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Find cheap one-way flights from Philadelphia to Chicago starting at US$20.

Book one-way or return flights from Philadelphia to Chicago from as little as US$20. 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.

When is the cheapest time to book flights from Philadelphia to Chicago?

We monitor flight fares to help you find the best deals effortlessly

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

Frontier Airlines
From US$20
Spirit Airlines
From US$33
American Airlines
From US$45
Southwest Airlines
From US$62
United Airlines
From US$73
Delta Air Lines
From US$78
Sun Country Airlines
From US$115
Jetblue Airways
From US$209
ANA airlines

Find more flights and airlines

Find cheap flights from Philadelphia to Chicago by different airports

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Philadelphia to Chicago.

  • Cheapest
    Frontier Airlines
    PHL
    22:59
    2h 17m
    Direct
    MDW
    00:16
    Philadelphia International Airport - Midway International Airport
    Tue, Apr 23Frontier Airlines
    US$20
  • Frontier Airlines
    PHL
    09:09
    2h 24m
    Direct
    ORD
    10:33
    Philadelphia International Airport - O'Hare International Airport
    Wed, May 22Frontier Airlines
    US$30
  • Frontier Airlines
    TTN
    21:59
    14h 53m
    1 transfer
    MDW
    11:52
    Trenton Mercer Airport - Midway International Airport
    Sat, Apr 13Frontier Airlines
    US$53
  • Frontier Airlines
    TTN
    21:59
    14h 53m
    1 transfer
    MDW
    11:52
    Trenton Mercer Airport - Midway International Airport
    Sat, Apr 13Frontier Airlines
    US$53
    Find More Flights

Frequently Asked Questions

  • When are flight tickets from Philadelphia (PHL) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Philadelphia to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
  • How much do flights from Philadelphia (PHL) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around $235.
  • How long does it take to fly from Philadelphia (PHL) to Chicago (CHI) and what is the distance?

    It takes around 2 hours 23 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. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14km. It takes about 30 minutes by taxi.
  • What are the most popular airlines that fly from Philadelphia (PHL) to Chicago (CHI)?

    Airlines with flights from Philadelphia (PHL) to Chicago (CHI): American Airlines, Southwest Airlines, Emirates, United Airlines, Royal Jordanian and All Nippon Airways.

Philadelphia to Chicago Flight Information

Cheapest nonstop flight price

$20

Cheapest round-trip ticket price

$45

Off-season for travel

January

Peak season for travel

June