Flights from Philadelphia to Chicago from $60

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Airfare Deals Philadelphia to Chicago

On HolidayPrice.com you will find 4 direct and 1 connecting flights from Philadelphia to Chicago at a price of from $60. You can compare airfare deals from airlines and multiple travel sites, book and save on cheap plane tickets and last minute offers. Also check out PHL - CHI flight schedule to find best flight time, convenient departure and arrival airports.

Sun

The cost of airline tickets from Philadelphia to Chicago (United States) and back without transfers can be found with the help of the calendar. Specify the search parameters: one way or round-trip, payment currency, click on the month/day you need and we will search for flights to Chicago.

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Cheap flights from Philadelphia
Cheap flights to Chicago
Airline tickets to United States

One way flight from Philadelphia to Chicago

Below are the prices of tickets for direct one-way flights from Philadelphia to Chicago. The cheapest flight from Philadelphia to Chicago starts from $60 – the departure date for this flight is 10 December 2025.

*Prices include: baggage, hand luggage, airline fees and charges.

Round trip from Philadelphia to Chicago

You can buy a round-trip ticket from Philadelphia to Chicago (United States) and back using the table below. The best offer starts from $449, the flight dates are: there on 27 December 2025 year and back on 27 December 2025 year.

Sort by: Departure date Cheap flights Trip time Direct flights

Spirit Airlines NK 1501 Day flight

Departure 01.02.26 14:52, Su

1 Stopover Trip 9 days

Return 10.02.26 11:15, Tu

Find Flights from $152

Frontier Airlines F9 3379 Day flight

Departure 14.12.25 16:07, Su

1 Stopover Trip 2 days

Return 16.12.25 22:22, Tu

Find Flights from $153

*Prices include: baggage, hand luggage, airline fees and charges.

From Philadelphia to Chicago from $82! Airfare Deals by American Airlines

from $82 left 80 days

Sales dates 01 December 2025 Flight dates: 25 February 2026

Philadelphia - Chicago One way, Economy - from $82

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Flight Schedule Philadelphia to Chicago 2025

The current flight schedule for the route from Philadelphia to Chicago for today, tomorrow and the next few days. This schedule will help you decide on the time of departure and arrival, the airline, the flight number and the day of the week.

More than 17 flights every day, from 2hours 0min. Local departure and arrival times are indicated.

05:30 → 06:30

Southwest Airlines WN1226

PHL → MDW

- - - - - - Su

Check price

05:55 → 07:00

Southwest Airlines WN3709

PHL → MDW

Mo - - Th Fr - -

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06:00 → 07:05

Southwest Airlines WN3709

PHL → MDW

- - - - - Sa -

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06:00 → 07:11

Frontier Airlines F91617

PHL → MDW

Mo - - Th Fr - Su

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06:30 → 07:52

United Airlines UA1741

PHL → ORD

Mo - - Th Fr Sa -

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06:30 → 07:52

United Airlines UA1328

PHL → ORD

Mo Tu We Th - - Su

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06:30 → 07:30

Southwest Airlines WN1226

PHL → MDW

- Tu We - - - -

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07:20 → 08:43

American Airlines AA3074

PHL → ORD

Mo Tu - Th Fr Sa Su

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07:20 → 08:41

American Airlines AA3074

PHL → ORD

- - We - - - -

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09:14 → 10:36

American Airlines AA2095

PHL → ORD

- - - - - Sa -

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09:16 → 10:38

American Airlines AA2095

PHL → ORD

Mo Tu We Th Fr - Su

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10:05 → 11:27

United Airlines UA622

PHL → ORD

- - We Th Fr Sa -

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Show all

*Schedule is indicated only for direct scheduled flights and low-cost airlines.

Flight Information

Flying to Chicago from Philadelphia takes 01:56 minutes (excluding transfers). The distance between Philadelphia and Chicago is 662 miles (1066 kilometers). Planes depart from Philadelphia between 00:20 and 23:56. The fastest flight from the company American Airlines with flight number AA 2098. Flies for just 02:00 minutes with departure from Philadelphia and arrival in O'Hare.

