Using the online timetable is an easy way to look at all the direct flights Toronto — Chicago
266 flights in a week
Departure and arrival times are local (Toronto and Chicago)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 00:55 | 01:45 | thu | CX3290 | Cathay Pacific | 1h 50m | Pearson International Airport — O'Hare International Airport | Select dates |
| 03:40 | 04:25 | thu | CX90 | Cathay Pacific | 1h 45m | Pearson International Airport — O'Hare International Airport | Select dates |
| 06:30 | 07:40 | thu, fri, sat | AA3351 | American Airlines | 2h 10m | Pearson International Airport — O'Hare International Airport | Select dates |
| 06:30 | 07:39 | daily | AA3351 | American Airlines | 2h 9m | Pearson International Airport — O'Hare International Airport | Select dates |
| 06:30 | 07:25 | daily | AA4409 | American Airlines | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 06:52 | 08:09 | mon, tue, thu, sat, sun | UA3436 | United Airlines | 2h 17m | Pearson International Airport — O'Hare International Airport | Select dates |
| 07:00 | 07:12 | fri | AC7070 | Air Canada | 1h 12m | Pearson International Airport — O'Hare International Airport | Select dates |
| 07:00 | 08:01 | mon, tue, wed, thu, fri | UA1584 | United Airlines | 2h 1m | Pearson International Airport — O'Hare International Airport | Select dates |
| 07:00 | 08:09 | sun | UA3662 | United Airlines | 2h 9m | Pearson International Airport — O'Hare International Airport | Select dates |
| 07:00 | 07:40 | thu | UA3882 | United Airlines | 1h 40m | Pearson International Airport — O'Hare International Airport | Select dates |
| 07:59 | 08:58 | mon, tue, wed, thu, fri, sun | UA490 | United Airlines | 1h 59m | Pearson International Airport — O'Hare International Airport | Select dates |
| 07:59 | 09:03 | sun | UA5450 | United Airlines | 2h 4m | Pearson International Airport — O'Hare International Airport | Select dates |
| 08:00 | 09:02 | daily | AC501 | Air Canada | 2h 2m | Pearson International Airport — O'Hare International Airport | Select dates |
| 08:00 | 09:02 | tue | AC501 | Air Canada Rouge | 2h 2m | Pearson International Airport — O'Hare International Airport | Select dates |
| 08:00 | 08:54 | tue, wed, thu, fri, sun | AC501 | Air Canada | 1h 54m | Pearson International Airport — O'Hare International Airport | Select dates |
| 08:03 | 08:42 | mon | NetJets | 1h 39m | Pearson International Airport — Chicago Executive Airport | Select dates | |
| 09:00 | 10:05 | daily | UA1538 | United Airlines | 2h 5m | Pearson International Airport — O'Hare International Airport | Select dates |
| 09:00 | 10:11 | daily | UA1538 | United Airlines | 2h 11m | Pearson International Airport — O'Hare International Airport | Select dates |
| 09:20 | 10:07 | mon, tue, wed, thu, fri | PD2387 | Porter | 1h 47m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 09:30 | 10:12 | fri | NetJets | 1h 42m | Pearson International Airport — Chicago Midway International Airport | Select dates | |
| 10:00 | 11:30 | daily | SX263 | FlyGTA Airlines | 2h 30m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 10:30 | 11:17 | sun | PD2387 | Porter | 1h 47m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 10:30 | 11:14 | thu | UA3905 | United Airlines | 1h 44m | Pearson International Airport — O'Hare International Airport | Select dates |
| 10:45 | 11:32 | sat | PD2387 | Porter | 1h 47m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 11:00 | 12:04 | daily | UA5454 | United Airlines | 2h 4m | Pearson International Airport — O'Hare International Airport | Select dates |
| 11:38 | 12:49 | daily | AA6050 | American Airlines | 2h 11m | Pearson International Airport — O'Hare International Airport | Select dates |
| 11:38 | 12:49 | mon | AA6050 | United Airlines | 2h 11m | Pearson International Airport — O'Hare International Airport | Select dates |
| 11:44 | 12:54 | thu, sat | AA3594 | American Airlines | 2h 10m | Pearson International Airport — O'Hare International Airport | Select dates |
| 11:44 | 12:53 | tue, wed, fri, sat | AA3594 | American Airlines | 2h 9m | Pearson International Airport — O'Hare International Airport | Select dates |
| 11:55 | 12:50 | daily | AA3426 | American Airlines | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 12:30 | 13:32 | daily | AC503 | Air Canada | 2h 2m | Pearson International Airport — O'Hare International Airport | Select dates |
| 12:30 | 13:32 | mon | AC503 | Air Canada Rouge | 2h 2m | Pearson International Airport — O'Hare International Airport | Select dates |
| 12:30 | 13:24 | mon, tue, wed, thu, sat, sun | AC503 | Air Canada | 1h 54m | Pearson International Airport — O'Hare International Airport | Select dates |
| 13:00 | 14:04 | tue, wed, thu, fri, sat, sun | UA4629 | United Airlines | 2h 4m | Pearson International Airport — O'Hare International Airport | Select dates |
