$89+ Cheap flights from Midway (MDW) to Philadelphia (PHL)
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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PHL
Jun 5 — Jun 121
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Philadelphia with Cheapflights
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Cheapest flights from Midway to PhiladelphiaExplore the most affordable flight options available from Midway to Philadelphia. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 6, 2026.
Explore the most affordable flight options available from Midway to Philadelphia. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 6, 2026.
This Expedia deal was found by Cheapflights users on 5/3. 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.
Wed 5/2012:04 pm
MDW
- PHL
1 stop9h 06m
Frontier
Sun 5/244:35 pm
PHL
- MDW
1 stop6h 27m
Frontier
Deal found 5/3![Frontier logo]()
$186
This Trip.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/212:27 pm
MDW
- PHL
1 stop5h 43m
Frontier
Tue 6/94:35 pm
PHL
- MDW
1 stop6h 36m
Frontier
Deal found 5/5![Frontier logo]()
$188
This Expedia deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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.
Tue 5/2612:27 pm
MDW
- PHL
1 stop8h 43m
Frontier
Tue 6/24:25 pm
PHL
- MDW
1 stop6h 37m
Frontier
Deal found 5/5![Frontier logo]()
$190
This Booking.com deal was found by Cheapflights users on 5/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:00 am
MDW
- PHL
1 stop5h 25m
Frontier
Thu 6/44:25 pm
PHL
- MDW
1 stop6h 37m
Frontier
Deal found 5/4![Frontier logo]()
$200
This Trip.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/306:00 am
MDW
- PHL
1 stop5h 25m
Frontier
Wed 6/34:25 pm
PHL
- MDW
1 stop6h 37m
Frontier
Deal found 5/5![Frontier logo]()
$201
This Orbitz deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:00 am
MDW
- PHL
1 stop5h 22m
Frontier
Sat 7/114:30 pm
PHL
- MDW
1 stop6h 38m
Frontier
Deal found 5/5![Frontier logo]()
$204
This Frontier deal was found by Cheapflights users on 5/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
MDW
- PHL
1 stop12h 10m
Frontier
Wed 6/106:25 am
PHL
- MDW
1 stop5h 44m
Frontier
Deal found 5/3![Frontier logo]()
$205
This Frontier deal was found by Cheapflights users on 5/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/156:00 am
MDW
- PHL
1 stop12h 14m
Frontier
Sat 5/164:35 pm
PHL
- MDW
1 stop6h 27m
Frontier
Deal found 5/1![Frontier logo]()
$206
This Trip.com deal was found by Cheapflights users on 5/3. 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.
Sat 7/1112:11 pm
MDW
- PHL
1 stop6h 09m
Frontier
Tue 7/144:30 pm
PHL
- MDW
1 stop6h 38m
Frontier
Deal found 5/3![Frontier logo]()
$209
This Frontier deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 7/296:00 am
MDW
- PHL
1 stop5h 22m
Frontier
Fri 7/316:30 am
PHL
- MDW
1 stop5h 37m
Frontier
Deal found 5/5![Frontier logo]()
$210
This Trip.com deal was found by Cheapflights users on 5/4. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2912:04 pm
MDW
- PHL
1 stop6h 10m
Frontier
Tue 6/26:30 am
PHL
- MDW
1 stop5h 42m
Frontier
Deal found 5/4![Frontier logo]()
$212
This Trip.com deal was found by Cheapflights users on 5/4. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:00 am
MDW
- PHL
1 stop5h 22m
Frontier
Sun 7/126:30 am
PHL
- MDW
1 stop5h 37m
Frontier
Deal found 5/4![Frontier logo]()
$215
Best flights from Midway to PhiladelphiaDiscover carefully curated flight deals from Midway to Philadelphia that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 6, 2026.
Discover carefully curated flight deals from Midway to Philadelphia that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 6, 2026.
This Southwest deal was found by Cheapflights users on 5/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/231:00 pm
MDW
- PHL
Nonstop2h 00m
Southwest
Sun 9/277:20 am
PHL
- MDW
Nonstop2h 00m
Southwest
Deal found 5/4![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 5/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/301:40 pm
MDW
- PHL
Nonstop2h 05m
Southwest
Sat 8/14:30 pm
PHL
- MDW
1 stop8h 10m
Southwest
Deal found 5/4![Southwest logo]()
$305
This Southwest deal was found by Cheapflights users on 5/2. 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.
