Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline United Airlines

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

  • United Airlines United Airlines
  • American Airlines American Airlines
  • Air Canada Air Canada
  • Porter Airlines Porter Airlines
  • WestJet WestJet
  • Air Transat Air Transat
  • Alaska Airlines Alaska Airlines
Cheapest Month February

Travel Period: January 2025 - December 2025

The cheapest month(s) to fly from Toronto to Chicago is February.

  • 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 Wednesday

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

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

Flight Schedules

Last Updated: Mon, 2 Dec, 2024

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      • Availability
        • M
        • T
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        • F
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        • S
      • 21:00 YYZ
        22:13 ORD
        2Hrs, 13m Direct
      • YYZToronto Lester B Pearson Intl Airport 21:00 - ORD 22:13 2h 13m Direct
      • YYZToronto Lester B Pearson Intl Airport 21:00
      • ORDChicago O'Hare International Airport 22:13
      • 2h 13m
      • Direct
      • United Airlines (UA 5728)Embraer 175
      • United Airlines (UA 5728)
        • M
        • T
        • W
        • T
        • 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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        • W
        • T
        • F
        • 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
        • T
        • W
        • 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
        • -
        • S
        • -
      • Airbus A220 300
      • 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
      • Air Canada (AC 501)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Airbus
      • 08:00 YYZ
        08:58 ORD
        1Hrs, 58m Direct
      • YYZToronto Lester B Pearson Intl Airport 08:00 - ORD 08:58 1h 58m Direct
      • YYZToronto Lester B Pearson Intl Airport 08:00
      • ORDChicago O'Hare International Airport 08:58
      • 1h 58m
      • Direct
      • Air Canada (AC 8901)Embraer Emb 175
      • Air Canada (AC 8901)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • Embraer Emb 175
      • 09:00 YYZ
        10:10 ORD
        2Hrs, 10m Direct
      • YYZToronto Lester B Pearson Intl Airport 09:00 - ORD 10:10 2h 10m Direct
      • YYZToronto Lester B Pearson Intl Airport 09:00
      • ORDChicago O'Hare International Airport 10:10
      • 2h 10m
      • Direct
      • United Airlines (UA 1538)Boeing 737 800
      • United Airlines (UA 1538)
        • M
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        • F
        • S
        • S
      • Boeing 737 800
      • 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)
        • -
        • T
        • -
        • -
        • F
        • -
        • S
      • Dehavilland Dash 8 400
      • 09:40 YTZ
        10:30 MDW
        1Hrs, 50m Direct
      • YTZToronto City Centre Airport 09:40 - MDW 10:30 1h 50m Direct
      • YTZToronto City Centre Airport 09:40
      • MDWChicago Midway Airport 10:30
      • 1h 50m
      • Direct
      • Porter Airlines (PD 2387)Dehavilland Dash 8 400
      • Porter Airlines (PD 2387)
        • -
        • -
        • -
        • T
        • -
        • S
        • -
      • Dehavilland Dash 8 400
      • 10:20 YTZ
        11:10 MDW
        1Hrs, 50m Direct
      • YTZToronto City Centre Airport 10:20 - MDW 11:10 1h 50m Direct
      • YTZToronto City Centre Airport 10:20
      • MDWChicago Midway Airport 11:10
      • 1h 50m
      • Direct
      • Porter Airlines (PD 2387)Dehavilland Dash 8 400
      • Porter Airlines (PD 2387)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • Dehavilland Dash 8 400
      • 11:00 YYZ
        12:13 ORD
        2Hrs, 13m Direct
      • YYZToronto Lester B Pearson Intl Airport 11:00 - ORD 12:13 2h 13m Direct
      • YYZToronto Lester B Pearson Intl Airport 11:00
      • ORDChicago O'Hare International Airport 12:13
      • 2h 13m
      • Direct
      • United Airlines (UA 5578)Embraer 175
      • United Airlines (UA 5578)
        • M
