$90+ Cheap flights from Philadelphia (PHL) to Midway (MDW)
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 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — MDW
Nov 29 — Dec 61
Round-trip
1 adult, Economy
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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 January or November, booked 37 days in advance, depart on a Wednesday or Saturday 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 October 30, 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 October 30, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:34 am -
1 stop9h 33m
Mon 12/76:11 pm -
1 stop13h 49m
Deal found 10/28![Frontier logo]()
$177
This Cheapflightsfares deal was found by Cheapflights users on 10/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:34 am -
1 stop9h 33m
Mon 12/76:11 pm -
1 stop27h 38m
Deal found 10/27![Frontier logo]()
$182
This Travelocity deal was found by Cheapflights users on 10/27. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/138:40 am -
1 stop8h 26m
Wed 12/1612:28 pm -
1 stop7h 39m
Deal found 10/27![Frontier logo]()
$185
This Cheapflightsfares deal was found by Cheapflights users on 10/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/108:40 am -
1 stop8h 26m
Sat 12/1212:28 pm -
1 stop9h 43m
Deal found 10/29![Frontier logo]()
$186
This Trip.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/78:40 am -
1 stop8h 26m
Wed 12/912:28 pm -
1 stop7h 39m
Deal found 10/30![Frontier logo]()
$187
This Expedia deal was found by Cheapflights users on 10/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:34 am -
1 stop9h 33m
Tue 12/812:28 pm -
1 stop7h 39m
Deal found 10/29![Frontier logo]()
$188
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/198:30 am -
1 stop10h 17m
Mon 11/238:42 pm -
1 stop10h 20m
Deal found 10/28![Frontier logo]()
$190
This Frontier deal was found by Cheapflights users on 10/27. 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.
Thu 11/198:30 am -
1 stop10h 17m
Thu 11/261:16 pm -
1 stop6h 21m
Deal found 10/27![Frontier logo]()
$192
This Cheapflightsfares deal was found by Cheapflights users on 10/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/188:30 am -
1 stop10h 17m
Wed 11/258:42 pm -
1 stop10h 20m
Deal found 10/27![Frontier logo]()
$194
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/164:31 pm -
1 stop6h 53m
Mon 12/218:35 pm -
1 stop10h 27m
Deal found 10/28![Frontier logo]()
$195
This Trip.com deal was found by Cheapflights users on 10/29. 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 12/15:01 am -
1 stop7h 32m
Thu 12/33:36 pm -
1 stop6h 19m
Deal found 10/29![Frontier logo]()
$196
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/78:40 am -
1 stop8h 26m
Fri 12/116:11 pm -
1 stop27h 38m
Deal found 10/28![Frontier logo]()
$197
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 October 30, 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 October 30, 2026.
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/91:25 pm -
Nonstop2h 15m
Wed 12/1611:25 am -
Nonstop1h 50m
Deal found 10/25![Southwest logo]()
$199
This Delta deal was found by Cheapflights users on 10/29. 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.
Wed 12/306:00 am -
1 stop3h 49m
Tue 1/56:40 pm -
1 stop3h 34m
Deal found 10/29![Delta logo]()
$260
This Southwest deal was found by Cheapflights users on 10/28. 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.
Wed 2/35:10 am -
2 stops12h 10m
Sat 2/66:40 am -
1 stop6h 15m
Deal found 10/28![Southwest logo]()
$224
This Southwest deal was found by Cheapflights users on 10/26. 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.
Wed 2/105:25 pm -
Nonstop2h 15m
Thu 2/117:10 pm -
Nonstop1h 55m
Deal found 10/26![Southwest logo]()
$239
This Southwest deal was found by Cheapflights users on 10/27. 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.
Fri 1/82:15 pm -
1 stop4h 20m
Sat 1/912:00 pm -
Nonstop2h 00m
Deal found 10/27![Southwest logo]()
$249
This Southwest deal was found by Cheapflights users on 10/26. 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.
Thu 12/36:00 am -
1 stop10h 30m
Sat 12/57:50 am -
2 stops11h 25m
Deal found 10/26![Southwest logo]()
$251
This Southwest deal was found by Cheapflights users on 10/26. 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.
Wed 12/25:05 pm -
1 stop6h 35m
Fri 12/411:30 am -
2 stops9h 40m
Deal found 10/26![Southwest logo]()
$260
This Southwest deal was found by Cheapflights users on 10/29. 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 12/36:00 am -
1 stop10h 30m
Mon 12/78:10 am -
Nonstop1h 55m
Deal found 10/29![Southwest logo]()
$260
This Southwest deal was found by Cheapflights users on 10/28. 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.
Mon 11/238:15 pm -
1 stop4h 55m
Fri 11/273:50 pm -
Nonstop1h 55m
Deal found 10/28![Southwest logo]()
$261
This Southwest deal was found by Cheapflights users on 10/29. 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 12/105:35 am -
2 stops13h 15m
Mon 12/143:50 pm -
1 stop4h 40m
Deal found 10/29![Southwest logo]()
$262
This Southwest deal was found by Cheapflights users on 10/29. 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.
Fri 11/206:25 pm -
Nonstop2h 10m
Mon 11/233:50 pm -
Nonstop1h 55m
Deal found 10/29![Southwest logo]()
$265
This Southwest deal was found by Cheapflights users on 10/29. 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 12/95:35 am -
2 stops9h 55m
Sun 12/136:30 am -
1 stop6h 20m
Deal found 10/29![Southwest logo]()
$285
Last-minute flights from Philadelphia to MidwayDiscover last-minute flight deals from Philadelphia to Midway. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Philadelphia to Midway. Data last updated October 30, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 10/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/105:14 pm -
1 stop7h 33m
Tue 11/176:42 pm -
1 stop11h 39m
Deal found 10/26![Frontier logo]()
$216
This Cheapflightsfares deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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.
