$38 Cheap Flights from Chicago (MDW) to Philadelphia (PHL)

View $38 flight on Mon, Nov 17, 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 $38 for one-way flights and $68 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Fri, Oct 31 - Thu, Nov 6
MDW
Chicago
PHL
Philadelphia
$68 Roundtrip, found 2 days ago
$68
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Oct 31 from Chicago to Philadelphia, returning Thu, Nov 6, priced at $68 found 2 days ago
Frontier Airlines
Thu, Nov 13 - Mon, Nov 17
MDW
Chicago
PHL
Philadelphia
$73 Roundtrip, found 20 hours ago
$73
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Thu, Nov 13 from Chicago to Philadelphia, returning Mon, Nov 17, priced at $73 found 20 hours ago
Frontier Airlines
Thu, Nov 13 - Mon, Nov 17
MDW
Chicago
PHL
Philadelphia
$83 Roundtrip, found 1 hour ago
$83
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Nov 13 from Chicago to Philadelphia, returning Mon, Nov 17, priced at $83 found 1 hour ago
Frontier Airlines
Fri, Nov 7 - Mon, Nov 17
MDW
Chicago
PHL
Philadelphia
$87 Roundtrip, found 2 days ago
$87
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Nov 7 from Chicago to Philadelphia, returning Mon, Nov 17, priced at $87 found 2 days ago
Frontier Airlines
Fri, Nov 14 - Mon, Nov 17
MDW
Chicago
PHL
Philadelphia
$92 Roundtrip, just found
$92
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Nov 14 from Chicago to Philadelphia, returning Mon, Nov 17, priced at $92 just found
Frontier Airlines
Fri, Oct 31 - Mon, Nov 3
MDW
Chicago
PHL
Philadelphia
$93 Roundtrip, found 1 hour ago
$93
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Oct 31 from Chicago to Philadelphia, returning Mon, Nov 3, priced at $93 found 1 hour ago
Frontier Airlines
Mon, Nov 3 - Mon, Nov 17
MDW
Chicago
PHL
Philadelphia
$97 Roundtrip, found 2 days ago
$97
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Nov 3 from Chicago to Philadelphia, returning Mon, Nov 17, priced at $97 found 2 days ago
Frontier Airlines
Fri, Nov 7 - Thu, Nov 13
MDW
Chicago
PHL
Philadelphia
$98 Roundtrip, found 2 days ago
$98
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Nov 7 from Chicago to Philadelphia, returning Thu, Nov 13, priced at $98 found 2 days ago
Frontier Airlines
Thu, Nov 13 - Fri, Nov 28
MDW
Chicago
PHL
Philadelphia
$99 Roundtrip, found 3 days ago
$99
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Nov 13 from Chicago to Philadelphia, returning Fri, Nov 28, priced at $99 found 3 days ago
Southwest Airlines
Wed, Dec 24 - Wed, Dec 31
MDW
Chicago
PHL
Philadelphia
$139 Roundtrip, just found
$139
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, Dec 24 from Chicago to Philadelphia, returning Wed, Dec 31, priced at $139 just found

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

October is typically the cheapest month to fly

From $75 - $258 per traveler.

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 $174
PHL
Philadelphia Intl.
CheapestClosest
Average driving time to city center17 min
Flights from $174

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Philadelphia Intl. Airport (PHL) cost?
Secure a cheap one-way flight from $38 or cheap return flight from $68 from Midway Intl. Airport (MDW) to Philadelphia Intl. Airport (PHL) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Philadelphia Intl. Airport (PHL)?
The cheapest month to fly from MDW to PHL is October, when demand is low. Off-peak months are usually when you'll find lower airfares between these airports.
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 Midway Intl. Airport (MDW) to Philadelphia Intl. Airport (PHL)?
Use the filters on Expedia to compare different airlines and find the cheapest carrier that'll fly you from MDW to PHL. Then, sort your results by "Price (lowest to highest)" to pick up a good deal.
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.

Travel information

Origin airport
Midway Intl.
Destination airport
Philadelphia Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$62
Distance
666 mi
Average flight time
2 hours 55 mins

Book with confidence

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 October. 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 $38 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.

 

Chicago to Philadelphia Flights

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*Available to One Key members.