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        • T
        • F
        • S
        • S
      • Embraer 175
      • 11:35 YYZ
        12:35 ORD
        2Hrs, 00m Direct
      • YYZToronto Lester B Pearson Intl Airport 11:35 - ORD 12:35 2h Direct
      • YYZToronto Lester B Pearson Intl Airport 11:35
      • ORDChicago O'Hare International Airport 12:35
      • 2h
      • Direct
      • American Airlines (AA 3604)Embraer 170
      • American Airlines (AA 3604)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Embraer 170
      • 11:40 YYZ
        12:40 ORD
        2Hrs, 00m Direct
      • YYZToronto Lester B Pearson Intl Airport 11:40 - ORD 12:40 2h Direct
      • YYZToronto Lester B Pearson Intl Airport 11:40
      • ORDChicago O'Hare International Airport 12:40
      • 2h
      • Direct
      • American Airlines (AA 3604)Embraer 170
      • American Airlines (AA 3604)
        • M
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        • T
        • F
        • -
        • S
      • Embraer 170
      • 12:20 YYZ
        13:18 ORD
        1Hrs, 58m Direct
      • YYZToronto Lester B Pearson Intl Airport 12:20 - ORD 13:18 1h 58m Direct
      • YYZToronto Lester B Pearson Intl Airport 12:20
      • ORDChicago O'Hare International Airport 13:18
      • 1h 58m
      • Direct
      • Air Canada (AC 8903)Embraer Emb 175
      • Air Canada (AC 8903)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Embraer Emb 175
      • 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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        • T
        • F
        • -
        • 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
        • -
        • -
        • T
        • F
        • S
        • S
      • Embraer 170
      • 14:00 YYZ
        14:58 ORD
        1Hrs, 58m Direct
      • YYZToronto Lester B Pearson Intl Airport 14:00 - ORD 14:58 1h 58m Direct
      • YYZToronto Lester B Pearson Intl Airport 14:00
      • ORDChicago O'Hare International Airport 14:58
      • 1h 58m
      • Direct
      • Air Canada (AC 8905)Embraer Emb 175
      • Air Canada (AC 8905)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Embraer Emb 175
      • 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
        • -
      • Airbus A220 300
      • 15:30 YYZ
        16:41 ORD
        2Hrs, 11m Direct
      • YYZToronto Lester B Pearson Intl Airport 15:30 - ORD 16:41 2h 11m Direct
      • YYZToronto Lester B Pearson Intl Airport 15:30
      • ORDChicago O'Hare International Airport 16:41
      • 2h 11m
      • Direct
      • United Airlines (UA 2364)Airbus
      • United Airlines (UA 2364)
        • M
        • -
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        • T
        • F
        • S
        • S
      • Airbus
      • 15:30 YYZ
        16:40 ORD
        2Hrs, 10m Direct
      • YYZToronto Lester B Pearson Intl Airport 15:30 - ORD 16:40 2h 10m Direct
      • YYZToronto Lester B Pearson Intl Airport 15:30
      • ORDChicago O'Hare International Airport 16:40
      • 2h 10m
      • Direct
      • United Airlines (UA 2364)Boeing 737 800
      • United Airlines (UA 2364)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 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
        • -
        • W
        • T
        • F
        • S
        • S
      • Dehavilland Dash 8 400
      • 17:30 YYZ
        18:43 ORD
        2Hrs, 13m Direct
      • YYZToronto Lester B Pearson Intl Airport 17:30 - ORD 18:43 2h 13m Direct
      • YYZToronto Lester B Pearson Intl Airport 17:30
      • ORDChicago O'Hare International Airport 18:43
      • 2h 13m
      • Direct
      • United Airlines (UA 3542)Embraer 170
      • United Airlines (UA 3542)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Embraer 170
      • 17:30 YYZ
        18:43 ORD
        2Hrs, 13m Direct
      • YYZToronto Lester B Pearson Intl Airport 17:30 - ORD 18:43 2h 13m Direct
      • YYZToronto Lester B Pearson Intl Airport 17:30
      • ORDChicago O'Hare International Airport 18:43
      • 2h 13m
      • Direct
      • United Airlines (UA 3542)Embraer 175
      • United Airlines (UA 3542)
        • M
        • T
        • W
        • T
        • F
