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$69+ 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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PHL
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to Philadelphia are usually found in September or August, booked 28 days in advance, depart on a Friday or Saturday and return on a Friday

Cheap 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 September 17, 2025.

Round-trip from

$116
(Cheapflightsfares)

One-way from

$69
(Cheapflightsfares)

Popular in

February

Cheapest in

September

Average price

$165

Good round-trip deal

$152 or less

Good one-way deal

$89 or less
From Chicago Midway to Philadelphia
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One-way flight from Chicago Midway to Philadelphia
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Highest demand for flights based on searches. 7% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago Midway to Philadelphia.
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Price to beat on a one-way flight from Chicago Midway to Philadelphia.
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Find flight deals from Midway to Philadelphia

Cheapest flights from Midway to Philadelphia
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 September 17, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/245:52 pmMDW - PHL
Nonstop2h 01mFrontier
Mon 10/279:48 pmPHL - MDW
Nonstop2h 15mFrontier
Deal found 9/16$116
This Booking.com deal was found by Cheapflights users on 9/16. 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.
Thu 10/168:25 amMDW - PHL
Nonstop2h 02mFrontier
Sun 10/195:05 pmPHL - MDW
1 stop17h 28mFrontier
Deal found 9/16$118
This Trip.com deal was found by Cheapflights users on 9/15. 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 10/218:05 amMDW - PHL
1 stop7h 30mFrontier
Sun 10/266:10 amPHL - MDW
Nonstop2h 15mFrontier
Deal found 9/15$120
This Priceline deal was found by Cheapflights users on 9/16. 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.
Fri 11/712:14 pmMDW - PHL
Nonstop2h 00mFrontier
Sun 11/97:00 amPHL - MDW
Nonstop2h 13mFrontier
Deal found 9/16$121
This Priceline deal was found by Cheapflights users on 9/15. 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.
Thu 10/3010:12 amMDW - PHL
1 stop7h 18mFrontier
Sun 11/25:15 amPHL - MDW
Nonstop2h 15mFrontier
Deal found 9/15$122
This Priceline deal was found by Cheapflights users on 9/15. 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.
Fri 10/38:15 amMDW - PHL
Nonstop2h 01mFrontier
Mon 10/66:00 amPHL - MDW
Nonstop2h 11mFrontier
Deal found 9/15$123
This Frontier deal was found by Cheapflights users on 9/17. 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 10/168:25 amMDW - PHL
Nonstop2h 02mFrontier
Mon 10/204:13 pmPHL - MDW
Nonstop2h 14mFrontier
Deal found 9/17$124
This Cheapflightsfares deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/175:28 pmMDW - PHL
1 stop6h 39mFrontier
Mon 10/204:13 pmPHL - MDW
Nonstop2h 14mFrontier
Deal found 9/15$125
This Priceline deal was found by Cheapflights users on 9/17. 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.
Thu 10/98:25 amMDW - PHL
Nonstop2h 02mFrontier
Sun 10/125:05 amPHL - MDW
1 stop7h 34mFrontier
Deal found 9/17$126
This Cheapflightsfares deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/168:25 amMDW - PHL
Nonstop2h 02mFrontier
Thu 10/236:37 pmPHL - MDW
1 stop6h 09mFrontier
Deal found 9/16$128
This Priceline deal was found by Cheapflights users on 9/17. 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 10/1811:31 amMDW - PHL
1 stop9h 56mFrontier
Mon 10/204:13 pmPHL - MDW
Nonstop2h 14mFrontier
Deal found 9/17$130

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 September 17, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Philadelphia that are best for you.

Fly from

Midway

Fly to

Philadelphia

Route

Depart

Return

Price

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Sat 10/25

5:35 pm-8:30 pm

Nonstop1h 55m

Philadelphia

Sun 10/26

6:00 am-7:05 am

Nonstop2h 05m

$158

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Fri 10/17

6:30 am-9:25 am

Nonstop1h 55m

Philadelphia

Tue 10/21

6:05 pm-7:10 pm

Nonstop2h 05m

$158

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Mon 11/3

8:10 am-11:05 am

Nonstop1h 55m

Philadelphia

Tue 11/4

11:40 am-12:50 pm

Nonstop2h 10m

$158

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Tue 10/14

2:50 pm-5:45 pm

Nonstop1h 55m

Philadelphia

Wed 10/15

5:25 am-6:30 am

Nonstop2h 05m

$159

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Thu 10/23

9:15 pm-12:10 am

Nonstop1h 55m

Philadelphia

Mon 10/27

8:35 pm-9:45 pm

Nonstop2h 10m

$177

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Fri 10/24

9:15 pm-12:10 am

Nonstop1h 55m

Philadelphia

Sun 10/26

6:00 am-7:05 am

Nonstop2h 05m

$177

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Wed 12/10

5:35 am-3:05 pm

2 stops8h 30m

Philadelphia

Sat 12/13

2:20 pm-3:30 pm

Nonstop2h 10m

$184

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Sat 10/18

9:55 am-12:50 pm

Nonstop1h 55m

Philadelphia

Tue 10/21

5:55 am-2:25 pm

2 stops9h 30m

$184

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Sat 10/18

11:10 am-4:35 pm

1 stop4h 25m

Philadelphia

Tue 10/21

6:18 pm-10:14 pm

1 stop4h 56m

$197

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Tue 11/11

8:10 am-11:05 am

Nonstop1h 55m

$70

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 19 results
1
2

The best insider tips for Chicago Midway Airport to Philadelphia flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to Philadelphia trip
Airlines
Frontier

