Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline American Airlines

The cheapest airline(s) flying from Toronto to Chicago is American Airlines.

  • American Airlines American Airlines
  • Porter Airlines Porter Airlines
  • United Airlines United Airlines
  • Air Canada Air Canada
  • Air Transat Air Transat
  • British Airways British Airways
  • Lufthansa Lufthansa
  • WestJet WestJet
  • Alaska Airlines Alaska Airlines
  • Copa Airlines Copa Airlines
Cheapest Month January

Travel Period: January 2025 - December 2025

The cheapest month(s) to fly from Toronto 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 Friday

The cheapest day(s) of the week to fly from Toronto to Chicago is Friday.

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

Flight Schedules

Last Updated: Sat, 2 Nov, 2024

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    • Airline Filter by Airline
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      • Availability
        • M
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        • F
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        • S
      • 21:00 YYZ
        22:07 ORD
        2Hrs, 07m Direct
      • YYZToronto Lester B Pearson Intl Airport 21:00 - ORD 22:07 2h 07m Direct
      • YYZToronto Lester B Pearson Intl Airport 21:00
      • ORDChicago O'Hare International Airport 22:07
      • 2h 07m
      • Direct
      • United Airlines (UA 5728)Embraer 175
      • United Airlines (UA 5728)
        • M
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        • F
        • -
        • S
      • Embraer 175
      • 06:15 YYZ
        07:30 ORD
        2Hrs, 15m Direct
      • YYZToronto Lester B Pearson Intl Airport 06:15 - ORD 07:30 2h 15m Direct
      • YYZToronto Lester B Pearson Intl Airport 06:15
      • ORDChicago O'Hare International Airport 07:30
      • 2h 15m
      • Direct
      • American Airlines (AA 3524)Embraer 170
      • American Airlines (AA 3524)
        • M
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        • T
        • -
        • S
        • S
      • Embraer 170
      • 06:52 YYZ
        08:05 ORD
        2Hrs, 13m Direct
      • YYZToronto Lester B Pearson Intl Airport 06:52 - ORD 08:05 2h 13m Direct
      • YYZToronto Lester B Pearson Intl Airport 06:52
      • ORDChicago O'Hare International Airport 08:05
      • 2h 13m
      • Direct
      • United Airlines (UA 3534)Embraer 175
      • United Airlines (UA 3534)
        • M
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        • T
        • F
        • S
        • S
      • Embraer 175
      • 08:00 YYZ
        08:57 ORD
        1Hrs, 57m Direct
      • YYZToronto Lester B Pearson Intl Airport 08:00 - ORD 08:57 1h 57m Direct
      • YYZToronto Lester B Pearson Intl Airport 08:00
      • ORDChicago O'Hare International Airport 08:57
      • 1h 57m
      • Direct
      • Air Canada (AC 501)Airbus A220 300
      • Air Canada (AC 501)
        • M
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        • T
        • F
        • S
        • S
      • Airbus A220 300
      • 09:00 YYZ
        10:05 ORD
        2Hrs, 05m Direct
      • YYZToronto Lester B Pearson Intl Airport 09:00 - ORD 10:05 2h 05m Direct
      • YYZToronto Lester B Pearson Intl Airport 09:00
      • ORDChicago O'Hare International Airport 10:05
      • 2h 05m
      • Direct
      • United Airlines (UA 1538)Boeing 737 Max 8 Passenger
      • United Airlines (UA 1538)
        • M
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        • F
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        • S
      • Boeing 737 Max 8 Passenger
      • 09:30 YTZ
        10:20 MDW
        1Hrs, 50m Direct
      • YTZToronto City Centre Airport 09:30 - MDW 10:20 1h 50m Direct
      • YTZToronto City Centre Airport 09:30
      • MDWChicago Midway Airport 10:20
      • 1h 50m
      • Direct
      • Porter Airlines (PD 2387)Dehavilland Dash 8 400
      • Porter Airlines (PD 2387)
        • M
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        • W
        • T
        • F
        • -
        • S
      • Dehavilland Dash 8 400
      • 11:00 YYZ
        11:59 ORD
        1Hrs, 59m Direct
      • YYZToronto Lester B Pearson Intl Airport 11:00 - ORD 11:59 1h 59m Direct
      • YYZToronto Lester B Pearson Intl Airport 11:00
      • ORDChicago O'Hare International Airport 11:59
      • 1h 59m
