Using the online timetable is an easy way to look at all the direct flights Toronto — Chicago
231 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 |
| 03:40 | 04:40 | thu | CX90 | Cathay Pacific | 2h 0m | Pearson International Airport — O'Hare International Airport | Select dates |
| 06:15 | 07:30 | daily | AA3524 | American Airlines | 2h 15m | Pearson International Airport — O'Hare International Airport | Select dates |
| 06:30 | 07:25 | daily | AA3524 | American Airlines | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 06:52 | 08:01 | tue, wed, fri, sat, sun | UA5345 | United Airlines | 2h 9m | Pearson International Airport — O'Hare International Airport | Select dates |
| 07:00 | 08:03 | daily | UA3449 | United Airlines | 2h 3m | Pearson International Airport — O'Hare International Airport | Select dates |
| 07:55 | 08:50 | mon, thu, sat | AC503 | Air Canada | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 07:55 | 08:45 | thu, sat | AC7231 | Air Canada | 1h 50m | Pearson International Airport — O'Hare International Airport | Select dates |
| 07:55 | 08:45 | thu, fri, sat, sun | PD2387 | Porter | 1h 50m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 08:00 | 08:57 | daily | AC501 | Air Canada | 1h 57m | Pearson International Airport — O'Hare International Airport | Select dates |
| 08:00 | 09:01 | daily | AC8901 | Air Canada | 2h 1m | Pearson International Airport — O'Hare International Airport | Select dates |
| 08:00 | 08:55 | tue, thu, fri, sat | AC8901 | Air Canada | 1h 55m | 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 | 10:04 | daily | UA1538 | United Airlines | 2h 4m | Pearson International Airport — O'Hare International Airport | Select dates |
| 09:00 | 10:01 | mon, sat, sun | UA1538 | United Airlines | 2h 1m | Pearson International Airport — O'Hare International Airport | Select dates |
| 09:30 | 10:12 | fri | NetJets | 1h 42m | Pearson International Airport — Chicago Midway International Airport | Select dates | |
| 09:30 | 10:20 | mon, tue, wed, thu, fri, sun | PD2387 | Porter Airlines Canada | 1h 50m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 09:30 | 10:20 | mon, wed, thu, fri | PD2387 | Porter | 1h 50m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 10:00 | 10:23 | sun | AC7331 | Air Canada | 1h 23m | Pearson International Airport — O'Hare International Airport | Select dates |
| 10:00 | 10:54 | sun | AC8903 | Air Canada | 1h 54m | Pearson International Airport — O'Hare International Airport | Select dates |
| 11:00 | 12:09 | daily | UA5578 | United Airlines | 2h 9m | Pearson International Airport — O'Hare International Airport | Select dates |
| 11:00 | 12:03 | daily | UA3529 | United Airlines | 2h 3m | Pearson International Airport — O'Hare International Airport | Select dates |
| 11:10 | 12:00 | sat | PD2387 | Porter Airlines Canada | 1h 50m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 11:10 | 12:00 | sat | PD2387 | Porter | 1h 50m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 11:32 | 12:27 | daily | AA3604 | American Airlines | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 12:00 | 12:54 | wed, sun | AC8905 | Air Canada | 1h 54m | Pearson International Airport — O'Hare International Airport | Select dates |
| 12:20 | 13:11 | daily | AC503 | Air Canada | 1h 51m | Pearson International Airport — O'Hare International Airport | Select dates |
| 12:20 | 12:46 | sat | BR659 | EVA Air | 1h 26m | Pearson International Airport — O'Hare International Airport | Select dates |
| 12:20 | 13:15 | mon, tue, wed, thu, fri | AC503 | Air Canada | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 13:00 | 14:05 | mon, tue, thu, fri, sun | UA3675 | United Airlines | 2h 5m | Pearson International Airport — O'Hare International Airport | Select dates |
| 13:00 | 14:07 | wed | UA3448 | United Airlines | 2h 7m | Pearson International Airport — O'Hare International Airport | Select dates |
| 13:00 | 14:06 | sun | UA3529 | United Airlines | 2h 6m | Pearson International Airport — O'Hare International Airport | Select dates |
| 13:15 | 14:10 | daily | AA3606 | American Airlines | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 13:30 | 13:40 | sat | LF333 | Contour Aviation | 1h 10m | Pearson International Airport — Chicago Midway 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 | 14:05 | sat | K4297 | Kalitta Air | 1h 15m | Hamilton Airport — O'Hare International Airport | Select dates |
| 13:50 | 13:49 | thu | K4297 | Kalitta Air | 59m | Hamilton Airport — O'Hare International Airport | Select dates |
| 13:50 | 14:02 | tue | K4297 | Kalitta Air | 1h 12m | Hamilton Airport — O'Hare International Airport | Select dates |
| 13:50 | 14:12 | sat | K4297 | Kalitta Air | 1h 22m | Hamilton Airport — O'Hare International Airport | Select dates |
| 13:50 | 13:36 | sun | K4295 | DHL | 46m | Hamilton Airport — O'Hare International Airport | Select dates |
| 14:00 | 14:51 | daily | AC505 | Air Canada | 1h 51m | Pearson International Airport — O'Hare International Airport | Select dates |
| 14:00 | 14:55 | mon, tue, sat, sun | AC505 | Air Canada | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 14:10 | 15:04 | fri, sun | AC8907 | Air Canada | 1h 54m | Pearson International Airport — O'Hare International Airport | Select dates |
| 14:10 | 15:05 | sun | AC507 | Air Canada | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 14:30 | 15:30 | mon, sat | BR658 | EVA Air | 2h 0m | 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 |
| 14:35 | 14:41 | wed | K4697 | Kalitta Air | 1h 6m | Hamilton Airport — O'Hare International Airport | Select dates |
| 14:45 | 15:51 | mon, tue, wed, fri, sat, sun | UA3404 | United Airlines | 2h 6m | 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 |
| 14:50 | 15:50 | wed | BR658 | EVA Air | 2h 0m | Pearson International Airport — O'Hare International Airport | Select dates |
| 15:10 | 16:05 | daily | AA3608 | American Airlines | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 15:50 | 16:40 | mon, tue, wed, thu, fri, sun | PD2393 | Porter Airlines Canada | 1h 50m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 15:50 | 16:40 | mon, wed, thu, fri, sun | PD2393 | Porter | 1h 50m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 16:00 | 17:25 | fri | K4697 | Kalitta Air | 2h 25m | 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 | |
| 16:30 | 17:24 | daily | AC8909 | Air Canada | 1h 54m | Pearson International Airport — O'Hare International Airport | Select dates |
| 16:45 | 17:54 | sun | K4697 | Kalitta Air | 2h 9m | Hamilton Airport — O'Hare International Airport | Select dates |
| 17:30 | 18:39 | daily | UA3542 | United Airlines | 2h 9m | Pearson International Airport — O'Hare International Airport | Select dates |
| 17:30 | 18:30 | daily | UA2064 | United Airlines | 2h 0m | Pearson International Airport — O'Hare International Airport | Select dates |
| 18:20 | 19:15 | daily | AA3610 | American Airlines | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 18:35 | 19:30 | daily | AC511 | Air Canada | 1h 55m | 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 |
| 22:00 | 22:35 | wed | UA3865 | United Airlines | 1h 35m | Pearson International Airport — O'Hare International Airport | Select dates |
| 22:00 | 22:50 | sat | AC7231 | Air Canada | 1h 50m | 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 |
| 23:05 | 23:55 | wed | 3S442 | DHL | 1h 50m | Pearson International Airport — O'Hare International Airport | Select dates |