$59 Cheap Flights from Chicago (MDW) to Philadelphia (PHL)

View $59 flight on Tue, Aug 19, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Philadelphia Intl. Airport (PHL)

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Cheap Flights from Chicago to Philadelphia (MDW-PHL)

Prices were available within the past 7 days and start at $59 for one-way flights and $117 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Aug 19 - Tue, Aug 26
MDW
Chicago
PHL
Philadelphia
$117 Roundtrip, found 9 hours ago
$117
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Tue, Aug 19 from Chicago to Philadelphia, returning Tue, Aug 26, priced at $117 found 9 hours ago
Southwest Airlines
Wed, Sep 24 - Mon, Sep 29
MDW
Chicago
PHL
Philadelphia
$118 Roundtrip, found 5 hours ago
$118
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Wed, Sep 24 from Chicago to Philadelphia, returning Mon, Sep 29, priced at $118 found 5 hours ago
Southwest Airlines
Thu, Oct 2 - Mon, Oct 6
MDW
Chicago
PHL
Philadelphia
$119 Roundtrip, found 5 hours ago
$119
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Thu, Oct 2 from Chicago to Philadelphia, returning Mon, Oct 6, priced at $119 found 5 hours ago
Southwest Airlines
Sun, Sep 7 - Sat, Sep 13
MDW
Chicago
PHL
Philadelphia
$123 Roundtrip, found 5 hours ago
$123
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Sun, Sep 7 from Chicago to Philadelphia, returning Sat, Sep 13, priced at $123 found 5 hours ago
Southwest Airlines
Fri, Sep 12 - Mon, Sep 15
MDW
Chicago
PHL
Philadelphia
$124 Roundtrip, found 3 hours ago
$124
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Fri, Sep 12 from Chicago to Philadelphia, returning Mon, Sep 15, priced at $124 found 3 hours ago
Southwest Airlines
Mon, Oct 20 - Wed, Oct 22
MDW
Chicago
PHL
Philadelphia
$128 Roundtrip, found 16 hours ago
$128
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Mon, Oct 20 from Chicago to Philadelphia, returning Wed, Oct 22, priced at $128 found 16 hours ago
Frontier Airlines
Fri, Sep 19 - Tue, Sep 23
MDW
Chicago
PHL
Philadelphia
$129 Roundtrip, found 19 hours ago
$129
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Fri, Sep 19 from Chicago to Philadelphia, returning Tue, Sep 23, priced at $129 found 19 hours ago
Southwest Airlines
Fri, Oct 3 - Sun, Oct 5
MDW
Chicago
PHL
Philadelphia
$129 Roundtrip, found 10 hours ago
$129
Roundtrip
found 10 hours ago
Select Southwest Airlines flight, departing Fri, Oct 3 from Chicago to Philadelphia, returning Sun, Oct 5, priced at $129 found 10 hours ago
Southwest Airlines
Wed, Sep 24 - Mon, Sep 29
MDW
Chicago
PHL
Philadelphia
$130 Roundtrip, found 5 hours ago
$130
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Wed, Sep 24 from Chicago to Philadelphia, returning Mon, Sep 29, priced at $130 found 5 hours ago
Southwest Airlines
Fri, Oct 3 - Sat, Oct 4
MDW
Chicago
PHL
Philadelphia
$134 Roundtrip, found 1 day ago
$134
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, Oct 3 from Chicago to Philadelphia, returning Sat, Oct 4, priced at $134 found 1 day ago

Find the cheapest month to fly from Chicago (MDW) to Philadelphia (PHL)

September is typically the cheapest month to fly

From $48 - $281 per traveler.

