Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline Porter Airlines

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

  • Porter Airlines Porter Airlines
  • Air Canada Air Canada
  • United Airlines United Airlines
  • American Airlines American Airlines
  • Air Transat Air Transat
  • WestJet WestJet
  • Frontier Airlines Frontier Airlines
  • British Airways British Airways
  • Lufthansa Lufthansa
  • Alaska Airlines Alaska Airlines
Cheapest Month December

Travel Period: December 2024 - November 2025

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

  • Dec 2024
  • Jan 2025
  • Feb 2025
  • Mar 2025
  • Apr 2025
  • May 2025
  • Jun 2025
  • Jul 2025
  • Aug 2025
  • Sep 2025
  • Oct 2025
  • Nov 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: Sat, 2 Nov, 2024

  • Time Earliest
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  • Stopover
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  • Availability
    • M
    • T
    • W
    • T
    • F
    • S
    • 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
    • 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
    • T
    • 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
    • T
    • W
    • 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
    • T
    • W
    • T
    • F
    • S
    • 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
    • T
    • 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 737 800
  • United Airlines (UA 1063)
    • M
    • T
    • W
    • T
    • F
    • 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
    • T
    • W
    • T
    • F
    • S
    • 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
    • T
    • W
    • T
    • F
    • S
    • 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
  • Embraer 170
  • 13:14 YYZ
    14:14 ORD
    2Hrs, 00m Direct
  • YYZToronto Lester B Pearson Intl Airport 13:14 - ORD 14:14 2h Direct
  • YYZToronto Lester B Pearson Intl Airport 13:14
  • ORDChicago O'Hare International Airport 14:14
  • 2h
  • Direct
  • American Airlines (AA 3606)Embraer 170
  • American Airlines (AA 3606)
    • -
    • T
    • W
    • -
    • -
    • 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
    • T
    • W
    • 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
    • T
    • W
    • T
    • -
    • S
    • 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 737 700
  • 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
    • -
    • -
    • T
    • 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
    • T
    • W
    • T
    • 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
    • T
    • W
    • T
    • F
    • S
    • 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
  • 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
    • S
  • Airbus A220 300
  • 19:40 YYZ
    23:20 ORD
    4Hrs, 40m 1 Stop (IAD)
  • YYZToronto Lester B Pearson Intl Airport 19:40 - ORD 23:20 4h 40m 1 Stop (IAD) Washington
  • YYZToronto Lester B Pearson Intl Airport 19:40
    IADWashington Dulles International Airport 22:16
  • IADWashington Dulles International Airport 21:19
    ORDChicago O'Hare International Airport 23:20
  • 4h 40m (57m)
  • 1 Stop IAD · Washington 57m
  • United Airlines (UA 3466)Embraer 175
    United Airlines (UA 1738)Boeing 737 800
  • United Airlines (UA 3466)
    • M
    • T
    • W
    • T
    • -
    • -
    • -
  • 19:40 YYZ
    23:20 ORD
    4Hrs, 40m 1 Stop (IAD)
  • YYZToronto Lester B Pearson Intl Airport 19:40 - ORD 23:20 4h 40m 1 Stop (IAD) Washington
  • YYZToronto Lester B Pearson Intl Airport 19:40
    IADWashington Dulles International Airport 22:16
  • IADWashington Dulles International Airport 21:19
    ORDChicago O'Hare International Airport 23:20
  • 4h 40m (57m)
  • 1 Stop IAD · Washington 57m
  • United Airlines (UA 3466)Embraer 175
    United Airlines (UA 1738)Boeing 737 900
  • United Airlines (UA 3466)
    • -
    • -
    • -
    • -
    • F
    • -
    • -
  • 19:40 YYZ
    23:20 ORD
    4Hrs, 40m 1 Stop (IAD)
  • YYZToronto Lester B Pearson Intl Airport 19:40 - ORD 23:20 4h 40m 1 Stop (IAD) Washington
  • YYZToronto Lester B Pearson Intl Airport 19:40
