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

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Flight deals from Philadelphia to Chicago

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Find the cheapest month to fly from Philadelphia to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Philadelphia to Chicago flights are currently cheapest in May.

Direct flights from Philadelphia to Chicago

Alternative Philadelphia to Chicago routes

Looking for the cheapest, fastest or easiest route from Philadelphia to Chicago? You could fly into the following airports instead.

Philadelphia to Chicago: Flight information

The things to know before you go.
Cheapest flight found$56
Cheapest month to flyMay
Average flight time2 hrs, 18 mins
Most popular airlineAmerican Airlines
Average flights per week616

Finding cheap flights from Philadelphia to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a round-trip flight from Philadelphia to Chicago is $56. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 18 minutes is the average flight time from Philadelphia to Chicago.
American Airlines, Southwest Airlines and United fly direct from Philadelphia to Chicago.
There are 604 flights per week flying from Philadelphia to Chicago, as of April 2024.
The cheapest month to fly from Philadelphia to Chicago is usually May.
If you're flying from Philadelphia, the cheapest airport near Chicago is Chicago Midway – which is 9.0 miles away from the center of Chicago. We've found flights to this airport from $56.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Philadelphia to Chicago on Wednesday, May 15, 2024.
Yes – the average flight time is 2 hours and 18 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In April, the average temperature is usually around 46°F. July is typically the warmest month in Chicago, when it usually averages around 80°F. You can expect the least rain in January. The coldest month is January, with temperatures averaging 18°F. The rainiest month is August.
The cheapest airline that flies to Chicago is Frontier Airlines.

Philadelphia to Chicago

Few cities in the United States are as unique as Philly, the southeastern Pennsylvanian municipality that borders Delaware and New Jersey. A long time economic and cultural hub for the region, the City of Brotherly Love has a steadily rising population of 1.5 million, though its larger metropolitan region caters to a total of 6 million; this includes the surrounding suburbs of the three adjacent states.

Once a highly influential railway transportation center in the 19th century, Philadelphia has grown to be one of the most modernized of America’s founding cities. The former meeting place for the country’s Founding Fathers and site of the signing of the U.S. Declaration of Independence and Constitution is now the headquarters for multiple Fortune 1000 companies and a plethora of outdoor sculptures, parks, and attractions.

Over 665 miles to the West lay The Windy City. Alaska Airlines, American Airlines, Continental Airlines, United Airlines, and US Airways are the carriers which offer direct with United typically featuring the shortest trip times. The flight averages 2 hours and 7 minutes, not accounting for potential delays.

Departing the Birthplace of America

US Airways’ second largest hub and the airliner’s chief international transport point, Philadelphia International provides non-stop routes to a multitude of global destinations, including those located in Canada, the Middle East, Europe, Latin America, and the Caribbean. While a majority of the airfield is housed in Philly, parts of it do extent outside the city limits.

Once the site of the first Air Force training field during World War II; Philadelphia International is now a major public-use airport responsible for the transportation of 30 million foreign and domestic passengers. The rate of growth experienced by the facility has been quite rapid in the 21st century, thus necessitating the implementation of multiple expansion projects.

A Day in Chicago

Unmatched dining, shopping, and sports attractions are a few of the things you will find in Chi-Town, but in order to experience the city in all its majestic wonder, do not forget to pay a visit to these following places: Millennium Park, Museum of Science and Industry, Sears Tower, the Chicago Symphony Orchestra, The Chicago Theatre, Buckingham Fountain, and last but not least, The Magnificent Mile!

There are plenty of fun things to see and do in the country’s third largest city. Book cheap flights from Philadelphia to Chicago with Skyscanner’s downloadable smartphone app to avoid running short on travel cash!


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Prices shown on this page are estimated lowest prices only. Found in the last 45 days.