        • S
        • -
      • Embraer 175
      • 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
        • F
        • S
        • 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
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        • T
        • F
        • -
        • S
      • Airbus A220 300
      • 19:40 YYZ
        23:25 ORD
        4Hrs, 45m 1 Stop (IAD)
      • YYZToronto Lester B Pearson Intl Airport 19:40 - ORD 23:25 4h 45m 1 Stop (IAD) Washington
      • YYZToronto Lester B Pearson Intl Airport 19:40
        IADWashington Dulles International Airport 22:20
      • IADWashington Dulles International Airport 21:21
        ORDChicago O'Hare International Airport 23:25
      • 4h 45m (59m)
      • 1 Stop IAD · Washington 59m
      • United Airlines (UA 3466)Embraer 175
        United Airlines (UA 1738)Boeing 757 200 Series
      • United Airlines (UA 3466)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 08:00 YYZ
        12:05 ORD
        5Hrs, 05m 1 Stop (BNA)
      • YYZToronto Lester B Pearson Intl Airport 08:00 - ORD 12:05 5h 05m 1 Stop (BNA) Nashville
      • YYZToronto Lester B Pearson Intl Airport 08:00
        BNANashville Airport 10:09
      • BNANashville Airport 09:14
        ORDChicago O'Hare International Airport 12:05
      • 5h 05m (55m)
      • 1 Stop BNA · Nashville 55m
      • Air Canada (AC 1715)Airbus
        United Airlines (UA 3434)Embraer 175
      • Air Canada (AC 1715)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 08:00 YYZ
        11:56 ORD
        4Hrs, 56m 1 Stop (BNA)
      • YYZToronto Lester B Pearson Intl Airport 08:00 - ORD 11:56 4h 56m 1 Stop (BNA) Nashville
      • YYZToronto Lester B Pearson Intl Airport 08:00
        BNANashville Airport 10:00
      • BNANashville Airport 09:14
        ORDChicago O'Hare International Airport 11:56
      • 4h 56m (46m)
      • 1 Stop BNA · Nashville 46m
      • Air Canada (AC 1103)Airbus A220 300
        United Airlines (UA 5714)Embraer 175
      • Air Canada (AC 1103)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 08:00 YYZ
        12:05 ORD
        5Hrs, 05m 1 Stop (BNA)
      • YYZToronto Lester B Pearson Intl Airport 08:00 - ORD 12:05 5h 05m 1 Stop (BNA) Nashville
      • YYZToronto Lester B Pearson Intl Airport 08:00
        BNANashville Airport 10:09
      • BNANashville Airport 09:14
        ORDChicago O'Hare International Airport 12:05
      • 5h 05m (55m)
      • 1 Stop BNA · Nashville 55m
      • Air Canada (AC 1103)Airbus A220 300
        United Airlines (UA 5714)Embraer 175
      • Air Canada (AC 1103)
        • M
        • T
        • -
        • T
        • F
        • -
        • S
      • 10:00 YYZ
        14:00 ORD
        5Hrs, 00m 1 Stop (IAD)
      • YYZToronto Lester B Pearson Intl Airport 10:00 - ORD 14:00 5h 1 Stop (IAD) Washington
      • YYZToronto Lester B Pearson Intl Airport 10:00
        IADWashington Dulles International Airport 12:40
      • IADWashington Dulles International Airport 11:41
        ORDChicago O'Hare International Airport 14:00
      • 5h (59m)
      • 1 Stop IAD · Washington 59m
      • United Airlines (UA 3416)Embraer 175
        United Airlines (UA 1581)Airbus
      • United Airlines (UA 3416)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 10:00 YYZ
        14:05 ORD
        5Hrs, 05m 1 Stop (IAD)
      • YYZToronto Lester B Pearson Intl Airport 10:00 - ORD 14:05 5h 05m 1 Stop (IAD) Washington
      • YYZToronto Lester B Pearson Intl Airport 10:00
        IADWashington Dulles International Airport 12:45
      • IADWashington Dulles International Airport 11:41
        ORDChicago O'Hare International Airport 14:05
      • 5h 05m (1h 04m)
      • 1 Stop IAD · Washington 1h 04m
      • United Airlines (UA 3416)Embraer 175
        United Airlines (UA 1581)Boeing 737 700
      • United Airlines (UA 3416)
        • M
        • -
        • -
        • -
        • F
        • -
        • -
      • 10:00 YYZ
        14:05 ORD
        5Hrs, 05m 1 Stop (IAD)
      • YYZToronto Lester B Pearson Intl Airport 10:00 - ORD 14:05 5h 05m 1 Stop (IAD) Washington
      • YYZToronto Lester B Pearson Intl Airport 10:00
        IADWashington Dulles International Airport 12:45
