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$96+ 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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PHL
Apr 22 — Apr 291
Wed 4/22
Wed 4/29
1 adult, Economy
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Find cheap flights from Midway to Philadelphia with Cheapflights

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Cheapflights Tip: The best prices from Chicago Midway to Philadelphia are usually found in October or January, booked 62 days in advance, depart on a Monday or Thursday and return on a Friday

Cheap 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 March 23, 2026.

This Trip.com deal was found by Cheapflights users on 3/22. 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 5/111:33 am
MDW
-
PHL
1 stop8h 58m
Frontier
Mon 5/116:30 am
PHL
-
MDW
1 stop5h 39m
Frontier
Deal found 3/22$184
This Southwest deal was found by Cheapflights users on 3/22. 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 5/1210:15 am
MDW
-
PHL
2 stops10h 45m
Southwest
Wed 5/136:45 pm
PHL
-
MDW
1 stop4h 30m
Southwest
Deal found 3/22$186
This Southwest deal was found by Cheapflights users on 3/23. 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 4/253:35 pm
MDW
-
PHL
Nonstop2h 00m
Southwest
Wed 4/296:20 am
PHL
-
MDW
1 stop6h 15m
Southwest
Deal found 3/23$187
This Southwest deal was found by Cheapflights users on 3/23. 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 5/117:40 am
MDW
-
PHL
Nonstop1h 55m
Southwest
Tue 5/1211:35 am
PHL
-
MDW
Nonstop2h 05m
Southwest
Deal found 3/23$189
This CheapOair deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/179:14 am
MDW
-
PHL
1 stop21h 27m
Frontier
Wed 4/2211:02 am
PHL
-
MDW
1 stop12h 12m
Frontier
Deal found 3/19$191
This Southwest deal was found by Cheapflights users on 3/23. 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 5/1612:45 pm
MDW
-
PHL
1 stop8h 20m
Southwest
Tue 5/195:45 pm
PHL
-
MDW
Nonstop2h 10m
Southwest
Deal found 3/23$192
This Trip.com deal was found by Cheapflights users on 3/22. 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 5/42:15 pm
MDW
-
PHL
1 stop9h 39m
Frontier
Mon 5/116:30 am
PHL
-
MDW
1 stop5h 39m
Frontier
Deal found 3/22$193
This Southwest deal was found by Cheapflights users on 3/23. 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 5/271:55 pm
MDW
-
PHL
1 stop7h 05m
Southwest
Sat 5/305:30 pm
PHL
-
MDW
1 stop6h 05m
Southwest
Deal found 3/23$197
This Southwest deal was found by Cheapflights users on 3/23. 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 5/197:55 am
MDW
-
PHL
Nonstop1h 55m
Southwest
Wed 5/2011:35 am
PHL
-
MDW
Nonstop2h 05m
Southwest
Deal found 3/23$199
This Frontier deal was found by Cheapflights users on 3/20. 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 5/2912:04 pm
MDW
-
PHL
1 stop9h 06m
Frontier
Sun 5/316:30 am
PHL
-
MDW
1 stop5h 42m
Frontier
Deal found 3/20$201
This Gotogate deal was found by Cheapflights users on 3/19. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/173:29 pm
MDW
-
PHL
1 stop7h 25m
Frontier
Mon 4/203:41 pm
PHL
-
MDW
1 stop7h 40m
Frontier
Deal found 3/19$202
This Booking.com deal was found by Cheapflights users on 3/22. 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.
Fri 5/111:33 am
MDW
-
PHL
1 stop19h 08m
Frontier
Sun 5/34:55 pm
PHL
-
MDW
1 stop6h 24m
Frontier
Deal found 3/22$203

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 March 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$184
(Trip.com)

One-way from

$96
(Southwest)

Popular in

February

Cheapest in

October

Average price

$334

Good round-trip deal

$287 or less

Good one-way deal

$154 or less
Provider with most accurate pricing for Chicago Midway-Philadelphia flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Philadelphia flights.
Search Deals
From Chicago Midway to Philadelphia
Search Deals
One-way flight from Chicago Midway to Philadelphia
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Philadelphia.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Philadelphia.
Search Deals

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 March 23, 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

Price

Cheapest round-trip

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Tue 5/12

8:00 am-4:50 pm

2 stops7h 50m

Philadelphia

Tue 5/12

6:35 pm-9:50 pm

1 stop4h 15m

$186
Quickest round-trip

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Fri 5/1

6:45 pm-9:45 pm

Nonstop2h 00m

Philadelphia

Mon 5/4

6:00 pm-7:10 pm

Nonstop2h 10m

$227

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Thu 5/7

9:00 am-4:45 pm

1 stop6h 45m

Philadelphia

Thu 5/14

5:25 pm-12:05 am

1 stop7h 40m

$236

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Fri 4/17

3:25 pm-6:25 pm

Nonstop2h 00m

Philadelphia

Fri 4/24

6:00 pm-7:10 pm

Nonstop2h 10m

$237

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Mon 5/11

6:36 pm-11:07 pm

1 stop3h 31m

Philadelphia

Tue 5/12

4:06 pm-9:09 pm

1 stop6h 03m

$257

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Mon 5/4

9:00 am-4:45 pm

1 stop6h 45m

Philadelphia

Mon 5/11

4:30 pm-10:45 pm

2 stops7h 15m

$262

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Wed 6/3

10:59 am-6:39 pm

1 stop6h 40m

Philadelphia

Sat 6/13

6:00 am-8:42 am

1 stop3h 42m

$267

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Tue 5/26

4:40 pm-10:00 pm

1 stop4h 20m

Philadelphia

Wed 6/3

6:35 pm-9:50 pm

1 stop4h 15m

$267

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Thu 4/16

3:25 pm-6:25 pm

Nonstop2h 00m

Philadelphia

Mon 4/20

4:30 pm-9:00 pm

1 stop5h 30m

$267
Cheapest one-way

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Wed 4/22

7:55 am-10:50 am

Nonstop1h 55m

$119

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/19

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy1 starTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • 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.
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 March 13, 2026.

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 62 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, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Philadelphia (average of $57). Flying from Chicago Midway Airport to Philadelphia in February is currently the most expensive (average of $232). 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 March 23, 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 22% 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 March 14, 2026.

Travelers seeking maximum savings on their Chicago Midway Airport to Philadelphia flight should consider departing on Friday 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.

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
Marisa Garcia

Marisa Garcia

Expert on Southwest and Frontier

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

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 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

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 March 23, 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.
Southwest
8.0
Very good
4,324 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,324 reviews
Southwest
8.0
Very good
4,324 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
3,020 reviews
Southwest
8.0
Very good
4,324 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 2 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 $186, Southwest can have you in Philadelphia from Chicago Midway Airport in 7h 50m. Chicago Midway Airport and Philadelphia are separated by a distance of 666 mi.

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

    Frontier, at $67, 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 74% 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 $113. While the most popular route (Chicago Midway - Philadelphia) can be booked for $161 on average, our data indicates $276 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, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Philadelphia (average of $57). Flying from Chicago Midway Airport to Philadelphia in February is currently the most expensive (average of $232). 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
Wildwood
Reading
King of Prussia
Camden
Ocean City
Lewes
Dewey Beach
Pottstown
Ephrata
Vineland
Milford
Cherry Hill
Dover
Elkton
Essington
Willow Grove
New Castle
Millville
Glen Mills
Chester

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.

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 March 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$67Average$160FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$168Average$324FlexibilityNo cancel feeOn-time63%

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