Airlines

Direct flight

There are 4 airlines that fly directly from Philadelphia to Chicago. The most popular company carrying out non-stop flights is American Airlines.

American Airlines: AA 2324, AA 934, AA 973
Southwest Airlines: WN 1355, WN 389, WN 2180
United Airlines: UA 2409, UA 549, UA 1741
Frontier Airlines: F9 815

*Flight number

Flights with Transfers

Flights with transfers from Philadelphia to Chicago can be bought from 1 airlines:

American Airlines: , Madison, Baltimore
: New York

*Transit cities

Airports

Airports serving the air communication between Philadelphia and Chicago. You can fly to Chicago from 2 Philadelphia airports. Planes arrive at 2 airport in Chicago.

Philadelphia airports:

Philadelphia ~ 11 km* from $ 23Trenton-Mercer Airport ~ 47 km* from $ 85

Chicago airports:

O'Hare ~ 25 km* from $ 51Chicago Midway ~ 14 km* from $ 84

*Distance from the airport to the city center

Aircraft

You can fly from Philadelphia to Chicago on board of 4 airlines that utilize 7 aircraft models.

Airbus A319
Airbus A320
Airbus A321

Boeing 737
Boeing 737-700
Boeing 737-800

Boeing 737-900

Connecting cities

The list of cities on transfer flights to Chicago from Philadelphia. The best options are to fly through: , Madison, Baltimore.

Madison

Baltimore

Cheap airline tickets from Philadelphia to United States

Here is a list of flights from Philadelphia to United States purchased on HolidayPrice.com in the past 48 hours. If you find an interesting offer for cheap tickets, do not delay your purchase, prices change every 15 minutes.

Philadelphia - New York AA 4702 American Airlines Embraer EMB 175

19:03 Philadelphia

in a way 0 hours 56 min Direct

19:59 LaGuardia

Flights
from $94 11 December 2025

Philadelphia - Los Angeles AA 497 American Airlines Airbus A321

13:40 Philadelphia

in a way 5 hours 20 min Direct

19:00 Los Angeles

Flights
from $99 17 January 2026

Philadelphia - Miami B6 975 JetBlue Airways Airbus A320

19:35 Philadelphia

in a way 2 hours 25 min Direct

22:00 Fort Lauderdale Executive Airport

Flights
from $37 11 December 2025

Philadelphia - Chicago AA 2098 American Airlines Boeing 737-800

14:00 Philadelphia

in a way 2 hours 0 min Direct

16:00 O'Hare

Flights
from $60 10 December 2025

Philadelphia - San Francisco AA 594 American Airlines Airbus A321

19:10 Philadelphia

in a way 5 hours 49 min Direct

00:59 San Francisco

Flights
from $100 21 February 2026

All flights from Philadelphia

Flights from United States to Chicago

Here are the cheapest flight bookings from United States to Chicago made by users of our website. If you didn’t find your flight destination, use the search bar at the top of the page.

New York - Chicago UA 761 United Airlines Boeing 737-800

13:00 LaGuardia

in a way 2 hours 0 min Direct

15:00 O'Hare

Flights
from $30 13 January 2026

Los Angeles - Chicago UA 910 United Airlines Boeing 737-800

10:23 Los Angeles

in a way 3 hours 37 min Direct

14:00 O'Hare

Flights
from $47 25 February 2026

Miami - Chicago AA 2796 American Airlines Boeing 767-300

17:05 Miami

in a way 2 hours 55 min Direct

20:00 O'Hare

Flights
from $24 11 December 2025

Miami - Chicago WN 1626 Southwest Airlines Boeing 737

13:35 Fort Lauderdale Executive Airport

in a way 3 hours 0 min Direct

16:35 Chicago Midway

Flights
from $24 11 December 2025

San Francisco - Chicago UA 1800 United Airlines Airbus A319

04:15 San Francisco

in a way 3 hours 45 min Direct

08:00 O'Hare

Flights
from $69 23 January 2026

All flights to Chicago

Tips for buying a ticket

Philadelphia – Chicago – Philadelphia round-trip route are always cheaper than tickets purchased there and back separately.

Cheap flights from Philadelphia to Chicago — Chicago city

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