    IADWashington Dulles International Airport 22:16
  • IADWashington Dulles International Airport 21:19
    ORDChicago O'Hare International Airport 23:20
  • 4h 40m (57m)
  • 1 Stop IAD · Washington 57m
  • United Airlines (UA 3466)Embraer 175
    United Airlines (UA 1738)Airbus
  • United Airlines (UA 3466)
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 19:40 YYZ
    23:20 ORD
    4Hrs, 40m 1 Stop (IAD)
  • YYZToronto Lester B Pearson Intl Airport 19:40 - ORD 23:20 4h 40m 1 Stop (IAD) Washington
  • YYZToronto Lester B Pearson Intl Airport 19:40
    IADWashington Dulles International Airport 22:16
  • IADWashington Dulles International Airport 21:19
    ORDChicago O'Hare International Airport 23:20
  • 4h 40m (57m)
  • 1 Stop IAD · Washington 57m
  • United Airlines (UA 3466)Embraer 175
    United Airlines (UA 1738)Boeing 737 700
  • United Airlines (UA 3466)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 07:45 YYZ
    11:46 ORD
    5Hrs, 01m 1 Stop (EWR)
  • YYZToronto Lester B Pearson Intl Airport 07:45 - ORD 11:46 5h 01m 1 Stop (EWR) New York City
  • YYZToronto Lester B Pearson Intl Airport 07:45
    EWRNewark Liberty International Airport 10:15
  • EWRNewark Liberty International Airport 09:30
    ORDChicago O'Hare International Airport 11:46
  • 5h 01m (45m)
  • 1 Stop EWR · New York City 45m
  • United Airlines (UA 3638)Embraer 175
    United Airlines (UA 1525)Boeing 737 900
  • United Airlines (UA 3638)
    • -
    • -
    • -
    • -
    • F
    • -
    • -
  • 08:00 YYZ
    11:55 ORD
    4Hrs, 55m 1 Stop (BNA)
  • YYZToronto Lester B Pearson Intl Airport 08:00 - ORD 11:55 4h 55m 1 Stop (BNA) Nashville
  • YYZToronto Lester B Pearson Intl Airport 08:00
    BNANashville Airport 10:05
  • BNANashville Airport 09:14
    ORDChicago O'Hare International Airport 11:55
  • 4h 55m (51m)
  • 1 Stop BNA · Nashville 51m
  • Air Canada (AC 1103)Airbus A220 300
    United Airlines (UA 1496)Boeing 737 800
  • Air Canada (AC 1103)
    • M
    • -
    • -
    • -
    • -
    • -
    • -
  • 08:00 YYZ
    11:55 ORD
    4Hrs, 55m 1 Stop (BNA)
  • YYZToronto Lester B Pearson Intl Airport 08:00 - ORD 11:55 4h 55m 1 Stop (BNA) Nashville
  • YYZToronto Lester B Pearson Intl Airport 08:00
    BNANashville Airport 10:05
  • BNANashville Airport 09:14
    ORDChicago O'Hare International Airport 11:55
  • 4h 55m (51m)
  • 1 Stop BNA · Nashville 51m
  • Air Canada (AC 1103)Airbus A220 300
    United Airlines (UA 1496)Boeing 737 700
  • Air Canada (AC 1103)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 08:00 YYZ
    11:55 ORD
    4Hrs, 55m 1 Stop (BNA)
  • YYZToronto Lester B Pearson Intl Airport 08:00 - ORD 11:55 4h 55m 1 Stop (BNA) Nashville
  • YYZToronto Lester B Pearson Intl Airport 08:00
    BNANashville Airport 10:05
  • BNANashville Airport 09:14
    ORDChicago O'Hare International Airport 11:55
  • 4h 55m (51m)
  • 1 Stop BNA · Nashville 51m
  • Air Canada (AC 1103)Airbus A220 300
    United Airlines (UA 1496)Airbus
  • Air Canada (AC 1103)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 08:50 YTZ
    12:58 ORD
    5Hrs, 08m 1 Stop (YOW)
  • YTZToronto City Centre Airport 08:50 - ORD 12:58 5h 08m 1 Stop (YOW) Ottawa
  • YTZToronto City Centre Airport 08:50
    YOWOttawa McDonald Cartier Intl Airport 11:25
  • YOWOttawa McDonald Cartier Intl Airport 09:46
    ORDChicago O'Hare International Airport 12:58
  • 5h 08m (1h 39m)
  • 1 Stop YOW · Ottawa 1h 39m
  • Air Canada (AC 7704)Dehavilland Dash 8 400
    United Airlines (UA 4437)Canadair Regional Jet 550
  • Air Canada (AC 7704)
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • 11:45 YYZ
    15:40 ORD
    4Hrs, 55m 1 Stop (CLT)
  • YYZToronto Lester B Pearson Intl Airport 11:45 - ORD 15:40 4h 55m 1 Stop (CLT) Charlotte
  • YYZToronto Lester B Pearson Intl Airport 11:45
    CLTCharlotte Airport 14:32
  • CLTCharlotte Airport 14:00
    ORDChicago O'Hare International Airport 15:40
  • 4h 55m (32m)
  • 1 Stop CLT · Charlotte 32m
  • American Airlines (AA 1720)Airbus
    American Airlines (AA 614)Boeing 737 800
  • American Airlines (AA 1720)
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • 12:45 YYZ
    16:54 ORD
    5Hrs, 09m 1 Stop (EWR)