Thu 6/46:00 pm
MDW
- PHL
1 stop4h 55m
Southwest
Sat 6/66:05 pm
PHL
- MDW
Nonstop2h 10m
Southwest
Deal found 5/2![Southwest logo]()
$305
This Southwest deal was found by Cheapflights users on 5/3. 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 5/2412:50 pm
MDW
- PHL
Nonstop1h 55m
Southwest
Mon 5/257:10 pm
PHL
- MDW
1 stop4h 35m
Southwest
Deal found 5/3![Southwest logo]()
$310
This Southwest deal was found by Cheapflights users on 5/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/201:00 pm
MDW
- PHL
Nonstop1h 55m
Southwest
Sat 5/237:45 am
PHL
- MDW
Nonstop2h 05m
Southwest
Deal found 5/4![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 5/2. 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.
Tue 6/305:20 pm
MDW
- PHL
1 stop4h 30m
Southwest
Mon 7/68:25 pm
PHL
- MDW
1 stop4h 40m
Southwest
Deal found 5/2![Southwest logo]()
$315
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/295:40 pm
MDW
- PHL
1 stop4h 25m
Southwest
Mon 6/17:10 pm
PHL
- MDW
1 stop4h 35m
Southwest
Deal found 5/5![Southwest logo]()
$320
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 8/11:15 pm
MDW
- PHL
2 stops9h 20m
Southwest
Mon 8/35:00 am
PHL
- MDW
2 stops8h 20m
Southwest
Deal found 5/5![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 5/1. 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 7/181:55 pm
MDW
- PHL
Nonstop2h 00m
Southwest
Mon 7/206:55 pm
PHL
- MDW
Nonstop2h 25m
Southwest
Deal found 5/1![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 5/1. 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 5/219:20 am
MDW
- PHL
1 stop6h 55m
Southwest
Sun 5/241:50 pm
PHL
- MDW
Nonstop2h 10m
Southwest
Deal found 5/1![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 5/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/303:35 pm
MDW
- PHL
Nonstop2h 00m
Southwest
Mon 6/15:25 pm
PHL
- MDW
1 stop7h 50m
Southwest
Deal found 5/4![Southwest logo]()
$342
This Southwest deal was found by Cheapflights users on 5/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2312:10 pm
MDW
- PHL
Nonstop1h 55m
Southwest
Mon 5/257:10 pm
PHL
- MDW
1 stop4h 35m
Southwest
Deal found 5/4![Southwest logo]()
$342
Last-minute flights from Midway to PhiladelphiaDiscover last-minute flight deals from Midway to Philadelphia. Data last updated May 6, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Philadelphia. Data last updated May 6, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 5/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/156:00 am
MDW
- PHL
1 stop12h 14m
Frontier
Sat 5/164:35 pm
PHL
- MDW
1 stop6h 27m
Frontier
Deal found 5/1![Frontier logo]()
$206
This Frontier deal was found by Cheapflights users on 5/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1611:59 am
MDW
- PHL
1 stop9h 11m
Frontier
Thu 5/216:10 am
PHL
- MDW
1 stop9h 02m
Frontier
Deal found 5/1![Frontier logo]()
$216
This Expedia deal was found by Cheapflights users on 5/3. 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.
Wed 5/2012:04 pm
MDW
- PHL
1 stop9h 06m
Frontier
Sun 5/244:35 pm
PHL
- MDW
1 stop6h 27m
Frontier
Deal found 5/3![Frontier logo]()
$186
This Expedia deal was found by Cheapflights users on 5/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/226:00 am
MDW
- PHL
1 stop12h 14m
Frontier
Tue 5/266:30 am
PHL
- MDW
1 stop5h 42m
Frontier
Deal found 5/4![Frontier logo]()
$215
This Frontier deal was found by Cheapflights users on 5/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2311:59 am
MDW
- PHL
1 stop9h 11m
Frontier
Fri 6/264:40 pm
PHL
- MDW
1 stop6h 31m
Frontier
Deal found 5/2![Frontier logo]()
$210
This Expedia deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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.
Tue 5/2612:27 pm
MDW
- PHL
1 stop8h 43m
Frontier
Tue 6/24:25 pm
PHL
- MDW
1 stop6h 37m
Frontier
Deal found 5/5![Frontier logo]()
$190
This Priceline deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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.