      • IADWashington Dulles International Airport 11:41
        ORDChicago O'Hare International Airport 14:05
      • 5h 05m (1h 04m)
      • 1 Stop IAD · Washington 1h 04m
      • United Airlines (UA 3416)Embraer 175
        United Airlines (UA 1581)Airbus
      • United Airlines (UA 3416)
        • -
        • T
        • W
        • T
        • -
        • -
        • -
      • 10:00 YYZ
        14:15 ORD
        5Hrs, 15m 1 Stop (IAD)
      • YYZToronto Lester B Pearson Intl Airport 10:00 - ORD 14:15 5h 15m 1 Stop (IAD) Washington
      • YYZToronto Lester B Pearson Intl Airport 10:00
        IADWashington Dulles International Airport 12:55
      • IADWashington Dulles International Airport 11:41
        ORDChicago O'Hare International Airport 14:15
      • 5h 15m (1h 14m)
      • 1 Stop IAD · Washington 1h 14m
      • United Airlines (UA 3416)Embraer 175
        United Airlines (UA 1581)Airbus
      • United Airlines (UA 3416)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 11:50 YYZ
        15:51 ORD
        5Hrs, 01m 1 Stop (CLT)
      • YYZToronto Lester B Pearson Intl Airport 11:50 - ORD 15:51 5h 01m 1 Stop (CLT) Charlotte
      • YYZToronto Lester B Pearson Intl Airport 11:50
        CLTCharlotte Airport 14:41
      • CLTCharlotte Airport 14:00
        ORDChicago O'Hare International Airport 15:51
      • 5h 01m (41m)
      • 1 Stop CLT · Charlotte 41m
      • American Airlines (AA 5020)Canadair Regional
        American Airlines (AA 614)Boeing 737 800
      • American Airlines (AA 5020)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 14:10 YYZ
        18:10 ORD
        5Hrs, 00m 1 Stop (PHL)
      • YYZToronto Lester B Pearson Intl Airport 14:10 - ORD 18:10 5h 1 Stop (PHL) Philadelphia
      • YYZToronto Lester B Pearson Intl Airport 14:10
        PHLPhiladelphia International Airport 16:38
      • PHLPhiladelphia International Airport 15:45
        ORDChicago O'Hare International Airport 18:10
      • 5h (53m)
      • 1 Stop PHL · Philadelphia 53m
      • Air Canada (AC 8932)Canadair Regional
        United Airlines (UA 308)Airbus
      • Air Canada (AC 8932)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 14:45 YYZ
        18:49 ORD
        5Hrs, 04m 1 Stop (IAD)
      • YYZToronto Lester B Pearson Intl Airport 14:45 - ORD 18:49 5h 04m 1 Stop (IAD) Washington
      • YYZToronto Lester B Pearson Intl Airport 14:45
        IADWashington Dulles International Airport 17:29
      • IADWashington Dulles International Airport 16:26
        ORDChicago O'Hare International Airport 18:49
      • 5h 04m (1h 03m)
      • 1 Stop IAD · Washington 1h 03m
      • United Airlines (UA 3637)Embraer 175
        United Airlines (UA 2497)Boeing 737 900
      • United Airlines (UA 3637)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 14:45 YYZ
        18:42 ORD
        4Hrs, 57m 1 Stop (IAD)
      • YYZToronto Lester B Pearson Intl Airport 14:45 - ORD 18:42 4h 57m 1 Stop (IAD) Washington
      • YYZToronto Lester B Pearson Intl Airport 14:45
        IADWashington Dulles International Airport 17:22
      • IADWashington Dulles International Airport 16:26
        ORDChicago O'Hare International Airport 18:42
      • 4h 57m (56m)
      • 1 Stop IAD · Washington 56m
      • United Airlines (UA 3637)Embraer 175
        United Airlines (UA 2497)Boeing 737 900
      • United Airlines (UA 3637)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 14:45 YYZ
        18:42 ORD
        4Hrs, 57m 1 Stop (IAD)
      • YYZToronto Lester B Pearson Intl Airport 14:45 - ORD 18:42 4h 57m 1 Stop (IAD) Washington
      • YYZToronto Lester B Pearson Intl Airport 14:45
        IADWashington Dulles International Airport 17:22
      • IADWashington Dulles International Airport 16:26
        ORDChicago O'Hare International Airport 18:42
      • 4h 57m (56m)
      • 1 Stop IAD · Washington 56m
      • United Airlines (UA 3637)Embraer 175
        United Airlines (UA 2497)Airbus
      • United Airlines (UA 3637)
        • -
        • T
        • -
        • -
        • F
        • -
        • -
      • 14:45 YYZ
        18:55 ORD
        5Hrs, 10m 1 Stop (IAD)
      • YYZToronto Lester B Pearson Intl Airport 14:45 - ORD 18:55 5h 10m 1 Stop (IAD) Washington