Graph displaying average flight prices per month

Alternative airports near Philadelphia

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Philadelphia Intl. PHL. Cheapest and Closest option available. Average driving time to city center is 17 minutes. Flights from $257
PHL
Philadelphia Intl.
CheapestClosest
Average driving time to city center17 min
Flights from $257
Flights from Chicago (MDW) to Philadelphia (PHL)
Origin airport
Midway Intl.
Destination airport
Philadelphia Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$117
Distance
666 mi
Average flight time
2 hours 58 mins

Chicago to Philadelphia Flights

The cheapest times to fly from Chicago to Philadelphia

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Philadelphia are during the month of August. You can find some of the cheapest flights from Chicago to Philadelphia with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Philadelphia

Sunday is one of the best days to book for cheap flights from Chicago to Philadelphia: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Philadelphia

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Philadelphia in 2025. You can also book with separate airlines for your outbound and return journeys, from $59 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Philadelphia flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Philadelphia airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Philadelphia Intl. Airport (PHL) cost?
Pick up cheap return tickets starting at $103 from Midway Intl. Airport (MDW) to Philadelphia Intl. Airport (PHL). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Frontier Airlines flight leaving MDW on July 11 2025 and touching down at PHL. The price was last updated on July 5 2025 and has not changed since.
What is the cheapest month to fly from MDW to PHL?
The cheapest flights from MDW to PHL are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Midway Intl. Airport (MDW) to Philadelphia Intl. Airport (PHL)?
You can fly directly from Midway Intl. Airport (MDW) to Philadelphia Intl. Airport (PHL) on a Southwest Airlines flight.
What is the cheapest airline that flies from MDW to PHL?
At the moment, the cheapest carrier operating one-way flights from MDW to PHL is Frontier Airlines. You can book a seat on this route from $54. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on September 29 2025. Prices were last updated on July 5 2025 and have not changed since.
How many flights per day from Midway Intl. Airport (MDW) to Philadelphia Intl. Airport (PHL)?
With, on average, 3 direct flights departing from Midway Intl. Airport (MDW) to Philadelphia Intl. Airport (PHL) each day, you'll be soaring through the skies in no time.
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to Philadelphia Intl. Airport (PHL)?
The 10 AM departures from MDW to PHL see the highest demand. Prices can be higher for these popular slots. If you want to save on your trip, pick a less crowded time to fly.
What day of the week has the most flights from MDW to PHL?
Friday has the most flights from Midway Intl. Airport (MDW) to Philadelphia Intl. Airport (PHL). Consider jetting off on this day and you'll have a greater chance of finding a schedule that works for you.
What is the earliest flight from Midway Intl. Airport (MDW) to Philadelphia Intl. Airport (PHL)?
Catch the earliest flight at around 8:35AM UTC-6, leaving from Midway Intl. Airport (MDW). You'll be traveling for around 1h 55m, landing at Philadelphia Intl. Airport (PHL) at approximately 11:30AM UTC-5.
How long does it take to fly from Midway Intl. Airport (MDW) to Philadelphia Intl. Airport (PHL)?
It takes about 1 hour and 52 minutes to cover the 670 mi from MDW to PHL.
What is the best time to fly from Midway Intl. Airport (MDW) to Philadelphia Intl. Airport (PHL)?
Book a flight from Midway Intl. Airport (MDW) to Philadelphia Intl. Airport (PHL) that takes off before 3 PM to reduce the likelihood of delays. Departures after this time are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Philadelphia from Midway Intl. Airport (MDW)?
If you're traveling on a direct flight from Midway Intl. Airport (MDW) to Philadelphia, Philadelphia Intl. Airport (PHL) is the only airport you can land at.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Philadelphia Intl. Airport (PHL) last-minute?
Booking your ticket from MDW to PHL right before your journey is typically more expensive. However, if there's some wiggle room with your itinerary, you could grab a cheap last-minute fare.
Is it cheaper to book a MDW to PHL flight and hotel package?
Compared with arranging flights and hotels separately, booking a MDW to PHL flight and hotel package with Expedia could result in significant savings. What's more, having it all in one place will take the stress out of travel planning. Just pick your flights and choose from our wide range of stays, then customize your trip with other add-ons like tours, car rentals and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Philadelphia Intl. Airport (PHL)?
Typically, you can cancel or modify your MDW to PHL flight. However, additional fees may apply, especially if you booked over 24 hours ago. Double-check your itinerary for the airline's guidelines and fees on flight changes, or if you'd like further details, go to our Customer Service portal.

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