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Cheap Flight Deals from Philadelphia to Chicago

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Round TripOne Way
PHL Philadelphia
CHI Chicago
From $74.98
Jan 13, 2026 - Jan 16, 2026
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PHL Philadelphia
CHI Chicago
From $114.98
Jan 21, 2026 - Jan 30, 2026
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PHL Philadelphia
CHI Chicago
From $175.99
Dec 30, 2025 - Jan 4, 2026
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ILG Wilmington
CHI Chicago
From $408.63
Mar 31, 2026 - Apr 4, 2026
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*All fares above were last found on:
Fares are one way/round trip. Fares incl. all fuel surcharges, taxes & fees and our service fees. Displayed fares are subject to change and cannot be guaranteed at the time of booking. See all booking terms and conditions.

When’s a good time to book a flight from Philadelphia to Chicago?

What’s the cheapest day of the week to fly from Philadelphia to Chicago?

What is the cheapest month to fly from Philadelphia to Chicago?

‡This information is based on historical data from the last 365 days.

Finding Affordable Flights from Philadelphia to Chicago
  • Plan Ahead - One of the keys to securing cheap flights from Philadelphia to Chicago is to plan your trip well in advance. Airlines often offer lower prices for those who book tickets months ahead. Keep an eye on special promotions and sales events, which can yield significant savings.
  • Flexibility is Key - Being flexible with your travel dates can also lead to substantial cost savings. Consider flying during off-peak seasons or on weekdays when prices tend to be lower.
  • Set Price Alerts - To keep tabs on flight prices, consider setting up fare alerts. These alerts will notify you when fares from Philadelphia to Chicago drop, giving you the opportunity to grab cheap deals.
  • Consider Nearby Airports - If Chicago has multiple airports, check the prices at each one. Sometimes, flying into a nearby airport and then taking a short train or bus ride to your destination can be a much cheaper option.
  • Bundle and Save - Booking your flight and accommodation together as a package can often result in significant savings. CheapOair offers these bundled deals, so make sure to explore this option.

When is the Cheapest Time to Book Flights from Philadelphia to Chicago?

Got flexible travel dates? Use our flight data from the past year to discover ideal times to fly from Philadelphia to Chicago. Find out which months and days typically offer lower fares and score our best savings.

CheapOair provides the predicted prices for one-way trips or round-trips with a duration of 7 days for domestic and 14 days for international trips based on historical data and available flight information. Graphs are estimates only. Prices are subject to change and can't be guaranteed until ticketed.
Estimated price for
Round-trip

‡Graphs are estimates only. Based on historical data and available flight information. Prices are subject to change and cannot be guaranteed until ticketed.

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Philadelphia to Chicago Flight Route Information

Travel Distance:6,111 Miles
Airlines Flying This Route: American Airlines, United Airlines, Frontier Airlines
Weekly Flights:259
Avg. Flight Duration:07.51 Hours

Insights About Flying from Philadelphia to Chicago

Q. Which is the high season to travel from Philadelphia to Chicago?

A. The month of July is considered the high season for flying from PHL to CHI. Traveling during the high season can affect ticket prices and availability, making this data crucial for trip planning.

Q. How many direct flights are available from PHL to CHI?

A. There are a total of 1063 direct flights from Philadelphia to Chicago. For travelers seeking convenience and shorter travel times, this data is important when choosing flight options.

Q. Which is the low season to travel from Philadelphia to Chicago?

A. February, December, July, March is considered the low season for traveling from Philadelphia to Chicago, Illinois. Travelers looking for cost-effective options and fewer crowds may consider traveling during this period.

Q. How many daily flights are there between Philadelphia to Chicago?

A. There are as many as 35 daily flights available for travelers between PHL to CHI. This data offers flexibility in choosing departure times that best suit your schedule.

Q. At what time does the last flight depart to Chicago?

A. The last flight to Chicago typically departs between 9:00PM - 10:00PM. Travelers who prefer late-night departures will find this information valuable for planning their journey.

Q. What percentage of travelers spent an average of 2 days in Chicago, Illinois?

A. Approximately 40.94% of travelers spent an average of 2 days exploring Chicago. This information can assist in planning the duration of your stay in Chicago

Q. What percentage of PHL to CHI flyers traveled with kids under 14?

A. About 4% of passengers on flights from Philadelphia to Chicago were accompanied by children under the age of 14. This information is useful if you're planning a family trip and want to know how common it is to travel with young children on this route.

Q. What percentage of Philadelphia to Chicago travelers were over 60 years old?

A. A notable 12% of travelers were aged 60 or older. This statistic provides insights for senior travelers or those seeking a mature travel demographic.