Mon 11/165:14 pm -
1 stop7h 33m
Tue 11/176:42 pm -
1 stop11h 39m
Deal found 10/25![Frontier logo]()
$198
This Cheapflightsfares deal was found by Cheapflights users on 10/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/188:30 am -
1 stop10h 17m
Wed 11/258:42 pm -
1 stop10h 20m
Deal found 10/27![Frontier logo]()
$194
This Cheapflightsfares deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/185:14 pm -
1 stop7h 33m
Mon 11/238:42 pm -
1 stop10h 20m
Deal found 10/30![Frontier logo]()
$214
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/198:30 am -
1 stop10h 17m
Mon 11/238:42 pm -
1 stop13h 41m
Deal found 10/28![Frontier logo]()
$190
This Frontier deal was found by Cheapflights users on 10/27. 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.
Thu 11/198:30 am -
1 stop10h 17m
Thu 11/261:16 pm -
1 stop6h 21m
Deal found 10/27![Frontier logo]()
$192
This Cheapflightsfares deal was found by Cheapflights users on 10/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/198:30 am -
1 stop10h 17m
Sun 11/228:42 pm -
1 stop13h 41m
Deal found 10/29![Frontier logo]()
$213
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2010:07 pm -
1 stop22h 40m
Mon 11/238:42 pm -
1 stop23h 11m
Deal found 10/28![Frontier logo]()
$215
This Cheapflightsfares deal was found by Cheapflights users on 10/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/217:21 am -
1 stop7h 24m
Thu 12/105:02 pm -
1 stop5h 38m
Deal found 10/26![Frontier logo]()
$201
This CheapOair deal was found by Cheapflights users on 10/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2110:07 pm -
1 stop22h 40m
Mon 11/238:42 pm -
1 stop27h 11m
Deal found 10/28![Frontier logo]()
$206
This Trip.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/217:06 am -
1 stop13h 41m
Thu 11/261:16 pm -
1 stop6h 21m
Deal found 10/30![Frontier logo]()
$212
This Frontier deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2311:27 am -
1 stop9h 20m
Tue 12/112:33 pm -
1 stop9h 36m
Deal found 10/30![Frontier logo]()
$209
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 October 30, 2026.
Search for one-way flight options from Philadelphia to Midway. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This Super.com deal was found by Cheapflights users on 10/27. 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.
Tue 12/15:01 am -
1 stop7h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:34 am -
1 stop9h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$92
This Super.com deal was found by Cheapflights users on 10/28. 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.
Thu 11/196:00 pm -
1 stop6h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Frontier logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/178:30 am -
2 stops27h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Frontier logo]()
$95
This Frontier deal was found by Cheapflights users on 10/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/138:40 am -
1 stop8h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Frontier logo]()
$96
This CheapOair deal was found by Cheapflights users on 10/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1812:36 pm -
1 stop6h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Frontier logo]()
$98
This Southwest deal was found by Cheapflights users on 10/29. 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 12/911:45 am -
Nonstop2h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Southwest logo]()
$100
This Cheapflightsfares deal was found by Cheapflights users on 10/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/176:37 pm -
1 stop6h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/87:16 am -
1 stop10h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$103
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 October 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $176 (Cheapflightsfares) |
One-way from | $90 (Super.com) |
Popular in | March |
Cheapest in | January |
Average price | $343 |
Good round-trip deal | $362 or less |
Good one-way deal | $201 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 7,457,451 searches. Data last updated October 30, 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 Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Tue 12/15
7:30 am-8:50 am
Nonstop2h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$100
Quickest round-trip
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Thu 11/26
1:25 pm-2:35 pm
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$116
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Mon 11/23
10:07 pm-7:47 pm
1 stop22h 40m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$123
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Thu 11/26
6:00 am-11:25 am
1 stop6h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$126
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Thu 11/19
1:25 pm-2:40 pm
Nonstop2h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$141
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Fri 12/4
2:45 pm-11:10 pm
2 stops9h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$151
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Wed 11/18
11:45 am-1:00 pm
Nonstop2h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$156
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Wed 12/9
1:25 pm-2:40 pm
Nonstop2h 15m
Chicago Midway
Wed 12/16
11:25 am-2:15 pm
Nonstop1h 50m
$199
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Wed 2/3
5:10 am-4:20 pm
2 stops12h 10m
Chicago Midway
Sat 2/6
6:40 am-1:55 pm
1 stop6h 15m
$224
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Wed 2/10
5:25 pm-6:40 pm
Nonstop2h 15m
Chicago Midway
Thu 2/11
7:10 pm-10:05 pm
Nonstop1h 55m
$239
Showing 1-10 of 19 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 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 |
- 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 36 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, January is the cheapest month in which you can book a flight from Philadelphia to Chicago Midway Airport (average of $248). 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 October 30, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 19% on flights from Philadelphia to Chicago Midway Airport by exploring options for tickets in the afternoon.
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 October 24, 2026.
Travelers seeking maximum savings on their Philadelphia to Chicago Midway Airport flight should consider departing on Saturday afternoons 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.
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 120 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?
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 October 30, 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.
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
7.9
Entertainment
7.4
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
7.9
Entertainment
7.4
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
7.9
Entertainment
7.4
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
7.9
Entertainment
7.4
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 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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Midway
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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 7,457,451 searches. Data last updated October 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$105 | Average$198 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$186 | Average$296 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$215 | Average$377 | FlexibilityNo cancel fee | On-time63% |