Cheap Flights from Philadelphia (PHL) to Chicago (PWK)

Popular airlines from Philadelphia Intl. Airport (PHL) to Chicago, IL (PWK-Chicago Executive)

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 $120
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $120
Select flight to Midway Intl. MDW. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $120
MDW
Midway Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $120

Frequently asked questions

How much does a flight from Philadelphia Intl. Airport (PHL) to Chicago Executive Airport (PWK) cost?
Grab a cheap one-way flight or cheap return flight from Philadelphia Intl. Airport (PHL) to Chicago Executive Airport (PWK) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Philadelphia Intl. Airport (PHL) to Chicago Executive Airport (PWK)?
Planning your trip for is a great way to save, as it's the cheapest month for flights between PHL and PWK. You'll often find the lowest prices during off-peak months.
How many flights per day from Philadelphia Intl. Airport (PHL) to Chicago Executive Airport (PWK)?
You'll need to hop on a flight with a layover if you're traveling from Philadelphia Intl. Airport (PHL) to Chicago Executive Airport (PWK). There are no daily direct flights on this route. However, simply filter your search to include one or more stops to discover an option that works for you.
What day of the week has the most flights from PHL to PWK?
You'll generally find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Philadelphia Intl. Airport (PHL) to Chicago Executive Airport (PWK)?
To land at Chicago Executive Airport (PWK) on time, opt for a flight that takes off from Philadelphia Intl. Airport (PHL) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**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)?
Catch a direct flight from Philadelphia Intl. Airport (PHL) to Chicago and touch down at O'Hare Intl. Airport (ORD). Another convenient gateway to this city is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Philadelphia Intl. Airport (PHL) to Chicago Executive Airport (PWK) last-minute?
Booking your flight from PHL to PWK right before your trip is typically more expensive. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a PHL to PWK flight and hotel package?
Booking a PHL to PWK flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip all in one place. Select from our impressive range of accommodations and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Philadelphia Intl. Airport (PHL) to Chicago Executive Airport (PWK)?
In most cases, you're able to reschedule or cancel your PHL to PWK flight. However, additional fees may apply, especially if you booked more than 24 hours ago. Double-check your itinerary for the airline's fees and rules on flight changes, or if you'd like more information, go to our Customer Service portal.

Travel information

Origin airport
Philadelphia Intl.
Destination airport
Chicago Executive
Distance
677 mi

Book with confidence

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 . 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 2025. You can also book with separate airlines for your outbound and return journeys, from 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.

 

Philadelphia to Chicago Flights

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*Available to One Key members.