| 13:12 | 14:21 | mon, wed, thu, sat | AA3333 | American Airlines | 2h 9m | Pearson International Airport — O'Hare International Airport | Select dates |
| 13:13 | 14:23 | tue, thu, fri, sat | AA3333 | American Airlines | 2h 10m | Pearson International Airport — O'Hare International Airport | Select dates |
| 13:15 | 14:10 | tue, wed, thu, fri, sat | AA3427 | American Airlines | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 14:35 | 15:37 | daily | AC505 | Air Canada | 2h 2m | Pearson International Airport — O'Hare International Airport | Select dates |
| 14:35 | 15:29 | mon, tue, wed, thu, sat, sun | AC505 | Air Canada | 1h 54m | Pearson International Airport — O'Hare International Airport | Select dates |
| 14:35 | 15:13 | wed | BR656 | EVA Air | 1h 38m | Pearson International Airport — O'Hare International Airport | Select dates |
| 15:00 | 16:11 | mon, tue, wed, thu, fri, sun | UA3608 | United Airlines | 2h 11m | Pearson International Airport — O'Hare International Airport | Select dates |
| 15:00 | 16:15 | mon, tue, wed, thu, fri, sun | UA3543 | United Airlines | 2h 15m | Pearson International Airport — O'Hare International Airport | Select dates |
| 15:07 | 16:02 | daily | AA3428 | American Airlines | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 15:30 | 16:20 | mon, tue, wed, thu, fri, sun | PD2393 | Porter | 1h 50m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 15:30 | 16:17 | wed | PD2393 | Porter | 1h 47m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 15:30 | 16:17 | mon, thu, sun | PD2393 | Porter | 1h 47m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 15:50 | 16:40 | sun | PD2393 | Porter | 1h 50m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 16:00 | 17:04 | mon, tue, wed, thu, fri, sun | UA3636 | United Airlines | 2h 4m | Pearson International Airport — O'Hare International Airport | Select dates |
| 16:30 | 17:12 | mon | NetJets | 1h 42m | Pearson International Airport — Chicago Midway International Airport | Select dates | |
| 16:37 | 17:48 | daily | AA6021 | American Airlines | 2h 11m | Pearson International Airport — O'Hare International Airport | Select dates |
| 16:40 | 17:49 | daily | AA3641 | American Airlines | 2h 9m | Pearson International Airport — O'Hare International Airport | Select dates |
| 16:44 | 17:54 | tue, wed | AA3641 | American Airlines | 2h 10m | Pearson International Airport — O'Hare International Airport | Select dates |
| 16:55 | 17:36 | mon | BR660 | EVA Air | 1h 41m | Pearson International Airport — O'Hare International Airport | Select dates |
| 16:55 | 17:39 | mon | BR660 | EVA Air | 1h 44m | Pearson International Airport — O'Hare International Airport | Select dates |
| 17:30 | 18:41 | daily | UA5599 | United Airlines | 2h 11m | Pearson International Airport — O'Hare International Airport | Select dates |
| 17:30 | 18:29 | daily | UA213 | United Airlines | 1h 59m | Pearson International Airport — O'Hare International Airport | Select dates |
| 18:15 | 19:02 | sat | PD2399 | Porter | 1h 47m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 18:19 | 19:14 | mon, tue, thu, fri, sun | AA3429 | American Airlines | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 18:20 | 19:31 | mon, thu, fri, sun | AA6086 | American Airlines | 2h 11m | Pearson International Airport — O'Hare International Airport | Select dates |
| 18:25 | 19:34 | mon, fri, sun | AA3602 | American Airlines | 2h 9m | Pearson International Airport — O'Hare International Airport | Select dates |
| 18:26 | 19:36 | thu, fri | AA3602 | American Airlines | 2h 10m | Pearson International Airport — O'Hare International Airport | Select dates |
| 18:35 | 19:29 | daily | AC509 | Air Canada | 1h 54m | Pearson International Airport — O'Hare International Airport | Select dates |
| 18:40 | 19:34 | mon | AC509 | Air Canada | 1h 54m | Pearson International Airport — O'Hare International Airport | Select dates |
| 18:55 | 19:49 | mon, tue | AC509 | Air Canada | 1h 54m | Pearson International Airport — O'Hare International Airport | Select dates |
| 19:55 | 20:05 | sat | AA6021 | American Airlines | 1h 9m | Pearson International Airport — O'Hare International Airport | Select dates |
| 19:56 | 20:55 | sun | UA3757 | United Airlines | 1h 59m | Pearson International Airport — O'Hare International Airport | Select dates |
| 20:15 | 21:00 | fri | CX2092 | Cathay Pacific | 1h 45m | Pearson International Airport — O'Hare International Airport | Select dates |
| 20:50 | 21:37 | tue | PD2395 | Porter | 1h 47m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 20:50 | 21:37 | mon, tue, wed, fri | PD2395 | Porter | 1h 47m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 21:00 | 22:04 | mon, tue, wed, thu, fri, sun | UA4631 | United Airlines | 2h 4m | Pearson International Airport — O'Hare International Airport | Select dates |