Fare Guide
Estimated lowest fares found within 7 days
The cheapest airline(s) flying from Toronto to Chicago is Porter Airlines.
Travel Period: December 2024 - November 2025
The cheapest month(s) to fly from Toronto to Chicago is December.
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Dec 2024
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Jan 2025
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Feb 2025
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Mar 2025
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Apr 2025
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May 2025
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Jun 2025
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Jul 2025
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Aug 2025
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Sep 2025
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Oct 2025
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Nov 2025
The cheapest day(s) of the week to fly from Toronto to Chicago is Wednesday.
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Sun Sunday
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Mon Monday
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Tue Tuesday
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Wed Wednesday
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Thu Thursday
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Fri Friday
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Sat Saturday
Flight Schedules
Last Updated: Sat, 2 Nov, 2024
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Time
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Availability
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21:00 YYZ22:07 ORD2Hrs, 07m Direct
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YYZToronto Lester B Pearson Intl Airport 21:00 - ORD 22:07 2h 07m Direct
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YYZToronto Lester B Pearson Intl Airport 21:00
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ORDChicago O'Hare International Airport 22:07
- 2h 07m
- Direct
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United Airlines (UA 5728)Embraer 175 -
United Airlines (UA 5728) -
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- Embraer 175
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06:15 YYZ07:30 ORD2Hrs, 15m Direct
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YYZToronto Lester B Pearson Intl Airport 06:15 - ORD 07:30 2h 15m Direct
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YYZToronto Lester B Pearson Intl Airport 06:15
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ORDChicago O'Hare International Airport 07:30
- 2h 15m
- Direct
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American Airlines (AA 3524)Embraer 170 -
American Airlines (AA 3524) -
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- Embraer 170
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06:52 YYZ08:05 ORD2Hrs, 13m Direct
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YYZToronto Lester B Pearson Intl Airport 06:52 - ORD 08:05 2h 13m Direct
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YYZToronto Lester B Pearson Intl Airport 06:52
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ORDChicago O'Hare International Airport 08:05
- 2h 13m
- Direct
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United Airlines (UA 3534)Embraer 175 -
United Airlines (UA 3534) -
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- Embraer 175
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08:00 YYZ08:57 ORD1Hrs, 57m Direct
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YYZToronto Lester B Pearson Intl Airport 08:00 - ORD 08:57 1h 57m Direct
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YYZToronto Lester B Pearson Intl Airport 08:00
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ORDChicago O'Hare International Airport 08:57
- 1h 57m
- Direct
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Air Canada (AC 501)Airbus A220 300 -
Air Canada (AC 501) -
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- Airbus A220 300
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09:00 YYZ10:05 ORD2Hrs, 05m Direct
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YYZToronto Lester B Pearson Intl Airport 09:00 - ORD 10:05 2h 05m Direct
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YYZToronto Lester B Pearson Intl Airport 09:00
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ORDChicago O'Hare International Airport 10:05
- 2h 05m
- Direct
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United Airlines (UA 1538)Boeing 737 Max 8 Passenger -
United Airlines (UA 1538) -
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- Boeing 737 Max 8 Passenger
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09:30 YTZ10:20 MDW1Hrs, 50m Direct
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YTZToronto City Centre Airport 09:30 - MDW 10:20 1h 50m Direct
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YTZToronto City Centre Airport 09:30
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MDWChicago Midway Airport 10:20
- 1h 50m
- Direct
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Porter Airlines (PD 2387)Dehavilland Dash 8 400 -
Porter Airlines (PD 2387) -
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- Dehavilland Dash 8 400
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11:00 YYZ11:59 ORD1Hrs, 59m Direct
