Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline Spirit Airlines

The cheapest airline(s) flying from Pittsburgh to Chicago is Spirit Airlines.

  • Spirit Airlines Spirit Airlines
  • JetBlue Airways JetBlue Airways
  • United Airlines United Airlines
  • American Airlines American Airlines
  • Southwest Airlines Southwest Airlines
  • Alaska Airlines Alaska Airlines
Cheapest Month January

Travel Period: January 2025 - December 2025

The cheapest month(s) to fly from Pittsburgh to Chicago is January.

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

The cheapest day(s) of the week to fly from Pittsburgh to Chicago is Tuesday.

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

Flight Schedules

Last Updated: Mon, 2 Dec, 2024

  • Time Earliest
    • Earliest
    • Latest
  • Depart Earliest
    • Earliest
    • Latest
  • Arrive
    • Earliest
    • Latest
  • Duration
    • Shortest
    • Longest
  • Stopover
    All
    • Airline Filter by Airline
      View All Airline
      • Availability
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 19:10 PIT
        19:40 MDW
        1Hrs, 30m Direct
      • PITPittsburgh International Airport 19:10 - MDW 19:40 1h 30m Direct
      • PITPittsburgh International Airport 19:10
      • MDWChicago Midway Airport 19:40
      • 1h 30m
      • Direct
      • Southwest Airlines (WN 3122)Boeing 737 800
      • Southwest Airlines (WN 3122)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 20:35 PIT
        21:05 MDW
        1Hrs, 30m Direct
      • PITPittsburgh International Airport 20:35 - MDW 21:05 1h 30m Direct
      • PITPittsburgh International Airport 20:35
      • MDWChicago Midway Airport 21:05
      • 1h 30m
      • Direct
      • Southwest Airlines (WN 3122)Boeing 737 800
      • Southwest Airlines (WN 3122)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 20:55 PIT
        21:25 MDW
        1Hrs, 30m Direct
      • PITPittsburgh International Airport 20:55 - MDW 21:25 1h 30m Direct
      • PITPittsburgh International Airport 20:55
      • MDWChicago Midway Airport 21:25
      • 1h 30m
      • Direct
      • Southwest Airlines (WN 3122)Boeing 737 700
      • Southwest Airlines (WN 3122)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 700
      • 21:25 PIT
        21:55 MDW
        1Hrs, 30m Direct
      • PITPittsburgh International Airport 21:25 - MDW 21:55 1h 30m Direct
      • PITPittsburgh International Airport 21:25
      • MDWChicago Midway Airport 21:55
      • 1h 30m
      • Direct
      • Southwest Airlines (WN 3122)Boeing 737 800
      • Southwest Airlines (WN 3122)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • Boeing 737 800
      • 06:19 PIT
        07:14 ORD
        1Hrs, 55m Direct
      • PITPittsburgh International Airport 06:19 - ORD 07:14 1h 55m Direct
      • PITPittsburgh International Airport 06:19
      • ORDChicago O'Hare International Airport 07:14
      • 1h 55m
      • Direct
      • American Airlines (AA 538)Airbus
      • American Airlines (AA 538)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • Airbus
      • 06:25 PIT
        07:20 ORD
        1Hrs, 55m Direct
      • PITPittsburgh International Airport 06:25 - ORD 07:20 1h 55m Direct
      • PITPittsburgh International Airport 06:25
      • ORDChicago O'Hare International Airport 07:20
      • 1h 55m
      • Direct
      • American Airlines (AA 538)Airbus
      • American Airlines (AA 538)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Airbus
      • 06:30 PIT
        07:00 MDW
        1Hrs, 30m Direct
      • PITPittsburgh International Airport 06:30 - MDW 07:00 1h 30m Direct
      • PITPittsburgh International Airport 06:30
      • MDWChicago Midway Airport 07:00
      • 1h 30m
      • Direct
      • Southwest Airlines (WN 611)Boeing 737 700
      • Southwest Airlines (WN 611)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 06:59 PIT
        07:53 ORD
        1Hrs, 54m Direct
      • PITPittsburgh International Airport 06:59 - ORD 07:53 1h 54m Direct
      • PITPittsburgh International Airport 06:59
      • ORDChicago O'Hare International Airport 07:53
      • 1h 54m
      • Direct
      • American Airlines (AA 538)Airbus
      • American Airlines (AA 538)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Airbus
      • 07:07 PIT
        08:05 ORD
        1Hrs, 58m Direct
