 pm
Nonstop2h 00m
$268
PhiladelphiaChicago
PHL - MDW
PHLMDW
Philadelphia
Sun 8/23
5:05 pm-6:10 pm
Nonstop2h 05m
Chicago Midway
Wed 9/2
5:55 pm-8:55 pm
Nonstop2h 00m
$274
PhiladelphiaChicago
PHL - MDW
PHLMDW
Philadelphia
Tue 8/25
2:45 pm-10:20 pm
2 stops8h 35m
Chicago Midway
Tue 9/1
6:00 am-1:10 pm
1 stop6h 10m
$282
PhiladelphiaChicago
PHL - MDW
PHLMDW
Philadelphia
Sat 9/12
2:15 pm-9:00 pm
1 stop7h 45m
Chicago Midway
Sun 9/13
8:20 pm-11:20 pm
Nonstop2h 00m
$284
PhiladelphiaChicago
PHL - MDW
PHLMDW
Philadelphia
Thu 10/22
2:35 pm-9:40 pm
1 stop8h 05m
Chicago Midway
Sun 10/25
8:15 pm-11:10 pm
Nonstop1h 55m
$284
PhiladelphiaChicago
PHL - MDW
PHLMDW
Philadelphia
Tue 9/1
7:15 am-3:25 pm
2 stops9h 10m
Chicago Midway
Sat 9/5
9:20 am-9:30 pm
2 stops11h 10m
$298
PhiladelphiaChicago
PHL - MDW
PHLMDW
Philadelphia
Fri 8/28
1:05 pm-8:15 pm
1 stop8h 10m
Chicago Midway
Sun 8/30
9:45 am-12:40 pm
Nonstop1h 55m
$301
PhiladelphiaChicago
PHL - MDW
PHLMDW
Philadelphia
Wed 10/21
6:00 am-12:05 pm
2 stops7h 05m
Chicago Midway
Fri 10/23
11:05 am-6:30 pm
2 stops6h 25m
$304
Quickest round-trip
PhiladelphiaChicago
PHL - MDW
PHLMDW
Philadelphia
Fri 8/28
8:00 am-9:05 am
Nonstop2h 05m
Chicago Midway
Mon 8/31
6:45 pm-9:40 pm
Nonstop1h 55m
$316
Showing 1-10 of 23 resultsSorted by cheapest first
Compare providers for flights from Philadelphia to Midway
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 Midway in July.
| 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 |
- Most accurate provider: When it comes to deals on Philadelphia-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Philadelphia-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Philadelphia-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Philadelphia-Chicago Midway Airport 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 Midway Airport 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 Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Philadelphia with our price prediction graph.
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 Midway Airport
Prices
Delays
How far ahead should I book a flight from Philadelphia to Chicago Midway Airport?
The price you pay for your flight from Philadelphia to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 17 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Philadelphia to Chicago Midway Airport?
Currently, November is the cheapest month in which you can book a flight from Philadelphia to Chicago Midway Airport (average of $224). Flying from Philadelphia to Chicago Midway Airport in March is currently the most expensive (average of $461). 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 MDW?
Find hourly flight availability from Philadelphia to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 31, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 13% on flights from Philadelphia to Chicago Midway Airport by exploring options for tickets at noon.
What is the cheapest day to fly from Philadelphia to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from Philadelphia to Midway. Price data was last updated on July 25, 2026.
Travelers seeking maximum savings on their Philadelphia to Chicago Midway Airport 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.
How often are flights from Philadelphia to Chicago delayed?
About 22% of weekly flights between Philadelphia and Chicago have experienced delays in the past year, with the average delay time being 123 minutes.
What is the most punctual flight time for Philadelphia to Chicago flights?
Historically, flights departing in the morning 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?
Tuesday 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, Southwest have had the lowest number of delays on this route, with just 21% of flights being delayed.
The best insider tips for Philadelphia to Chicago Midway Airport 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 Midway Airport trip
Our travel experts
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated July 31, 2026.
Read reviews from past customers who have flown Southwest,Delta, andFrontier from Philadelphia to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
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 Midway. 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 Midway Airport?
Book flights to Chicago Midway Airport 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
Complete your trip
Flights by cabin class
Midway flight routes
Other flight options
Other flights from Philadelphia
Popular flights
Alternative routes for Philadelphia to Midway
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Midway by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Philadelphia to Midway by cabin class
Find flights from Philadelphia to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on July 31, 2026.
Philadelphia and Midway flights
Browse other Philadelphia and Midway flight options. Last updated on July 31, 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 July 31, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Philadelphia to Midway
Discover the top 3 airlines that operate flights from Philadelphia to Midway. 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 2,558,603 searches. Data last updated July 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$82 | Average$176 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$169 | Average$364 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$186 | Average$266 | FlexibilityNo cancel fee | On-timeN/A |