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YYZToronto Lester B Pearson Intl Airport 11:00 - ORD 11:59 1h 59m Direct
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YYZToronto Lester B Pearson Intl Airport 11:00
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ORDChicago O'Hare International Airport 11:59
- 1h 59m
- Direct
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United Airlines (UA 1063)Boeing 737 800 -
United Airlines (UA 1063) -
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- Boeing 737 800
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11:10 YTZ12:00 MDW1Hrs, 50m Direct
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YTZToronto City Centre Airport 11:10 - MDW 12:00 1h 50m Direct
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YTZToronto City Centre Airport 11:10
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MDWChicago Midway Airport 12:00
- 1h 50m
- Direct
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Porter Airlines (PD 2387)Dehavilland Dash 8 400 -
Porter Airlines (PD 2387) -
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- -
- -
- -
- -
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- Dehavilland Dash 8 400
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11:37 YYZ12:37 ORD2Hrs, 00m Direct
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YYZToronto Lester B Pearson Intl Airport 11:37 - ORD 12:37 2h Direct
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YYZToronto Lester B Pearson Intl Airport 11:37
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ORDChicago O'Hare International Airport 12:37
- 2h
- Direct
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American Airlines (AA 3604)Embraer 170 -
American Airlines (AA 3604) -
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- Embraer 170
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12:20 YYZ13:11 ORD1Hrs, 51m Direct
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YYZToronto Lester B Pearson Intl Airport 12:20 - ORD 13:11 1h 51m Direct
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YYZToronto Lester B Pearson Intl Airport 12:20
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ORDChicago O'Hare International Airport 13:11
- 1h 51m
- Direct
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Air Canada (AC 503)Airbus A220 300 -
Air Canada (AC 503) -
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- Airbus A220 300
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13:10 YYZ14:10 ORD2Hrs, 00m Direct
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YYZToronto Lester B Pearson Intl Airport 13:10 - ORD 14:10 2h Direct
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YYZToronto Lester B Pearson Intl Airport 13:10
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ORDChicago O'Hare International Airport 14:10
- 2h
- Direct
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American Airlines (AA 3606)Embraer 170 -
American Airlines (AA 3606) -
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- Embraer 170
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13:14 YYZ14:14 ORD2Hrs, 00m Direct
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YYZToronto Lester B Pearson Intl Airport 13:14 - ORD 14:14 2h Direct
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YYZToronto Lester B Pearson Intl Airport 13:14
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ORDChicago O'Hare International Airport 14:14
- 2h
- Direct
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American Airlines (AA 3606)Embraer 170 -
American Airlines (AA 3606) -
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- Embraer 170
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14:00 YYZ14:51 ORD1Hrs, 51m Direct
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YYZToronto Lester B Pearson Intl Airport 14:00 - ORD 14:51 1h 51m Direct
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YYZToronto Lester B Pearson Intl Airport 14:00
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ORDChicago O'Hare International Airport 14:51
- 1h 51m
- Direct
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Air Canada (AC 505)Airbus A220 300 -
Air Canada (AC 505) -
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15:30 YYZ16:30 ORD2Hrs, 00m Direct
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YYZToronto Lester B Pearson Intl Airport 15:30 - ORD 16:30 2h Direct
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YYZToronto Lester B Pearson Intl Airport 15:30
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ORDChicago O'Hare International Airport 16:30
- 2h
- Direct
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United Airlines (UA 2364)Airbus -
United Airlines (UA 2364) -
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15:30 YYZ16:29 ORD1Hrs, 59m Direct
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YYZToronto Lester B Pearson Intl Airport 15:30 - ORD 16:29 1h 59m Direct
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YYZToronto Lester B Pearson Intl Airport 15:30
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ORDChicago O'Hare International Airport 16:29
- 1h 59m
- Direct
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United Airlines (UA 2364)Boeing 737 700 -
United Airlines (UA 2364) -
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- Boeing 737 700
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15:50 YTZ16:40 MDW1Hrs, 50m Direct
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YTZToronto City Centre Airport 15:50 - MDW 16:40 1h 50m Direct
