Cheap Flights from Philadelphia to Chicago from CAD 27️ 2024

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Find Philadelphia to Chicago flights starting at CAD 27.

Book one-way or return flights from Philadelphia to Chicago from as little as CAD 27. Choose from the popular airlines below and book your flight today!

One way
Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Searching for the best last minute flight from Philadelphia to Chicago? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Philadelphia to Chicago. Stay updated on price trends and snag the best deals for your upcoming trip.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Find Cheapest Airlines Flying from Philadelphia to Chicago

View airlines operating flights from Philadelphia to Chicago. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Spirit Airlines

From CAD 47

Frontier Airlines

From CAD 50

American Airlines

From CAD 89

Delta Air Lines

From CAD 93

Southwest Airlines

From CAD 98

Sun Country Airlines

From CAD 116

United Airlines

From CAD 120

Jetblue Airways

From CAD 127

ANA airlines

Find more flights and airlines

Alternative Routes for Philadelphia to Chicago Flights

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Philadelphia to Chicago.

Cheapest
PHL
17:49
2h 13m
Direct
MDW
19:02
Philadelphia International Airport - Midway International Airport
Wed, Jun 5Frontier Airlines
CAD 37
PHL
09:09
2h 24m
Direct
ORD
10:33
Philadelphia International Airport - O'Hare International Airport
Wed, Jun 5Frontier Airlines
CAD 50
TTN
21:59
14h 53m
1 transfer
MDW
11:52
Trenton Mercer Airport - Midway International Airport
Wed, May 1Frontier Airlines
CAD 65
TTN
21:59
14h 53m
1 transfer
MDW
11:52
Trenton Mercer Airport - Midway International Airport
Wed, May 1Frontier Airlines
CAD 65
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How do I find the cheapest flights?

When are flight tickets from Philadelphia (PHL) to Chicago (CHI) the cheapest?
Airlines adjust prices for flights from Philadelphia to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much are flights from Philadelphia (PHL) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around CAD 256.
How long is the flight from Philadelphia (PHL) to Chicago (CHI)?
It takes about 2 hours 24 minutes to fly from Philadelphia (PHL) to Chicago (CHI).
What is the transportation method from the main airport to downtown in Chicago?
- The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
- The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
What are the most popular airlines that fly from Philadelphia (PHL) to Chicago (CHI)?
Airlines with flights from Philadelphia (PHL) to Chicago (CHI): Emirates, American Airlines, United Airlines, Alaska Airlines, Qatar Airways, Royal Jordanian and Southwest Airlines.
What's the most popular airline for direct flights from Philadelphia (PHL) to Chicago (CHI)?
American Airlines operates 2 direct flights from Philadelphia (PHL) to Chicago (CHI).
How many airports in Chicago (CHI)?
There are 5 airport(s) in Chicago (CHI): Chicago Du Page County Airport, Midway International Airport, O'Hare International Airport, Chicago Palwaukee Airport and Chicago Rockford International Airport.

How to find a cheap flight from Philadelphia to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Philadelphia to Chicago. Book your flights at the right time and save more.

Book Early

Once prices are gone, they're gone. Lock in deals while you can!

Compare Flight Prices

Compare prices on travel agency and airline websites.

Look Out for Deals

Check airline and travel agency websites for latest flight deals

Check One-way Fares

Buying two cheap one-way flights can sometimes be a better deal than a round-trip.

Try Different Dates

Flying during the week, early in the morning, or late at night can help save money.

Use the Trip.com App

Save up to £10 per person when booking your flights on Trip.com

Flight Information for Philadelphia to Chicago Flights

Cheapest direct flight price	CAD 26
Cheapest return ticket price	CAD 52
Cheapest month	January
Peak season for travel	October
Flight distance	1,065.25km
Average flight time	2 hours 24 minutes
Popular airline	Frontier Airlines