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$61+ 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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PHL
Jan 8 — Jan 151
Thu 1/8
Thu 1/15
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Chicago Midway to Philadelphia are usually found in October or August, 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 December 9, 2025.

This Southwest deal was found by Cheapflights users on 12/9. 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 12/242:30 pmMDW - PHL
Nonstop1h 50mSouthwest
Wed 1/712:15 pmPHL - MDW
Nonstop2h 15mSouthwest
Deal found 12/9$149
This Southwest deal was found by Cheapflights users on 12/8. 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 12/316:05 pmMDW - PHL
Nonstop1h 55mSouthwest
Wed 1/145:40 amPHL - MDW
Nonstop2h 20mSouthwest
Deal found 12/8$158
This Southwest deal was found by Cheapflights users on 12/9. 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 12/3111:05 amMDW - PHL
Nonstop1h 55mSouthwest
Thu 1/111:40 amPHL - MDW
Nonstop2h 10mSouthwest
Deal found 12/9$174
This Delta deal was found by Cheapflights users on 12/9. 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 12/316:08 pmMDW - PHL
1 stop4h 09mDelta
Thu 1/16:00 amPHL - MDW
1 stop3h 49mDelta
Deal found 12/9$177
This Delta deal was found by Cheapflights users on 12/9. 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 12/246:08 pmMDW - PHL
1 stop4h 09mDelta
Wed 1/76:00 amPHL - MDW
1 stop3h 52mDelta
Deal found 12/9$178
This Trip.com deal was found by Cheapflights users on 12/7. 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.
Thu 12/256:12 amMDW - PHL
1 stop7h 49mFrontier
Fri 1/305:30 amPHL - MDW
1 stop7h 15mFrontier
Deal found 12/7$210
This Expedia deal was found by Cheapflights users on 12/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:12 amMDW - PHL
1 stop9h 57mFrontier
Sat 12/208:36 pmPHL - MDW
1 stop26h 14mFrontier
Deal found 12/9$212
This CheapOair deal was found by Cheapflights users on 12/7. 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.
Sun 12/146:15 amMDW - PHL
1 stop5h 48mFrontier
Sun 12/2110:00 pmPHL - MDW
1 stop24h 58mFrontier
Deal found 12/7$213
This CheapOair deal was found by Cheapflights users on 12/8. 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 12/243:10 pmMDW - PHL
1 stop22h 36mFrontier
Tue 12/3010:00 pmPHL - MDW
1 stop24h 58mFrontier
Deal found 12/8$214

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 December 9, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$128
(Flightnetwork)

One-way from

$61
(Kiwi.com)

Popular in

July

Cheapest in

October

Average price

$215

Good round-trip deal

$220 or less

Good one-way deal

$145 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. 3% potential increase in price ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 9, 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

Wed 1/14

5:30 pm-8:20 pm

Nonstop1h 50m

Philadelphia

Fri 1/16

6:20 pm-7:35 pm

Nonstop2h 15m

$168

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Wed 12/31

11:05 am-2:00 pm

Nonstop1h 55m

Philadelphia

Thu 1/1

11:40 am-12:50 pm

Nonstop2h 10m

$174

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Wed 12/24

6:08 pm-11:17 pm

1 stop4h 09m

Philadelphia

Thu 12/25

6:00 am-8:49 am

1 stop3h 49m

$177

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Thu 1/15

9:40 am-12:35 pm

Nonstop1h 55m

Philadelphia

Sun 1/18

5:40 am-7:00 am

Nonstop2h 20m

$177

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Wed 1/14

5:31 pm-12:21 am

1 stop5h 50m

Philadelphia

Fri 1/16

6:15 am-1:09 pm

1 stop7h 54m

$187

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Fri 1/9

9:50 am-5:57 pm

1 stop7h 07m

Philadelphia

Tue 1/13

12:11 pm-4:29 pm

1 stop5h 18m

$187

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Wed 1/7

5:30 pm-8:20 pm

Nonstop1h 50m

Philadelphia

Fri 1/9

5:45 pm-7:00 pm

Nonstop2h 15m

$188

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Mon 1/12

9:32 am-4:28 pm

1 stop5h 56m

Philadelphia

Fri 1/16

6:15 am-1:09 pm

1 stop7h 54m

$197

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Thu 1/8

11:21 am-7:41 pm

1 stop7h 20m

Philadelphia

Sun 1/11

6:00 am-8:52 am

1 stop3h 52m

$197

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Fri 2/6

5:01 pm-12:52 am

1 stop6h 51m

$65

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/8

Showing 1-10 of 16 results
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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Philadelphia flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 December 5, 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 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Philadelphia (average of $44). Flying from Chicago Midway Airport to Philadelphia in February is currently the most expensive (average of $170). 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 December 9, 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 24% 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 December 6, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to Philadelphia flight should consider departing on Monday afternoons when fares are most often at their lowest. Sunday 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
Airlines
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
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
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 Southwest and Frontier

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

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 December 9, 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
7.9
Good
4,252 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

7.9

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,252 reviews
Southwest
7.9
Good
4,252 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

7.9

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,085 reviews
Southwest
7.9
Good
4,252 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

7.9

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 $168, Southwest can have you in Philadelphia from Chicago Midway Airport in 1h 50m. Chicago Midway Airport and Philadelphia are separated by a distance of 666 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 72% 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 $69. While the most popular route (Chicago Midway - Philadelphia) can be booked for $158 on average, our data indicates $221 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Philadelphia (average of $44). Flying from Chicago Midway Airport to Philadelphia in February is currently the most expensive (average of $170). 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
Pottstown
King of Prussia
Reading
Ocean City
Cherry Hill
Lewes
Dewey Beach
Ephrata
Camden
Vineland
Milford
Dover
Elkton
Essington
Willow Grove
New Castle
Newark
Millville
Chester

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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 December 9, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$78Average$157FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$177Average$305FlexibilityNo cancel feeOn-time63%

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