      • Direct
      • United Airlines (UA 1063)Boeing 737 Max 8 Passenger
      • United Airlines (UA 1063)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 11:00 YYZ
        11:59 ORD
        1Hrs, 59m Direct
      • YYZToronto Lester B Pearson Intl Airport 11:00 - ORD 11:59 1h 59m Direct
      • YYZToronto Lester B Pearson Intl Airport 11:00
      • ORDChicago O'Hare International Airport 11:59
      • 1h 59m
      • Direct
      • United Airlines (UA 1063)Boeing 737 800
      • United Airlines (UA 1063)
        • -
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        • S
        • S
      • Boeing 737 800
      • 11:10 YTZ
        12:00 MDW
        1Hrs, 50m Direct
      • YTZToronto City Centre Airport 11:10 - MDW 12:00 1h 50m Direct
      • YTZToronto City Centre Airport 11:10
      • MDWChicago Midway Airport 12:00
      • 1h 50m
      • Direct
      • Porter Airlines (PD 2387)Dehavilland Dash 8 400
      • Porter Airlines (PD 2387)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Dehavilland Dash 8 400
      • 11:37 YYZ
        12:37 ORD
        2Hrs, 00m Direct
      • YYZToronto Lester B Pearson Intl Airport 11:37 - ORD 12:37 2h Direct
      • YYZToronto Lester B Pearson Intl Airport 11:37
      • ORDChicago O'Hare International Airport 12:37
      • 2h
      • Direct
      • American Airlines (AA 3604)Embraer 170
      • American Airlines (AA 3604)
        • M
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        • F
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        • S
      • Embraer 170
      • 12:20 YYZ
        13:11 ORD
        1Hrs, 51m Direct
      • YYZToronto Lester B Pearson Intl Airport 12:20 - ORD 13:11 1h 51m Direct
      • YYZToronto Lester B Pearson Intl Airport 12:20
      • ORDChicago O'Hare International Airport 13:11
      • 1h 51m
      • Direct
      • Air Canada (AC 503)Airbus A220 300
      • Air Canada (AC 503)
        • M
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        • S
      • Airbus A220 300
      • 13:10 YYZ
        14:10 ORD
        2Hrs, 00m Direct
      • YYZToronto Lester B Pearson Intl Airport 13:10 - ORD 14:10 2h Direct
      • YYZToronto Lester B Pearson Intl Airport 13:10
      • ORDChicago O'Hare International Airport 14:10
      • 2h
      • Direct
      • American Airlines (AA 3606)Embraer 170
      • American Airlines (AA 3606)
        • M
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        • T
        • -
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        • S
      • Embraer 170
      • 14:00 YYZ
        14:51 ORD
        1Hrs, 51m Direct
      • YYZToronto Lester B Pearson Intl Airport 14:00 - ORD 14:51 1h 51m Direct
      • YYZToronto Lester B Pearson Intl Airport 14:00
      • ORDChicago O'Hare International Airport 14:51
      • 1h 51m
      • Direct
      • Air Canada (AC 505)Airbus A220 300
      • Air Canada (AC 505)
        • M
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        • T
        • F
        • S
        • S
      • Airbus A220 300
      • 15:30 YYZ
        16:30 ORD
        2Hrs, 00m Direct
      • YYZToronto Lester B Pearson Intl Airport 15:30 - ORD 16:30 2h Direct
      • YYZToronto Lester B Pearson Intl Airport 15:30
      • ORDChicago O'Hare International Airport 16:30
      • 2h
      • Direct
      • United Airlines (UA 2364)Airbus
      • United Airlines (UA 2364)
        • M
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        • -
        • -
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        • S
      • Airbus
      • 15:30 YYZ
        16:29 ORD
        1Hrs, 59m Direct
      • YYZToronto Lester B Pearson Intl Airport 15:30 - ORD 16:29 1h 59m Direct
      • YYZToronto Lester B Pearson Intl Airport 15:30
      • ORDChicago O'Hare International Airport 16:29
      • 1h 59m
      • Direct
      • United Airlines (UA 2364)Boeing 737 800
      • United Airlines (UA 2364)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 800
      • 15:30 YYZ
        16:29 ORD
        1Hrs, 59m Direct
      • YYZToronto Lester B Pearson Intl Airport 15:30 - ORD 16:29 1h 59m Direct
      • YYZToronto Lester B Pearson Intl Airport 15:30
      • ORDChicago O'Hare International Airport 16:29
      • 1h 59m
      • Direct
      • United Airlines (UA 2364)Boeing 737 700
      • United Airlines (UA 2364)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • Boeing 737 700
