$64 Cheap Flights from Philadelphia (PHL) to Chicago (MDW)

View $64 flight on Wed, Jan 28, 2026Opens in a new window

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

Cheap Flights from Philadelphia to Chicago (PHL-MDW)

Prices were available within the past 7 days and start at $64 for one-way flights and $128 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Tue, Jan 27 - Tue, Feb 3
PHL
Philadelphia
MDW
Chicago
$128 Roundtrip, found 13 hours ago
$128
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Tue, Jan 27 from Philadelphia to Chicago, returning Tue, Feb 3, priced at $128 found 13 hours ago
Frontier Airlines
Wed, Jan 28 - Mon, Feb 2
PHL
Philadelphia
MDW
Chicago
$138 Roundtrip, just found
$138
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Jan 28 from Philadelphia to Chicago, returning Mon, Feb 2, priced at $138 just found
Southwest Airlines
Tue, Jan 13 - Sat, Jan 17
PHL
Philadelphia
MDW
Chicago
$139 Roundtrip, just found
$139
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Jan 13 from Philadelphia to Chicago, returning Sat, Jan 17, priced at $139 just found
Southwest Airlines
Wed, Feb 11 - Thu, Feb 12
PHL
Philadelphia
MDW
Chicago
$144 Roundtrip, found 5 hours ago
$144
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Wed, Feb 11 from Philadelphia to Chicago, returning Thu, Feb 12, priced at $144 found 5 hours ago
Frontier Airlines
Wed, Mar 4 - Sat, Mar 7
PHL
Philadelphia
MDW
Chicago
$145 Roundtrip, found 1 day ago
$145
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Mar 4 from Philadelphia to Chicago, returning Sat, Mar 7, priced at $145 found 1 day ago
Frontier Airlines
Thu, Jan 15 - Mon, Jan 19
PHL
Philadelphia
MDW
Chicago
$148 Roundtrip, just found
$148
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Jan 15 from Philadelphia to Chicago, returning Mon, Jan 19, priced at $148 just found
Southwest Airlines
Sat, Jan 17 - Sun, Jan 18
PHL
Philadelphia
MDW
Chicago
$149 Roundtrip, found 2 hours ago
$149
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Sat, Jan 17 from Philadelphia to Chicago, returning Sun, Jan 18, priced at $149 found 2 hours ago
Southwest Airlines
Sat, Feb 28 - Thu, Mar 5
PHL
Philadelphia
MDW
Chicago
$151 Roundtrip, just found
$151
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, Feb 28 from Philadelphia to Chicago, returning Thu, Mar 5, priced at $151 just found
Frontier Airlines
Tue, Jan 27 - Fri, Jan 30
PHL
Philadelphia
MDW
Chicago
$153 Roundtrip, found 5 hours ago
$153
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Tue, Jan 27 from Philadelphia to Chicago, returning Fri, Jan 30, priced at $153 found 5 hours ago
Delta
Wed, Feb 4 - Sat, Feb 7
PHL
Philadelphia
MDW
Chicago
$158 Roundtrip, found 2 hours ago
$158
Roundtrip
found 2 hours ago
Select Delta flight, departing Wed, Feb 4 from Philadelphia to Chicago, returning Sat, Feb 7, priced at $158 found 2 hours ago

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

October is typically the cheapest month to fly

From $78 - $209 per traveler.

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $251
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $251
Flights from Philadelphia (PHL) to Chicago (MDW)
Origin airport
Philadelphia Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$128
Distance
666 mi
Average flight time
1 hour 10 mins

Philadelphia to Chicago Flights

The cheapest times to fly from Philadelphia to Chicago

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 Philadelphia to Chicago are during the month of January. You can find some of the cheapest flights from Philadelphia to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Philadelphia to Chicago

Sunday is one of the best days to book for cheap flights from Philadelphia to Chicago: 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 Philadelphia to Chicago

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 Philadelphia to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $64 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 Philadelphia to Chicago 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 Philadelphia to Chicago 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 Philadelphia Intl. Airport (PHL) to Midway Intl. Airport (MDW) cost?
Secure a cheap one-way flight from $64 or cheap return flight from $128 from Philadelphia Intl. Airport (PHL) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Philadelphia Intl. Airport (PHL) to Midway Intl. Airport (MDW)?
Flying in January is a good way to save, as it's the cheapest month for flights between PHL and MDW. You'll often find the lowest prices during the off-season.
Which airlines fly direct from Philadelphia Intl. Airport (PHL) to Midway Intl. Airport (MDW)?
When jetting out of Philadelphia Intl. Airport (PHL), you can board a direct flight to Midway Intl. Airport (MDW) with Southwest Airlines.
What is the cheapest airline that flies from Philadelphia Intl. Airport (PHL) to Midway Intl. Airport (MDW)?
To find the cheapest airline that'll fly you from PHL to MDW, use Expedia's filter tool. Tailor your search based on your travel needs, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to discover the cheapest flight right away.
How many flights per day from Philadelphia Intl. Airport (PHL) to Midway Intl. Airport (MDW)?
When departing from Philadelphia Intl. Airport (PHL), you can take your pick from an average of 3 daily nonstop flights to Midway Intl. Airport (MDW).
What are the most popular departure times for flights from Philadelphia Intl. Airport (PHL) to Midway Intl. Airport (MDW)?
The 6 AM departures from PHL to MDW are the top choice for many travelers. Greater demand means you'll likely pay more for these departures. If you're looking to save, pick a less crowded time to fly.
What day of the week has the most flights from PHL to MDW?
If you depart on a Friday, you'll get the widest range of options for flights from Philadelphia Intl. Airport (PHL) to Midway Intl. Airport (MDW).
What is the earliest flight from Philadelphia Intl. Airport (PHL) to Midway Intl. Airport (MDW)?
The earliest flight out of Philadelphia Intl. Airport (PHL) is at around 6:00AM UTC-5. Hop on this flight and you'll touch down at Midway Intl. Airport (MDW) at approximately 7:20AM UTC-6. The entire trip takes 2h 20m.
How long does it take to fly from Philadelphia Intl. Airport (PHL) to Midway Intl. Airport (MDW)?
It takes about 2 hours and 18 minutes to fly the 670 mi from PHL to MDW.
What is the best time to fly from Philadelphia Intl. Airport (PHL) to Midway Intl. Airport (MDW)?
To avoid possible delays on the Philadelphia Intl. Airport (PHL) to Midway Intl. Airport (MDW) route, aim to travel before 3 PM. Later departures have a 22% higher chance of cancellation.**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 Chicago from Philadelphia Intl. Airport (PHL)?
You can arrive at O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW) when you travel to Chicago on a direct flight from Philadelphia Intl. Airport (PHL).
Is it cheaper to buy a plane ticket from Philadelphia Intl. Airport (PHL) to Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from PHL to MDW just before your trip is typically more expensive. But if you're flexible with your departure times and dates, you could land a cheap last-minute fare.
Is it cheaper to book a PHL to MDW flight and hotel package?
You'll typically save money by booking a PHL to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one convenient place. After choosing your preferred accommodations and flights, consider adding extras like tours, activities and car rentals.
Can I cancel or change the date of my flight from Philadelphia Intl. Airport (PHL) to Midway Intl. Airport (MDW)?
If you reserved your PHL to MDW flight within the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the type of ticket you have, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal for further details.

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Chicago nearby Airports

Chicago

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*Available to One Key members.