Wed 5/276:00 am
MDW
- PHL
1 stop5h 25m
Frontier
Thu 5/281:32 pm
PHL
- MDW
1 stop9h 30m
Frontier
Deal found 5/5![Frontier logo]()
$204
This Trip.com deal was found by Cheapflights users on 5/4. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2912:04 pm
MDW
- PHL
1 stop6h 10m
Frontier
Tue 6/26:30 am
PHL
- MDW
1 stop5h 42m
Frontier
Deal found 5/4![Frontier logo]()
$212
This Trip.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/306:00 am
MDW
- PHL
1 stop5h 25m
Frontier
Wed 6/34:25 pm
PHL
- MDW
1 stop6h 37m
Frontier
Deal found 5/5![Frontier logo]()
$201
This Booking.com deal was found by Cheapflights users on 5/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:00 am
MDW
- PHL
1 stop5h 25m
Frontier
Thu 6/44:25 pm
PHL
- MDW
1 stop6h 37m
Frontier
Deal found 5/4![Frontier logo]()
$200
This Trip.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/212:27 pm
MDW
- PHL
1 stop5h 43m
Frontier
Tue 6/94:35 pm
PHL
- MDW
1 stop6h 36m
Frontier
Deal found 5/5![Frontier logo]()
$188
This Frontier deal was found by Cheapflights users on 5/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
MDW
- PHL
1 stop5h 25m
Frontier
Sun 6/74:25 pm
PHL
- MDW
1 stop6h 37m
Frontier
Deal found 5/3![Frontier logo]()
$205
One-way flights from Midway to PhiladelphiaSearch for one-way flight options from Midway to Philadelphia. Find affordable one-way fares based on user searches. Data last updated May 6, 2026.
Search for one-way flight options from Midway to Philadelphia. Find affordable one-way fares based on user searches. Data last updated May 6, 2026.
This Super.com deal was found by Cheapflights users on 5/2. 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 6/36:00 am
MDW
- PHL
1 stop5h 25m
Frontier
Deal found 5/2![Frontier logo]()
$89
This Frontier deal was found by Cheapflights users on 5/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
MDW
- PHL
1 stop5h 25m
Frontier
Deal found 5/4![Frontier logo]()
$90
This Super.com deal was found by Cheapflights users on 5/4. 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.
Tue 7/76:00 am
MDW
- PHL
1 stop5h 22m
Frontier
Deal found 5/4![Frontier logo]()
$94
This Frontier deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 7/86:00 am
MDW
- PHL
1 stop5h 22m
Frontier
Deal found 5/5![Frontier logo]()
$95
This Frontier deal was found by Cheapflights users on 5/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1611:59 am
MDW
- PHL
1 stop9h 11m
Frontier
Deal found 5/1![Frontier logo]()
$96
This Trip.com deal was found by Cheapflights users on 5/3. 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.
Wed 5/2712:04 pm
MDW
- PHL
1 stop9h 06m
Frontier
Deal found 5/3![Frontier logo]()
$98
This Super.com deal was found by Cheapflights users on 5/4. 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.
Tue 5/2612:27 pm
MDW
- PHL
1 stop8h 43m
Frontier
Deal found 5/4![Frontier logo]()
$100
This Super.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/16:00 am
MDW
- PHL
1 stop5h 25m
Frontier
Deal found 5/5![Frontier logo]()
$108
This Frontier deal was found by Cheapflights users on 5/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1112:11 pm
MDW
- PHL
1 stop6h 09m
Frontier
Deal found 5/4![Frontier logo]()
$109
Find flight deals from Midway to Philadelphia
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Philadelphia (PHL). 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 May 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $186 (Expedia) |
One-way from | $89 (Super.com) |
Popular in | February |
Cheapest in | October |
Average price | $303 |
Good round-trip deal | $311 or less |
Good one-way deal | $155 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Philadelphia 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 May 6, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Philadelphia that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoPhiladelphia
MDW - PHL
MDWPHL
Chicago Midway
Wed 9/23
1:00 pm-4:00 pm
Nonstop2h 00m
Philadelphia
Sun 9/27
7:20 am-8:20 am
Nonstop2h 00m
$301
ChicagoPhiladelphia
MDW - PHL
MDWPHL
Chicago Midway
Thu 7/30
1:40 pm-4:45 pm
Nonstop2h 05m
Philadelphia
Sat 8/1
4:30 pm-11:40 pm
1 stop8h 10m
$305
ChicagoPhiladelphia
MDW - PHL
MDWPHL
Chicago Midway
Thu 6/4
6:00 pm-11:55 pm
1 stop4h 55m
Philadelphia
Sat 6/6
6:05 pm-7:15 pm
Nonstop2h 10m
$305
ChicagoPhiladelphia
MDW - PHL
MDWPHL
Chicago Midway
Sun 5/24
12:50 pm-3:45 pm
Nonstop1h 55m
Philadelphia
Mon 5/25
7:10 pm-10:45 pm