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YTZToronto City Centre Airport 15:50
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MDWChicago Midway Airport 16:40
- 1h 50m
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Porter Airlines (PD 2393)Dehavilland Dash 8 400 -
Porter Airlines (PD 2393) -
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16:44 YYZ17:44 ORD2Hrs, 00m Direct
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YYZToronto Lester B Pearson Intl Airport 16:44 - ORD 17:44 2h Direct
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YYZToronto Lester B Pearson Intl Airport 16:44
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ORDChicago O'Hare International Airport 17:44
- 2h
- Direct
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American Airlines (AA 3608)Embraer 170 -
American Airlines (AA 3608) -
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17:30 YYZ18:37 ORD2Hrs, 07m Direct
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YYZToronto Lester B Pearson Intl Airport 17:30 - ORD 18:37 2h 07m Direct
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YYZToronto Lester B Pearson Intl Airport 17:30
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ORDChicago O'Hare International Airport 18:37
- 2h 07m
- Direct
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United Airlines (UA 3542)Embraer 175 -
United Airlines (UA 3542) -
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- Embraer 175
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18:20 YYZ19:20 ORD2Hrs, 00m Direct
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YYZToronto Lester B Pearson Intl Airport 18:20 - ORD 19:20 2h Direct
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YYZToronto Lester B Pearson Intl Airport 18:20
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ORDChicago O'Hare International Airport 19:20
- 2h
- Direct
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American Airlines (AA 3610)Embraer 170 -
American Airlines (AA 3610) -
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18:35 YYZ19:32 ORD1Hrs, 57m Direct
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YYZToronto Lester B Pearson Intl Airport 18:35 - ORD 19:32 1h 57m Direct
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YYZToronto Lester B Pearson Intl Airport 18:35
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ORDChicago O'Hare International Airport 19:32
- 1h 57m
- Direct
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Air Canada (AC 509)Airbus A220 300 -
Air Canada (AC 509) -
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19:40 YYZ23:20 ORD4Hrs, 40m 1 Stop (IAD)
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YYZToronto Lester B Pearson Intl Airport 19:40 - ORD 23:20 4h 40m 1 Stop (IAD) Washington
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YYZToronto Lester B Pearson Intl Airport 19:40IADWashington Dulles International Airport 22:16
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IADWashington Dulles International Airport 21:19ORDChicago O'Hare International Airport 23:20
- 4h 40m (57m)
- 1 Stop IAD · Washington 57m
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United Airlines (UA 3466)Embraer 175 United Airlines (UA 1738)Boeing 737 800 -
United Airlines (UA 3466) -
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19:40 YYZ23:20 ORD4Hrs, 40m 1 Stop (IAD)
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YYZToronto Lester B Pearson Intl Airport 19:40 - ORD 23:20 4h 40m 1 Stop (IAD) Washington
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YYZToronto Lester B Pearson Intl Airport 19:40IADWashington Dulles International Airport 22:16
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IADWashington Dulles International Airport 21:19ORDChicago O'Hare International Airport 23:20
- 4h 40m (57m)
- 1 Stop IAD · Washington 57m
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United Airlines (UA 3466)Embraer 175 United Airlines (UA 1738)Boeing 737 900 -
United Airlines (UA 3466) -
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19:40 YYZ23:20 ORD4Hrs, 40m 1 Stop (IAD)
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YYZToronto Lester B Pearson Intl Airport 19:40 - ORD 23:20 4h 40m 1 Stop (IAD) Washington
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YYZToronto Lester B Pearson Intl Airport 19:40IADWashington Dulles International Airport 22:16
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IADWashington Dulles International Airport 21:19ORDChicago O'Hare International Airport 23:20
- 4h 40m (57m)
- 1 Stop IAD · Washington 57m
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United Airlines (UA 3466)Embraer 175 United Airlines (UA 1738)Airbus -
United Airlines (UA 3466) -
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19:40 YYZ23:20 ORD4Hrs, 40m 1 Stop (IAD)
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YYZToronto Lester B Pearson Intl Airport 19:40 - ORD 23:20 4h 40m 1 Stop (IAD) Washington
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YYZToronto Lester B Pearson Intl Airport 19:40IADWashington Dulles International Airport 22:16
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IADWashington Dulles International Airport 21:19ORDChicago O'Hare International Airport 23:20
- 4h 40m (57m)
- 1 Stop IAD · Washington 57m
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United Airlines (UA 3466)Embraer 175 United Airlines (UA 1738)Boeing 737 700 -
United Airlines (UA 3466) -
