Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline Frontier Airlines
Cheapest Month June
Cheapest Day of the Week Saturday
Cheapest Airline Frontier Airlines

The cheapest airline(s) flying from Philadelphia to Chicago is Frontier Airlines.

  • Frontier Airlines Frontier Airlines
  • JetBlue Airways JetBlue Airways
  • American Airlines American Airlines
  • Spirit Airlines Spirit Airlines
  • Southwest Airlines Southwest Airlines
  • United Airlines United Airlines
  • Sun Country Airlines Sun Country Airlines
  • Alaska Airlines Alaska Airlines
Cheapest Month June

Travel Period: May 2025 - April 2026

The cheapest month(s) to fly from Philadelphia to Chicago is June.

  • May 2025
  • Jun 2025
  • Jul 2025
  • Aug 2025
  • Sep 2025
  • Oct 2025
  • Nov 2025
  • Dec 2025
  • Jan 2026
  • Feb 2026
  • Mar 2026
  • Apr 2026
Cheapest Day of the Week Saturday

The cheapest day(s) of the week to fly from Philadelphia to Chicago is Saturday.

  • Sun Sunday
  • Mon Monday
  • Tue Tuesday
  • Wed Wednesday
  • Thu Thursday
  • Fri Friday
  • Sat Saturday

Flight Schedules

Last Updated: Wed, 2 Apr, 2025

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    • Airline Filter by Airline
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      • Availability
        • M
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        • S
      • 20:45 PHL
        21:55 MDW
        2Hrs, 10m Direct
      • PHLPhiladelphia International Airport 20:45 - MDW 21:55 2h 10m Direct
      • PHLPhiladelphia International Airport 20:45
      • MDWChicago Midway Airport 21:55
      • 2h 10m
      • Direct
      • Southwest Airlines (WN 3338)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3338)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 Max 8 Passenger
      • 21:17 PHL
        22:47 ORD
        2Hrs, 30m Direct
      • PHLPhiladelphia International Airport 21:17 - ORD 22:47 2h 30m Direct
      • PHLPhiladelphia International Airport 21:17
      • ORDChicago O'Hare International Airport 22:47
      • 2h 30m
      • Direct
      • American Airlines (AA 1327)Boeing 737 800
      • American Airlines (AA 1327)
        • M
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        • T
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        • S
        • S
      • Boeing 737 800
      • 05:00 PHL
        06:24 ORD
        2Hrs, 24m Direct
      • PHLPhiladelphia International Airport 05:00 - ORD 06:24 2h 24m Direct
      • PHLPhiladelphia International Airport 05:00
      • ORDChicago O'Hare International Airport 06:24
      • 2h 24m
      • Direct
      • American Airlines (AA 1652)Boeing 737 800
      • American Airlines (AA 1652)
        • M
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        • S
      • Boeing 737 800
      • 05:50 PHL
        06:55 MDW
        2Hrs, 05m Direct
      • PHLPhiladelphia International Airport 05:50 - MDW 06:55 2h 05m Direct
      • PHLPhiladelphia International Airport 05:50
      • MDWChicago Midway Airport 06:55
      • 2h 05m
      • Direct
      • Southwest Airlines (WN 418)Boeing 737 700
      • Southwest Airlines (WN 418)
        • M
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        • -
        • -
      • Boeing 737 700
      • 06:00 PHL
        07:18 MDW
        2Hrs, 18m Direct
      • PHLPhiladelphia International Airport 06:00 - MDW 07:18 2h 18m Direct
      • PHLPhiladelphia International Airport 06:00
      • MDWChicago Midway Airport 07:18
      • 2h 18m
      • Direct
      • Frontier Airlines (F9 1617)Airbus A320 Neo
      • Frontier Airlines (F9 1617)
        • -
        • -
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        • -
        • -
        • -
        • S
      • Airbus A320 Neo
      • 06:25 PHL
        07:35 MDW
        2Hrs, 10m Direct
      • PHLPhiladelphia International Airport 06:25 - MDW 07:35 2h 10m Direct
      • PHLPhiladelphia International Airport 06:25