Q. What percentage of PHL to CHI travelers were millennials?

A. Millennials make up a significant portion of travelers on this route, accounting for 41% of all passengers. If you're a millennial looking to connect with like-minded travelers, this statistic might interest you.

Q. What percentage of Philadelphia to Chicago travelers were female?

A. Almost half of the passengers, approximately 49% were female. Knowing the gender distribution can be useful for solo female travelers or those interested in gender-related travel insights.

Q. What percent of Philadelphia to Chicago travellers booked first or business class?

A. 2% of travelers booked first or business class on this route.

Q. At what time the earliest flight departs from Philadelphia?

A. The earliest flight departs at 7:00AM - 8:00AM.

Q. Which is the most popular airport for connecting flights between Philadelphia to Chicago?

A. Nashville International Airport is the most popular airport for connecting flights between PHL to CHI.

Q. On which days one can have the most flight options in Chicago?

A. Monday offer the most flight options in Chicago.

§ All flight facts are based on last 3 months' data except the highest and lowest booking months that are based on last 3 months' data.

Cheap Flights from Philadelphia to Chicago

Looking for flights from Philadelphia to Chicago? Look no more, for you�re at the right place. Book cheap flights from Philadelphia to Chicago on CheapOair and enjoy great discounts. Whether its leisure or a business trip, we offer the most competitive rates on flight tickets to destinations around the world. Grab PHI to CHI flight deals, and save big! Hurry, our cheap rates are not going to last forever, so make your bookings right away!

Airports in Philadelphia

Philadelphia is served by two airports- Philadelphia International Airport, and the Northeast Philadelphia Airport. The Philadelphia International Airport is the primary airport serving the Delaware Valley. It is Located between the city of Philadelphia and Tinicum Township in Pennsylvania. The airport offers scheduled domestic and international flights to Canada, the Caribbean, Latin America, Europe, and the Middle East. Travelers can avail seamless connectivity between the airport and the city through the train and bus service operated by South Eastern Pennsylvania Transit Authority (called SEPTA) and taxis. The Northeast Philadelphia Airport serves as a general aviation reliever airport for Philadelphia International Airport.

Explore Chicago

Chicago is the third-most populous city in the United States. It is located along Lake Michigan in the state of Illinois. Its picture-perfect waterfront skyline (led by Willis Tower, the second tallest building in the Western Hemisphere) and a vibrant nightlife have earned the city the nickname of global architecture capital. Chicago�s unbeatable leadership is further powered by a stellar presence of 20th century architectural and artistic masterpieces. Also of note in the city is the Chicago Park District that consists of more than 570 parks, 31 sand beaches, several museums, two conservatories and 50 nature zones.

Things to do in Chicago

Millennium Park

Millennium Park is a prominent civic center in Chicago. This lakeside attraction along Lake Michigan is home to a wide range of public art and is known for its four postmodern architectural highlights- the Jay Pritzker Pavilion, Cloud Gate, the Crown Fountain and the Lurie Garden. The Jay Pritzker Pavilion is a state-of-the-art pavilion with a picturesque stage framed by curving plates of stainless steel. This pavilion hosts the famous Grant Park Music Festival, a 10-week classical music concert series every year in summer season.

Navy Pier

Built in 1916, the Navy Pier tops the rankings of tourist attractions in Chicago. This 3300 foot-long lakeside attraction along Lake Michigan comprises over fifty acres of parks, restaurants, gardens, shops and exhibition facilities. Some of its top highlights are the Chicago Children's Museum, the Chicago Shakespeare Theater and scores of art works like an anchor from the naval vessel USS Chicago.

Art Institute of Chicago

The Art Institute of Chicago is one of the oldest and largest art museums in the United States. It was founded in 1879 and is now home to an encyclopedic collection of 300000 artworks spanning more than 5000 years of history and corresponding to various cultures around the world. Some popular highlights here include works by Pablo Picasso and about 25000 pieces of European artworks dating back to 1100 AD.

Best Time to fly to Chicago

The best times to visit Chicago are early summer (in April and May) and the fall season (in September and October). It is warm and sunny with maximum daylight hours and full of several cultural festivals like Chicago Comic & Entertainment Expo (April), Chicago Jazz Festival and Oktoberfest Chicago (in September) and the Chicago International Film Festival (October). Budget travelers can visit the city in winter season from November to March to avail cheaper hotel and flight rates. It is freezing cold but one can also enjoy events like The Magnificent Mile Lights Festival (in November) during this time.

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