      • 15:50 YTZ
        16:40 MDW
        1Hrs, 50m Direct
      • YTZToronto City Centre Airport 15:50 - MDW 16:40 1h 50m Direct
      • YTZToronto City Centre Airport 15:50
      • MDWChicago Midway Airport 16:40
      • 1h 50m
      • Direct
      • Porter Airlines (PD 2393)Dehavilland Dash 8 400
      • Porter Airlines (PD 2393)
        • M
        • -
        • -
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        • F
        • -
        • S
      • Dehavilland Dash 8 400
      • 16:44 YYZ
        17:44 ORD
        2Hrs, 00m Direct
      • YYZToronto Lester B Pearson Intl Airport 16:44 - ORD 17:44 2h Direct
      • YYZToronto Lester B Pearson Intl Airport 16:44
      • ORDChicago O'Hare International Airport 17:44
      • 2h
      • Direct
      • American Airlines (AA 3608)Embraer 170
      • American Airlines (AA 3608)
        • M
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        • W
        • -
        • F
        • S
        • S
      • Embraer 170
      • 17:30 YYZ
        18:37 ORD
        2Hrs, 07m Direct
      • YYZToronto Lester B Pearson Intl Airport 17:30 - ORD 18:37 2h 07m Direct
      • YYZToronto Lester B Pearson Intl Airport 17:30
      • ORDChicago O'Hare International Airport 18:37
      • 2h 07m
      • Direct
      • United Airlines (UA 3542)Embraer 175
      • United Airlines (UA 3542)
        • M
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        • W
        • T
        • F
        • S
        • S
      • Embraer 175
      • 18:15 YYZ
        19:15 ORD
        2Hrs, 00m Direct
      • YYZToronto Lester B Pearson Intl Airport 18:15 - ORD 19:15 2h Direct
      • YYZToronto Lester B Pearson Intl Airport 18:15
      • ORDChicago O'Hare International Airport 19:15
      • 2h
      • Direct
      • American Airlines (AA 3610)Embraer 170
      • American Airlines (AA 3610)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Embraer 170
      • 18:20 YYZ
        19:20 ORD
        2Hrs, 00m Direct
      • YYZToronto Lester B Pearson Intl Airport 18:20 - ORD 19:20 2h Direct
      • YYZToronto Lester B Pearson Intl Airport 18:20
      • ORDChicago O'Hare International Airport 19:20
      • 2h
      • Direct
      • American Airlines (AA 3610)Embraer 170
      • American Airlines (AA 3610)
        • M
        • T
        • W
        • -
        • F
        • S
        • -
      • Embraer 170
      • 18:35 YYZ
        19:32 ORD
        1Hrs, 57m Direct
      • YYZToronto Lester B Pearson Intl Airport 18:35 - ORD 19:32 1h 57m Direct
      • YYZToronto Lester B Pearson Intl Airport 18:35
      • ORDChicago O'Hare International Airport 19:32
      • 1h 57m
      • Direct
      • Air Canada (AC 509)Airbus A220 300
      • Air Canada (AC 509)
        • M
        • T
        • W
        • T
        • F
        • S
        • -
      • Airbus A220 300
      • 18:40 YYZ
        19:37 ORD
        1Hrs, 57m Direct
      • YYZToronto Lester B Pearson Intl Airport 18:40 - ORD 19:37 1h 57m Direct
      • YYZToronto Lester B Pearson Intl Airport 18:40
      • ORDChicago O'Hare International Airport 19:37
      • 1h 57m
      • Direct
      • Air Canada (AC 509)Airbus A220 300
      • Air Canada (AC 509)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Airbus A220 300
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      What’s the fastest flight time from Toronto to Chicago?

      The fastest flight time for direct flights from Toronto to Chicago is 1 hour 50 minutes. Check latest flight schedules & prices on Wego.

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

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

      How far is Chicago from Toronto?

      The flight distance between Toronto and Chicago is 701km. Check all available flights on Wego.

      When is the earliest and latest flight of the day?

      The earliest flight of the day departs at 06:15. The last flight of the day departs at 21:00. See the full list of flight times on Wego.

      How many airlines offer direct flights from Toronto to Chicago?

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

      Popular Airlines flying from Toronto to Chicago

      SkyWest Airlines ‏()
      United Airlines ‏()
      American Airlines ‏()
      Air Canada ‏()

      Popular Destinations from Chicago

      Popular Destinations from Toronto

      Popular Hotels in Chicago

      Hotels In Popular Destinations