      • MDWChicago Midway Airport 07:35
      • 2h 10m
      • Direct
      • Southwest Airlines (WN 1474)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1474)
        • -
        • -
        • -
        • -
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        • -
      • Boeing 737 Max 8 Passenger
      • 06:30 PHL
        07:40 MDW
        2Hrs, 10m Direct
      • PHLPhiladelphia International Airport 06:30 - MDW 07:40 2h 10m Direct
      • PHLPhiladelphia International Airport 06:30
      • MDWChicago Midway Airport 07:40
      • 2h 10m
      • Direct
      • Southwest Airlines (WN 1474)Boeing 737 700
      • Southwest Airlines (WN 1474)
        • -
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        • -
        • -
        • -
      • Boeing 737 700
      • 06:41 PHL
        08:05 ORD
        2Hrs, 24m Direct
      • PHLPhiladelphia International Airport 06:41 - ORD 08:05 2h 24m Direct
      • PHLPhiladelphia International Airport 06:41
      • ORDChicago O'Hare International Airport 08:05
      • 2h 24m
      • Direct
      • United Airlines (UA 1857)Boeing 737 Max 9 Passenger
      • United Airlines (UA 1857)
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        • -
      • Boeing 737 Max 9 Passenger
      • 06:41 PHL
        08:05 ORD
        2Hrs, 24m Direct
      • PHLPhiladelphia International Airport 06:41 - ORD 08:05 2h 24m Direct
      • PHLPhiladelphia International Airport 06:41
      • ORDChicago O'Hare International Airport 08:05
      • 2h 24m
      • Direct
      • United Airlines (UA 1857)Boeing 737 800
      • United Airlines (UA 1857)
        • -
        • -
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        • -
        • -
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        • S
      • Boeing 737 800
      • 07:25 PHL
        08:49 ORD
        2Hrs, 24m Direct
      • PHLPhiladelphia International Airport 07:25 - ORD 08:49 2h 24m Direct
      • PHLPhiladelphia International Airport 07:25
      • ORDChicago O'Hare International Airport 08:49
      • 2h 24m
      • Direct
      • American Airlines (AA 2095)Boeing 737 800
      • American Airlines (AA 2095)
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        • S
      • Boeing 737 800
      • 07:35 PHL
        08:40 MDW
        2Hrs, 05m Direct
      • PHLPhiladelphia International Airport 07:35 - MDW 08:40 2h 05m Direct
      • PHLPhiladelphia International Airport 07:35
      • MDWChicago Midway Airport 08:40
      • 2h 05m
      • Direct
      • Southwest Airlines (WN 1474)Boeing 737 700
      • Southwest Airlines (WN 1474)
        • -
        • -
        • -
        • -
        • -
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        • S
      • Boeing 737 700
      • 09:31 PHL
        10:55 ORD
        2Hrs, 24m Direct
      • PHLPhiladelphia International Airport 09:31 - ORD 10:55 2h 24m Direct
      • PHLPhiladelphia International Airport 09:31
      • ORDChicago O'Hare International Airport 10:55
      • 2h 24m
      • Direct
      • United Airlines (UA 622)Boeing 737 800
      • United Airlines (UA 622)
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      • Boeing 737 800
      • 09:39 PHL
        11:05 ORD
        2Hrs, 26m Direct
      • PHLPhiladelphia International Airport 09:39 - ORD 11:05 2h 26m Direct
      • PHLPhiladelphia International Airport 09:39
      • ORDChicago O'Hare International Airport 11:05
      • 2h 26m
      • Direct
      • American Airlines (AA 3313)Boeing 737 800
      • American Airlines (AA 3313)
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      • Boeing 737 800
      • 10:48 PHL
        12:19 ORD
        2Hrs, 31m Direct
      • PHLPhiladelphia International Airport 10:48 - ORD 12:19 2h 31m Direct
      • PHLPhiladelphia International Airport 10:48
      • ORDChicago O'Hare International Airport 12:19
      • 2h 31m
      • Direct
      • American Airlines (AA 471)Boeing 737 800