      • PITPittsburgh International Airport 07:07 - ORD 08:05 1h 58m Direct
      • PITPittsburgh International Airport 07:07
      • ORDChicago O'Hare International Airport 08:05
      • 1h 58m
      • Direct
      • United Airlines (UA 3461)Embraer 170
      • United Airlines (UA 3461)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Embraer 170
      • 07:10 PIT
        07:50 ORD
        1Hrs, 40m Direct
      • PITPittsburgh International Airport 07:10 - ORD 07:50 1h 40m Direct
      • PITPittsburgh International Airport 07:10
      • ORDChicago O'Hare International Airport 07:50
      • 1h 40m
      • Direct
      • United Airlines (UA 1803)Boeing 737 800
      • United Airlines (UA 1803)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 07:10 PIT
        08:04 ORD
        1Hrs, 54m Direct
      • PITPittsburgh International Airport 07:10 - ORD 08:04 1h 54m Direct
      • PITPittsburgh International Airport 07:10
      • ORDChicago O'Hare International Airport 08:04
      • 1h 54m
      • Direct
      • United Airlines (UA 1803)Boeing 737 700
      • United Airlines (UA 1803)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • Boeing 737 700
      • 07:10 PIT
        08:04 ORD
        1Hrs, 54m Direct
      • PITPittsburgh International Airport 07:10 - ORD 08:04 1h 54m Direct
      • PITPittsburgh International Airport 07:10
      • ORDChicago O'Hare International Airport 08:04
      • 1h 54m
      • Direct
      • United Airlines (UA 1803)Airbus
      • United Airlines (UA 1803)
        • -
        • -
        • -
        • -
        • -
        • S
        • S
      • Airbus
      • 07:40 PIT
        08:42 ORD
        2Hrs, 02m Direct
      • PITPittsburgh International Airport 07:40 - ORD 08:42 2h 02m Direct
      • PITPittsburgh International Airport 07:40
      • ORDChicago O'Hare International Airport 08:42
      • 2h 02m
      • Direct
      • American Airlines (AA 4769)Embraer Emb 175
      • American Airlines (AA 4769)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Embraer Emb 175
      • 07:55 PIT
        08:25 MDW
        1Hrs, 30m Direct
      • PITPittsburgh International Airport 07:55 - MDW 08:25 1h 30m Direct
      • PITPittsburgh International Airport 07:55
      • MDWChicago Midway Airport 08:25
      • 1h 30m
      • Direct
      • Southwest Airlines (WN 611)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 611)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 08:10 PIT
        08:45 MDW
        1Hrs, 35m Direct
      • PITPittsburgh International Airport 08:10 - MDW 08:45 1h 35m Direct
      • PITPittsburgh International Airport 08:10
      • MDWChicago Midway Airport 08:45
      • 1h 35m
      • Direct
      • Southwest Airlines (WN 3286)Boeing 737 700
      • Southwest Airlines (WN 3286)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • Boeing 737 700
      • 08:13 PIT
        09:10 ORD
        1Hrs, 57m Direct
      • PITPittsburgh International Airport 08:13 - ORD 09:10 1h 57m Direct
      • PITPittsburgh International Airport 08:13
      • ORDChicago O'Hare International Airport 09:10
      • 1h 57m
      • Direct
      • United Airlines (UA 3461)Embraer 175
      • United Airlines (UA 3461)
        • -
        • -
        • -
        • -
        • F
        • S
        • S
      • Embraer 175
      • 08:20 PIT
        08:55 MDW
        1Hrs, 35m Direct
      • PITPittsburgh International Airport 08:20 - MDW 08:55 1h 35m Direct
      • PITPittsburgh International Airport 08:20
      • MDWChicago Midway Airport 08:55
      • 1h 35m
      • Direct
      • Southwest Airlines (WN 611)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 611)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 08:50 PIT
        09:39 ORD
        1Hrs, 49m Direct
      • PITPittsburgh International Airport 08:50 - ORD 09:39 1h 49m Direct
      • PITPittsburgh International Airport 08:50
      • ORDChicago O'Hare International Airport 09:39
      • 1h 49m
      • Direct
      • United Airlines (UA 3461)Embraer 175
      • United Airlines (UA 3461)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Embraer 175
      • 10:39 PIT
        11:25 ORD
        1Hrs, 46m Direct
      • PITPittsburgh International Airport 10:39 - ORD 11:25 1h 46m Direct
      • PITPittsburgh International Airport 10:39
      • ORDChicago O'Hare International Airport 11:25
      • 1h 46m
      • Direct