Frontier's UpFront Plus seats guarantee an empty middle seat for added comfort.


Frontier offers no in-flight entertainment; bring your own device pre-loaded with content.

Read more about Frontierby Marisa Garcia
Southwest

Enjoy free snacks and non-alcoholic drinks, plus a complimentary drink on special occasions.


Southwest offers free messaging and high-speed Wi-Fi for a fee on all flights.

Read more about Southwestby Marisa Garcia
Airports
MDW

Order food via the airport’s mobile system directly to your gate to avoid missing boarding and losing seat choice on Southwest.

Read more about MDWby Ramsey Qubein
PHL

Use SEPTA for efficient travel to Center City Philadelphia; stations are near arrival gates and operate until midnight.

Read more about PHLby Mark Chesnut
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Frontier and Southwest

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Mark Chesnut

Mark Chesnut

Expert on PHL

Mark Chesnut

Mark Chesnut

Mark Chesnut is a travel writer and public speaker with more than 30 years of experience. The 2019 winner of the NLGJA Excellence in Travel Writing Award, Mark is the author of the book “Prepare for Departure” and has covered air travel for multiple top consumer and trade media outlets.

Read more

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.
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

How far ahead should I book a flight from Chicago Midway Airport to Philadelphia?

Use this chart to determine the optimal time to book a round-trip flight from Midway to Philadelphia. Price data was last updated on September 12, 2025.

The price you pay for your flight from Chicago Midway Airport to Philadelphia may vary depending on when you book. For the best chance of a lower fare, look to book 27 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 Chicago Midway Airport to Philadelphia?

Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Philadelphia (average of $236). Flying from Chicago Midway Airport to Philadelphia in March is currently the most expensive (average of $295). 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 September 17, 2025.

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 20% 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 September 14, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to Philadelphia flight should consider departing on Saturday at noon when fares are most often at their lowest. Wednesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 September 17, 2025.
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.
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,173 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • What airport do you fly into for flights to Philadelphia from Chicago Midway?

    If you book a flight to Philadelphia from Chicago Midway, you will be flying to Philadelphia, which is the city’s only airport. Philadelphia (PHL) is located 7.0 mi from the center of Philadelphia. There are 4 flights from Chicago Midway to Philadelphia per day from 2 different airlines.

  • How long is the flight from Chicago Midway Airport to Philadelphia?

    For as low as $158, Southwest can have you in Philadelphia from Chicago Midway Airport in 1h 55m. Chicago Midway Airport and Philadelphia are separated by a distance of 666 mi. Most flights are nonstop.

  • What are the cheapest airlines flying from Chicago Midway Airport to Philadelphia round-trip?

    Frontier, at $77, was found to be the cheapest airline from Chicago Midway Airport to Philadelphia. An alternate airline flying to your destination would be Southwest. Users have found that Frontier is 67% cheaper than the other options available to this destination.

  • What are the cheapest flights from Chicago Midway Airport to Philadelphia?

    Looking at all options, your cheapest flight can be booked for $61. While the most popular route (Chicago Midway - Philadelphia) can be booked for $68 on average, our data indicates $153 when flying from Chicago Midway Airport to Philadelphia.

  • Can I find deals for flights from Midway to Philadelphia that include hotel bookings?

    Yes. In addition to deals on Midway to Philadelphia flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Philadelphia?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Philadelphia.

  • Can I find deals for business class flights from Midway to Philadelphia?

    Yes. Cheapflights offers flight deals from Midway to Philadelphia by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Philadelphia?

    Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Philadelphia (average of $236). Flying from Chicago Midway Airport to Philadelphia in March is currently the most expensive (average of $295). 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.

See more FAQs

Traveling to a place near Philadelphia?

Book flights to Philadelphia if you plan to visit one of these locations
Vineland
Wildwood
King of Prussia
Pottstown
Reading
Dewey Beach
Ephrata
Camden
Ocean City
Cherry Hill
Dover
Elkton
Essington
Willow Grove
Newark
Millville
Chester
Exton
Havre de Grace
Plymouth Meeting

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Midway to Philadelphia

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$77Average$166FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$172Average$302FlexibilityNo cancel feeOn-time63%

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