      • YYZToronto Lester B Pearson Intl Airport 14:45
        IADWashington Dulles International Airport 17:35
      • IADWashington Dulles International Airport 16:26
        ORDChicago O'Hare International Airport 18:55
      • 5h 10m (1h 09m)
      • 1 Stop IAD · Washington 1h 09m
      • United Airlines (UA 3637)Embraer 175
        United Airlines (UA 2497)Boeing 737 900
      • United Airlines (UA 3637)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 14:45 YYZ
        18:42 ORD
        4Hrs, 57m 1 Stop (IAD)
      • YYZToronto Lester B Pearson Intl Airport 14:45 - ORD 18:42 4h 57m 1 Stop (IAD) Washington
      • YYZToronto Lester B Pearson Intl Airport 14:45
        IADWashington Dulles International Airport 17:22
      • IADWashington Dulles International Airport 16:26
        ORDChicago O'Hare International Airport 18:42
      • 4h 57m (56m)
      • 1 Stop IAD · Washington 56m
      • United Airlines (UA 3637)Embraer 175
        United Airlines (UA 2497)Airbus
      • United Airlines (UA 3637)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 14:45 YYZ
        18:55 ORD
        5Hrs, 10m 1 Stop (IAD)
      • YYZToronto Lester B Pearson Intl Airport 14:45 - ORD 18:55 5h 10m 1 Stop (IAD) Washington
      • YYZToronto Lester B Pearson Intl Airport 14:45
        IADWashington Dulles International Airport 17:35
      • IADWashington Dulles International Airport 16:26
        ORDChicago O'Hare International Airport 18:55
      • 5h 10m (1h 09m)
      • 1 Stop IAD · Washington 1h 09m
      • United Airlines (UA 3637)Embraer 175
        United Airlines (UA 2497)Airbus
      • United Airlines (UA 3637)
        • -
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        • -
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        • S
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      • 14:45 YYZ
        18:40 ORD
        4Hrs, 55m 1 Stop (BNA)
      • YYZToronto Lester B Pearson Intl Airport 14:45 - ORD 18:40 4h 55m 1 Stop (BNA) Nashville
      • YYZToronto Lester B Pearson Intl Airport 14:45
        BNANashville Airport 16:45
      • BNANashville Airport 16:01
        ORDChicago O'Hare International Airport 18:40
      • 4h 55m (44m)
      • 1 Stop BNA · Nashville 44m
      • Air Canada (AC 8855)Canadair Regional
        United Airlines (UA 771)Airbus
      • Air Canada (AC 8855)
        • M
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      • 16:05 YYZ
        20:07 ORD
        5Hrs, 02m 1 Stop (PHL)
      • YYZToronto Lester B Pearson Intl Airport 16:05 - ORD 20:07 5h 02m 1 Stop (PHL) Philadelphia
      • YYZToronto Lester B Pearson Intl Airport 16:05
        PHLPhiladelphia International Airport 18:35
      • PHLPhiladelphia International Airport 17:40
        ORDChicago O'Hare International Airport 20:07
      • 5h 02m (55m)
      • 1 Stop PHL · Philadelphia 55m
      • American Airlines (AA 5884)Er4 Embraer Rj145 Amazon
        American Airlines (AA 490)Airbus
      • American Airlines (AA 5884)
        • M
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      • 16:30 YYZ
        20:25 ORD
        4Hrs, 55m 1 Stop (DCA)
      • YYZToronto Lester B Pearson Intl Airport 16:30 - ORD 20:25 4h 55m 1 Stop (DCA) Washington
      • YYZToronto Lester B Pearson Intl Airport 16:30
        DCAWashington Ronald Reagan National Airport 19:00
      • DCAWashington Ronald Reagan National Airport 18:07
        ORDChicago O'Hare International Airport 20:25
      • 4h 55m (53m)
      • 1 Stop DCA · Washington 53m
      • Air Canada (AC 8784)Canadair Regional
        United Airlines (UA 3488)Embraer 175
      • Air Canada (AC 8784)
        • M
        • -
        • W
        • T
        • F
        • S
        • S
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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 Porter 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 19:40. 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

      Porter Airlines ‏()
      United Airlines ‏()
      Air Canada ‏()

      Popular Destinations From Chicago

      Popular Destinations From Toronto

      Popular Hotels in Chicago

      Hotels In Popular Destinations