      • American Airlines (AA 471)
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      • Boeing 737 800
      • 11:10 PHL
        12:20 MDW
        2Hrs, 10m Direct
      • PHLPhiladelphia International Airport 11:10 - MDW 12:20 2h 10m Direct
      • PHLPhiladelphia International Airport 11:10
      • MDWChicago Midway Airport 12:20
      • 2h 10m
      • Direct
      • Southwest Airlines (WN 1327)Boeing 737 700
      • Southwest Airlines (WN 1327)
        • -
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        • -
      • Boeing 737 700
      • 11:50 PHL
        12:55 MDW
        2Hrs, 05m Direct
      • PHLPhiladelphia International Airport 11:50 - MDW 12:55 2h 05m Direct
      • PHLPhiladelphia International Airport 11:50
      • MDWChicago Midway Airport 12:55
      • 2h 05m
      • Direct
      • Southwest Airlines (WN 2807)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2807)
        • M
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        • -
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      • Boeing 737 Max 8 Passenger
      • 12:15 PHL
        13:20 MDW
        2Hrs, 05m Direct
      • PHLPhiladelphia International Airport 12:15 - MDW 13:20 2h 05m Direct
      • PHLPhiladelphia International Airport 12:15
      • MDWChicago Midway Airport 13:20
      • 2h 05m
      • Direct
      • Southwest Airlines (WN 418)Boeing 737 800
      • Southwest Airlines (WN 418)
        • -
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      • Boeing 737 800
      • 12:50 PHL
        14:12 ORD
        2Hrs, 22m Direct
      • PHLPhiladelphia International Airport 12:50 - ORD 14:12 2h 22m Direct
      • PHLPhiladelphia International Airport 12:50
      • ORDChicago O'Hare International Airport 14:12
      • 2h 22m
      • Direct
      • United Airlines (UA 2394)Boeing 737 900
      • United Airlines (UA 2394)
        • M
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      • Boeing 737 900
      • 12:50 PHL
        14:14 ORD
        2Hrs, 24m Direct
      • PHLPhiladelphia International Airport 12:50 - ORD 14:14 2h 24m Direct
      • PHLPhiladelphia International Airport 12:50
      • ORDChicago O'Hare International Airport 14:14
      • 2h 24m
      • Direct
      • United Airlines (UA 2394)Boeing 737 900
      • United Airlines (UA 2394)
        • -
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        • -
      • Boeing 737 900
      • 13:45 PHL
        15:03 ORD
        2Hrs, 18m Direct
      • PHLPhiladelphia International Airport 13:45 - ORD 15:03 2h 18m Direct
      • PHLPhiladelphia International Airport 13:45
      • ORDChicago O'Hare International Airport 15:03
      • 2h 18m
      • Direct
      • American Airlines (AA 470)Airbus
      • American Airlines (AA 470)
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      • Airbus
      • 14:40 PHL
        15:45 MDW
        2Hrs, 05m Direct
      • PHLPhiladelphia International Airport 14:40 - MDW 15:45 2h 05m Direct
      • PHLPhiladelphia International Airport 14:40
      • MDWChicago Midway Airport 15:45
      • 2h 05m
      • Direct
      • Southwest Airlines (WN 3338)Boeing 737 800
      • Southwest Airlines (WN 3338)
        • M
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        • -
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        • -
        • -
      • Boeing 737 800
      • 15:45 PHL
        16:55 MDW
        2Hrs, 10m Direct
      • PHLPhiladelphia International Airport 15:45 - MDW 16:55 2h 10m Direct
      • PHLPhiladelphia International Airport 15:45
      • MDWChicago Midway Airport 16:55
      • 2h 10m
      • Direct
      • Southwest Airlines (WN 4654)Boeing 737 800
      • Southwest Airlines (WN 4654)
        • -
        • -
        • -
        • -
        • -
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        • S
      • Boeing 737 800
      • 16:04 PHL
        17:30 ORD
        2Hrs, 26m Direct