1 stop4h 35m
$310
ChicagoPhiladelphia
MDW - PHL
MDWPHL
Chicago Midway
Wed 5/20
1:00 pm-3:55 pm
Nonstop1h 55m
Philadelphia
Sat 5/23
7:45 am-8:50 am
Nonstop2h 05m
$311
ChicagoPhiladelphia
MDW - PHL
MDWPHL
Chicago Midway
Tue 6/30
5:20 pm-10:50 pm
1 stop4h 30m
Philadelphia
Mon 7/6
8:25 pm-12:05 am
1 stop4h 40m
$315
ChicagoPhiladelphia
MDW - PHL
MDWPHL
Chicago Midway
Fri 5/29
5:40 pm-11:05 pm
1 stop4h 25m
Philadelphia
Mon 6/1
7:10 pm-10:45 pm
1 stop4h 35m
$320
ChicagoPhiladelphia
MDW - PHL
MDWPHL
Chicago Midway
Sat 8/1
1:15 pm-11:35 pm
2 stops9h 20m
Philadelphia
Mon 8/3
5:00 am-12:20 pm
2 stops8h 20m
$326
ChicagoPhiladelphia
MDW - PHL
MDWPHL
Chicago Midway
Sat 7/18
1:55 pm-4:55 pm
Nonstop2h 00m
Philadelphia
Mon 7/20
6:55 pm-8:20 pm
Nonstop2h 25m
$327
ChicagoPhiladelphia
MDW - PHL
MDWPHL
Chicago Midway
Thu 5/21
9:20 am-5:15 pm
1 stop6h 55m
Philadelphia
Sun 5/24
1:50 pm-3:00 pm
Nonstop2h 10m
$332
Showing 1-10 of 23 resultsSorted by cheapest first
Compare providers for flights from Midway to Philadelphia
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 Midway to Philadelphia in May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Philadelphia flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Philadelphia flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Philadelphia flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Philadelphia 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 Chicago Midway Airport-Philadelphia 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 Midway to Philadelphia
Have a flexible travel schedule? Discover the best time to fly to Philadelphia from Midway with our price prediction graph.
MDW-PHL
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 Chicago Midway Airport to Philadelphia
What is the cheapest month to book a flight from Chicago Midway Airport to Philadelphia?
Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Philadelphia (average of $116). Flying from Chicago Midway Airport to Philadelphia in February 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 MDW to PHL?
Find hourly flight availability from Midway to Philadelphia. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 6, 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago Midway Airport to Philadelphia in the afternoon. If you’re flexible enough to do this you can expect to save up to 25% on your trip compared to booking a flight in the evening.
What is the cheapest day to fly from Chicago Midway Airport to Philadelphia?
Use this chart to determine the cheapest time to fly round-trip from Midway to Philadelphia. Price data was last updated on May 2, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Philadelphia flight should consider departing on Thursday mornings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Chicago Midway Airport to Philadelphia 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 Chicago Midway Airport to Philadelphia trip
Our travel experts
Reviews of airlines servicing Philadelphia
Get insights into the airlines that provide service to Philadelphia. 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 Philadelphia. Reviews last updated May 6, 2026.
See what other customers who have flown with Southwest and Frontier from Chicago Midway Airport to Philadelphia have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Midway to Philadelphia. 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 Philadelphia?
Book flights to Philadelphia if you plan to visit one of these locationsWildwood
King of Prussia
Reading
Camden
Ocean City
Lewes
Dewey Beach
Pottstown
Vineland
Ephrata
Milford
Dover
Elkton
Essington
Willow Grove
New Castle
Millville
Glen Mills
Chester
Newark
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Midway and Philadelphia flights
Browse other Midway and Philadelphia flight options. Last updated on May 6, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on May 6, 2026.
Other flights to Philadelphia
Explore flights to Philadelphia departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 6, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Midway to Philadelphia
Discover the top 2 airlines that operate flights from Midway to Philadelphia. 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 May 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$67 | Average$161 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$168 | Average$358 | FlexibilityNo cancel fee | On-time63% |