      • American Airlines (AA 4383)Embraer Emb 175
      • American Airlines (AA 4383)
        • -
        • -
        • -
        • T
        • F
        • S
        • S
      • Embraer Emb 175
      • 10:55 PIT
        11:38 ORD
        1Hrs, 43m Direct
      • PITPittsburgh International Airport 10:55 - ORD 11:38 1h 43m Direct
      • PITPittsburgh International Airport 10:55
      • ORDChicago O'Hare International Airport 11:38
      • 1h 43m
      • Direct
      • United Airlines (UA 4554)Canadair Regional Jet 550
      • United Airlines (UA 4554)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Canadair Regional Jet 550
      • 11:00 PIT
        11:55 ORD
        1Hrs, 55m Direct
      • PITPittsburgh International Airport 11:00 - ORD 11:55 1h 55m Direct
      • PITPittsburgh International Airport 11:00
      • ORDChicago O'Hare International Airport 11:55
      • 1h 55m
      • Direct
      • United Airlines (UA 3686)Embraer 175
      • United Airlines (UA 3686)
        • -
        • -
        • -
        • T
        • F
        • S
        • S
      • Embraer 175
      • 12:47 PIT
        13:35 ORD
        1Hrs, 48m Direct
      • PITPittsburgh International Airport 12:47 - ORD 13:35 1h 48m Direct
      • PITPittsburgh International Airport 12:47
      • ORDChicago O'Hare International Airport 13:35
      • 1h 48m
      • Direct
      • American Airlines (AA 4393)Embraer Emb 175
      • American Airlines (AA 4393)
        • -
        • -
        • -
        • T
        • F
        • -
        • S
      • Embraer Emb 175
      • 12:51 PIT
        13:39 ORD
        1Hrs, 48m Direct
      • PITPittsburgh International Airport 12:51 - ORD 13:39 1h 48m Direct
      • PITPittsburgh International Airport 12:51
      • ORDChicago O'Hare International Airport 13:39
      • 1h 48m
      • Direct
      • American Airlines (AA 4069)Embraer 170
      • American Airlines (AA 4069)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Embraer 170
      • 13:15 PIT
        14:01 ORD
        1Hrs, 46m Direct
      • PITPittsburgh International Airport 13:15 - ORD 14:01 1h 46m Direct
      • PITPittsburgh International Airport 13:15
      • ORDChicago O'Hare International Airport 14:01
      • 1h 46m
      • Direct
      • American Airlines (AA 3688)Embraer Emb 175
      • American Airlines (AA 3688)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Embraer Emb 175
      • 14:00 PIT
        14:55 ORD
        1Hrs, 55m Direct
      • PITPittsburgh International Airport 14:00 - ORD 14:55 1h 55m Direct
      • PITPittsburgh International Airport 14:00
      • ORDChicago O'Hare International Airport 14:55
      • 1h 55m
      • Direct
      • United Airlines (UA 3432)Embraer 170
      • United Airlines (UA 3432)
        • -
        • -
        • -
        • T
        • F
        • S
        • S
      • Embraer 170
      • 14:10 PIT
        14:35 MDW
        1Hrs, 25m Direct
      • PITPittsburgh International Airport 14:10 - MDW 14:35 1h 25m Direct
      • PITPittsburgh International Airport 14:10
      • MDWChicago Midway Airport 14:35
      • 1h 25m
      • Direct
      • Southwest Airlines (WN 3286)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3286)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 14:15 PIT
        14:55 ORD
        1Hrs, 40m Direct
      • PITPittsburgh International Airport 14:15 - ORD 14:55 1h 40m Direct
      • PITPittsburgh International Airport 14:15
      • ORDChicago O'Hare International Airport 14:55
      • 1h 40m
      • Direct
      • United Airlines (UA 660)Boeing 737 700
      • United Airlines (UA 660)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 14:15 PIT
        14:40 MDW
        1Hrs, 25m Direct
      • PITPittsburgh International Airport 14:15 - MDW 14:40 1h 25m Direct
      • PITPittsburgh International Airport 14:15
      • MDWChicago Midway Airport 14:40
      • 1h 25m
      • Direct
      • Southwest Airlines (WN 3286)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3286)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 15:20 PIT
        15:45 MDW
        1Hrs, 25m Direct
      • PITPittsburgh International Airport 15:20 - MDW 15:45 1h 25m Direct
      • PITPittsburgh International Airport 15:20
      • MDWChicago Midway Airport 15:45
      • 1h 25m
      • Direct
      • Southwest Airlines (WN 611)Boeing 737 700