      • PHLPhiladelphia International Airport 16:04 - ORD 17:30 2h 26m Direct
      • PHLPhiladelphia International Airport 16:04
      • ORDChicago O'Hare International Airport 17:30
      • 2h 26m
      • Direct
      • American Airlines (AA 3063)Boeing 737 800
      • American Airlines (AA 3063)
        • -
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        • -
      • Boeing 737 800
      • 16:10 PHL
        17:26 MDW
        2Hrs, 16m Direct
      • PHLPhiladelphia International Airport 16:10 - MDW 17:26 2h 16m Direct
      • PHLPhiladelphia International Airport 16:10
      • MDWChicago Midway Airport 17:26
      • 2h 16m
      • Direct
      • Frontier Airlines (F9 1617)Airbus A320 Neo
      • Frontier Airlines (F9 1617)
        • -
        • -
        • -
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        • F
        • -
        • -
      • Airbus A320 Neo
      • 16:13 PHL
        17:36 ORD
        2Hrs, 23m Direct
      • PHLPhiladelphia International Airport 16:13 - ORD 17:36 2h 23m Direct
      • PHLPhiladelphia International Airport 16:13
      • ORDChicago O'Hare International Airport 17:36
      • 2h 23m
      • Direct
      • American Airlines (AA 3063)Airbus
      • American Airlines (AA 3063)
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      • Airbus
      • 16:35 PHL
        17:45 MDW
        2Hrs, 10m Direct
      • PHLPhiladelphia International Airport 16:35 - MDW 17:45 2h 10m Direct
      • PHLPhiladelphia International Airport 16:35
      • MDWChicago Midway Airport 17:45
      • 2h 10m
      • Direct
      • Southwest Airlines (WN 3338)Boeing 737 700
      • Southwest Airlines (WN 3338)
        • -
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        • -
        • -
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        • -
      • Boeing 737 700
      • 17:01 PHL
        18:25 ORD
        2Hrs, 24m Direct
      • PHLPhiladelphia International Airport 17:01 - ORD 18:25 2h 24m Direct
      • PHLPhiladelphia International Airport 17:01
      • ORDChicago O'Hare International Airport 18:25
      • 2h 24m
      • Direct
      • United Airlines (UA 308)Boeing 737 800
      • United Airlines (UA 308)
        • M
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        • S
      • Boeing 737 800
      • 17:01 PHL
        18:25 ORD
        2Hrs, 24m Direct
      • PHLPhiladelphia International Airport 17:01 - ORD 18:25 2h 24m Direct
      • PHLPhiladelphia International Airport 17:01
      • ORDChicago O'Hare International Airport 18:25
      • 2h 24m
      • Direct
      • United Airlines (UA 308)Boeing 737 Max 9 Passenger
      • United Airlines (UA 308)
        • -
        • -
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        • -
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      • Boeing 737 Max 9 Passenger
      • 18:00 PHL
        19:23 ORD
        2Hrs, 23m Direct
      • PHLPhiladelphia International Airport 18:00 - ORD 19:23 2h 23m Direct
      • PHLPhiladelphia International Airport 18:00
      • ORDChicago O'Hare International Airport 19:23
      • 2h 23m
      • Direct
      • United Airlines (UA 2665)Airbus
      • United Airlines (UA 2665)
        • -
        • -
        • -
        • -
        • -
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        • S
      • Airbus
      • 18:30 PHL
        19:40 MDW
        2Hrs, 10m Direct
      • PHLPhiladelphia International Airport 18:30 - MDW 19:40 2h 10m Direct
      • PHLPhiladelphia International Airport 18:30
      • MDWChicago Midway Airport 19:40
      • 2h 10m
      • Direct
      • Southwest Airlines (WN 3338)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3338)
        • -
        • -
        • -
        • -
        • -
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        • -
      • Boeing 737 Max 8 Passenger
      • 18:31 PHL
        19:55 ORD
        2Hrs, 24m Direct