  • YYZToronto Lester B Pearson Intl Airport 12:45 - ORD 16:54 5h 09m 1 Stop (EWR) New York City
  • YYZToronto Lester B Pearson Intl Airport 12:45
    EWRNewark Liberty International Airport 15:15
  • EWRNewark Liberty International Airport 14:30
    ORDChicago O'Hare International Airport 16:54
  • 5h 09m (45m)
  • 1 Stop EWR · New York City 45m
  • United Airlines (UA 3649)Embraer 175
    United Airlines (UA 1144)Boeing 757 200 Series
  • United Airlines (UA 3649)
    • M
    • T
    • W
    • T
    • F
    • -
    • S
  • 14:45 YYZ
    18:35 ORD
    4Hrs, 50m 1 Stop (IAD)
  • YYZToronto Lester B Pearson Intl Airport 14:45 - ORD 18:35 4h 50m 1 Stop (IAD) Washington
  • YYZToronto Lester B Pearson Intl Airport 14:45
    IADWashington Dulles International Airport 17:21
  • IADWashington Dulles International Airport 16:24
    ORDChicago O'Hare International Airport 18:35
  • 4h 50m (57m)
  • 1 Stop IAD · Washington 57m
  • United Airlines (UA 3637)Embraer 175
    United Airlines (UA 2497)Airbus
  • United Airlines (UA 3637)
    • M
    • T
    • W
    • T
    • F
    • S
    • -
  • 14:45 YYZ
    18:35 ORD
    4Hrs, 50m 1 Stop (IAD)
  • YYZToronto Lester B Pearson Intl Airport 14:45 - ORD 18:35 4h 50m 1 Stop (IAD) Washington
  • YYZToronto Lester B Pearson Intl Airport 14:45
    IADWashington Dulles International Airport 17:21
  • IADWashington Dulles International Airport 16:24
    ORDChicago O'Hare International Airport 18:35
  • 4h 50m (57m)
  • 1 Stop IAD · Washington 57m
  • United Airlines (UA 3637)Embraer 175
    United Airlines (UA 2497)Boeing 737 800
  • United Airlines (UA 3637)
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 16:07 YYZ
    20:04 ORD
    4Hrs, 57m 1 Stop (PHL)
  • YYZToronto Lester B Pearson Intl Airport 16:07 - ORD 20:04 4h 57m 1 Stop (PHL) Philadelphia
  • YYZToronto Lester B Pearson Intl Airport 16:07
    PHLPhiladelphia International Airport 18:35
  • PHLPhiladelphia International Airport 17:42
    ORDChicago O'Hare International Airport 20:04
  • 4h 57m (53m)
  • 1 Stop PHL · Philadelphia 53m
  • American Airlines (AA 5884)Er4 Embraer Rj145 Amazon
    American Airlines (AA 490)Airbus
  • American Airlines (AA 5884)
    • M
    • -
    • -
    • T
    • F
    • -
    • S
  • 16:30 YYZ
    20:25 ORD
    4Hrs, 55m 1 Stop (BNA)
  • YYZToronto Lester B Pearson Intl Airport 16:30 - ORD 20:25 4h 55m 1 Stop (BNA) Nashville
  • YYZToronto Lester B Pearson Intl Airport 16:30
    BNANashville Airport 18:30
  • BNANashville Airport 17:44
    ORDChicago O'Hare International Airport 20:25
  • 4h 55m (46m)
  • 1 Stop BNA · Nashville 46m
  • Air Canada (AC 1105)Airbus A220 300
    United Airlines (UA 3482)Embraer 175
  • Air Canada (AC 1105)
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 16:30 YYZ
    20:14 ORD
    4Hrs, 44m 1 Stop (DCA)
  • YYZToronto Lester B Pearson Intl Airport 16:30 - ORD 20:14 4h 44m 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 20:14
  • 4h 44m (53m)
  • 1 Stop DCA · Washington 53m
  • Air Canada (AC 8784)Canadair Regional
    United Airlines (UA 2665)Airbus
  • Air Canada (AC 8784)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 16:30 YYZ
    20:25 ORD
    4Hrs, 55m 1 Stop (BNA)
  • YYZToronto Lester B Pearson Intl Airport 16:30 - ORD 20:25 4h 55m 1 Stop (BNA) Nashville
  • YYZToronto Lester B Pearson Intl Airport 16:30
    BNANashville Airport 18:30
  • BNANashville Airport 17:44
    ORDChicago O'Hare International Airport 20:25
  • 4h 55m (46m)
  • 1 Stop BNA · Nashville 46m
  • Air Canada (AC 1105)Airbus
    United Airlines (UA 3482)Embraer 175
  • Air Canada (AC 1105)
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • 16:30 YYZ
    20:14 ORD
    4Hrs, 44m 1 Stop (DCA)
  • YYZToronto Lester B Pearson Intl Airport 16:30 - ORD 20:14 4h 44m 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 20:14
  • 4h 44m (53m)
  • 1 Stop DCA · Washington 53m
  • Air Canada (AC 8784)Canadair Regional
    United Airlines (UA 2665)Airbus
  • Air Canada (AC 8784)
    • M
    • T
    • W
    • T
    • F
    • -
    • 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 Air Canada. 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.