Compare Cheap Flights from Philadelphia to Chicago
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Round Trip Flights from Philadelphia to Chicago
Last updated on Saturday 09/13/2025 at 05:00 AM, the fares mentioned above are for flight tickets and inclusive of fuel surcharges, service fee and taxes. Based on historical data, these fares are subject to change without prior notice and cannot be guaranteed at the time of booking. Kindly go through our terms and conditions before booking.
Book Philadelphia To Chicago Flights
Chicago, the largest city in the US, is located amidst the serene shores of Lake Michigan. Known for its dynamic skyline, Chicago houses the eight tallest skyscrapers in America. This is also known as the birthplace of skyscrapers. The Willis Tower is one of the major highlights of Chicago’s skyline, featuring a Skydeck that overlooks the city. It is not just the skyline but also the architecture that makes Chicago one of the most fascinating cities in the USA. Places such as the Rookery Building, Chicago Cultural Center, Tribune Tower, and Merchandise Mart are among the top buildings that are known for their unique architecture.
What does Chicago have for tourists? There is everything from history, culture, and art that makes it a city worth exploring. To start with, the Field Museum, Chicago Union Station, Adams House, and Chicago Board of Trade Building are among the top historical places you can visit. Art lovers will find Chicago the most artistic city with museums and galleries in every nook and cranny. The Chicago Arts District is a hub where you will find locals and travelers admiring the artwork. The Renaissance Society, Ukrainian Institute of Modern Art, and Chinatown Square are a few popular places to enjoy the artwork and exhibition. Coming to entertainment, Chicago is one of the liveliest cities with Chicago Broadway shows, live music, jazz, and stand-up comedy. You can explore its 77 community areas to explore and experience everything the city has to offer.
Chicago is the best to explore during the summer, i.e., June to August. With pleasant weather and great outdoors, this becomes the peak time for tourists. This also means expensive flights from Philadelphia to Chicago. To save on your flight tickets, fly during the shoulder season, i.e., April to May and September to October. Flights depart from Philadelphia International Airport (PHL) to Chicago O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW). For more information on Philadelphia to Chicago flights, you can give us a call. We are available 24/7 to assist our customers.
Finding Cheap Flights From Philadelphia To Chicago : Frequently Asked Questions
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How much are round-trip flights from Philadelphia to Chicago?
Average cost of a round-trip flight from Philadelphia to Chicago is around $308.
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Which upcoming date is cheapest to fly from Philadelphia to Chicago?
In the next 90 days, flights from Philadelphia to Chicago on will be the cheapest on October 11, 2025, September 29, 2025, and October 04, 2025.
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What?s the cheapest day of the week to fly from Philadelphia to Chicago?
On an average, flights from Philadelphia to Chicago tend to be cheapest on Wednesday.
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Which airlines offers the cheapest fares from Philadelphia to Chicago?
At the moment, FRONTIER AIRLINES and SPIRIT AIRLINES offer the cheapest flights from Philadelphia to Chicago.
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When is the peak season for traveling from Philadelphia to Chicago?
September to November is the peak season to travel from Philadelphia to Chicago.
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Cheapest Months to fly to Chicago
The cheapest months to visit Chicago are from October through December.
* The mentioned flight facts are based on the last 3 months' data. Information regarding the highest and lowest booking months is based on the last 12 months' data.
Major Carriers Operating Flights From Philadelphia To Chicago
SPIRIT AIRLINES
$76
$212
UNITED AIRLINES
$107
$226
AMERICAN AIRLINES
$79
$212
Low Cost Carriers Operating Flights From Philadelphia To Chicago
FRONTIER AIRLINES
$62
$179
SPIRIT AIRLINES
$76
$212
AMERICAN AIRLINES
$79
$212
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