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07:45 YYZ11:46 ORD5Hrs, 01m 1 Stop (EWR)
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YYZToronto Lester B Pearson Intl Airport 07:45 - ORD 11:46 5h 01m 1 Stop (EWR) New York City
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YYZToronto Lester B Pearson Intl Airport 07:45EWRNewark Liberty International Airport 10:15
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EWRNewark Liberty International Airport 09:30ORDChicago O'Hare International Airport 11:46
- 5h 01m (45m)
- 1 Stop EWR · New York City 45m
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United Airlines (UA 3638)Embraer 175 United Airlines (UA 1525)Boeing 737 900 -
United Airlines (UA 3638) -
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08:00 YYZ11:55 ORD4Hrs, 55m 1 Stop (BNA)
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YYZToronto Lester B Pearson Intl Airport 08:00 - ORD 11:55 4h 55m 1 Stop (BNA) Nashville
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YYZToronto Lester B Pearson Intl Airport 08:00BNANashville Airport 10:05
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BNANashville Airport 09:14ORDChicago O'Hare International Airport 11:55
- 4h 55m (51m)
- 1 Stop BNA · Nashville 51m
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Air Canada (AC 1103)Airbus A220 300 United Airlines (UA 1496)Boeing 737 800 -
Air Canada (AC 1103) -
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08:00 YYZ11:55 ORD4Hrs, 55m 1 Stop (BNA)
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YYZToronto Lester B Pearson Intl Airport 08:00 - ORD 11:55 4h 55m 1 Stop (BNA) Nashville
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YYZToronto Lester B Pearson Intl Airport 08:00BNANashville Airport 10:05
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BNANashville Airport 09:14ORDChicago O'Hare International Airport 11:55
- 4h 55m (51m)
- 1 Stop BNA · Nashville 51m
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Air Canada (AC 1103)Airbus A220 300 United Airlines (UA 1496)Boeing 737 700 -
Air Canada (AC 1103) -
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08:00 YYZ11:55 ORD4Hrs, 55m 1 Stop (BNA)
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YYZToronto Lester B Pearson Intl Airport 08:00 - ORD 11:55 4h 55m 1 Stop (BNA) Nashville
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YYZToronto Lester B Pearson Intl Airport 08:00BNANashville Airport 10:05
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BNANashville Airport 09:14ORDChicago O'Hare International Airport 11:55
- 4h 55m (51m)
- 1 Stop BNA · Nashville 51m
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Air Canada (AC 1103)Airbus A220 300 United Airlines (UA 1496)Airbus -
Air Canada (AC 1103) -
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08:50 YTZ12:58 ORD5Hrs, 08m 1 Stop (YOW)
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YTZToronto City Centre Airport 08:50 - ORD 12:58 5h 08m 1 Stop (YOW) Ottawa
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YTZToronto City Centre Airport 08:50YOWOttawa McDonald Cartier Intl Airport 11:25
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YOWOttawa McDonald Cartier Intl Airport 09:46ORDChicago O'Hare International Airport 12:58
- 5h 08m (1h 39m)
- 1 Stop YOW · Ottawa 1h 39m
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Air Canada (AC 7704)Dehavilland Dash 8 400 United Airlines (UA 4437)Canadair Regional Jet 550 -
Air Canada (AC 7704) -
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11:45 YYZ15:40 ORD4Hrs, 55m 1 Stop (CLT)
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YYZToronto Lester B Pearson Intl Airport 11:45 - ORD 15:40 4h 55m 1 Stop (CLT) Charlotte
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YYZToronto Lester B Pearson Intl Airport 11:45CLTCharlotte Airport 14:32
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CLTCharlotte Airport 14:00ORDChicago O'Hare International Airport 15:40
- 4h 55m (32m)
- 1 Stop CLT · Charlotte 32m
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American Airlines (AA 1720)Airbus American Airlines (AA 614)Boeing 737 800 -
American Airlines (AA 1720) -
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12:45 YYZ16:54 ORD5Hrs, 09m 1 Stop (EWR)
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YYZToronto Lester B Pearson Intl Airport 12:45 - ORD 16:54 5h 09m 1 Stop (EWR) New York City
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YYZToronto Lester B Pearson Intl Airport 12:45EWRNewark Liberty International Airport 15:15
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EWRNewark Liberty International Airport 14:30ORDChicago O'Hare International Airport 16:54
- 5h 09m (45m)
- 1 Stop EWR · New York City 45m
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United Airlines (UA 3649)Embraer 175 United Airlines (UA 1144)Boeing 757 200 Series -
United Airlines (UA 3649) -
- M
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14:45 YYZ18:35 ORD4Hrs, 50m 1 Stop (IAD)
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YYZToronto Lester B Pearson Intl Airport 14:45 - ORD 18:35 4h 50m 1 Stop (IAD) Washington
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YYZToronto Lester B Pearson Intl Airport 14:45IADWashington Dulles International Airport 17:21
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IADWashington Dulles International Airport 16:24ORDChicago O'Hare International Airport 18:35
- 4h 50m (57m)
- 1 Stop IAD · Washington 57m