      • PHLPhiladelphia International Airport 18:31 - ORD 19:55 2h 24m Direct
      • PHLPhiladelphia International Airport 18:31
      • ORDChicago O'Hare International Airport 19:55
      • 2h 24m
      • Direct
      • United Airlines (UA 2665)Boeing 737 800
      • United Airlines (UA 2665)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 18:31 PHL
        19:55 ORD
        2Hrs, 24m Direct
      • PHLPhiladelphia International Airport 18:31 - ORD 19:55 2h 24m Direct
      • PHLPhiladelphia International Airport 18:31
      • ORDChicago O'Hare International Airport 19:55
      • 2h 24m
      • Direct
      • United Airlines (UA 2665)Airbus
      • United Airlines (UA 2665)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • Airbus
      • 18:31 PHL
        19:55 ORD
        2Hrs, 24m Direct
      • PHLPhiladelphia International Airport 18:31 - ORD 19:55 2h 24m Direct
      • PHLPhiladelphia International Airport 18:31
      • ORDChicago O'Hare International Airport 19:55
      • 2h 24m
      • Direct
      • United Airlines (UA 2665)Airbus
      • United Airlines (UA 2665)
        • -
        • -
        • -
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        • -
        • -
        • -
      • Airbus
      • 18:35 PHL
        19:45 MDW
        2Hrs, 10m Direct
      • PHLPhiladelphia International Airport 18:35 - MDW 19:45 2h 10m Direct
      • PHLPhiladelphia International Airport 18:35
      • MDWChicago Midway Airport 19:45
      • 2h 10m
      • Direct
      • Southwest Airlines (WN 2570)Boeing 737 700
      • Southwest Airlines (WN 2570)
        • -
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        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 18:35 PHL
        20:01 ORD
        2Hrs, 26m Direct
      • PHLPhiladelphia International Airport 18:35 - ORD 20:01 2h 26m Direct
      • PHLPhiladelphia International Airport 18:35
      • ORDChicago O'Hare International Airport 20:01
      • 2h 26m
      • Direct
      • American Airlines (AA 490)Airbus
      • American Airlines (AA 490)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Airbus
      • 18:55 PHL
        20:10 MDW
        2Hrs, 15m Direct
      • PHLPhiladelphia International Airport 18:55 - MDW 20:10 2h 15m Direct
      • PHLPhiladelphia International Airport 18:55
      • MDWChicago Midway Airport 20:10
      • 2h 15m
      • Direct
      • Southwest Airlines (WN 4146)Boeing 737 800
      • Southwest Airlines (WN 4146)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 800
      No Schedules Sorry, there are no schedules matching your filters. Try removing one. reset
      What’s the fastest flight time from Philadelphia to Chicago?

      The fastest flight time for direct flights from Philadelphia to Chicago is 2 hours 5 minutes. Check latest flight schedules & prices on Wego.

      What’s the most popular airline flying from Philadelphia to Chicago?

      The most popular airline flying from Philadelphia to Chicago is Frontier Airlines. Find the latest flight deals on Wego.

      How far is Chicago from Philadelphia?

      The flight distance between Philadelphia and Chicago is 1069km. Check all available flights on Wego.

      When is the earliest and latest flight of the day?

      The earliest flight of the day departs at 05:00. The last flight of the day departs at 20:45. See the full list of flight times on Wego.

      How many airlines offer direct flights from Philadelphia to Chicago?

      There are 4 airlines that offer direct flights from Philadelphia to Chicago. Find out the list of airlines on Wego.

      All Airports in Philadelphia

      Philadelphia International Airport PHL

      Wings Field Airport BBX

      Popular Airlines Flying From Philadelphia to Chicago

      Frontier Airlines ‏()

      Popular Destinations From Chicago

      Popular Destinations From Philadelphia

      Popular Hotels in Chicago

      Hotels In Popular Destinations