Using the online timetable is an easy way to look at all the direct flights Toronto — Chicago
237 flights in a week
Departure and arrival times are local (Toronto and Chicago)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 00:15 | 01:05 | mon | 3S442 | AeroLogic | 1h 50m | Pearson International Airport — O'Hare International Airport | Select dates |
| 00:15 | 01:05 | mon | 3S442 | DHL | 1h 50m | Pearson International Airport — O'Hare International Airport | Select dates |
| 06:30 | 07:25 | daily | AA3524 | American Eagle | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 06:30 | 07:26 | daily | AA3524 | American Eagle | 1h 56m | Pearson International Airport — O'Hare International Airport | Select dates |
| 06:44 | 07:39 | thu | AA3524 | American Eagle | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 07:00 | 07:59 | daily | UA490 | United Airlines | 1h 59m | Pearson International Airport — O'Hare International Airport | Select dates |
| 07:50 | 08:39 | mon, tue, wed, thu, sun | PD2387 | Porter | 1h 49m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 07:50 | 08:39 | wed, sun | PD2387 | Porter Airlines Canada | 1h 49m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 07:55 | 08:45 | daily | PD2387 | Porter Airlines Canada | 1h 50m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 07:55 | 08:45 | tue, wed, thu, fri, sat, sun | PD2387 | Porter | 1h 50m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 08:03 | 08:42 | mon | NetJets | 1h 39m | Pearson International Airport — Chicago Executive Airport | Select dates | |
| 08:15 | 09:09 | daily | AC503 | Air Canada Express | 1h 54m | Pearson International Airport — O'Hare International Airport | Select dates |
| 08:15 | 09:08 | mon, tue, wed, thu, fri, sat | AC8901 | Air Canada Express | 1h 53m | Pearson International Airport — O'Hare International Airport | Select dates |
| 09:00 | 09:59 | daily | UA1538 | United Airlines | 1h 59m | Pearson International Airport — O'Hare International Airport | Select dates |
| 09:00 | 09:55 | mon, wed, thu, fri, sat | UA1538 | United Airlines | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 09:00 | 09:50 | fri | PD2387 | Porter | 1h 50m | 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 | 10:40 | thu | UA3929 | United Airlines | 1h 40m | Pearson International Airport — O'Hare International Airport | Select dates |
| 10:00 | 10:53 | daily | AC8903 | Air Canada Express | 1h 53m | Pearson International Airport — O'Hare International Airport | Select dates |
| 10:15 | 10:45 | tue | UA3287 | United Airlines | 1h 30m | Pearson International Airport — O'Hare International Airport | Select dates |
| 11:00 | 12:01 | sat, sun | UA5563 | United Airlines | 2h 1m | Pearson International Airport — O'Hare International Airport | Select dates |
| 11:00 | 12:03 | tue, wed, fri, sat, sun | UA5676 | United Airlines | 2h 3m | Pearson International Airport — O'Hare International Airport | Select dates |
| 11:44 | 12:39 | daily | AA6488 | American Eagle | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 12:20 | 13:13 | tue, wed, thu, fri, sat, sun | AC505 | Air Canada Express | 1h 53m | Pearson International Airport — O'Hare International Airport | Select dates |
| 12:20 | 13:14 | daily | AC505 | Air Canada Express | 1h 54m | Pearson International Airport — O'Hare International Airport | Select dates |
| 13:00 | 14:01 | mon, tue, wed, thu, fri, sun | UA3605 | United Airlines | 2h 1m | Pearson International Airport — O'Hare International Airport | Select dates |
| 13:00 | 13:54 | wed | AA9868 | American Eagle | 1h 54m | Pearson International Airport — O'Hare International Airport | Select dates |
| 13:15 | 14:10 | mon, tue, thu, sat | AA4770 | American Eagle | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 13:16 | 14:12 | daily | AA4770 | American Eagle | 1h 56m | Pearson International Airport — O'Hare International Airport | Select dates |
| 13:50 | 14:11 | wed | BR657 | EVA Air | 1h 21m | Pearson International Airport — O'Hare International Airport | Select dates |
| 13:50 | 14:04 | wed | K4295 | DHL | 1h 14m | Hamilton Airport — O'Hare International Airport | Select dates |
| 13:50 | 13:36 | sun | K4295 | DHL | 46m | Hamilton Airport — O'Hare International Airport | Select dates |