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United Airlines (UA 3637)Embraer 175 United Airlines (UA 2497)Airbus -
United Airlines (UA 3637) -
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14:45 YYZ18:35 ORD4Hrs, 50m 1 Stop (IAD)
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YYZToronto Lester B Pearson Intl Airport 14:45 - ORD 18:35 4h 50m 1 Stop (IAD) Washington
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YYZToronto Lester B Pearson Intl Airport 14:45IADWashington Dulles International Airport 17:21
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IADWashington Dulles International Airport 16:24ORDChicago O'Hare International Airport 18:35
- 4h 50m (57m)
- 1 Stop IAD · Washington 57m
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United Airlines (UA 3637)Embraer 175 United Airlines (UA 2497)Boeing 737 800 -
United Airlines (UA 3637) -
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16:07 YYZ20:04 ORD4Hrs, 57m 1 Stop (PHL)
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YYZToronto Lester B Pearson Intl Airport 16:07 - ORD 20:04 4h 57m 1 Stop (PHL) Philadelphia
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YYZToronto Lester B Pearson Intl Airport 16:07PHLPhiladelphia International Airport 18:35
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PHLPhiladelphia International Airport 17:42ORDChicago O'Hare International Airport 20:04
- 4h 57m (53m)
- 1 Stop PHL · Philadelphia 53m
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American Airlines (AA 5884)Er4 Embraer Rj145 Amazon American Airlines (AA 490)Airbus -
American Airlines (AA 5884) -
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16:30 YYZ20:25 ORD4Hrs, 55m 1 Stop (BNA)
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YYZToronto Lester B Pearson Intl Airport 16:30 - ORD 20:25 4h 55m 1 Stop (BNA) Nashville
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YYZToronto Lester B Pearson Intl Airport 16:30BNANashville Airport 18:30
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BNANashville Airport 17:44ORDChicago O'Hare International Airport 20:25
- 4h 55m (46m)
- 1 Stop BNA · Nashville 46m
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Air Canada (AC 1105)Airbus A220 300 United Airlines (UA 3482)Embraer 175 -
Air Canada (AC 1105) -
- -
- -
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16:30 YYZ20:14 ORD4Hrs, 44m 1 Stop (DCA)
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YYZToronto Lester B Pearson Intl Airport 16:30 - ORD 20:14 4h 44m 1 Stop (DCA) Washington
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YYZToronto Lester B Pearson Intl Airport 16:30DCAWashington Ronald Reagan National Airport 19:00
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DCAWashington Ronald Reagan National Airport 18:07ORDChicago O'Hare International Airport 20:14
- 4h 44m (53m)
- 1 Stop DCA · Washington 53m
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Air Canada (AC 8784)Canadair Regional United Airlines (UA 2665)Airbus -
Air Canada (AC 8784) -
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16:30 YYZ20:25 ORD4Hrs, 55m 1 Stop (BNA)
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YYZToronto Lester B Pearson Intl Airport 16:30 - ORD 20:25 4h 55m 1 Stop (BNA) Nashville
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YYZToronto Lester B Pearson Intl Airport 16:30BNANashville Airport 18:30
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BNANashville Airport 17:44ORDChicago O'Hare International Airport 20:25
- 4h 55m (46m)
- 1 Stop BNA · Nashville 46m
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Air Canada (AC 1105)Airbus United Airlines (UA 3482)Embraer 175 -
Air Canada (AC 1105) -
- M
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16:30 YYZ20:14 ORD4Hrs, 44m 1 Stop (DCA)
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YYZToronto Lester B Pearson Intl Airport 16:30 - ORD 20:14 4h 44m 1 Stop (DCA) Washington
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YYZToronto Lester B Pearson Intl Airport 16:30DCAWashington Ronald Reagan National Airport 19:00
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DCAWashington Ronald Reagan National Airport 18:07ORDChicago O'Hare International Airport 20:14
- 4h 44m (53m)
- 1 Stop DCA · Washington 53m
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Air Canada (AC 8784)Canadair Regional United Airlines (UA 2665)Airbus -
Air Canada (AC 8784) -
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The fastest flight time for direct flights from Toronto to Chicago is 1 hour 50 minutes. Check latest flight schedules & prices on Wego.
The most popular airline flying from Toronto to Chicago is Air Canada. Find the latest flight deals on Wego.
The flight distance between Toronto and Chicago is 701km. Check all available flights on Wego.
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.
There are 4 airlines that offer direct flights from Toronto to Chicago. Find out the list of airlines on Wego.
All Airports in Toronto
Toronto John C Munro Hamilton Airport YHM
Toronto City Centre Airport YTZ
All Airports in Chicago
Popular Airlines flying from Toronto to Chicago
Popular Destinations from Chicago
Popular Destinations from Toronto
Popular Hotels in Chicago
- Clarion Inn Elmhurst - Oak Brook near I-88, I-290, I-294
- The Royal Sonesta Chicago Downtown
- Club Quarters Hotel Central Loop
- The Ritz-Carlton, Chicago
- Fairmont Chicago at Millennium Park Gold Experience
- Swissôtel Chicago
- Pendry Chicago
- Hotel Felix Chicago
- Hotel Saint Clair
- Best Western River North Hotel