      • Southwest Airlines (WN 611)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • Boeing 737 700
      • 17:13 PIT
        18:01 ORD
        1Hrs, 48m Direct
      • PITPittsburgh International Airport 17:13 - ORD 18:01 1h 48m Direct
      • PITPittsburgh International Airport 17:13
      • ORDChicago O'Hare International Airport 18:01
      • 1h 48m
      • Direct
      • American Airlines (AA 4386)Embraer Emb 175
      • American Airlines (AA 4386)
        • -
        • -
        • -
        • T
        • F
        • S
        • S
      • Embraer Emb 175
      • 17:44 PIT
        18:32 ORD
        1Hrs, 48m Direct
      • PITPittsburgh International Airport 17:44 - ORD 18:32 1h 48m Direct
      • PITPittsburgh International Airport 17:44
      • ORDChicago O'Hare International Airport 18:32
      • 1h 48m
      • Direct
      • United Airlines (UA 1398)Boeing 737 700
      • United Airlines (UA 1398)
        • -
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 700
      • 17:44 PIT
        18:32 ORD
        1Hrs, 48m Direct
      • PITPittsburgh International Airport 17:44 - ORD 18:32 1h 48m Direct
      • PITPittsburgh International Airport 17:44
      • ORDChicago O'Hare International Airport 18:32
      • 1h 48m
      • Direct
      • United Airlines (UA 1398)Airbus
      • United Airlines (UA 1398)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Airbus
      • 17:44 PIT
        18:36 ORD
        1Hrs, 52m Direct
      • PITPittsburgh International Airport 17:44 - ORD 18:36 1h 52m Direct
      • PITPittsburgh International Airport 17:44
      • ORDChicago O'Hare International Airport 18:36
      • 1h 52m
      • Direct
      • United Airlines (UA 3704)Embraer 170
      • United Airlines (UA 3704)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Embraer 170
      • 17:50 PIT
        18:33 ORD
        1Hrs, 43m Direct
      • PITPittsburgh International Airport 17:50 - ORD 18:33 1h 43m Direct
      • PITPittsburgh International Airport 17:50
      • ORDChicago O'Hare International Airport 18:33
      • 1h 43m
      • Direct
      • United Airlines (UA 2248)Boeing 737 800
      • United Airlines (UA 2248)
        • M
        • T
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 17:50 PIT
        18:33 ORD
        1Hrs, 43m Direct
      • PITPittsburgh International Airport 17:50 - ORD 18:33 1h 43m Direct
      • PITPittsburgh International Airport 17:50
      • ORDChicago O'Hare International Airport 18:33
      • 1h 43m
      • Direct
      • United Airlines (UA 2248)Boeing 737 900
      • United Airlines (UA 2248)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 900
      • 18:57 PIT
        19:42 ORD
        1Hrs, 45m Direct
      • PITPittsburgh International Airport 18:57 - ORD 19:42 1h 45m Direct
      • PITPittsburgh International Airport 18:57
      • ORDChicago O'Hare International Airport 19:42
      • 1h 45m
      • Direct
      • American Airlines (AA 3459)Embraer Emb 175
      • American Airlines (AA 3459)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Embraer Emb 175
      No Schedules Sorry, there are no schedules matching your filters. Try removing one. reset
      What’s the fastest flight time from Pittsburgh to Chicago?

      The fastest flight time for direct flights from Pittsburgh to Chicago is 1 hour 25 minutes. Check latest flight schedules & prices on Wego.

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

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

      How far is Chicago from Pittsburgh?

      The flight distance between Pittsburgh and Chicago is 659km. Check all available flights on Wego.

      When is the earliest and latest flight of the day?

      The earliest flight of the day departs at 06:19. The last flight of the day departs at 19:10. See the full list of flight times on Wego.

      How many airlines offer direct flights from Pittsburgh to Chicago?

      There are 3 airlines that offer direct flights from Pittsburgh to Chicago. Find out the list of airlines on Wego.

      All Airports in Pittsburgh

      Pittsburgh International Airport PIT

      Popular Airlines Flying From Pittsburgh to Chicago

      United Airlines ‏()
      Southwest Airlines ‏()

      Popular Destinations From Chicago

      Popular Destinations From Pittsburgh

      Popular Hotels in Chicago

      Hotels In Popular Destinations