| 13:50 | 13:54 | wed | K4295 | Kalitta Air | 1h 4m | Hamilton Airport — O'Hare International Airport | Select dates |
| 13:50 | 13:38 | sun | K4295 | DHL | 48m | Hamilton Airport — O'Hare International Airport | Select dates |
| 13:50 | 13:44 | fri | K4295 | Kalitta Air | 54m | Hamilton Airport — O'Hare International Airport | Select dates |
| 13:50 | 13:28 | thu | K4297 | Kalitta Air | 38m | Hamilton Airport — O'Hare International Airport | Select dates |
| 14:10 | 15:04 | daily | AC507 | Air Canada Express | 1h 54m | Pearson International Airport — O'Hare International Airport | Select dates |
| 14:30 | 15:20 | sat | BR659 | EVA Air | 1h 50m | Pearson International Airport — O'Hare International Airport | Select dates |
| 14:30 | 14:10 | sat | BR683 | EVA Air | 40m | Pearson International Airport — O'Hare International Airport | Select dates |
| 14:45 | 15:35 | wed | BR683 | EVA Air | 1h 50m | Pearson International Airport — O'Hare International Airport | Select dates |
| 14:45 | 15:48 | daily | UA5258 | United Airlines | 2h 3m | Pearson International Airport — O'Hare International Airport | Select dates |
| 14:45 | 14:37 | tue | K4297 | Kalitta Air | 52m | Hamilton Airport — O'Hare International Airport | Select dates |
| 14:50 | 15:22 | fri | K4295 | Kalitta Air | 1h 32m | Hamilton Airport — O'Hare International Airport | Select dates |
| 14:50 | 14:07 | fri | K4295 | Kalitta Air | 17m | Hamilton Airport — O'Hare International Airport | Select dates |
| 15:10 | 16:05 | mon, tue, wed, thu, fri, sat | AA3608 | American Eagle | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 15:11 | 16:05 | daily | AA3608 | American Eagle | 1h 54m | Pearson International Airport — O'Hare International Airport | Select dates |
| 15:35 | 16:24 | mon, tue, wed, thu, fri, sun | PD2393 | Porter Airlines Canada | 1h 49m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 15:35 | 16:24 | tue | PD2393 | Porter | 1h 49m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 15:45 | 15:36 | fri | K4295 | DHL | 51m | Hamilton Airport — O'Hare International Airport | Select dates |
| 16:30 | 17:12 | mon | NetJets | 1h 42m | Pearson International Airport — Chicago Midway International Airport | Select dates | |
| 16:40 | 17:37 | mon, tue, wed, thu, fri, sun | AC8909 | Air Canada Express | 1h 57m | Pearson International Airport — O'Hare International Airport | Select dates |
| 16:40 | 17:33 | tue, thu, fri, sat, sun | AC8909 | Air Canada Express | 1h 53m | Pearson International Airport — O'Hare International Airport | Select dates |
| 16:45 | 17:42 | sat | AC8909 | Air Canada Express | 1h 57m | Pearson International Airport — O'Hare International Airport | Select dates |
| 17:15 | 18:15 | tue, thu, fri, sat, sun | UA1371 | United Airlines | 2h 0m | Pearson International Airport — O'Hare International Airport | Select dates |
| 17:15 | 18:12 | daily | UA2121 | United Airlines | 1h 57m | Pearson International Airport — O'Hare International Airport | Select dates |
| 17:15 | 18:22 | fri, sun | UA5536 | United Airlines | 2h 7m | Pearson International Airport — O'Hare International Airport | Select dates |
| 18:21 | 19:22 | mon, tue, fri, sat, sun | AA4530 | American Eagle | 2h 1m | Pearson International Airport — O'Hare International Airport | Select dates |
| 18:29 | 19:24 | mon, thu, fri, sun | AA3610 | American Eagle | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 18:35 | 19:29 | daily | AC511 | Air Canada Express | 1h 54m | Pearson International Airport — O'Hare International Airport | Select dates |
| 20:36 | 21:32 | thu | UA3752 | United Airlines | 1h 56m | Pearson International Airport — O'Hare International Airport | Select dates |
| 21:00 | 22:06 | mon, tue, wed, thu, fri, sun | UA3640 | United Airlines | 2h 6m | Pearson International Airport — O'Hare International Airport | Select dates |
| 21:00 | 22:05 | mon, tue, wed, thu, fri, sun | UA3640 | United Airlines | 2h 5m | Pearson International Airport — O'Hare International Airport | Select dates |
| 21:00 | 22:07 | mon, tue, wed, thu, fri, sun | UA5928 | United Airlines | 2h 7m | Pearson International Airport — O'Hare International Airport | Select dates |
| 23:05 | 23:55 | wed | 3S442 | AeroLogic | 1h 50m | Pearson International Airport — O'Hare International Airport | Select dates |